Advances in

Carbohydrate Chemistry and Biochemistry

Volume 54
Cumulative Subject and Contributor Indexes
and Tables of Contents
Volumes 1-53
This Page Intentionally Left Blank
 Advances in
Carbohydrate Chemistry
and
Biochemistry
Editor
DEREK HORTON
The American University
Washington, DC

Board of Advisors
LAURENS ANDERSON DAVtD R. BUNDLE
STEPHENJ. ANGYAL STEPHEN HANESSIAN
HANSH. BAER BENGTLINDBERG
CLINTON E. BALLOU HANSPAULSEN
JOHNS. BRIMACOMBE NATHAN SHARON
J. GRANTBUCHANAN J. F. G. VLIEGENTHART
ROYL. WHISTLER

Volume 54
Cumulative Subject and Contributor Indexes
and Tables of Contents
Volumes 1-53

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 CONTENTS

PREFACE .............. vii

CONTENTS OF VOLUMES 1-53 ....ix
SUBJECT INDEX ........... 1
CONTRIBUTOR INDEX ..... .533

V
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 PREFACE

This 54th volume of Advances in Carbohydrate Chemistry and Biochemistry

is an index volume that covers all previous volumes in the series, with a cumula-
tive subject index of the content of all published chapters, along with an index of
authors contributing the chapters.
The series began with the 1945 appearance of Volume 1 of Advances in Car-
bohydrate Chemistry under the editorship of Ward Pigman and Melville Wol-
from, and was the first serial publication of a new company named Academic
Press, founded by Kurt Jacoby. The stated policy was to have the individual
contributors furnish critical, integrating reviews rather than mere literature sur-
veys, and to have the articles presented in such a form as to be intelligible to the
average chemist rather than only to the specialist. The series was to cover the
broad field of carbohydrates, including sugars, polysaccharides, and glycosides,
and to include biochemical, industrial, and analytical developments.
The founding policy has been sustained throughout the subsequent evolution
of the series, under the editorship of Wolfrom for most of the volumes until his
death in 1969, of R. Stuart Tipson from 1954 until 1990, and of the present edi-
tor since 1969. The essential component of biochemical aspects was emphasized
when the title was changed, in 1969, to Advances in Carbohydrate Chemistry
and Biochemistry. The field of carbohydrates has undergone enormous expan-
sion during the half-century that Advances has been in existence, and the pages
of the past 53 volumes have recorded important developments in practically all
aspects of carbohydrate science. Some of the articles have constituted status re-
ports on areas still under active expansion, while others record definitive infor-
mation of permanent reference value.
To enhance the utility of Advances as a reference source, the provision of
good indexes has been an important objective, and each volume has contained a
comprehensive name index of all authors cited in the individual chapters, along
with a detailed subject index. Responsibility for compiling the subject indexes
from the outset and for more than four decades was largely entrusted to a leading
expert on indexing and nomenclature, Dr. Leonard T. Capell of Chemical Ab-
stracts Service. These subject indexes were integrated into cumulative indexes of
principal topics and have appeared in selected issues, with volume 29 containing
 ...
Vlll PREFACE

such an index for volumes 1-29, while those appearing in volumes 35, 40, 45,
and 50 refer in each case to the preceding five volumes.
The present index volume largely follows the model used successfully for the
Methods in Enzymology series published by Academic Press, and the cumulative
subject index has been compiled directly from subject indexes in the individual
volumes. It is recognized that a lack of total uniformity is inevitable as a conse-
quence of unevenness in some of the indexes, and most importantly, from the
progress that has been made toward uniformity in carbohydrate nomenclature.
Current nomenclature recommendations are recorded in the 1996 document
Nomenclature of Carbohydrates, issued by the International Union of Pure and
Applied Chemistry and the International Union of Biochemistry and Molecular
Biology, which has been published in Volume 52 of Advances in Carbohydrate
Chemistry and Biochemistry.
This index volume is complemented by a cumulative contributor index, and it
is hoped that the volume will facilitate the retrieval of information and signifi-
cantly enhance the utility of the entire series.

Washington, DC DEREKHORTON
June 1999
 CONTENTS OF VOLUMES 1-53

VOLUME 1

The Fischer Cyanohydrin Synthesis and the Configurations

ofHigher-Carbon Sugars and Alcohols ........................................... 1
C. S. HUDSON

The Altrose Group of Substances . . . . . .. . . . . . . . . .. .... . . . . . . .. .... .. . . . . .. .. . .. .. 37

NELSONK. RICHTMYER

CarbohydrateOrthoesters ..................................................... 77
EUGENEPACSU

Thio-and Seleno-sugars ....................................................... 129

ALBERT L. RAYMOND

The Carbohydrate Components of the Cardiac Glycosides .. ... .. .. .. .... .. . . .. . .. .. 147

ROBERT c. ELDERFIELD
Metabolism of the Sugar Alcohols and Their Derivatives . .. .. .. . . . . . .. .. . . . . . . . ... . . 175
CARRA N D JOHNC. KRANTZ,
C. JELLEFF JK.

The Chemistry of the Nucleic Acids . . . .. .. . .. .. .. . ......... .. .. . .. .. .. .. . . . .. .. .. 193

R. STUART
TIPSON

TheFractionationofStarch .................................................... 247

THOMASJOHNSCHOCH

Preparation and Properties of Starch Esters . .. . . . .. .. . . . .. .. . .. .. . . .. . . .. .. .. .. . . 279

ROYL. WHISTLER

Cellulose Esters of Organic Acids . . . . . . . . . . . . . . . . ..... . . . . .. . . . . . . . . . . . . . .. . .. .. 309

CHARLES R. FORDYCE

A Discussion of Methods of Value in Research on Plant Polyuronides .. .. .. . . . .. . . . .. . 329

ERNESTANDERSON AND LILASANDS

VOLUME 2

Melezitose and Turanose .. .. . . . . . . . .. . . . .. . . . .. .. . .. . . . . . .. .. . . . .. .. . .. .. . . . .. . 1

C. S.HUDSON

ix
X CONTENTS OF VOLUMES 1-53

The Chemistry of Anhydro Sugars .............................................. 37

STANLEYPEAT

AnalogsofAscorbic Acid ...................................................... 79

F. SMITH

Synthesis of Hexitols and Pentitols from Unsaturated Polyhydric Alcohols ............. 107
R. LESPLEAU

The Interrelation of Carbohydrate and Fat Metabolism ............................. 119

HARRYJ. DEUEL,JR., AND MARGARET G. MOREHOUSE

The Chemistry of Mucopolysaccharides and Mucoproteins .......................... 161

M. STACEY

Bacterial Polysaccharides ...................................................... 203

TAYLOR H. EVANSAND HAROLD HIBBERT

The Chemistry of Pectic Materials ............................................... 235

E. L. HIRSTAND J. K. N. JONES

The Polyfructosans and Difructose Anhydrides .................................... 253

EMMAJ. MCDONALD

Cellulose Ethers of Industrial Significance ........................................ 279

JOSEPHF. HASKINS

VOLUME 3
Historical Aspects of Emil Fischers Fundamental Conventions for
Writing Stereo-Formulas in a Plane ............................................. 1
C. S. HUDSON

The Structure and Reactivity of the Hydrazone

and Osazone Derivatives of the Sugars ........................................... 23
E. G. V. PERCIVAL

The Chemistry and Configuration of the Cyclitols .................................. 45

HEWITTG. FLETCHER, JR.

TritylEthersofCarbobydrates ................................................. 79
BURCKHARDT HELFERICH

Glutose and the Unfermentable Reducing Substances in Cane Molasses ............... 113
LOUISSATTLER

The Halogen Oxidation of Simple Carbohydrates,

Excluding the Action of Periodic Acid ............................................ 129
JOHNW. GREEN
 CONTENTS OF VOLUMES 1-53 xi

The Molecular Constitution of Cellulose . . .. . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . .. . .. . . . 185

JACKCOMPTON

Isotopic Tracers in the Study of Carbohydrate Metabolism .. . . . .... . .. . . . . . . .. . .. .. . 229

SAMUEL GURM

Products of the Enzymic Degradation of Starch and Glycogen .. . .. . . .. . .. .. .. .. . .. .. 253

KARLMYREIACK

The Polysaccharides of Mycobacterium Tuberculosis ... . . . . .. . ... . .. . .. .. . . . .. .... . 31 1

M. STACEY AND P. W. KENT

The Chemistry of Streptomycin . . . . . . . . . . . . . . . . .. .. . ... .. . .. . . . . . .. .. . . .. . . . .. . . 337

R. U. LEMIEUXAND M. L. WOLFROM

VOLUME 4

The Structure and Configuration of Sucrose

(a-D-~~ucopyranosy~-~-D-fructofuranoside) ....................................... 1
IRVINGLEVIA N D CLIFFORDB. Pmvts

Blood Group Polysaccharides . . . . . .. . . . . . . . .. . . . .. .. . . . . . . . . .. . . . . . .. . . . . . . . . .. . 37

H. G. BRAYAND M. STACEY

Apiose and the Glycosides of the Parsley Plant.. . .. .. . .. . . . . . . . . . . . . . . . . . . . . . . . ... . 57

C. S. HUDSON

Biochemical Reductions a t the Expense of Sugars .. ... ... .. .. . . . .. . . . . . . . . . . . . .. .. . 75

CARLNEUBERG

The Acylated Nitriles of Aldonic Acids and Their Degradation .. . . .. . .. . . . .. .. .. . . ... 119
VENANCIO DEULOFEU

Wood Saccbarification ......................................................... 154

ELWINE. HARRIS

The Use of Boric Acid for the Determination

of the Configuration of Carbohydrates . .. .. . .. . . . .. ... .. . . . .. . .. .. .. . . . .. .. . . ... . 189
J. BOESEKEN

The Hexitols and Some of Their Derivatives . . . . .. . .. . .. . . . .. .. . .. .. .. .. . . . .. .. . .. . 211

ROLLAND LOHMAR AND R. M. GOEPP.JR.

Plant Gums and Mucilages . . . . . . . . . . . . . . .. . .. .. ... .. . . . .. . . . .. . . . .. .. . . . .. . . .. . 243

J. K. N. JONES AND F. SMITH

The Utilization of Sucrose . . .. . . . . . . . . . . . . . . .. . .. .... . . .. . . . . . .. . . . .. .. . . . . . . .. . 293

L. F. WIGGMS
xii CONTENTS OF VOLUMES 1-53

VOLUME 5

Applications in the Carbohydrate Field of Reductive

Desulfurization by Raney Nickel ..... .. . .. .. . . .. . . . . . . . .. .. .. .. .. .. .. .. . . .. .. ... 1
HEWIT?G. FLETCHER, JR., AND NELSONK. RICHTMYER

Enzymatic Synthesis of Sucrose and Other Disaccharides . . . ..... . .. .. .. .. . .. ..... .. 29

W. Z. HASSIDAND M. DOUDOROFF

Principles Underlying Enzyme Specificity in the Domain of Carbohydrates .. .. . . . . . . . . 49

ALFRED GOITSCHALK

Enzymes Acting on Pectic Substances .. . . . . . . . . . . .. .. .. . .. .. .. .. .. .. . . .. .. ... .. .. 79

AND R. J. MCCOLLOCH
Z. I. KERTESZ

The Relative Crystallinity of Celluloses .. . . .. .. .. . . . ... . ..... .. .. .. ... . . . .. .. .. . . . 103

R. F. NICKERSON

The Commercial Production of Crystalline Dextrose .. .. .. .. ... .. .. .. .. .. .. . . ..... . 127

G. R. DEANAND J. B. GOTTFRIED

The Methyl Ethers of D-GlUCOSe . . .. . . .. .. .. . .. .. .. .. .. . . . .. .. .. .... ... .. . . .. .. . . 145

E. J. BOURNE
AND STANLEY PEAT

Anhydrides of the Pentitols and Hexitols.. . .. .. . . . . .. ... . . .... .. .... . . .. . .. .. .. .. . 191

L. F. WIGGINS

.
Action of Certain Alpha Amylases . . .. .. . . . . . .. . . .. .. . . . .... .. .. .. .. .. .... .. .. . . 229
MARYL. CALDWELL AND MILDRED ADAMS

Xylan ................... .. ................... ... .............. ......... ..... 269

ROYL. WHISTLER

VOLUME 6

Obituary of Walter Norman Haworth . . .. .. .. .. .... . . . .. .. .. .. . . . .. .... . .. .. . .. .. 1

E. L. HIRST

The Methyl Ethers of he galactose .. . . .. .... . ... .. . . . .. ... .. .... . . .. .. .. .... . . ... 11
D. J. BELL

Thesynthesis ofOligosaccbarides ............................................... 27

W. L. EVANS,D. D. REYNOLDS,AND E. A. TALLEY

The Formation of Furan Compounds from Hexoses . . .. .. .. .. . . . .. . . .. ... ... .. .. .. . 83

F. H. NEWTH

Cuprammonium-Glycoside Complexes .. ....... . .. .. . . . .. .... .. .. .. .. .. . .. .. .. ... 107

E. REEVES
RICHARD
 ...
CONTENTS OF VOLUMES 1-53 xi11

TheChemistryofRibose ....................................................... 135

ROGERW. JEANLOZAND HEWITT JR.
G. FI.ETCIIER.

The 2-(Aldo-polydroxyalkyl)benzimidazoles . . .. . . .. .. ... . . . .. .. . . . . . . . . ... . .. . . . .. 195

NELSON K. RICHTMYER

Trends in the Development of Granular Adsorbents for Sugar Refining .. . . .. . . . . . . . . . 205

ELLIOTT P. BARRETT

Acoritic Acid, a By-product in the Manufacture of Sugar.. . . . . .. ... . . . . .. .. .. .. . .. . . 231

ROBERT ELLSWORTH MILLER A N D SIDNEYM. CANTOR

Friedel-Crafts and Grignard Processes in the Carbohydrate Series .. . .. . . . . .. .. .. . .. . 251

WILLIAM A. BONNER

The Nitromethane and 2-Nitroethanol Syntheses . .. .. . .. . .. .. . . . . . .. . . . . .. .. . .. . . . . 291

JOHNC. SOWDEN

VOLUME 7

The Methyl Ethers of the Aldopentoses and of Rhamnose and Fucose .. . . . . . .. . . . .. . . . 1

R. A. LAIDLAWAND (THELATE) E. G. V. PERCIVAL

1,6-Anhydrohexofuranoses, a New Class of Hexosans . .. . .. . . . . .. . . .. . . . . . .. .. . .. . . . 37

R. J. DIMLER

Fructose and Its Derivatives .. . . .

. . . . . . .. . . ... . . . .. . . . . . . .. .... . . . . . . . . . . .. .. . .. 53
C. P. BARRYAND JOHNHONEYMAN

Psicose, Sorbose, and Tagatose . . . . .. .. . . . . . .. . . . .. . . . . . . . . .. .. . .. .. . . . .. . . . . . . . . 99

J. V. KARABINOS

Acetals and Ketals of the Tetritols, Pentitols, and Hexitols . . . . . . . . .. . . . ... . . . . .. . . . . . 137
S. A. BARKER AND E. J. BOURNE

TheGlycals .................................................................. 209

BURCKHARDT HELFERICH

The Chemistry of the 2-Amino Sugars (2-Amino-2-deoxy-sugars) .. . . . . . . . . . . . . .. .. .. . 247

A. B. FOSTER
AND M. STACEY

The Size and Shape of Some Polysaccharide Molecules.. . .. . . . . . .. . . . . . . .. . . .. . .. . .. 289

C. T. GREENWOOD

VOLUME 8

Relative Reactivities of Hydroxyl Groups of Carbohydrates . . . .. . . . .. . . . . . .. . . . . . . . . 1

JAMES M. SUGIHARA
xiv CONTENTS OF VOLUMES 1-53

The Chemistry of the 2-Desoxysugars ............................................ 45

W. G. OVEREND AND M. STACEY

Sulfonic Esters of Carbohydrates ................................................ 107

R. STUART TIPSON

The Methyl Ethers of o-Mannose ................................................ 217

G. 0. ASPINALL

The Chemical Synthesis of o-Glucuronic Acid ..................................... 231

C. L. MEHLTRETTER

o-Glucuronic Acid in Metabolism ............................................... 251

H. G. BRAY

The Substituted-Sucrose Structure of Melezitose ................................... 277

EDWARD J. HEHRE

Composition of Cane Juice and Cane Final Molasses ............................... 291

W. W. BINKLEY AND M. L. WOLFROM

SeaweedPolysaccharides ....................................................... 315

T. MOM

VOLUME 9

Some Implications in Carbohydrate Chemistry of Theories Relating

to the Mechanisms of Replacement Reactions ..................................... 1
R. U. LEMIEUX

Alkali-Sensitive Glycosides ..................................................... 59

CLINTON E. BALLOU

The 2-Hydroxyglycals ......................................................... 97

MARYGRACEBLAIR

The Methyl Ethers of Hexuronic Acids ........................................... 131

G. 0.ASPINALL

The Raffinose Family of Oligosaccharides ........................................ 149

DEXTERFRENCH

The Conjugates of o-Glucuronic Acid of Animal Origin ............................. 185

ROBERTS. TEAGUE

Color and Turbidity of Sugar Products ........................................... 247

R. W. LIGGETTAND VICTOR R. DEITZ
 CONTENTS OF VOLUMES 1-53 XV

Carboxymethylcellulose . . .. . . . . . . . . . . .. . .. .. . . . . . .. . . . . . . . . .. . . . . . .. . . . . .. . . .. 28.5
A N D MARJORIE
J. V. KARABINOS Hmmu

Paper Chromatography of Carbohydrates and Related Compounds . . . . .. .. . .. .. . . . . . 304

GEORGE N. KOWKABANY

VOLUME 10

The Stereochemistry of Cyclic Derivatives of Carbohydrates .. . . . . . . . . . . . .. . . . . . . . . . . 1

J. A. MILLS

Column Chromatography of Sugars and Their Derivatives . . . . . . . . . . . . . . . . . . . . . . . . .. 55

W. W. B~NKLEV

.
Glycosylamines . . . .. . . . . . .. .
. . . .. . . . . . . ... .. . .. . . . . . . . .. . . . .. .. . ... . .. .. . . . . . 95
G. P. ELLISAND JOHN HONEYMAN

The Amadori Rearrangement ................................................... 169

JOHNE. HODGE

The Glycosyl Halides and Their Derivatives . . . .. . .. ... .. . . . . . . . . . . .. .. .. . . . . . . . .. . 207

L. J. HAYNES
AND F. H. NEWTH

The Methyl Ethers of the Aldopentoses and of Rhamnose and Fucose . . . . . .. . . . .. . . .. . 257
GEORGE G. MAHER

The Methyl Ethers of D-Galactose . . .. .. .. . . . .. . .. .. . . . . . .. .. . . . . . .. . . . .. .. . . . . . . 273

GEORGE G. MAHER

Polysaccharides Associated with Wood Cellulose . . .. . .. .. . .. . . .. . . . .. . . .. . . . .. . . . .. 283

W. J. POLGLASE

Thechemistry ofHeparin ..................................................... 335

A. B. FOSTERA N D A. J. HUGGARD

VOLUME 11

Periodate Oxidation of Carbohydrates . .. . . ... .. . .. .. . . . ... .. .. . . . .. . . .. . . . . . . . .. 1

' M. BOBBITT

TheOsones . ..
..... ... ...... .. . . .. . .. .. .. . ..... . .... .. ... ............ .. . .. ... 43
S. BAYNE
AND J. A. FEWSTER

Reactions of Monosaccharides with P-Ketonic Esters and Related Substances . . . . . . . . .. 97

F. GARCIA CONZALEZ
xvi CONTENTS OF VOLUMES 1-53

Kojic Acid ................................................................... 145

ANDREW BEELIK

The Biosynthesis of the Monosaccharides .. ... .. .. .. .. .. .. . . ... .. .. .. .. .. .. . .. .. . . 185

L. HOUGHAND J. K. N. JONES

Branched-Chain Sugars of Natural Occurrence . .. .. . . . .. . . . . .. .. .. . . .... .. .. .. .. . . 263

F. SHAFIZADEH

Nucleic Acids ................................................................ 285

G. R. BARKER

Aspects of the Physical Chemistry of Starch .. .. .. . .. .. . . . ... . . .. .. .. .... .. .. ... .. . 335

C. T. GREENWOOD

Addendum .................................................................. 385

The Size and Shape of Some Polysaccharide Molecules

VOLUME 12

InfraredSpectraofCarbohydrates .............................................. 13
W. BROCKNEELY

The Saccharinic Acids .... .. .. .. . . ... .. .... . ... .. .. .. .... . ... .... . .. .. .. . . .. . . . 35
JOHNC. SOWDEN

Zone Electrophoresis of Carbohydrates ... ... .. .. .. .. .. .. .. . . .. .. .. ... . ... . . .. .. . 85

A. B. FOSTER

SugarNitrates ................................................................ 117

JOHNHONEYMAN AND J. W. W. MORGAN

BenzylEthers ofsugars ........................................................ 137

CHESTERM. MCCLOSKEY

Methyl and Phenyl Glycosides of the Common Sugars .. .. .. .. ........ . .. . .. .. .. .. . . 158

AND c . A. M A R S H
J. CONCHIE, G. A. LEVVY,

The Schardinger Dextrins .. .. .. .. ..... . . .. . . .. .. .. .. . . . . . . . .. .. . . .... .. ... .. . . . 189

DEXTERFRENCH

The Molecular Structure of Glycogens . .. ...... . .. .. .. .. .. .. .. .... .. .... . . .. .. .. . 261

D. J. MANNERS

The Biosynthesis of Hyaluronic Acid .. .. . . ... .. . . ... . .. .. .. .. .. .. .. .... .. .. .. .. . . 299

ROYL. WHISTLER AND E. J. OLSON
 CONTENTS OF VOLUMES 1-53 xvii

VOLUME 13

Formation and Cleavage of the Oxygen Ring in Sugars .. . . . . . .. . . . . . .. . .. .. . . . .. . . . 9

F. SHAFIZADEH

The Lobry De Bruyn-Alberda Van Ekenstein Transformation . . . . . . . . . .. .. . . . . . . . . .. 63

JOHNC. SPECK,JR.

The Formazan Reaction in Carbohydrate Research .. . . .. . . . .. . . . .. . . . . .. . . . .. .. . .. 105

L. MESTER

The Four-Carbon Saccharinic Acids . . . . . . . .. .. .. . .. .. . . . . . . . . . .. . . . ... . . . . . . . .. . 169

JAMESD. CRUM

The Methyl Ethers of 2-Amino-2-deoxy Sugars . . .. .. . . . . . . . . .. .. .. .. .. .. . .. . . . . . .. 189

ROGERW. JEANLOZ

Glycosyl Ureides . .. . . . .. .. . .. .. . . . . . . . . . .. . . . . . . . . .. .. . .. .. .. .. . . . . . . . . . .. .. . . 215

IRVINGGOODMAN

.
The Nonulosaminic Acids . . . .. . . . . . .. . . . .. .. . . ... .. .. .. . .... . . . . . . . . . . . .. . . . .. 237
F. ZILLIKEN
AND M. W. WHITEHOUSE

Neuraminic Acids and Related Compounds (Sialic Acids) . . . . . . .. . . . . . .. .. . . .. . . .. . . 237

F. ZILLIKEN
AND M. W. WHITEHOUSF

Polysaccharide Hydrocolloids of Commerce . . . .. . . . .. . . . . . .. ... . . . . .. . . . . .. . .. . . . . 265

LEONARD STOLOFF

Alkaline Degradation of Polysaccharides . .. . . . . . . .... . . . . . . . .. . . . . . .. . . . . . . . . . .. . 289

ROYL. WHISTLER AND J. N. BEMILLFR

Starch Nitrate ................................................................ 331

GEORGE V. CAESAR

VOLUME 14

Action of Lead Tetraacetate on the Sugars . . . . .. .. . . ... . ... . .. . . . . . . . .. .. .. .. . .. . . 9

A. S. PERLIN

TheMaillard Reaction. ........................................................ 63

G. P. ELLIS

TheCyclitols ................................................................. 135

s. J. ANGYALAND LAURENSANDERSON
Aspects of the Chemistry of the Amino Sugars . . .. . . . .. .. . . . .. . . . .. .. . .. . . .. . . . . . . . 213
A. B. FOSTERAND D. HORTON
xviii CONTENTS OF VOLUMES 1-53

PyrimidineNucleosides ........................................................ 283

J. J. FOX AND I. WEWEN

Preparation and Properties of P-Glucuronidase .. .. .. .. . .. . . . . .. .. .. .... .. . .. . . .. . 381

G. A. LEVVY AND C. A. MARSH

Structural Chemistry of the Hemicelluloses .. ... . . . .. . . . . .. .. . . .. .. .. .. .. .. .. .. .. . 429

G. 0. ASPINALL

VOLUME 15

Constitution and Physicochemical Properties of Carbohydrates . . . .. .. . . . . . .. .. .. .. . . 11

B. CAPONAND W. G. OVEREND

Methods in Structural Polysaccharide Chemistry . . . ... . . .. . . . ... . . .. . . . . . . .. . . .. .. 53

HANS0. BOWENFAND BENFTLINDBERC

The Carbonates and Thiocarbonates of Carbohydrates .. . . .... .. . . . . . .. ... ... . . .. .. 91

L. HOUGH,J. E. PRIDDLE.
AND R. S. THEOBALD

Tables of Properties of 2-Amino-2-deoxy Sugars and Their Derivatives .. .. .. . . . .. ... .. 159

D. HORTON

Bacterial Nucleosides and Nucleotides .. .. . . . . . .. .. . ... .. .. . . .. .. .. .. .. .... . . . ... . 201

J. JONSEN A N D S . LALAND

The Biosynthesis of Aromatic Compounds from o-Glucose .. . . .. . . . .. . . .. . .... . . ... . 235

DAVID B. SPRINSON

Polysaccharides of Gram-Negative Bacteria .. .. . . . .. .. .. ... . . . ..... . . .. . . . . .. .. . . . 271

D. A. L. DAVIES

Dextran: Structure and Synthesis .. . . . .. .. . . . . . .. .. . . . . .. .. .. .. .. ... . . . . . ....... 341

W. BROCK NEELY

Chitin. ...................................................................... 371

A. B. FOSTER
AND J. M. WEBBER

VOLUME 16

Radiation Chemistry of Carbohydrates . . . . . . . . . . . . .. .. .. .. .. .. . . . .. .. .. .... 13

GLYN0.PHILLIPS

Applications of Trifluoroacetic Anhydride in

Carbohydratechemistry ...................................................... 59
T. G. BONNER
 CONTENTS OF VOLUMES 1-53 XIX

Glycosyl Fluorides and Azides . . . . . . . . . . .. . . . .. . .. .. . . . . . . . . . . . . . . . .. . . . .. . . ... . 85

FRITZMICHEEL AND ALMLITH k E M t K

The Dialdehydes from the Periudate Oxidation of Carbohydrates . .. .. . .. .... .. . .. .. 105

R. D. GUTHRIE

Lactose ..................................................................... 159

JOHNL. HICKSON,
JOHNR. CLAMP, L. HOUGH, AND ROY L. WHISTLER

Glycolipids of Acid-Fast Bacteria . . . . . . . . . .. . . . . . . . . . . . . . . .. . . . . . . . . . . .. .. .. . . . . . 207

EDGARLEDERER

Galactosidases ............................................................... 239

KURTWALLENFELS AND OM PRAKASti MALHOTRA

The Fractionation of Starch .. . . . . . . . . . . . .. . . .. .. ... .. .. . . .. . . .. .. .. .. . . . . . .. .. . 299

J. MUETGEERT

Carbohydrates in the Soil . .. . . . . . . . . . . . . . . . . .. .. . . . . . . .. .. .. .. . . .. . . . .. .. . ., 335

.. .
N. C. MEHTA,P. DUBACH, AND H. D w t i

VOLUME 17

Higher-Carbon Sugars ........................................................ 15

J. M. WEBBER

The Sugars of the Cardiac Glycosides . . . . . . . . . . . . . . .. . . . . . .. .. . . . . . .. .. . . .. . .. . . . 65

T. REICHSTEINAND EKKEHARC WEKS

Oligosaccharides ............................................................. 121

R. W. BAILEYAND J. B. PIUDHAM

Selective Catalytic Oxidation of Carbohydrates, Employing Platinum Catalysts . . . . .. . . . 169

K. HEWS AND H. PAULSEN

Dicarhonyl Carbohydrates ..................................................... 223

OLOFTHEANDER

PurineNucleosides ............................................................ 301

JOHNA. MONTGOMERY AND H. JEANETTETHOMAS

Enzymic Synthesis and Degradation of Starch and Glycogen . . .. . . . . . . . .. . .. .. . . . .. .. 371

D. J. MANNERS

VOLUME 18

Photochemistry of Carbohydrates . . . .. . . . .. . .. . . . .. . . . .. . . . .. . . . . . . . . . . I 9
GLYN0. PHILLIPS
xx CONTENTS OF VOLUMES 1-53

Paper Electrophoresis of Carbohydrates .......................................... 61

H. WEIGEL

Chemistry of Osotriazoles ...................................................... 99

HASSANEL KHADEM

Developments in the Chemistry of Thio Sugars .................................... 123

D. HORTONAND D. H. HUTSON

Trehaloses ................................................................... 201

GORDONG. BIRCH

Naturally Occurring C-Glycosyl Compounds ...................................... 227

L. J. HAYNES

Chemistry of the Amino Sugars Derived from Antibiotic Substances .................. 259
JAMESD. DUTCHER

Biosynthesis of Saccharides from Glycopyranosyl

Esters of Nucleotides (Sugar Nucleotides) ....................................... 309
ELIZABETH F. NEUFELD AND W. Z. HASSID

Physical Properties of Solutions of Polysaccharides ................................. 357

W. BANKSAND C. T. GREENWOOD

VOLUME 19

Crystal-Structure Analysis in Carbohydrate Chemistry ............................. 7

G. A. JEFFREYAND R. D. ROSENSTEIN

Infrared Spectroscopy and Carbohydrate Chemistry ............................... 23

H. SPEDDINC

NuclearMagneticResouance ................................................... 51
L. D. HALL

Gas-Liquid Chromatography of Carbohydrate Derivatives .......................... 95

C. T. BISHOP

The Action of Hydrogen Peroxide on Carbohydrates and Related Compounds .......... 149
G. J. MOODY

3-Deoxyglycosuloses(3-Deoxyglycosones)and
the Degradation ofcarbohydrates ............................................... 181
E. F. L. J. ANET

Structure and Some Reactions of Cellulose ........................................ 219

DAVIDM. JONES
 CONTENTS OF VOLUMES 1b.53 xx1

Wood Hemicelluloses: Part I . . . . . . . .. . . . . .. . ... .. . . . . . . .. . . . .. . . . . . .. . . . . . . . . . .. 247

T. E. TIMELL

The Pneumococcal Polysaccharides . . . .. . . . . . . ... . . . .. . . . . . .. . . . . .. . . . .. .. . . . . . . . 303

M. J. H O W , J. S. BRIMACOMBE,
AN11 M. STACEY

VOLUME 20

Chemical and Physical Studies of Cyclitols Containing

Four or Five Hydroxyl Groups .................................................. 11
G. E. MCCASLAND

Unsaturated Sugars ........................................................... 67

R. J. FERRIER

ChemistryofOsazones ........................................................ 139

HASSANEL KHADEM

Sulfates of the Simple Sugars . . . . . . . .. . . . . . . . . .. .. . . . . . . . . . . . . . . . . . . . . . .. .. .. . . . 183

J. R. TURVEY

Cyclic Acetals of the Aldoses and Aldosides . . , . . . . . .. .. . . . . . .. . . . . . .. . .. . . . .. .. ... 219

A. N. DE BELDER

Reactions of Amino Sugars with P-Dicarhonyl Compounds . . . . . .. . . . . . . . .. .. . . . .. . . . 303

F. GARCiA GONZALEZ AND A. GOMIZSANCHEZ

Naturally Occurring C-Glycosyl Compounds . .. .. . . .. . . .. . . . . . . . . . . . . . . . . .. .. ... .. 357

L. J. HAYNES

Phenol-Carbohydrate Derivatives in Higher Plants . ... .. . . . . . . . .. .. . .. .. . . . . . . .. .. . 371

J . B. PRIDHAM

.
Wood Hemicelluloses: Part I1 . . . . . . . .. . . . . . .. . .. .. . . . .. . . . . .. . .. . . . . . . .. .. .. .. . 410
T. E. TIMELL

VOLUME 21

Emil Fischer and His Contribution to Carbohydrate Chemistry . . . . . . . . .. .. . . . . . .. . .. 1

KARLFREUDENBERG
Mass Spectrometry of Carbohydrate Derivatives .. . .. .. .. . .. . . ... .. .. .. . . . . . . . .. .. 39
N. K. KOCHETKOVAND 0. S. CHIZIIOV

TheGlycofuranosides ......................................................... 95
JOHNW. GREEN 95
xxii CONTENTS OF VOLUMES 1-53

Deoxy Sugars ................................................................ 143

STEPHENHANESSIAN

Complexes of Alkali Metals and Alkaline-Earth Metals with Carbohydrates . .... . ... .. 209
J. A. RENDLEMAN,JR.

Syntheticcardenolides ........................................................ 273

W. WERNER ZORBACH AND K. VENKATRAMANA
BHAT

TheTeichoic Acids ............................................................ 323

A. R. ARCHIBALDAND J. BADDILEY

The Effects of Plant-Growth Substances on Carbohydrate Systems ... .. .... ... . . .... , 377
H. W. HILTON

Chemical Synthesis of Poiysaccharides . .. .. . . .. . . . .. .. . . .. . . ..... .. .. . . .. .. .. .. . . 431

I. J. GOLDSTEIN
AND T. L. HULLAR

VOLUME 22

Fred Smith(1911-1965) ....................................................... 1

REXMONTGOMERY

Acetolysis ................................................................... 11
R. D. GUTHRIE
AND J. F. MCCARTHY

Acid-Catalyzed Hydrolysis of Glycosides . .. .. .. .. .. ... . ... .. .. .. .. . ... .. .. .. . . . .. 25

J. N. BEMILLER

Neighboring-Group Participation in Sugars . ... .. .. .. . .. .. .. .... .. .. .. .... . .. .. .. . 109

LEONGOODMAN

Halogenated Carbohydrates . .. .. . . .. . . . .. .. .. . . .. . . . .. .. .. . .. .. .. ..... .. .. .. .. . 177

J. E. G. BARNETT

o-Fructose and Its Derivatives .. .. . . . .. .. ... . ... . . .. .. .. .. . . . .. .. . . . .... .. . . . .. . 229

L. M. J. VERSTRAETEN

TheMononucleotides...... .................................................... 307

TOHRUUEDAAND JACKJ. Fox

X-Ray Structure of Polysaccharides . . .. . .. .. .. .. .. .. . .. .. .. .. .. . . . . ... .. .. .. .. . . 421

R. H. MARCHESSAULT AND A. SARKO

The Thermal Degradation of Starch . .. .. . ... . .. .. . . .. . .. .. . . .. .. . . .. .. . ... ... .. . 483

C. T. GREENWOOD483
 CONTENTS OF VOLUMES 1-53 xxiii

VOLUME 23

Clifford Burrough Purves(1902-1965) ........................................... 1

A. S. PERLIN

Mutarotation of Sugars in Solution: Part 1

History, Basic Kinetics, and Composition of Sugar Solutions ......................... 11

WARDPIGMAN AND HORACES. ~ S B E L ~

Application of the 0 x 0 Reaction to Some Carbohydrate Derivatives .................. 59

ALEXROSENTHAL

Cyclic Monosaccharides Having Nitrogen or Sulfur in the Ring ...................... 115

H. PAULSENAND K. TODT

Sulfonic Esters of Carbohydrates: Part I ......................................... 233

D. H. BALLAND F. w. PARRlSH

Starch Degrading and Synthesizing Enzymes: A Discussion of Their

Properties and Action Pattern .................................................. 281
C. T. GREENWOOD AND E. A. MILNF

Structural Chemistry of Fungal Polysaccharides ................................... 367

P. A. J. GORIN
A N D J. F. T. SPENCER

Pyrolysis and Combustion of Cellulosic Materials .................................. 419

F. SIMFIZADEM

VOLUME 24

RichardKuhn(1900-1967) ..................................................... 1
HANSH. BAER

Mutarotation of Sugars in Solution: Part II

Catalytic Processes, Isotope Effects, Reaction Mechanisms,
andBiochemica1 Aspects ....................................................... 13
HOKACES. ISBELLAND WARDPIGMAN

TheNitroSugars ............................................................. 67
HANSH. BAER

Sulfonic Esters of Carbohydrates: Part I1 ......................................... 139

D. H. BALLAND F. W. PARR~SH

Unsaturated Sugars ........................................................... 199

R. J. FERRIER
xxiv CONTENTS OF VOLUMES 1-53

Structure, Conformation, and Mechanism in the Formation

of Polysaccharide Gels and Networks ............................................ 267
D. A. REES

GumsandMucilages .......................................................... 333

G. 0.ASPINALL

Glycosphingolipids
(Sugar-Sphingosine Conjugates) ................................................ 381
J. KISS

Protein-Carbohydrate Compounds in Human Urine ............................... 435

E. H. F. MCGME

VOLUME 25

Stanley Peat (1902-1969). ...................................................... 1

J. R. TURVEY

Gel Chromatography of Carbohydrates .......................................... 13

SHIRLEYC. CHURMS

Crystal-Structure Data for Simple Carbohydrates

and Their Derivatives ......................................................... 53
GERALD STRAHS

Oxirane Derivatives of Aldoses .................................................. 109

NEILR.WILLIAMS

2,s-Anhydrides of Sugars and Related Compounds ................................. 181

J. DEFAYE

Alditol Anhydrides ............................................................ 229

S. SOLTZBERG

TheSugarsofHoney .......................................................... 285

I. R. SIDDIQUI

Reactions of Free Sugars with Aqueous Ammonia.. ................................ 311

M. J. KORT

Synthesis of Nitrogen Heterocycles from Saccharide Derivatives ...................... 351

HASSANEL KHADEM

Aspects of the Structure and Metabolism of Glycoproteins .......................... 407

R. D. MARSHALL AND A. NEUBERGER
 CONTENTS OF VOLUMES 1-53 xxv

VOLUME 26

Melville Lawrence Wolfrom (1900-1969) ......................................... 1

DEREKHORTON

Conformational Analysis of Sugars and Their Derivatives ........................... 49

L. DURETTEAND DEKEK
PHILIPPE HORTON

Cyclic Acyloxonium Ions in Carbohydrate Chemistry .............................. 127

HANSPAULSEN

Cyclic Acetals of Ketoses ....................................................... 197

ROBERT F. BRADY,JR.

Tables of the Properties of Deoxy Sugars and Their Simple Derivatives ................ 279
ROGERF. BUTTERWORTH AND STEPHEN HANESSIAN

Morphology and Biogenesis of Cellulose and Plant Cell Walls ........................ 297
AND G. D. MCGINNIS
F. SHAFIZADEH

Biosynthesis of Saccharides from Glycopyranosyl Esters of Nucleoside

Pyrophosphates (Sugar Nucleotides) ........................................... 351
H. N~KAIDO AND W. Z. HASSID

VOLUME 27

William Werner Zorbach ( 1 9 1 f ~ Y 7 0 ) ........................................... 1

G. A. JAMIESON

Proton Magnetic Resonance Spectroscopy: Part 1 .................................. 7

BRUCECOXON

Non-aqueous Solvents for Carbohydrates ......................................... 85

C. J. MOVE

Sugars Specifically Labeled with Isotopes of Hydrogen ............................. 127

J. E. G. BARNETTAND D. L. CORMA

The Use of Carbohydrates in the Synthesis and Configurational Assignments

of Optically Active, Non-carbohydrate Compounds ................................ 191
T. D. INCH

The Wittig Reaction in Carbohydrate Chemistry .................................. 227

Yu. A. ZHDANOV, Yu. E. ALEXEEV,AND V. G. ALEXEEVA

Glycoenzymes: Enzymes of Glycoprotein Structure ................................ 301

JOHNH. PAZURAND N. N. ARONSON. JK.
xxvi CONTENTS OF VOLUMES 1-53

VOLUME 28

Lbsz16 Vargha(1903-1971) ..................................................... 1

JANOS KUSZMANN

Applications of GasLiquid Chromatography

toCarb0hydrates:PartI ....................................................... 11
GUYG. S. DUTTON

Dehydration ReactionsofCarbohydrates ......................................... 161

MILTONs. FEATHER AND JOHNF. HARRIS

Deoxyhalogeno Sugars ......................................................... 225

WALTER A. SZAREK

Glycosyl Esters of Nucleoside Pyrophosphates . . .. .. .. .. .... . .... .. .. .... .. . .. ... .. 307

NICOLAIK. KOCHETKOV AND VLADIMIR N. SHIBAEV

a-o-Mannosidase ............................................................. 401

SYBILM. SNAITHAND GUILDFORD
A. LEVVY

VOLUME 29

BernardRandallBaker(1915-1971) ............................................. 1
LEONGOODMAN

Solutions to the Hidden-Resonance Problem in

Proton Nuclear Magnetic Resonance Spectroscopy . .. .. .. .. .. .. ...... .. .. .... . . .. .. 11
LAURANCE D. HALL

Mass Spectrometry in Structural Analysis of Natural Carbohydrates . .. .. .. .. .. .. . . . . 41

J ~ R G ELONNGREN
N .AND SICFRlD SVENSSON

The Electrochemistry of Carbohydrates and Their Derivatives . .. .. .. .. .. . . .. .. .. . . .. 107

MICHALFEDOROGKO

Synthesis and Utilization of Formose Sugars . .. ... . . . . . . .. . . .. .. .. .. .. . ......... .. 173

TAKASHI MIZUNOA N D ALVINH. WEISS

P-Eliminative Degradation of Carbohydrates

Containing Uronic Acid Residues .. .. .. . . .
. .. . .. .. . . .. . . .. .. . . . . . .. .. .. .. .. .... .. 230
JOSEPHGss

Chemically Reactive Derivatives of Polysaccharides ... .. .. . . .... .. .. . . .. .. . . . . ... .. 305

JOHNF. KENNEDY
 CONTENTS OF VOLUMES 1-53 xxvii

VOLUME 30

DavidJamesBell(1905-1972) .................................................. 1
JOHNS. D. BACONAND DAVIDJ. MANNERS

Applications of Gas-Liquid Chromatography to Carbohydrates: Part I1 ............... 9

GUYG. S. DUTTON

Structures and Syntheses of Aminoglycoside Antibiotics ............................ 111

SUMIO UMEZAWA

Biochemical Mechanism of Resistance to Aminoglycosidic Antibiotics ................. 183

HAMAOUMEZAWA

The Metabolism of a,u-Trehalose ............................................... 227

ALAND.ELBEIN

Application of Enzymic Methods to the Structural

Analysis of Polysaccharides: Part I .............................................. 257
J. JOHN MARSHALL

Dextrans .................................................................... 371

RAMON L. SIDEBOTHAM

Bibliography of Crystal Structures of Carbohydrates, Nucleosides,

andNucleotides 1970-1972 ..................................................... 445
GEORGE A. JEFFREYAND MUTTAIYA SUNDARALIFIGAM

VOLUME 31

Hewitt Grenville Fletcher, Jr. (1917-1973) ........................................ 1

CORNELIS P. J. GLAUUEMANS

Deamination of Carbohydrate Amines and R'elated Compounds ...................... 9

J. MICHAELWILLIAMS

The Reaction of Ammonia with Acyl Esters of Carbohydrates ....................... 81

MARIAE. GELPIAND RAULA. C A ~ E N A S

Chemistry and Biochemistry of Apiose ........................................... 135

RONALD R. WATSON AND NEILS. ORENSTEIN

Specific Degradation of Polysaccharides .......................................... 185

BENGTLINDBERG, JORGEN L~NNGREN, A N D SIGFRID SVENSSON

Chemistry and Interactions of Seed Galactoniannans ............................... 241

IAN C.M. DEAA N D ANTHONY MORRISON
xxviii CONTENTS OF VOLUMES 1-53

The Interaction of Homogeneous, Murine Myeloma Immunoglobulins

with Polysaccharide Antigens ................................................... 313
CORNELIS P. J. GLAUDEMANS

Bibliography of Crystal Structures of Carbohydrates,

Nucleosides, and Nucleotides, 1973 .............................................. 347
GEORGE A. JEFFREYAND MUTTAIYA SLINDARALINGAM

VOLUME 32

William Zev Hassid (1899-1974) ................................................ 1

C L ~ T OE.NBALLOUAND HORACE A. BARKER

Dithioacetals ofsugars ........................................................ 15

JOSEPHD. WANDER AND DEREKHORTON

TheUtilizationofSugarsbyYeasts .............................................. 125

JAMESA. BARNETT

Noncytotoxic, Antitumor Polysaccharides ......................................... 235

ROYL. WHISTLER, ALFRED A. BUSHWAY, PREMP. SMGH,WARONAKAHARA,
AND REIKOTOKUZEN

Hemieellulases: Their Occurrence, Purification,

Properties,andModeofAction ................................................. 277
ROBERTF. H. DEKKER AND GEOFFREY N. RICHARDS

Bibliography of Crystal Structures of Carbohydrates,

Nucleosides, and Nucleotides, 1974 .............................................. 353
GEORGE A. JEFFREYAND MUTTAIYA SUNDARALMGAM

VOLUME 33

Alfred Gottschalk (1894-1973) .................................................. 1

ALBERT NEUBERGER

Relative Reactivities of Hydroxyl Groups in Carbohydrates ......................... 11

ALANH. HAINES

Synthesis of Naturally Occurring C-Nucleosides, Their Analogs,

and Functionalized C-Glycosyl Precursors ........................................ 11 1
STEPHENHANESSIAN AND ANDRB G. PERNET

Reactions of ~-Glucofuranurono-6,3-~actone ...................................... 189

KARLDAXAND HANSWEIDMANN
 CONTENTS OF VOLUMES 1-53 xxix

TheChemistryofSucrose ...................................................... 235

k A Z KHAN

The Pneumococcal Polysaccharides: A Re-examination . . . . . . .. ... .. . . . . . .. .. .. . . . .. 295

OLLELARMAND BENGT LINDBERC

Pectic Enzymes ............................................................... 323

REXOVA-BENKOVA
~ B O M ~ R A AND OSKAR
MARKOVI~.

Bibliography of Crystal Structures of Polysaccharides 1967-1974 . . . . . . . . . .. . . ..... . . 387

ROBERT H. MARCHESSAULT AND PUDUPADI R. SUNDARARAJAN

VOLUME 34

EdwardJohnBourne(1922-1974) ............................................... 1
HELMUTWEIGEL

1,6-Anhydro Derivatives of Aldohexoses . . . . .. . . . . . ... .. . . . .. .. . . . .. ... .. .. . . . . ,. . 23

MILOSLAV ~ E R N YAND JANSTANEK,JR.

Cyclic Acetals of the Aldoses and Aldosides .. .. . . . ... . . . .. .. . . . . .. .. .. .... .. . .. .. . 179

ANTHONY N. DE BELDER

The Koenigs-Knorr Reaction .. .. .. . . . .. . . . .. . . . .. . .... . . . .. . .. .. . . .. ... . . .. ... . 243

KIKUOIGARASHI

Metabolism of D-Fructose .. .. .. ... .. . . . . . .. .. . .. ... .. ... . . .. . . . .. ... .. . .. . . . .. . 285

MNSHEN CHENAND ROYL. WHISTLER

Bibliography of Crystal Structures of Carbohydrates,

Nucleosides, and Nucleotides, 1975 . . ... .. ... .. . . .. .. .. ... .. . . . .. .. .. . . . . .. 345
GEORGE A. JEFFREYAND MUTTAIYA SUNDARALINGAM

VOLUME 35

.
Edmund Langley Hirst (1898-1975) . . . . . . . . . . . . . . . .... . . . .. . .. . . . . ... .. .. .. . .. . 1
MAURICESTACEY AND DAVID J. MANNERS

CarbohydrateBoronates ....................................................... 31
ROBERTJ. FERRIER

Biosynthesis of Sugar Components of Antibiotic Substances . . . .. ... .. . .. ... .. .. . . . .. 81

HANSGRISEBACH

The Lectins: Carbohydrate-Binding Proteins of Plants and Animals . . . . .. .. . .. .. . .. .. 127

IRWINJ. GOLDSTEIN AND COLLEEN E. HAYES
xxx CONTENTS OF VOLUMES 1-53

Biochemistry of Plant Galactomannans .. ... .. .. .. .. .. .. ... . . .. . . .. .... .. .. .. .. . .. 341

PRAKASHM. DEY

Bibliography of Crystal Structures of Polysaccharides, 1975 . .. .. .. .. .. .. ,.... . . . .. .. 377

PUDUPADI R. SUNDARARAJAN AND ROBERT H. MARCHESSAULT

VOLUME 36

JohnArcherMills(1919-1977) .................................................. 1
STEPHEN
J. ~ G Y A L

Joseph VincentKarabinos(192~1977) ........................................... 9

WENDELL W. BINKLEY

Nutritive Sweeteners Made from Starch .. .. . . . . . .. .. .. .. . .... .... .... .. .. .. .. .. .. 15

ROBERT V. MACALLISTER

Glycosiduronic Acids and Related Compounds .. .. .. .. .. . .. .. .. .. .. ....... .. .... .. 57

DINAKECLEVI~

. . .. .. .. .. .. . ...... .. .. .. . .. .. .. .. . .. .. .... . 135

The Synthesis of Polynucleotides . . ..
MORIOIKEHARA, EIKOOHTSUKA, F. MARKHAM
AND ALEXANDER

The Hemicelluloses of Grasses and Cereals . . . .. .. .. . .. .. .. .... ... .. .. .. .... .. . .. . . 215

KENNETHC. B. WILKIE

Exocellular, Microbial Polysaccharides . . . .. .. .. . .. . . .. .. .. .. .. .. .... .. .. ..... . .. . 265

PAULA. SANDFORD

Bibliography of Crystal Structures of Polysaccharides, 1976 . . ... ... . ..... .. ..... . ... 315
PUDUPADl R. SUNDARARAJAN AND ROBERT H. MARCHESSALTLT

VOLUME 37

William Ward Pigman (1910-1977) .... . .. . . .. .. . .. .. .... .. .. . . .. . . .. .. . . . . ... .. . 1

ANTHONY HEW

Free-Radical Reactions of Carbohydrates as Studied by Radiation Techniques . . . ... . .. 7

CLEMENS VON SONNTAG

. . . .. .. .. .. .. ... .. . ... .. .. .. .. . . .. .. . ... .. ....

Synthesis of L-Ascorbic Acid . . . . .. 79
THOMAS C. CRAWFORD A N D SALLYANNCRAWFORD

Primary Structure of Glycoprotein Glycans:

Basis for the Molecular Biology of Glycoproteins .. .. . . ...... ... .... .. ... .. .. ... . .. 157
JEANMONTREUIL
 CONTENTS OF VOLUMES 1-53 xxxi

Neoglycoproteins: The Preparation and Application of Synthetic Glycoproteins ......... 225

CHRISTOPHER P.STOWELL AND YUAN CHUAN LEE

Biochemistry of a-D-Galactosidic Linkages in the Plant Kingdom ..................... 284

PRAKASH M. DEY

Bibliography of Crystal Structures of carbohydrates,

Nucleosides, and Nucleotides 1976 ............................................... 373
GEORGE A. JEFFREYAND MUTTAIYA SUNDARALINGAM

VOLUME 38

EmilHardegger(1913-1978) ................................................... 1
HASSANS. EL KHADEM

Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Polysaccharides ............. 13

PHILIP A. .I.GORIN

Photochemical Reactions of Carbohydrates ....................................... 105

ROGERW. BINKLEY

Fluorinatedcarbohydrates ..................................................... 195

ANNAA. E. PENGLIS

The Gulono-1,4-lactones: A Review of Their Synthesis,

Reactions, and Related Derivatives .............................................. 287
THOMAS C. CRAWFORD

The Chemistry and Biological Significance of

3-Deoxy-o-rnanno-2-octu~osonicAcid (KDO) ...................................... 323
FRANKM. UNGER

Methylation Techniques in the Structural Analysis

ofGlycoproteinsandGlycolipids ................................................ 389
HEIKKIRAUVALA, JUKU FINNE,TOMKRusius, JORMA KARKKAINEN,
AND JOHAN JARNEFELT

Bibliography of Crystal Structures of Carbohydrates, Nucleosides,

andNucleotides:1977and1978 ................................................. 417
GEORGE A. JEFFREYAND MUTTAIYA SUNDARALINGAM

VOLUME 39

KarlPaulGerhardtLink(1901-1978) ............................................ 1
CLINTONE. BALLOU
xxxii CONTENTS OF VOLUMES 1-53

The Selective Removal of Protecting Groups in Carbohydrate Chemistry .............. 13

ALANH. HAINES

The Reactivity of Cyclic Acetals of Aldoses and Aldosides ........................... 71

JACQUESGELAS

Synthesis and Polymerization of Anhydro Sugars .................................. 157

CONRAD SCHUERCH

The ChemistryofMaltose ...................................................... 213

RLU KHAN

Chemistry and Biochemistry of D- and L-Fucose ................................... 279

HAROLD M. FLOWERS

The Utilization of Disaccharides and Some Other Sugars by Yeasts ...................

JAMESA. BARNETT

Affinity Chromatography of Macromolecular Substances on

Adsorbents Bearing Carbohydrate Ligands ....................................... 405
JOHNH. PAZUR

VOLUME 40

The Synthesis of Sugars from Non-carbohydrate Substrates ......................... 1

ALEKSANDER ZAMOJSKI, ANNABANASZEK, AND GRZEGORZ GRYNKIEWICZ

Chemistry, Metabolism, and Biological Functions of Sialic Acids ..................... 131

ROLANDSCHAUER

Biosynthesis and Catabolism of Glycosphingolipids ................ .......... .. 235

Yu-TEHLI AND SU-CHENLr

The Lipid Pathway of Protein Glycosylation and Its Inhibitors:

The Biological Significance of Protein-Bound Carbohydrates ..... .......... .. 287
RALPHT. SCHWARZ AND ROELFDATEMA

Bibliography of Crystal Structures of

Polysaccharides 1977-1979 ................................. .......... .. 381
PUDUPADI R. SUNDARARAJAN AND ROBERT H. MARCHESSAULT

VOLUME 41

John Kenyon Netherton Jones (1912-1977) ............................. .... 1

WALTER A. SZAREK,MAURICE STACEY, AND GEORGE W. HAY
 CONTENTS OF VOLUMES 1-53 xxxiii

Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Monosaccharides . .. .. ... .. .. 27

KLAUSBOCKAND CHRISTIAN PEDERSEN

Structural Chemistry of Polysaccharides from Fungi and Lichens . .. .. .. .. . . . . ... .. .. 67

ELIANA BARRETO-BERGTER AND PHILIP A. J. GORIN

Biosynthesis of Cellulose .. .. .. .. . . . . . . .. .... . .. ... .. ... .. . .. .. .. .. .. .. .. .. . .... 105

DEBORAH P. DELMER

Capsular Polysaccharides as Human Vaccines .. . . . .. . . . .. .. . . . . . ..... .. ... ... . . .. . 155

HAROLD J. J E N N ~ G S

High-Resolution, 'H Nuclear Magnetic Resonance Spectroscopy as a Tool

in the Structural Analysis of Carbohydrates Related to Glycoproteins . .. .. .. . ... 209
JOHANNES F. G. VLIEGENTHART, LAMBERTUS DORLAND, AND HERMAN VAN HALBEEK

VOLUME 42

DexterFrench(1918-1981) ..................................................... 1
JOHNH. PAZUR

The Composition of Reducing Sugars in Solution ........ .. . .. .. .. . .. .. .. .. .. . . .... 15

STEPHENJ. ANGYAL

SynthesisofBranched-Chain Sugars ............................................. 69

JUJIYOSHIMURA

Sugar Analogs Having Phosphorus in the Hemiacetal Ring .. .. ... . . . . . . .. . . . . ... .. .. 135
HlROSHl YAMAMOTO AND SABURO INOKAWA

Carbon-13 Nuclear Magnetic Resonance Data for Oligosaccharides . . . .. .. .. .. ... ..... 193
K L A U S BOCK,CHRISTIAN PEDERSEN, A N D HENRIK
PEDERSEN

Ketonucleosides .............................................................. 227

KOSTASANTONAKIS

Plant Cell Walls .............................................................. 265

PRAKASHM. DEYAND KENBIUNSON

L-Arabinosidases . .. .... . . . .. . . . . . .. .. . .. . .. .. ..... . . . .. . .. .. .. . . .. .. . . . .. .. .. 383

AKlU h J l

VOLUME 43

Natural-Abundance, "C Nuclear Magnetic Resonance-Spectral Studies of

Carbohydrates Linked to Amino Acids and Proteins . .... ... .. . .... ... ... .. .. . .. .. . 1
KlLlAN DILL,ELISHABERMAN, AND ANDRB A. PAVIA
xxxiv CONTENTS OF VOLUMES 1-53

Structure and Biological Activity of Heparin ...................................... 51

BENITOCAW

Synthetic N- and 0-Glycosyl Derivatives of L-Asparagine,

L-Serine, and L-Threonine ...................................................... 135
HAMG. GARGAND ROGERW. JEANLOZ

Bibliography of Crystal Structures of Carbohydrates, Nucleosides,

and Nucleotides for 1979 and 1980; Addenda and Errata for 1970-1978;
andIndexfor1935-1980 ....................................................... 203
GEORGE A. JEFFREYAND MUTTAIYA SUNDARALINGAM

VOLUME 44

FredShafuadeb,1924-1983 ....................................................
GARYD. MCGINNIS

VibrationalSpectraofCarbohydrates ............................................
MOHAMED MATHLOUTHI AND JACKL. KOENIG

Monosaccharide Isothiocyanates and Thiocyanates: Synthesis,

Chemistry, and Preparative Applications .........................................
ZBIGNIEWJ. WITCZAK

Enzymic Analysis of Polysaccharide Structure ..................................... 147

BARRYV. MCCLEARY AND NORMAN K. MATHESON

Biosyntbesis of Bacterial Polysaccharide Chains

Composed of Repeating Units ................................................... 277
VLADIMIR N. SHIBAEV

Lipid-Linked Sugars as Intermediates in the Biosynthesis

of Complex Carbohydrates in Plants ............................................. 341
RAFAEL PONTLEZICA, GUSTAVO R. DALEO,AND PRAKASH M. DEY

Glycolipids of Marine Invertebrates ............................................. 387

NICOLAI K. KOCHETKOV AND GALINA P. SMIRNOVA

VOLUME 45

Burckhardt Helferich, 1887-1982 ............................................... 1

HERMANN STETTER

Francisco Garcia Gonzalez, 1902-1983 ........................................... 7

ANTONIO G6MEZ-SANCHEZ AND JOSE FERNANDEZ-BOLAROS
 CONTENTS OF VOLUMES 1-53 xxxv

F.a.b.-Mass Spectrometry of Carbohydrates .. .. .. ... . .. .. .. . .. .. . ... . .. . . . . . . . . .. 19

ANNEDELL

The Circular Dichroism of Carbohydrates . . ... . . ... . .. .. . . . .... . . .. ..... .. .. . . . .. 73

W. CURTISJOHNSON, JR.

Proton Spin-Lattice Relaxation Rates in the Structural Analysis of

Carbohydrate Molecules in Solution .. .. . . . . . . . . .. ... .. . .. .. . . . . .. .. . . . . . .. .. . .. 125
.
PHOTISDAISAND ARTHUR S. PERLIN

I3C Nuclear Magnetic Resonance-Spectral Studies of Labeled Glycophorins . .. .. . . . . . .. 169

KILIANDILL

The Chemistry and Biochemistry of the Sweetness of Sugars . ... .. .. .. . .. . . . ... .. .. . . 199
CHEANG-KUAN LEE

VOLUME 46

KonoshinOnodera,1910-1983 .................................................. 1
TOIiRU KOMANO
AND NAOKIG S H I M U R A

VenancioDeulofeu,1902-1984 .................................................. 11
ROSAM. DE LEDERKREMER AND EDUARDOG. GROS

High-Performance Liquid Chromatography of Carbohydrates . .. . .. .. . . .. . . .. .. . .. .. 17

KEVINB. HICKS

NMR Spectroscopy of Fluorinated Monosaccharides . .. .. . . . . . . .. . . .. . . . . . . . .. . .. . . 73

RENECSUKAND BRIGITTE I. GLANZER

Applications of Photosensitive Protecting Groups in

Carbohydratechemistry ...................................................... 179
URIZEHAVI

Inclusion Complexes of the Cyclomalto-oligosaccharides (Cyclodextrins) .. .. . . .. .. .. . . 205

RONALD J. CLARKE,
JOHNH. COATES,AND STEPHEN F. LINCOLN

Hydrolysis and Other Cleavages of Glycosidic Linkages in Polysaccharides .. . . .. .. .... 251

CHRISTOPHER J. BIERMANN

Aqueous, High-Temperature Transformation of Carbohydrates

Relative to Utilization of Biomass . .. . .. . . . .
. . . .. . . . .. . . .. . . . . . .. . . . .. . . . .. .. . . . . . 273
OLOFTHEANDER AND DAVID A. NELSON

Addendum to Article 3: References Published after 1986

(AddedatProofStage) ........................................................ 327
KEVINB. HICKS
xxxvi CONTENTS OF VOLUMES 1-53

AddendumtoArticle4 ........................................................ 331

RE& CSUKAND BRIGITTEI. GLANZER

AddendumtoArticle6 ........................................................ 333

RONALDJ. CLARKE,JOHNH. COATES,AND STEPHEN
F. LINCOLN

VOLUME 47

Complexes of Metal Cations with Carbohydrates in Solution ......................... 1

STEPHENJ. ANGYAL

Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry ..................... 45

IGORTVAROSKA AND TOMASBLEHA

13C Nuclear Magnetic Resonance-Spectral Studies of the Interactions of Metal

Ions with Carbohydrates: Use of Relaxation Probes ................................ 125
KILIANDILLAND R. DOUGLAS CARTER

Application of Anhydrous Hydrogen Fluoride for the

Structural Analysis of Polysaccharides........................................... 167
YURIYA. KNIREL, EVGENY V. VINOGRADOV,
AND ANDREW J. MORT

The Thermal Decomposition of Carbohydrates. Part I. The Decomposition of

Mono-, Di-, and Oligo-saccharides ............................................... 203
PIOTRTOMASIK,
MIECZYSKAW
PALASINSKI,
AND STANISLAW
WIEJAK

The Thermal Decomposition of Carbohydrates. Part 11.

The Decomposition of Starch ................................................... 279
PIOTRTOMASIK,STANISLAW WIEJAK,AND MIECZYSLAW PALASINSKI

The Macrostructure of Mucus Glycoproteins in Solution ............................ 345

STEPHENE. HARDING

VOLUME 48

HamaoUmezawa,1914-1986 ................................................... 1
TSUTOMU
TSUCHIYA,KENJIMAEDA,AND DEREKHORTON

Chemistry of Carba-sugars (Pseudo-sugars) and Their Derivatives ................... 21

TETSUOSUAMI AND SEIICHIROOGAWA

Chemistry and Developments of Fluorinated Carbohydrates ......................... 91

TSUTOMU TSUCHIYA

Components of Bacterial Polysaccharides ......................................... 279

BENGTLINDBERG
 CONTENTS OF VOLUMES 1-53 xxxvii

Glycoside Hydrolases: Mechanistic Information from Studies with

Reversible and Irreversible Inhibitors............................................ 319
GUNTERLECLER

VOLUME 49

Rezs8 Bognar, 1913-1990 ...................................................... 3

A N D ~LIPTAX,
S PALNANASI,AND FERENCSZTARICSKAI

Jean Emile Courtois, 1907-1989 ................................................. 11

FRANCOISPERCHERON

The Composition of Reducing Sugars in Solution: Current Aspects ................... 19

STEPHENJ. ANCYAL

Radical-Mediated Brominations at Ring Positions of Carbohydrates .................. 37

LASZLOSOMSAKAND ROBERTJ. FERRIER

1,4:3,6-Dianhydrohexitols ...................................................... 93
PETERSTOSSAND REINHARD
HEMMER

Enzymic Methods in Preparative Carbohydrate Chemistry .......................... 176

SERGEDAVID,CLAUDINE AucB, AND CHRISTINEGAUTHERON

Structure of Collagen Fibril-Associated, Small Proteoglycans

ofMammalian Origin ......................................................... 239
HARl GARCAND NANCYLYON

VOLUME 50

How Emil Fischer Was Led to the Lock and Key

Concept for Enzyme Specificity ................................................. 1
RAYMOND U. LEMIELJX
AND ULRIKE SPOHR

Anomeric-Oxygen Activation for Glycoside Synthesis:

The Trichloroacetimidate Method ............................................... 21
RICHARD R. SCHMIDT AND W ~ L L~Y Z Y

SyntheticReactionsofAldonolactones ........................................... 125

ROSAM. DE LEDERKREMER AND OSCAR VARELA

Molecular Structure of Lipid A, the Endotoxic Center

of Bacterial Lipopolysaccharides ................................................ 211
ULRICHZAHRINCER, BUKOLINDNER, AND ERNST TH. RIETSCHEL
xxxviii CONTENTS OF VOLUMES 1-53

Developments in the Synthesis of Glycopeptides Containing

Glycosyl L-Asparagine, L-Serine, and L-Threonine ................................. 277
HARIG. GARG,KARSTENVON DEM BRUCH,AND HORSTKUNZ

Physicochemical Analyses of Oligosaccharide Determinants of Glycoproteins ...........311

ELIZABETH F. HOUNSELL

VOLUME 51

HoraceS.Isbell,1898-1992 ..................................................... 1
HASSANS. EL KHADEM

Carbon-Proton Coupling Constants in the Conformational

Analysis of Sugar Molecules .................................................... 15
IGORTVAROSKA AND FRANCOIS R. TARAVEL

Carbon-13 Nuclear Magnetic Relaxation and Motional Behavior of

Carbohydrate Molecules in Solution ............................................. 63
PHOTlS DAIS

Mechanisms in the Glucansucrase Synthesis of Polysaccharides and

Oligosaccharides from Sucrose .................................................. 133
JOHNF. ROBYT

The Variable Surface Glycolipids of Mycobacteria: Structures,

...................................
Synthesis of Epitopes, and Biological Properties 169
GERALD 0. ASPINALL, DELPHICHATTERJEE, AND PATRICKJ. BRENNAN

Nonconventional Methods of Modification of Starch .................. ....... 243

PIOTRTOMASIK AND MARKF. ZARANYIKA

VOLUME 52

MauriceStacey,1907-1994 ....................................... ............ 1

PAULFTNCH AND W. GEORGE OVEREND

Nomenclature of Carbohydrates .................................. ............ 47

Thioglycosides as Glycosyl Donors in Oligosaccharide Synthesis ........ ............ 179

PERJ. GAREGG

DihexuloseDianhydrides ....................................................... 207

MERILYN MANLEY-HARRIS AND GEOFFREY
N. RICHARDS

Sugars and Nucleotides and the Biosynthesis of Thiamine ........................... 267

SERGEDAVIDAND BERNARD ESTRAMAREIX
 CONTENTS OF VOLUMES 1-53 xxxix

Molecular Architecture of Polysaccharide Helices in Oriented Fibers .................311

RENCASWAMI CI-IANDRASEKARAN

Sucrose Decomposition in Aqueous Solution and Losses in

Sugar Manufacture and Refining ..................................... .. ......... 441
MARGARET A. CLARKE,LESLIEA. E D Y E , A N D GILI I A N EGGLESTON

VOLUME 53

John E.Hodge,1914-1996 .......................................... ......... 1

MILTON S. FEATHER

AlleneR.Jeanes,1906-1995 ......................................... .. ......... I

NINAM. ROSCHER
AND PAULA. SANDFORD

HarrietL.Frush,1903-1996 ......................................... 13
HASSANS. EL KHADEM

Applications of Tin-Containing Intermediates to Carbohydrate Chemistry 117

T. BRUCE GRINDLEY

Synthetic Applications of Selenium-Containing Sugars ............................ .. 143

ZBIGNIEW J. WITCZAKA N D STANISLASCL~RNECKI

Anti-carbohydrate Antibodies with Specificity for Monosaccharide and

Oligosaccharide Units of Antigens ............................................. 201
JOHN H. PAZUR

Complexes of Starch with Inorganic Guests ..................................... 263

PIOTR TOMASIK AND CHRISTOPHER H. SCtIILLINCI

Complexes of Starch with Organic Guests ...................................... .. 345

PIOTRTOMASIK AND CHRISTOPHER H. SCHILLING
This Page Intentionally Left Blank
 SUBJECT INDEX
Boldface numc~rulsindicate volume n 1 4 n 1 h w
A with enol ethers. 34:188
Aaptos papillulu lectins, isolation and
properties, 35:3 16
Abequose, 21:187, 180-190, 23:272,
SO: 173-1 74
2- and 4-O-methyl-, synthesis of. 30:23
ester of cytidinc pyrophosphate, isolation of,
2 8 3 16
gas-liquid chromatography of, 28:Oi
residues in lipopolysaccharides, 26:42 I
Abequoside, methyl p-, 23:272
Abramov reaction, 3 4 9 8
Abrin
carbohydrate-binding specificity, 3S:255
immunization 10 toxic, 35: I29
isolation and purification, affinity
chromatography, 35:138
purification and properties, 35:254 257
.4h m r precutorius
lectin, see Abrin
seed extracts, hemagglutinating and toxlc
activities, 35:254-257
Abscission, 21:429
Acut~rhamoebcr.cellulose biosynthesia. 41 : I 08,
128
Acarbose, 48:24-25, 348
inhibition of sucrase by, 48:88
synthesis, 48:84
Acceptor products. structures, 51: 15 I I 55
Acceptor reaction, 51 :15 I I52
- cyclic
applications, 51: 162-163
Aceric acid. 4S:67
Accsulfame-K, 45:299
Acetalation, see also Acetonation
Benzylidenation; Transacetalatioii
I ,2-acetoxonium ion in, 34: 190
by 2-acetoxypropene, 39:76
agents, 39:76
and aldonolactones, 50: 125-126
of 1,6-anhydrohexopyaiioses,3 4 : W 03
catalysts, 39:80
of u-fructose, mechanism of; 26:? I X 220
I
with gem-dihalides and base, 34: 188-1 90
ofhexoses and heuitols. 28:4
methods of, 26:211-218, 34:191
of nitro sugars, 24: I 16
principle governing, 34: 180-1 82
selective. 33:71 -72
o f i -sorbose, mechanism of. 26:205
Acetaldehyde. 46:32 1
i n aqueous solution. 42:30
reaction with ii-allose, 34: 183-1 84
formation, 51 :28 1
Acetals
acetolysis, 22: 12, 39324-26
of alditols. mass spectrometry of. 29:75-77
aldofuranoside formation from, 21:l I I
alkyl monothio-, fonnation in
demercaptalation. 32:69
preparation of, 32:72
ofanhydroalditols, fonnation and behavior
of, 25:205
of2.5-aiih~droaldoses,synthesis of. 33: 126
benzylidene, reaction with .Y-
bromosuccinimide. 26: 163-1 68
bicyclic. hydrogenolysis. 39: 133
carbohydrate
mass spectrometry and configuration of,
29:43
photochemical reactions. 38: 142 -147, 170
cleavage of p-nitro. 24: 125
acetobroiiiinolysis, 39: 1 I4
Grignard reagent cleavage, 39: I53
halogenation, 39:95-121. 115-121
hydrogenolysis, 39:121-138, 136-138
maltose derivatives, 393237-238
migration, 39: I I 5
oxidation by chromium trloxlde,
39:82-85
oxidation by potassium permanganate,
39:82
oxidation by triphenylrnethyl
fluoroborate, 39:85 86
2 SUBJECT INDEX
Acetals (uintinued)
ozonolysis, 39:8 1-82
peroxide-induced rearrangement,
39: 150
photolysis, 39:86-95
polymerization, 39: I52
as protecting groups, and as functional
groups, 39:155-156
reaction with bromine, 39: 1 18
reaction with dibromomethyl methyl
ether, 39:119-121
reaction with hydrogen fluoride,
39:117
reaction with N-bromosuccinimide,
39:96-107
reaction with N-chlorosuccinimide,
39:118
reaction with 1,3,5-trichloro- 1,3,5-
triazine-2,4,6-trionc, 39: 1 18
reaction with triphenylmethyl
fluoroborate, 39: 107-1 13
reactivity, of aldoses and aldosides,
39:71-156
synthesis, 39:73
acetolysis of, 34:206
of aldoses and aldosides, 34: 179-24 I
applications of, 34:207-209
cleavage by trityl fluoroborate, 34:207
conformational analysis of, 34: 197
con formational eq u i I i bna of.
34: 198-202
degradation of, 34:8
diastereoisomerism of, 34: 195-197
formation of, 34: 180-1 82
hydrogenolysis of, 34:205
hydrolysis by acids, mechanism of,
34:202
mass spectrometry and structure of,
34~192-194
methanolysis of, 34:206
migration in, 34:205
nuclear magnetic resonance
spectroscopy and structure of,
34: 195-198
oxidation of, 34:207
ozonolysis of, 34:207
photolysis of, 34:207
reactions with N-bromosuccinimide,
34:206
synthesis of, 34:8, 182-192
from alditols, 36:4
of the aldoses and aldosides. 20:219-302
di-, hydrolysis of, 34:203-204
of ketoses, 26:197-277
hydrolysis of, 26:203
preparation of, 26: 199
selective etherification of, 33:53
of sucrose, 33:255
stability of. 26:202
sugar, conformations of, 26: 1 I X
of o-fructose, 22:245
esters and ethers, 22:289-290
dithio-
acetylated, gas-liquid chromatography of,
28:66, 12 I
acylation of, 32:45
conformations of, 32:9&92
formation and reactions of alkylidene
acetals of, 32:52-55
formation of, 32:17-19
glycosides and thioglycosides from,
32:66-70
history, 32: 16-17
Iiydrogenolysis by Raney nickel,
32:75-7
mass spectrometry of, 32:2 ~7
methylation of, 32:47
micro method of preparation of, 32:96
nucleophilic reactions, 32:3743
oxidation of hydroxyl groups in sugar
residue, 32:8&82
oxidation of sulfur atoms of. 32:82-88
physical constants of alduronic acids
and derivatives, 32: 1 16- I I8
physical constants of discaccharides and
their peracetates. 32: 1 I6
physical constants of substituted
monosaccharides, 32: 1 18-1 23
physical constants of unsubstituted
monosaccharides and their
peracetates, 32: 102-1 I5
physical properties of, 32:98
reactions of amino groups in,
32:55-57
reactions of hydroxyl and other groups
in sugar, 32:44-60
reaction with bases, 32:57-60
replacement of alkylthio groups by
halogens, 32:70-75
replacement of alkylthio groups by
 SUBJECT INDEX
mineral and Lewis acids, 32:60 70
spectroscopic properties of, 32:8X 98
ofsugars, 32:IS-123
sulfonic esters, fonnation and reaciions
of, 3248-52
in synthesis, 32: 16
tritylation of, 32:46
of 2-amino-2-deoxyaldoses, deamination
of, 25: 192
gas-liquid chromatography of, 30:33
glycoside synthesis by alcoholysis of
acyclic sugar. 34:244
mass spectra of sugar, 29:7 1-73
photolysis. 38: 150-1 53
selective esterification of carbohydrate,
33:4041
selective methylation of carbohydraic.
33:65-66
sugar, 26: I3
in 1-thioglycosiduronic acid prcparation,
36: 10&102
exchange of, 34: 186-1 88, 192
gas-liquid chromatographic detemii nation
of, 30:35
of hexitols, pentitols, and tetritols,
7: 137-207
hydrolysis
(acid-catalyzed) of, 22:30, 59, I 13
selective, 39: 14-24
isomerization, 39:26-28
isopropylidene. in gas-liquid
chromatography, 28:37
mercaptalation of, 32:28
of monosaccharides, mass spcctra of,
21:74
nomenclature, 52: 123-1 24
cyclic, 52:121-122
of polyhydric alcohols, mass spectra of.
21:79
of polysaccharides, preparation of: 29:339
preparation
from dithioacetals, 32:65
from en01 ethers, 34: 1 88
propane- I ,3-diyl dithio-, preparation of,
3239
protection as, 46: 182-1 X9
rearrangements of, 26:220
synthesis of, 34: 182-1 92
trimethylene dithio-, preparation of,
32: 37-38
3
w-deoxy sugars by catalytic reduction of,
21:176
Acetamide
N-[5-( I ,2-dihydroxyethyl)-3-furyl]-.
formation of, 28:202
~~,O-bis(trimethylsilyl)-. trimethylsilylation
with, 28:26
trifluoro-N-methyl-N-(trimethylsily1)-.
trimethylsilylation with, 28:28
trifluoro-N.0-bis(triniethylsily1)-, as
trimethylsilylating agent, 28:27, 80
Acetamidodeoxyhexosidase, in Tay-Sachs
discasc, 31:6
Acetamido group
effect on acyloxoniurn rearrangements.
26:161
oligosaccharides containing, ' T - N M R data
for, 42:209-2 I0
participation i n sugar reactions, 22: 127
Acetanilide, metabolism, 36:9 1
2-Acetate. trorworiented. nucleophilic attack
on carbonyl group, 51:7. 10
Acetates
circular dichroism. 45: 120- 122
gas-liquid chromatography of
alditol, 30:30 -32
mass spectrometry of, 30:40
of methylated alditols, 30:89-98
of niethylated aldononitriles, 30: I00
of niethylated methyl glycosides. 30:26,
82
of methylated sugars, 30:29. 86
mass spectrometry of, aldononitrile.
methylated. 30:43
Acetic acid
(2,3-0-isopropylidene-P-r~-ribofuranosyl)-,
ethyl ester, preparation of, 33:157
bromo-. cellulose ester, preparation of,
29:337
bromo (2,3,4,6-tetra-O-acety 1-P-o-
glucopyranosy1)-, methyl ester,
preparation of, 33:146-147
as catalyst in osazone formation, 22:264
chloro-
as catalyst for polymerization of 1.6-
anhydro sugars, 2 1 :486
as solvent for sucrose, 27: 104
(4-chloro-2-methy1phenoxy)-
effect on sugarcane. 21 :427
4 SUBJECT INDEX
Acetic acid (continued)
as herbicide, 21:392
(2-chlorophenoxy)-, as plant-growth
substance, 21:398
(3-chlorophenoxy)-, as plant-growth
substance, 21:398
(4-chlorophenoxy)-, as plant-growth
substance, 21:398
cyclodextrin inclusion complexes with,
46:22 1
(5-deoxy-5-adenosine-5-yl)-, 43:335
(2,4-dichlorophenoxy)-,
effect on sugarcane, 21:424
as herbicide, 21:392
metabolism by plant tissue, 21:396
(3,5-dichlorophenoxy)-, as herbicide, 21:394
~~-(2,3-@isopropy~idene-p-~~-
ribofuranosy1)-, methyl ester,
preparation of, 33:163
o~-tetrahydropyran-2-y1-, preparation of,
33:145
esterification of D-glucose with, 33:44
esters of sugar dithioacetals, preparation of,
32:45
ethoxylyfluoro-, ethyl ester, carbohydrate
substrate, 40:10&105
(ethy1enedinitrilo)tetra-
effect on a-amylase action, 30:286
inhibitor of protein glycosylation, 40:297
2-formyl-5-(hydroxymethyl)pyrrole-I-,
formation of, 46:312-314
2-formyl-5-methylpyrrole-l-, formation of, N- Acetimidoyl groups, bacterial
4 6 ~ 12-3
3 14
gas-liquid chromatographic determination
of, 30:36
in hydrolysis of polysaccharides, 28: 17
iodo-, cellulose ester, preparation of, 29:338
liquid chromatography of, 46:53-54
pH of aqueous solutions of, 46:252
as solvent for sugars, 27: 102
(2,3,4,6-tetra-O-acetyl-~-~-g~ucopyranosyl)-, Acetobacter xylinum
preparation of, 33: 146-147
trichloro-
in hydrolysis of glycoproteins, 28: 17
as plant-growth substance, 21:402
(2,4,5-trichlorophenoxy)-
effect on abscission and ripening, 21:429
on sugarcane, 21:424
as herbicide, 21:392
trifluoro-
anhydride
1,6-anhydrohexopyranose cleavage by,
34:66
applications of, in carbohydrate
chemistry, 16:59-84
for hydrolysis of cyclic acetals, 34:205
in organic syntheses, 34:s
catalytic action on trimethylsilylation,
28:25
in hydrolysis of plant cell walls, 28: 16
(2,3,5-tri-O-benzoyl-a-~- and p-D-
ribofuranosy1)-
ethyl esters, preparation of, 33: 156, 162
preparation of, 33: 162
(2,3,5-tri-O-benzyl-a-~- and p-D-
ribofuranosy1)-, ethyl esters, preparation
of, 33:158
triphenylmethoxy-, anhydride with 2,4,6-
triisopropylbensenesulfonylchloride, in
esterification of nucleosides, 33: 13
vinyl-, see 3-Butenoic acid
Acetic acid-I4C, (2,4-dichlorophenoxy)-,
metabolism by plant tissue, 21:396
Acetic acid-sulfuric acid, cyclitol
rearrangement in, 26: 188-191
Acetic anhydride
in acetolysis, 22:11
reaction with amino group in dithioacetals,
32:55
zinc chloride, rearrangements of saccharides
in, 26: 192
polysaccharides, 48:307
Acetoacetic acid, ethyl ester, condensation
products with D-fructose, 22:288,305
Acetobacter suboxydans
in dendroketose synthesis, 42: 129
oxidative specificity toward aldose
dithioacetals, 32:81-82
selective oxidation of alditols with, 33: 100
cellulose assembly model, 41: 113
cellulose biosynthesis, 41:106-107, 116,
119, 124, 128
high-molecular-weight precursors,
41:135-137, 141
lipid intermediates involvement,
41:132-133
Acetobrominolysis, 22:22
of cyclic acetals, 39: 114
 SUBJECT INDEX
Acetohalogeno carbohydrates, 4 5 5
Acetohydroximate
1-thio-P-D-ghcopyranosyl2-phenyl-.
biosynthesis of, 26:441
1-thio-2-phenyl-, biosynthesis of, 26:44 1
Acetoin
formation, 46:294
from hydrothermolyzed cellulose,
46:304305
Acetol
formation of, 28:200,46:293
high-temperature transformation, in alkali
conditions, 46:284
Acetolysis, 22: 11-23
acetal, 39:24-26
of alkylthio groups of dithioacetals, 32:69
of aminodeoxy 1,6-anhydrohexopyranoses,
34:128
of 1,6-anhydrohexopyranoses,34:65, 162
and anomerization, 31: 197-200
henzyl ethers, selective, 39:45
of cyclic acetals, 34:206
of cyclic monosaccharides, ring contraction
in, 23: 187
in degradation of polysaccharides,
31:197-200
and epimerization, 31:200
and f.a.b.-mass spectrometry, application to
preliminary screening of glycoproteins
for sugar type, 45:5&5 1
glycosidic linkage cleavage, 46:269-270
monitoring with f.a.b.- mass spectrometry,
45:49
of monosaccharide derivatives, 22: I2
of polysaccharides, 22:20, 24:339
reagents, 39:25
rearrangements during, 22: 19
structural analysis, 38:396,409
of tragacanthic acid, 24:362
usefulness of, 22:21
Acetonation, see also Acetalation
of D-allose, 34: 183
of o-galactose, 34: 185
Of D-ghlCOSe, 34: 182-183
of D-ribose, 34:18&185
of D-talose, 34: 184
Acetone
enolization of, in water and in deuterium
oxide, 24:29
photochemical cycloaddition with 3,4-6-tri-
5
0-acetyl-D-glucal, 38:106, 117
photochemical reaction with carbohydrate
acetals, 38: 143-145
reaction with methyl 2-0-methyl-~-
glucofuranoside, 30:4
solubility of sucrose in, 27: 107
solubility of sugars in, effect of zinc chloride
on, 27:95
sugar and alditol compounds, 21: 19
Acetonitrile
cyclodextrin inclusion complexes with,
46:221
solvent for trimethylsilylation, 28:29
trichloro-
intermediate in nucleotide formation,
36: 157
as solvent for sugars, 27: 1 13
Acetophenone
a-(D-arabinofuran0syl)-p- methoxy-,
preparation of, 33: 154-155
a-(D-galactofuranosyl-p-methoxy)-,
preparation of, 33: 154-155
a-(D-glucofuranosy1)-p-methoxy-,
preparation of, 33: 154-155
(~-(2,3;5,6-di-0-isopropylidene-a-~-and p-D-
mannofuranosy1)-p-methoxy-,
preparation of, 33:154-155
Acetoxonium ion
in acetal preparation, 34:190
in mercaptalation, 32:32
Acetoxonium salts, 26: 130
Acetoxy group
displacement in carbohydrates by halogen,
22:181
participation in sugar reactions, 22: I 16,
122
Acetoxyl group
elimination from peracetylated glycosides in
mass spectrometry, 29:46
reactivity of, in acyloxonium salt formation,
26:131
Acetoxymethylpyran-2-one, 3-acetoxy-6-,
50: 165- 166
I -0-Acetyl, activation, 3-0-glycosidic linkage
formation, 50:292-293
1-0-Acetyl-a-oi-carba-glucopyranose,
48:6 1-62
Acetylation
of alditols, effect of borate complexes on,
28:34
6 SUBJECT INDEX
Acetylation (continued)
of amino sugars, effect on behavior in
solution, 42:47
of 1,6-anhydrohexopyranoses,34:83
of carbohydrate boronates, 35:53
of o-fructose derivatives, 22:250
f.a.b.-mass spectrometry of, 45:53
of methyl glycosides, 30:26
of polysaccharides, 29:329-333
N-Acetyl-P-o-glucosamine antibodies,
53:230-23 1
N-Acetyl-P-o-glucosamine-1 -P, 53:252-253
Acetyl bromide, reaction with carbohydrates,
22:22
Acetyl chloride
chloro-, in esterification of thymidine, 33: 14
reaction with carbohydrates, 22:22
Acetyl chloridechlorodiphenyl-, in
esterification of thymidine, 33: 13
Acetylcoenzyme A, from aerobic catabolism of
D-glucose, 32: 163
N-Acetyl-2,3-dehydroneuraminic acid, 48:35 1
N-Acetyl-9-deoxy-9-fluorone~uaminic acid,
"C-NMR data for, 46: 177
Acetylene compounds, o-glucopyransoylation
of, 25:242
Acetylenic precursors, for sugar syntheses,
40:34
Acetyl esterase, 44: 162
Acetylformoin, from dehydration of o-fructose,
28:176, 180
N-Acetylfucosamine, glycosidic linkages,
47: 195-196
N-Acetylgalactosamine, trichloroacetimidates,
synthesis, 50:84,93-98
N-Acetyl-o-galactosamine, 47: 195, 200-20 1
Acetylgentiobiose, octa-0-, Helferich's work
on, 45:4
N-Acetylglucosamine
glycosidic, in glycoproteins, 46:257
linked to L-asparagine, N-glycosylic linkage,
46:255
naturally occurring glycosidic linkages,
50:61, 68
residues, 47:181-182
Acetylglucosaminidase H, endo-P-N-, 44:370
Acetyl group
determination of
in carbohydrates, 26: 15
in N-polysaccharides, 29:343
effect on antitumor activity of
polysaccharides, 32:261
hindered rotation of, in monosaccharides,
23:193, 197
N-Acetyl groups, gas-liquid chromatographic
determination of, 30:36
N- Acetylhexosamines, glycosidic linkages,
47: 188
Acetylimino group, monosaccharides
containing, 23: 166
Acetylium ion
in acetolysis, 22: 1 1
in mass spectra of alditol acetates, 29:5 1
N-Acetyllactosamine, trichloroacetimidates,
synthesis, 50:73,78-80
N-Acetylmannosamine
functional derivatives, 49:195, 197-199
synthesis of derivatives, 49:201-203
N-Acetylmuramic acid, circular dichroism,
45:113
Acetylneuraminic acid
N-, 48:114
biosynthesis, 49: 1 9 4 1 9 5
circular dichroism, 45: 111-1 12
methyl a-and P-o-ketopyranosides,
circular dichroism, 45: 112
synthesis, 49:200
2-0-methyl a-N-, 51:97-98
a-(2+6)-linked N-Acetylneuraminic acid
glycosides, synthesis, 48: 1 15
Acetylpentopyranosylamines, 2,3,4-tri-0-,
47:57
2-AcetyIpyrrole, formation of, 46:3 12-3 13
1-Acetylrubranitrose, 43:333
N-Acetyltetrapeptide, 51:229
Acid anhydrides, in selective esterification of
carbohydrate, 33: 1 3 4 2
Acid chlorides, in selective esterification of
carbohydrate, 33: 1 3 4 2
Acid degradation, monosaccharides,
52:457459
Acid factor, 47:3 18
a-Acid glycoprotein
oligosaccharides, liquid chromatography
separation, 46:4243
structural analysis, 43: 17-20
Acid glycosaminoglycans, quantitation of
uronic acids in, 46:258
Acid hydrolysis
di-o-fructose dianhydrides and per-O-methyl
 SUBJECT INDEX
derivatives, 52:232
sucrose, 52:455456
Acidic sugars, 48:292-293
glyculosonic acids, 48:295-298
glycuronic acids, 48:293-295
Acid invertase in plant cell walls, 42:301
Acid phosphatase
Helferichs work on, 455
in plant cell walls, 42:301-302
Acids, see also specific types
a,P-unsaturated, chemical and physical
properties, 27:260-267
synthesis by Wittig reaction, 27:253-260
a-keto, polarography of, 29:147
carboxylic, as catalysts for mutarotation,
24:27,34
catalysis of mutarotation of sugars by,
24:14
catalytic coefficients for anions of weak,
24:17, 18
in catalytic hydrolysis of glycosides, 22:25
effect on reducing sugars in solution, 42:34
hydroxy
of high optical purity, preparation of,
27:199-20 1
from hydrocellulose, mass spectrometry
of, 30:38
ketonucleoside stability in, 42:245-246
organic, as solvents and reaction media.
21:102
reactions of mineral, with dialkyl
dithioacetals, 32:60
Ackers equation, 25:25
Aclacinomycins, 48:10
Acofriose, L-, from Rhodopseudomonos
cupsulatu lipopolysaccharide, 29:67
Aconitase, inhibition of, 22:210
Aconitic acid, 6:23 1-249
Acosamine
N-acetyl-ix-, synthesis, 40:2425
N-acetyl-r-, synthesis, 40:1 I5
Acrusieae, polysaccharides of, 23:368
Acridine Orange, 53:383-384
5-iodocyisylyl-(3+5)-guanosine,hydrate,
crystal structure, 43:301
sodium cytidylyl-(3 +5 )-guanosine,
hexacosyhydrate, 43:335
a-Acritol, see Mannitol, DL-
Acrocylindrium, crystalline endo-o-
galacturonanase from, 33:363
7
Acrolein
acetal, hydrogenolysis and regioselectivity,
39: I31
1,6-anhydrohexopyranosesfrom, 34: 1 12
Diels-Alder condensation and reduction of,
34:48
dimer, monosaccharides prepared from,
28:296
or-threonic acid synthesis, 40:5
reaction with sucrose, effect of zinc chloride
on, 27:95
Acroscyphus sphaerophoroides.
polysaccharide, 41:76
a-Acrose, see Fructose
P-Acrose, see Sorbose
Acrylaldehyde, reactions with nitro alcohols,
40:105-106
Acrylamide
polymers, gels
in chromatography, 25: 14
fractionation ranges of, 25:19
selective etherification of cellulose with,
33:67
Acrylic acid
Diels-Alder cycloaddition, racemic carba-
sugars, synthesis, 48:29-36
3-(3,4,6-tri-0-benzoyl-o-arabinofi1ranosyl)-,
ethyl ester, preparation of, 33:136
Acrylonitrile, selective etherifications with,
33:66-67
Actinamine, synthesis of, 30:137,35:1 19
Actinomycetes
a,-a-trehalose in, 30:23 I , 234,253
teichoic acid from, 21:363
Actinomycin
complex with 2-deoxyguanosine,
dodecahydrate, crystal structure
bibliography. 30:460
research, 29:2
Actinospectacin. see Spectinomycin
Actinospectinoic acid, structure, 35:1 19
Actinospectose, 21:19 1
Activation energy. 22:32,66,76,82
in polarography, 29: I38
Activation entropy, in polarography, 29:138
Activation parameters, glycoside hydrolysis,
48:323-324
Activation volumes, apparent, starch pastes,
51:257
Actodigin, crystal structure, 43:263-264
8 SUBJECT INDEX
Acute myelogenous leukemia cells, f.a.b.-mass
spectrometry
complex ohgosaccharide, 45:6&61
0-linked oligosaccharides, 45:64
Acyclic carbonyl forms of reducing sugars in
solution, 42:1617,29-30
determination of, 42:20-22
Acyclic diols, 53:129-131, 133
Acyclic model compounds, conformational
energy, 47:77-8 1
Acylalkyl radicals
hydrogen-abstraction reactions, by radiation,
37~18-19
oxidation, by transition-metal ions, 37: 19
radical-radical reactions by radiation, 37: 18
radical-scavenger reactions, by radiation,
37~18-23
reduction by phenoxides, 37:19
by transition-metal ions, 37: 19-20
Acylamido group, participation in sugar
reactions, 22: 127, 143
Acylamido groupin cyclic monosaccharide
formation, 23: 117
Acylating agents, selectivity, cyclic acetals in
study of, 34:207
Acylation
aldonolactones, 50: 132-1 34
of deoxynitroalditols, 24: 1 15
of dithioacetals, 32:45
isosorbide, 4 9 1 2 6 127
selective, of anhydroalditols, 25:262
Acyl azides, selective esterification of
nucleosides with, 33:45
Acyl cyanides, in selective esterification of
carbohydrate, 33:45
Acylglycals, 3,4-frans-di-O-, treatment with
pyridinium poly(hydrogen fluoride),
48: 102-103
Acyl groups
bacterial polysaccharides, 48:3063 11
effect on mercaptalation, 32:29
migration in o-galactose series, 30:4
Acyl halides
nomenclature, 52: 105
reactions with ethanol, 33:18
Acyl migration, 21:24
in acylated carbohydrates, 33:lOl-107
in detritylation of sucrose acetates, 33:246
during detritylation with acetic anhydride,
33:239
in ~-glucofuranosidurono-6,3-lactone esters,
33:214
imidazole-catalyzed in selective acylation,
33:42
in methylation of sucrose acetates, 33:244
N-Acylneuraminate-9(7)-O-acetyltransferase,
40: 184
Acylneuraminate pyruvate-lyase, 40: 158, 177,
211~214,219
Acyloxonium ions
in fluorination of carbohydrates, 38:20 1
formations from 1,6-anhydrohexopyranoses,
34:87-89
Acyloxy group
neighboring-group reactions of, 26: 128
participation in sugar reactions, 22: 116
reactivities of, 26: 131
Acylpyrrole formation, from 3-deoxy-hexos-2-
dose, by Strecker degradation,
46:3 11-312
Acyl substituents, location, glycopeptidolipids,
51:198-200
Acyl-thiocarbamide, bitterness, 45:3 10
Acylthio group, participation in sugar reactions,
22:141, 168
I-Adamantanecarbonyl chloride, in
esterification of nucleosides, 33: 13
Adamantenecarboxylic acid, cyclodextrin
inclusion complexes with, 46:221
N-( 1-Adamantyl) sulfamate, taste properties,
45300
Additive model of atomic interaction, 44:40, 52
Adenine
L-apiosyl-, bacteriostatic for Escherichia coli
and Staphylococcus aureus, 31: 153
4-amino-2-P-o-arabinofuranosy~-,
preparation of, 33: 186
4-amino-8-P-~-arabinofuranosyl-,
preparation of, 33: 188
9-P-o-arabinofuranosy1-
biosynthesis, 35:123-124
and hydrochloride, crystal structure
bibliography, 32:375-376
preparation of, 29:6
9-(2-chloro-2-deoxy-~-arabinofuranosyl)-,
synthesis of, 28:8
9-(4-thio-P-o-arabinofuranosyl)-,23:224
arabinofuranosyl-, biosynthesis of, 42:230
9-P-o-arabinosyI-, biosynthesis of, 42:262
arabinosyl-, biosynthesis, 35: 124
 SUBJECT INDEX
crystal structure bibliography, 32373,375
dinucleotide with nicotinamide, proton
magnetic resonance spectroscopy of,
27:37,57
6-(2-furfurylamino)-, as plant-growth
substance, 21:420
9-(P-~-ghcopyranosy~uronamide) conjugate,
preparation, 36: 129
~ - ~ I u c o s Y21:23
~-,
9-(6-deoxy-P-~-elythro-hex-5-
enulofkanosyl)-, 21: 174
9-(2-deoxy-~-arubino-hexopyranosyl)-, in
cancer chemotherapy, 21: 145
keto derivatives of, synthesis, 42:234
9-P-~-lyxofuranosyl-,22: 122
9-(2,3-anhydro-5-deoxy-P-~-lyxofurano-
syl)-,preparation of, 33:34
9-[2,3-O-isopropylidene-5-O-
(methylsulfonyl)-P-~-~yxofuranosy~]-,
displacement reactions of, 24: 187
9-a-o-mannopyranosyI-, hydrochloride,
conformation of, 26: 108
9 (5-deoxy-2,3-O-isopropylidene-P-~-
erythro-pent-4-enofuranosyl)-, 24: 148
9-(2,3-dideoxy-P-~-glycero-pent-2-
enofuranosyQ, 24:166,32:373,375
9-(5-deoxy-P-o-elythro-pent-4-
enofuranosy1)-, 24: 148
9-(5-deoxy-2,3-O-(ethoxymethylidene)-P-o-
elythro-pent-4-enofuranosyl)-, 24: 148
2-P-~-pentofuranosyl-,preparation of,
33: 186
4-amIno-8-(2-deoxy-P-~-eryfhro-
pentofuranosy1)-, preparation of, 33: 1 88
8-P-o-pentofuranosyl-, preparation and
structure of, 33: 187
9-(2-deoxy-o-erythro-pentofuranosyl)-,
synthesis of anomers, 31:4
9-(3,5-anhydro-2-deoxy-P-~-threo-
pentofuranosy1)-, 24: I74
9-(3-deoxy-a-~-threo-pentofuranosyl)-,
preparation of, 29:290
(2-keto-threo-pentofuranosyl)-, synthesis of,
42:232
9-(3,4-di-O-acetyl-2-deoxy-P-~-er,vthro-
pentopyranosy1)-, 24:2 12
9-(4-thio-P-~-rihoforanosyl)-, 23:222
N3.5-anhydro-9-(2,3-O-isopropylidene-P-o-
ribofuranosy1)-,p-toluenesulfonate,
22:371
9
4-amin0-2-P-o-ribofuranosy~-.preparation
of, 33: I86
4-amino-8-~-~-ribohranosy~-, preparation
of, 33: 187-1 88
8-P-n-ribofuranosyl-, crystal structure
bibliography, 37:436
9-(2,3-anhydro-P-o-ribofuranosyl)-,
preparation of, 29:5
9-(2-amino-2-deoxy-o-~-ribofuranosyl)-,
monohydrate, crystal structure
bibliography, 30:462
9-(4-acetamido-4-deoxy-P-~-ribofuranosyl)-,
23: 187
9-[5-deoxy-2,3-O-isopropylidene-5-
(phenylthi0)-P-o-ribofuranosyl]-,
irradiation, 38: 152
9-a-o-ribofuranosy~-,5-phosphate. 22373
9-( P-o-ribofuranosyhronic acid) conjugate,
preparation, 36: 127
7-(5-S-methyl-5-thio-P-~-ribosyl)-,
biological activity and structure of,
42: 135
2-chloro-9-[3-C-(hydroxymethyl)-a-r.-
threofuranosyl]-, preparation of, 31: 184
9-[3-C-(hydroxymethyl)-P-~-
threofuranosyl]-, synthesis of, and
bacteriostatic action of, 31: 184
9-P-~-xylofuranosyl-,synthesis of, 29:4
9-(2,3-anhydro-5-deoxy-P-~-xylofurano-
syl)-, 23~246
9-(4-acetamido-4-deoxy-~-~-xylofurano-
~yl)-,23~183
9-(4-thio-~-xylofuranosyl)-,23:224
9-(5-deoxy-P-xylofuranosyl)-,sulfonylation
of, 23:246
9-( 5-deoxy-2,3-di-O-p-tolylsulfony~-P-~-
xylofuranosy1)-, 23:246
9-( 5-deoxy-3-O-p-tolylsuIfonyl-~-~-
xylofuranosy1)-, 23:246
9-(5-deoxy-P-o-xylofuranosyl)-,p-
toluenesulfonylation of, 33:34
9-(5-thio-~-xylopyranosyl)-, 23:2 1 1
Adenine nucleoside, antiviral activity of,
42131
Adenosine
5-(2-acetamido-2-deoxy-a-~-
glucopyranosyl pyrophosphate),
enzymic preparation of, 28:3 15, 342
reaction with 2-acetoxy-2-methylpropanoyl
chloride or bromide, 33:84
10 SUBJECT INDEX
Adenosine (continued)
adenylyl-(3 '+5 ')-
adenylyl-(3 '+S')-
hexahydrate, crystal structure
bibliography, 37:432434
hydrate, crystal structure bibliography,
31:362
proton magnetic resonance spectroscopy
of, 27:36
5 '-(a-D-galactopyranosyl pyrophosphate),
enzymic synthesis of, 28:340
5 '-(a-o-glucopyranosyl pyrophosphate),
enzymic synthesis of, 28:337
occurrence and isolation of, 28:3 14
structure of, 28:309
in sucrose synthesis, 28:395
5 '-(a-o-mannopyranosyl pyrophosphate),
enzymic synthesis of, 28:339
5 '-(a-o-xylopyranosyl pyrophosphate),
enzymic synthesis of, 28:343
3 '-amino-3 '-deoxy-
antitumor activity, 29:4
biosynthesis, 35:123
deamination of, 31:57
reaction with phosphoryl chloridetriethyl
phosphate, 33:80
5'-amino-5'-deoxy-, 23: 141
5'-(2-amino-2-deoxy-a-~-glucopyranosyl
pyrophosphate), enzymic preparation of,
28:338
3 '-amino-2,'3 '-dideoxy-, preparation of,
29:5
8-(2-aminoethylamino)-,3' , S I -
monophosphate tetrahydrate, crystal
structure bibliography, 38:5 19-520
3,S'-anhydro-, 23: 141
5',8-anhydro-2,'3 '-0-isopropylidene-8-endo-
mercapto-, hydrate, crystal structure
bibliography, 31:371
8,5 '-anhydro-2,'3 '-0-isopropylidene-8-
mercapto-, crystal structure
bibliography, 30:466
5'-(arabinosyl pyrophosphate), occurrence
of, 28:315
5'-azido-5'-deoxy-4'-fluoro-2,'3'-O-
isopropylidene-, preparation of,
28:273
barium 5 '-monophosphate heptahydrate,
crystal structure bibliography, 37:415
benzoylation of, 33:33
N6-benzoyl-3',5 '-di-0-(chloroacety1)-,
selective deacylation, 39:43
N6-benzoyl-3 '-0-(3-benzoylpropanoyl)-2'-
deoxy-, preparation, 39:43
5' (benzyl hydrogen phosphate), 22:327
bis(pyridine) osmate(VI), crystal structure
bibliography, 32:384
p-L-.5'-phosphate, 22:337
8-bromo-
5 ' -(a-o-glucopyranosyl pyrophosphate),
preparation of, 28:355
crystal structure bibliography, 30:459
2' ,3 '-0-isopropylidene. crystal structure
bibliography, 37:424
monohydrate, crystal structure
bibliography, 37:424
2'-0-(triisopropylphenylsulfonyl)-,
43:374
monohydrate, 43:374
S'-O-trityl-, sulfonylation of, 33:34
reaction with sodium hydride-
triisopropylbenzenesulfonyl chloride,
33:34
5 '-bromo-S '-deoxy-, riboflavine complex
trihydrate, crystal structure
bibliography, 30:459
5-hromouracil, crystal structure bibliography,
38:522
5-bromouridine monohydrate, crystal
structure bibliography, 31:370
[N6-(1-carboxy-2-hydroxyethyl)amino-
carbonyll-, crystal structure
bibliography, 38:496-497
5 '-carboxylate, isopropyl3 '-deoxy-3'-eno-,
preparation of, 29:275
[N6-(carboxymethyl)aminocarbonyl]-,
crystal structure bibliography, 38:496
complex formation with phenylboronic acids,
35:49
crystal structure bibliography, 30:460
2',3'-cyclic phosphate, 22:357
3',5'-cyclic phosphate, 22:319,358
crystal structure bibliography, 31:370
hydrolysis, 39:61
cyclic 3',5'-phosphate, in enzyme
biosynthesis, 30:224
7-deaza-, configuration of, 24: 187
2'-deoxy-
benzoylation of, 33:33
3 ',S'-diphosphate, 22:348
 SUBJECT INDEX
monohydrate, crystal structure
bibliography, 31:370
3-0-p-tolylsulfonyl-, displacement
reaction of, 24:166, 174
3-phosphate, 22:343,348
5-phosphate, 2 2 3 1 I, 343, 348
5-phosphate sodium salt hexahydrate,
crystal structure bibliography, 34:368
preparation of, 29:5-6
proton magnetic resonance spectroscopy
of, 2 7 s I
selective oxidation with chromium
trioxide, 33:99
5-(sodium phosphate) hexahydrate,
crystal structure bibliography, 31:357
3-deoxy-, see Cordycepin
5-(2-deoxyuridin-2-yl phosphate),
tetrahydrate, crystal structure
bibliography, 31:37 1
NO,N6-dibenzoyl-2,3,5-tri-U-benzoyl-,
selective deacylation, 39:39
2,3-dideoxy-, 24: 166
preparation of, 29:5
diethidium 5-iodouridylyl-(3,5)-, 27
hydrate, crystal structure bibliography,
38:501-502
N6-dimethyl-, 5-phosphate, 22:337
3,5-di-O-acetyl-
2-deoxy-, selective deacylation, 39:36
preparation, 39:40
reaction with morpholine, 39:38
3,5-di-O-benzoyI-, preparation, 39:39
2,5-diphosphate, 22321, 366
3,5-diphosphate,22:321, 366
5-diphosphate
glycosly esters, 44:280; see also Glycosyl
nucleotides
trihydrate, 43:334
5-(o-mannitol 1 -pyrophosphate), isolation
of, 28:333
4-fluro-
2,3-0-isopropylidene-, preparation of,
28:273
5-0-sulfamoyl-, synthesis of, 28:226,273
5-(a-~-glucopyranosyl pyrophosphate),
enzymic preparation of, 28:338
synthesis of, 28:s
N-formyl-2,3 -0-isopropylidene-5 - 0 - p -
tolylsulfonyl-, displacement reaction of,
24: 187
II
fusion reaction with 2,3,5-tri-O-
acetyladenosine, 39:37
5 -(galactosyl pyrophosphate), occurrence
and isolation of, 28:3 15
hydrochloride, crystal structure bibliography,
31:357
N6-hydroxy-, 5 -(a-D-glucopyranosyl
pyrophosphate), preparation of, 28:355
8-( 1-hydroxyisopropyl)-, dihydrate, crystal
structure bibliography, 38:52 1-522
8-hydroxy-2-O-p-tolylsulfonyl-.
displacement reaction of, 24: 188
iodide
3,5-anhydro-2,3-0-isopropylidene-,
crystal structure bibliography,
31:371
5 -deoxy-5 -(methy1ammonium)-,
monohydrate, crystal structure
bibliography, 30:462
5-iodouridylyl-(3+5)-, ethidium complex,
methanolate hydrate, crystal structure
bibliography, 34:377
5 -(mannosy1pyrophosphate, occurrence and
isolation of, 28:3 15
P m e t h o x y - , 5-(a-~-glucopyranosyl
pyrophosphate), preparation of, 28:355
N1-methyl-,5-(a-o-glucopyranosyl
pyrophosphate), preparation of, 28:355
N6-methyl-, 5-phosphate, 22337
5methyl-
phosphate
crystal structure bibliography,
38:5 16-5 17
hemihydrate, crystal structure,
43:289-290
5-thio-, crystal structure bibliography,
38:515-516
5 -monophosphate
copper(I1) iminodipyridine. crystal
structure bibliography, 38:528
monohydrate, crystal structure
bibliography, 37:4 18
p-toluenesulfonylation of, 33:33
3 ,5 monophosphate P, 0-ethyl ester
monohydrate, crystal structure
bibliography. 34:370
reaction with N-(benzyloxycarbony1)-
phenylalanine, 33:45
nickel 5-monophosphate hexahydrate,
crystal structure bibliography, 34:374
12 SUBJECT INDEX
Adenosine (continued)
3-O-acetyl-
acyl migration in. 33: 105
crystal structure bibliography, 30:463
2-deoxy-5 -0-p-tolylsulfonyl-,
displacement reaction of, 24: 185
54-acetyl-
acylation and sulfonylation of, 33:3 1-32
2- and 3 -p-nitrobenzenesulfonate,
23:246
8-bromo-, sulfonylation of, 33:34
fusion reaction with 2,3,5-tri-O-
acetyladenosine, 39:37
preparation, 39:38
5 -0-benzoyl-8-bromo-, sulfonylation of,
33:34
2,3 -0-[(2-~arboxyethyl)ethylidene]-,
crystal structure bibliography, 38:529
2,3-O-(ethoxymethylidene)-5-0-p-
tolylsulfonyl-, displacement reaction of,
24: 148
3O-formyl-, acyl migration in, 33: 105
2,3 -0-isopropylidene-
crystal structure bibliography, 38:520-52 1
5-(dibenzyl phosphate), 22:337
5 -0-p-tolylsulfonyl-, displacement
reactions of, 24: 147
5-phosphate, 22:327
p-toluenesulfonylation of, 24: 185
5-S-phenyl-5-thio-. photolysis
mechanism, 38: 153
2,3-0-( I-methoxyethy1idene)- reaction
with pivaloyl chloride, 28:279
2-0-methyl-, crystal structure bibliography,
37:421
2-O-(tetrahydropyranyl)-,crystal structure
bibliography, 31:37 1
2-O-tetrahydropyran-2-yl-, esterification
with pivaloyl chloride, 33: 13
5 -0-trityl-
acetylation of, 33:32
preparation, 3 5 5 5
2-phosphate, 22:308,321,349-350
3-phosphate, dihydrate, crystal structure
bibliography, 31:371
5-phosphate, 22:3 11,326-327, 336-338,
373
monobydrate, crystal structure
bibliography, 31:371
preparation, 3 9 5 4
proton magnetic resonance spectroscopy
of, 27:81
spin-lattice relaxation of I3C nuclei in,
21:59
5-phosphoropiperidate, in synthesis of
glycosyl nucleoside pyrophosphates,
28:346
5 -phosphoro(P+N)phenylalanine, in
synthesis of glycosyl nucleoside
pyrophosphates, 28:346
5-(potassium diphosphate), dihydrate,
43:334
crystal structure, 43:323-324
3,5-pyrophosphate, in marine algae, 26:404
5 -pyrophosphate glycosyl esters, occurrence
and enzymic synthesis of, 26:356
rubidium 5 -diphosphate monohydrate,
crystal structure bibliography, 37:418
selective reactions
bromination with N-bromosuccinimide
and triphenylphosphine. 33:78
esterification with acyl azides, 33:45
methylation with diazomethane, 33:69-70
oxidation of, 33:88
phosphorylation of, 33:4849
2-S-methyl-2-thio-, preparation of, 29:6
sulfonylation and halogenation of, 33:83
2-thio-, preparation of, 29:6
3-thio-, preparation of, 29:6
4-thio-
D-, 23:222
L-, 23~222
5 -(triethylammonium phosphorothioate), p-
nitrophenyl ester crystal structure,
43:299-300
2,3,5-tri-O-acetyI-
fusion reaction with 5 -0-acetyladenosine,
39:37
with adenosine, 39:37
hydrazinolysis, 39:40
selective deacylation, 39:36
2,3,5-triphosphate, 22:366
5-triphosphate
in cellulose synthesis, 26:322
formation in yeast catabolism of sugars,
32:127
P3-1-(2-nitrobenzyl), 46:204
P3-l-(2-nitrophenylethyl), 46:204
triphosphate disodium salt trihydrate, crystal
structure bibliography, 30:46 I
 SUBJECT INDEX
5 -[tris(hydroxymethyl)methylammonium
diphosphate], dihydrate, crystal
structure, 43:321-322
N6-trityl-5-O-trityl-, selective benzylation
of, 33:59
uridylyl- (345)-, hemihydrate, crystal
structure bibliography, 30:464
5-zinc(I1) (2,2-dipyridyl triphosphate),,
tetrahydrate, 43:335
Adenosine deaminase, action on I.-
apiosyladenine nucleotide, 31: 153
S-Adenosyl-L-methionine, as methyl donor,
42:321
Adenylic acid, 22:327
muscle, 22:309
yeast, 22:3 12
Adenylylation, of gentamicins, 30:204-208
AdenylyL(3 -5 )-adenosine phosphate
bis(proflavin hemisulfate), 43:373
Adhesives
from copolymers of levoglucosan with
alcohols and ethers, 34:73
dextrins as, 47:323
Adipic acid, starch ester in food industry.
29:330
Adipose tissue, o-fructose metabolism in,
34:297
Adiposin, 48:2&25
synthesis, 48535
Admantoates, of dithioacetals, preparation of,
32:48
Adonitol, 21:17
Adonose, purification of, 26:236
Adriamycin analogs, 46328
Adsorbents, granular, for sugar refining,
6:205-230
Aerobacter aerogenes, polysaccharide,
methylation analysis of, 30: 12
Aerobic growth, of yeast in presence of sugar,
32: I42
Aerobic respiration, of yeast, 32: 143- 144, 23 1
Aesculus hippocastanum, oligosaccharides
from seeds of, mass spectrometry of,
29:96
Affinity absorbents, 53:203-204
Affinity chromatography
adsorbent preparation, 39:406-409
adsorbents with carbohydrate ligands for
macromolecular substances,
39:405447
13
applications, 39:437443
of enzymes, 39:441443
of lectins, 39:444445
techniques, 39:410412
anti-carbohydrate antibodies, 53:203-209
of concanavalin A, 35: 157
in lectin isolation and purification, 35: 137
polysaccharide derivatives as matrices,
29:388-399
protocol for, 53:204-205
in purification of immunoglobulins.
31~323-325
Agar, 44: 186
acetobrominolysis of, 22:23
3,6-anhydro-~-galactoseresidues in, 22:4
carbon-I 3 nuclear magnetic resonance,
spectra, 38:77-78
constitution of, 25:6
degradation by mercaptolysis or
methanolysis, 31: 190
desulfation of, 29:337
diffusion, 53:205-206
galactomannans interaction with
polysaccharides of, 3 1:29 1-30 1
gelation mechanism, 24:32 1
in gel chromatography, 25: 14
pyrolysis of, 34:45
pyruvic acid assay in, by enzymic method,
30:284
separation into components, 29:398
structure of, 24:277
substitute for, 25:7
Agar-agar, see Agar
Agarase, 44: 187- 190
Agaricus bisporus lectin, see Mushroom lectin
Agaricus campestris. a-L-arabinohranosidas
of, 42:387
Agarobiose, 24:277
4,6-0-( 1-carboxyethylidene)-, dimethyl
acetal, 24:279
6-O-methyl-, dimethyl acetal, 24:278
preparation by mercaptolysis or methanolysis
of agar, 31 :190
Agaropectin, 44: 186-1 87
complex with chitosan, 29:398
Agarose, 24:277, 52:368-370,420
acetylated, separation from agar. 29:329
activation by 1,1 -bis(imidazole),
39:415416
by bisoxirane method, 39:415
14 SUBJECT INDEX
Agarose (continued)
by cyanogen bromide, 39:414,430-43 1
by divinyl sulfone, 39:415
affinity chromatography adsorbent, 39:407,
410,413416
circular dichroism, at various temperatures,
4591-93
cross-linked, 29:355,357
crystal structure bibliography of, and
derivatives, 33:404
epichlorohydrin, reaction with, 29:326
gelation
ofagars by, 24:321
and liquefaction of, 31:292-301
gels, in chromatography, 25: 14
immobilization on, 49: 181-1 86
iodine complex, laser-Raman spectroscopy,
44:84
0-(2-diethylaminoethyl)-, gels, as media for
electrophoresis and
immunoelectrophoresis, 29:323
related polysaccharides, structure, enzymic
analysis, 44: 18C190
structure of, 31:291
enzymic analysis, 44: 186-190
Agave Vera cruz, o-fructose from, 22:232
Agglutination, of red blood cells, effect of
influenza virus on, 33:&5
Agglutinins, see also Lectins
plant, history, 35: 128
Aglycon
character, 47:62-65
effect on hydrolysis of glycosidic bond,
22:71, 78
on rate of hydrolysis of glycosides,
22:4849
non-sugar, 48:299-300
staggered orientations, 4750-5 1
AGMGP, f.a.b.-mass spectrometry, 4 5 2 1-23
Agricultural chemistry, carbohydrate chemistry
and, 21:378
Agrobacteria, p-(1+2)-glucans, f.a.b.-mass
spectrometry, 45:68
Agronomy, carbohydrate chemistry and,
21:378
AH,B hypothesis, 45:20&201,213-223, 231,
246,257-261,264,271,283-285,292,
297-299,303-307,322,341
A-396-1 (antibiotic)
discovery of, 30: 112
isolation and structure of, 30: 134
Ajugose, isolation, 37:307-308
Alanine
3-(3-amino-S-triazolyl)-, L-, 21:40 1
W(benzyloxycarbony1) phenyl-, reaction
with adenosine, 33:45
D-
in glycoprotein from sheep and ox, 33:7
sweetness, 45233
L-
AH, B system in, 45221
carbohydrate precursor, 40: 117
in cell-wall glycoproteins, 42:298
configurational relationship with 2-amino-
2-deoxy-~-glucose,27:206
N-(2-furoylmethyl)-, 46:3 19
N-acetyl-, preparation of, 32:79
3-[(9-~-~-ribofuranosylpurin-6-yl)glycyl]-~-,
sesquihydrate, crystal structure
bibliography, 37:425
Alanine amidase, N-acetylmuramoyl-L-, 44: 196
Alaria esculenta, stipes, material from, circular
dichroism, 45:lOX-109
Albersheim model for plant primary-wall
structure, 42:275, 303-304, 338
discussion of, 42:309-314
Albumin
carbohydrate linkage in, 2 5 4 2 0 , 4 4 4 4 5
effect on a-o-mannosidase activity, 28:427,
429
hen egg, glycoprotein, 'H-NMR
spectroscopy, 41:344,346,348-350,
357,359-361
Alcaligenes faecalis
curdlan, preparation, properties, and uses,
36:307-3 10
0-specific polysaccharide, 47: 199
Alcian blue, complexes with
glycosaminoglycans, 29:401
Alcoholates
carbohydratealkali metal complexes, 21:256
of carbohydrates, preparation of, 21:263
Alcohols
amino, sphingosine-related, 24:39&393
configuration determination of, 27:201
copolymerization with levoglucosan, 34:72
fluoro, mass spectrometry of esters of, 30:38
halogenation of, 28:240
higher-carbon sugar, configurations of,
1:l-36
 SUBJECT INDEX
iodination of, 28:281
methylation with diazornethane, 33:68
nitro, reactions with acrylaldehyde,
40: 105-106
reactions with sodium glyoxylate,
40:10&107
as 0-nucleophiles, see Nucleophiles, 0-
optically active secondary, preparation of,
27: 196
organic complexes, 53:360-361, 363-364
oxidation ofpolyhydric, 41:9
pol yhydric
from formose, 29: 174, 178
mass spectra and stereochemistry of,
21:79
oxidation of, 31:3
and radiation-generated electrons, 37:74
as solvents for sugars, 27:98
unsaturated, 2: 107-1 I8
racemic, aldonic acids in gas-liquid
chromatography of, 30:37
radiolysis and free-radical reactions,
37:26-32
as reaction media, 27:99
reactions with
aldonolactones, 50: 149-15 1
(a1koxymethylene)dirnethyliminiurn
halides, 28:254
with carbon tetrachloride and tertiary
phosphines, 28:246
with cyanuric chloride, 28:258
with dichlorocarbene, 28:260
with N-(2-chloro-l, 1,2-trifluoroethyl)-
diethylamine, 28:258
with N,N -dicyclohexyl-N-
methylcarbodiimidium iodide, 28:260
glycals, 24:2 15
as solvents
in ammonolysk, 31: 102
of sugars, 27:96-102
alkoxy, 27538
as solvents for sucrose, 27:87
as solvents for sugars, 27:96, 99
w-aminoalkyl, 27:99
starch complexes, 53:283
Alcohol ysis
of ~-g~ucofuranurono-6,3-lactones, 33:2 12
of gulono-1,4-lactones, 38:301
Aldaric acids, 52:51, 110-1 12
2,5-anhydro-, preparation of, 33: 1 18
1s
gas-liquid chromatography of, 28: 7 1-78
high-performance liquid chromatography of,
46~33-35
mass spectrometry of, 29:79
deoxy-, 29:79
Aldehydes, 53:36S-366
preparation by oxidation of hydroxymethyl
groups, 33:78
protection of, 46: 195-1 98
reaction with
alditols, 39:21
aldonolactones, 50: 125- I27
carbohydrates, 38: 122- I29
gulono-l,4-lactones, 38:303
selective derivatization with N,N-di-
phenylethylenediamine, 33: 122
synthesis, 36: 10
Aldehydo fonn of reducing sugars in solution,
42:29-30,35
determination of, 4220-22
Aldehydrol. 23:25
formation in aqueous solution, 42:30
Ald-3-enopyranoside, alkyl 3,4-dideoxy-o~-
cis-hydroxylation, 40:5455
epoxidation, and oxirane-ring opening,
40:5&59
synthesis, 40:48-59
AId-2-enopyranosio-4-ulose, methyl, reduction,
selectivity, 40:71
Ald-2-enos-4-ulose, synthesis, 40:65
Ald-3-enulosonic acids, alkyl esters, chemical
properties of, 27:268
synthesis by Witting reaction, 27:267
Aldgamycin C, periodate oxidation, 35:90
Aldgamycin E, components, and degradation,
35:89-91
Aldgarose
D-, biosynthesis, 35:89-9 1
natural occurrence of, 4 2 7 3
structure of, 42:71, 78
synthesis of, 42:8 I
Aldgarose methyl glycoside, synthesis of,
3238
Alditol-cation complexes, crystal structures,
47:26
Alditols, 52:51. 103-106
acetals
mass spectrometry of, 29:75-77
methylated, chemical-ionization mass
spectra, 38:401
16 SUBJECT INDEX
Alditols (continued)
mass fragmentograms, 38:404
rearrangements of, 26:221
sulfonylation of, 23:241
acetamidodeoxy-
gas-liquid chromatography of, 28:84-87
per-0-(trimethylsilyl) derivatives,
gas-liquid chromatography, 28: 145
acetates
carbon-I 3 nuclear magnetic resonance
spectroscopy, 41:59-60
conformation of, 26:72
gas-liquid chromatography of. 28:34,
59-65, 122-129
and trimethylsilyl ethers, gas-liquid
chromatography of, 28:43
gas-liquid chromatography of methylated,
30:30-32,89-98
mass spectromern of methylated, 30:40
mass spectra of, 21239
of monosaccharide, mass spectra of,
295-55
partially methylated, mass spectrometry
Of, 29~58-71
acetylenic, 24:262
1,l -bis-(acylamido)- 1-deoxy-, configuration
of, 31:109
mechanism of formation of, 31:110-121
aldonolactone reduction to, 50: 157-161
amino-
gas-liquid chromatography of, 28:78
trifluoroacetyl derivatives, gas-liquid
chromatography of, 28: 1 14
aminoanhydrodeoxy-, carbon- 13 nuclear
magnetic resonance spectroscopy, 41:61
1-amino-I-deoxy-, deamination of, 31:60
2-amino-2-deoxy-, deamination of, 25: 191
aminodeoxy-
carbon- 13 nuclear magnetic resonance
spectroscopy, 41:61
peracetylated, gas-liquid chromatography
of, 28:145-146
2-amino-l,2-dideoxy-l -nitro-, 24: 133
anhydro, carbon-I 3 nuclear magnetic
resonance spectroscopy, 41:60-6 1
2,Sanhydro-
in nucleoside synthesis, 25:218
preparation of, 33:119-125
properties of, 25:220-229
reactivity of, 25:211
anhydro-, 25229-283
acetals, 25:265
configurations (revised) of, 25264
infrared spectra of, 25:250-252
isomerization of, 25258
rearrangements in hydrogen fluoride,
26:173-175
ring opening of, 25:256
uses, industrial, 25:267
anhydrodeoxy-, 23:74,77,79,94
a,w-dibromo-a,w-dideoxy-, sulfonylation of,
23:239
with benzaldehyde, 21: 19
boronates
acetates and benzoates, 3 5 5 3
preparation and structure of, 35:42,53
properties, of, 3577-78
preparation, 35:40
catabolism by yeasts, 32210-219, 234
column chromatography, boronic acids in,
35:63
complex-formation, 47: 13-14
compounds with acetone, 21:19
conformations of, 25: 105
and crystal-structure analyses of, 26:69
crystallography of, 2 9 6 0
dehydration of, 33: I 19-125
1-deoxy-
l-nitro-
optical rotatory dispersion and circular
dichroism of, 24: 134
synthesis of, 24:70
2-O-methyl-l-nitro-, 24: 133
preparation of, 3 2 7 5
2-deoxy-2-nitro-, 24:72
deoxynitro-
acylation of, 24: 115
anbydridization of, 24: 119
dehydroacetylation of, 24: 127
3,6-dideoxy-, gas-liquid chromatography of,
28:63
dideoxy-, 21:189
preparation of, 3 2 7 6
disaccharide, trifluoroacetyl derivatives,
gas-liquid chromatography of, 28: 1 13
electrophoresis
in metal salt solutions, 21:232
sulfonylated phenylboronic acids in, 3 9 6 2
electrosynthesis, from monosaccharides,
29: 109-1 17
 SUBJECT INDEX
enzymic determination by kinases, 30:282
gas-liquid chromatography, 28: 56-57
boronic acids in, 35:65
gel chromatography, 2 5 3 1
glycosyl-, per-O-(trimethylsilyI) derivatives,
gas-liquid chromatography of,
28:156-157
1-halo- 1-thio-, preparation from
dithioacetals, 32:70-7 1
irradiation of unprotected, 38: 147-149
isolation, 47: 179-180
lectins, interaction with, 35: 180
liquid chromatograhy, 46:33
pre-column derivatization procedures,
46:68
methylene acetals, acetolysis of, 22: 12
methyl ethers, mass spectrometry of, 29:56
from oligosaccharides,
per(trimethylsily1)ated. gas-liquid
chromatography of, 28:133-134
1-[2-( p-aminophenyl)ethyl]amino- I -deoxy-,
as affinity chromatography adsorbents,
39:420,426-427,431
paper chromatography, phenylboronic acid
in, 3 5 6 0
permethylated, mass spectrometry of, 30:42
permethylated oligosaccharide, mass
spectrometry of, 29:89-91
per-0-trimethylsilyl, mass spectrometry of,
30:38
per(trimethylsilyl)ated, mass spectra of,
29:58
per(trimethylsily1) derivatives, gas-liquid
chromatography of, 28: 1 19-120
phosphates, bacterial polysaccharides,
48~316-317
preparation of, 26: 15
1-S-ethyl- I-thio-, peracetates, 32:78
I-t, 21:129
2-2, 21: 129
reactions with aldehydes, 39:21
with ketones, 39:21
rearrangements in hydrogen fluoride,
26:173-176
selective oxidation with Acetobacter
suboxyduns, 33: 100
with lead tetraacetate, 33:96
selective phosphorylation of, 33:50
separation
on ion-exchange columns, 47:38
17
of methylated sugars as, 30:22
sulfonic esters, solvolysis of, 25207
sweetness-structure relationship, 45293-295
synthesis of
trifluoracetic acid in, 34:8
by yeasts from sugars, 32:128
transport into Rhodotorula glutinis, 32: 157
trifluoroacetates
gas-liquid chromatography of, 28:37,65,
113
of methylated, gas-liquid chromatography
of, 30:32,99
mass spectrometry of, 30:42
of monosaccharide, mass spectrometry of,
2955
trimethylsilyl ethers
gas-liquid chromatography of, 28:57
of methylated, gas-liquid chromatography
of, 30:30, 88
of oligosaccharide, mass spectrometry of,
29:96-97
unsaturated, synthesis by Witting reaction,
27237
from uronic acids, acetates, gas-liquid
chromatography of, 28: 129
utilization by yeasts, 32: 147
and associations of abilities, 32:225-228
Aldobioses, acyl esters, ammonolysis of, 31539
Aldobiosylamines, N-acyl-, configuration of,
31:105
Aldobiouronic acid anhydride, mass
spectrometry of trimethylsilyl derivative,
30:38
Aldobiouronic acids
from acidic xylans, 36:237-238
from dextrans, 30:408
hydrolysis kinetics of, gas-liquid
chromatography of, 28:46
permethylated, mass spectra of, 29:85
preparation by acid hydrolysis of uronic acid
residues, 3 1:193
Aldofuranoses
4-acetamido-4-deoxy-, hindered rotations of
acetyl groups, 23: 196-197
2,3-anhydro-, nuclear magnetic resonance
spectra, 25: 172
in aqueous solution, NMR spectroscopy,
42: 19
ethylidene-, fragmentation patterns of,
34: 194
18 SUBJECT INDEX
Aldofuranoses (continued)
monoisopropylidene-, fragmentation patterns
of, 34: 194
Aldofuranosides
formation of
mechanism of, 21:117
rate of, 21:106
synthesis, 21:96
from furanose esters and halides, 21: 121
hydrolysis of, 21 :129
by alkali, 21:137
rate constants for, 22:42
phenyl, melting points and specific optical
rotations of, 21:141
Aldoheptoses, composition in aqueous solution,
42:35-36,6445
Aldohexofuranoses, 1,6-anhydro-P-o-,
preparation, properties, and conformation
of, 34:24
Aldohexofuranosides
conformation of, 21:lOO
oxidation of glycol groups in, 21: 133
Aldohexonic acids, 2-amino-2-deoxy-o-,
deamination of, 25:191,31:58
Aldohexopyranoses, see also Hexopyranose
5-amino-l,6-anhydro-5-deoxy-, 23: 132
2-amino-2-deoxy-, deamination of, 25: 184
I ,6-anhydro-p-o-
conformations of, 26: 116
stereoselective oxidation of, 33:90
6-bromo-6-deoxy- or 6-deoxy-6-iodo-,
reaction with silver fluoride, 33:263
complex, axialkquatorial equilibrium,
47:5940
conformational analysis of, 26:67
conformational equilibria, 26:91
ethylidene-, fragmentation patterns of,
34: I94
free energies of, 24:58
preparation, properties, and conformation of,
34:24
relative free energies of, 4225-26
Aldohexopyranosides
6-deoxy-, proton magnetic resonance
spectroscopy of, 27:70
methyl 01-D-, oxidation with potassium
ferrate, 33:lOO
methyl 3,6-anhydro-, sweetness-structure
relationship, 45:273
methyl 4,6-0-benzylidene-
(Y-D-, conformations of, 26: 115
hydrolysis of, 34:202
Aldohexopyranosyl cyanides, per-0-acetylated,
laser-Raman spectroscopy, 4 4 9 1
Aldohexoses, 49:25-26
4-acetamido-4-deoxy-, 23: 179
5-acetamido-5-deoxy-, 23: 174
composition in aqueous solution, 4 2 5 1
2,5-anhydro-, 25: 183
preparation by intramolecular
displacement of sulfonate groups,
33~125-131
1,6-anhydro derivatives, 34:23-177
in aqueous solutions
composition, 4234-35,6344
NMR spectroscopy, 42: 18
crystallography of, 25:61
cyclization by acids, 34:3437
2-deoxy-, determination of, 28: 184
deoxy-, composition in aqueous solution,
42:35
1,4:3,6-dianhydro-, formation by pyrolysis of
monosaccharides, 34:46
gel chromatography of, 25:3 1
irradiation of unprotected, 38: 147-149
ketonucleosides from, 42237-240
mass spectrometry of trimethylsilyl
derivatives of, 30:38
oligosaccharides containing
I3C-NMR data for, 42200-202, 205-207
glycosides of, 13C-NMR data for,
42:211-212
5-O-methyl, in aqueous solution, 42:16
per-0-trimethylsilylated, mass spectrometry
of, 29:48
polarography of, 29: 126
pyrolysis of reducing, anhydride formation
by, 34:45
rate constants and equilibrium constants in
polarography of, 29: 141-143
reactions of glycosidic linkages, 47: 169
ring opening, mechanism of, 29:138
synthesis of, 33:88
2,3,4,5-tetra-O-methyl, in aqueous solution,
4229, 3 1
4-thio-, 23:224
2,3,6-trideoxy-4-C-(2-hydroxyacetyl)-~-
threo-, 35:96
Aldohydroximo-lactones, 50: 1 5 6 157
Aldoketoses, nomenclature, 52:79-80
 SUBJECT INDEX
Aldol addition in branched-chain sugar
synthesis, 42:104-105
Aldolases
control enzyme in o-fructose metabolism in
liver, 34:296
and hydrogen-isotope action on sugars,
27:156
inhibition of, anhydroalditols in, 25:269
Aldol reactions, see Formose reaction
Aldonamides, preparation, 50: 15 1
Aldonic acids, 5251, 103-106
2,-amino-2-deoxy-. deamination of. in
preparation of 2,5-anhydroaldonate
derivatives, 31:70
a,P-unsaturated, synthesis of, 27:261
acid decomposition, 46:252
2-acylamino, synthesis and chemistry of,
31:6
acylated nitriles of, 4: 1 19-1 5 1
from aldoses by electro-oxidation,
29: 118-120
amino-, deamination of, 33: 1 16, I I9
2-amino-2-deoxy-, deamination of, 25:373,
33:116-119
analysis of, 28:22
high-performance liquid chromatography,
46:33-34
2,Sanhydro-
preparation of by deamination, 33: 1 I6
preparation from glycosyl cyanides,
33: 131-142
synthetic routes to, 33: I 1 4 1 15
properties of, 25:22&229
carbon- 13 nuclear magnetic resonance
spectroscopy, 41:63
characterization of, 25373
deoxy, mass spectrometry of, 29:79
2-deoxy-, and lactones, 22:206
epimerization of, 21:Il, 33:211
gas-liquid chromatography, 38:3 I8
and lactones, 28:71-78
high-performance liquid chromatography,
38:3 I9
ion-exchange chromatography, 38:3 I9
mass spectrometry of, 29:79-80,38:3 I8
trimethylsilyl derivatives, 30:3 8
paper chromatography, 38:318
polarography of, and lactones, 29: 162
preparation
and benzimidazole derivatives, 39:5
19
by catalytic oxidation of aldoses, 33:87
thin-layer chromatography, 38:3 18
trimethylsilyl derivatives, gas-liquid
chromatography of, 28: 138-140
ultraviolet-absorbances of, 46:65
Aldonolactones. 50:125-201
acylation and etheritication, 50: 132-134
2-amino-2-deoxy. deamination of, 25: 189
p-elimination. 50: 162-1 66
benzoylated, benzoic acid elimination,
50: 167-1 68
carbon-I 3 nuclear magnetic resonance
spectroscopy, 41:63
carbonyl group, chain elongation,
50:136- 148
formy laminomethylenat ion of
aldonolactones, 50: 146148
methylenation of aldonolactones,
50:143-146
reaction with organomagnesium and
organolithium reagents, 50: 138-143
Reformatsky-type reactions, 50:136-138
as chiral precursors for synthesis of natural
products, 50: 181-20 1
?i-butenolides, 50: 190-1 92
y-butenolides, 50: 182-190
nucleosides, amino acids, and other N-
containing products, 50:195-201
from o-ribono-~,4-~actone, 50: 192-195
gas-liquid chromatography of methylated,
30:29, 87
glycosylation, 50: 179-1 8 1
intramolecular reaction yielding lactams,
50:15&155
lactone group, reaction with
ammonia and amines, 50: I5 1-1 53
hydrazine and derivatives, 50: 155-157
mass spectrometry of trimethylsilyl
derivatives, 30:38
methylenation, 50: 143-146
per(trimethylsilyl) derivatives, gas-liquid
chromatography of, 28: 136-138
reaction with
alcohols, 50:149-151
aldehydes, 50: 125-127
hydrogen bromide, 50: 13&136
ketones, 50:127-130
reduction
to aldoses and alditols, 50:157-161
by borane, 50: 159-160
20 SUBJECT INDEX
Aldonolactones (continued)
isotopic labeling and substitution at
anomeric center of aldoses,
50: 16 1-162
by sodium amalgam, 50: 157
reversible inhibitors of glycosidases,
48:327-333
synthesis of deoxy sugars, 50: 17G179
use of acetals for sugar derivative synthesis,
50: 130-132
Aldono-l,4-lactones, as inhibitors of a+-
mannosidase activity, 28:420
Aldono- 1,5-1actones,48:328-330
as inhibitors of a-o-mannosidase activity,
28:4 19
as plant-growth substances, 21:416
Aldononitriles
acetates
chemical-ionization mass spectra of
partially methylated, 38:402
mass spectrometry of, 29:73
of methylated, gas-liquid chromatography
of, 30: 100
mass spectrometry of, 30:43
acetylates, gas-liquid chromatography of,
28:66, 120
gas-liquid chromatography of, 28:56,30:33
separation of methylated sugars as, 30:22
Aldopentofuranoses, 4-deoxy-4-phosphiny1,
synthesis and structures of, 42:181-183
Aldopentofuranosides
formation of, 21:109
methyl, conformations of, 21:99
oxidation of glycol groups in, 21: 132
Aldopentofuranosylpyrimidines, keto
derivatives of, 42:227-229
Aldopentopyranoses
anomeric effect and conformational
equilibria of, 26: 103-104
conformation of, 26:59
analysis of, 26:67
equilibria, 26:91-98
in solution, 26:85
electric charges on atoms of, 25: 100
proton spin-lattice relaxation rates, 45: 151
relative free energies of, 42:25-26
tetraacetates, conformation, 24:58
in chloroform solution, 26:86
Aldopentopyranosides, 2,3-anhydro-4-azido-4-
deoxy-, 23: 184
Aldopentoses, 49:25-26
4-acetamido-4-deoxy-, 23: 179
5-acetamido-5-deoxy-, 23: 166
acid decomposition, 46:252
2,5-anhydro-, dithioacetals, preparation of,
32:48
4,5-bis (acetamido)-4,5-dideoxy-, 23: 166
composition in aqueous solution, 42:34-35,
6344
gel chromatography of, 25:3 1
high-temperature transformation,
46:275-284
ketonucleosides of, 42:229-230
mass spectrometry of trimethylsilyl
derivatives, 30:38
methylated, separation of, 30:18
methyl ethers of, 7: 1-36, 10:257-272
polarography and reactions with hydrazine,
semicarbazide, and hydroxylamine,
29: 152
polarography of, 29: 127
rate constants and equilibrium constants in
polarography of, 29:141-143
ring opening, mechanism of, 29:138
4-thio-, 23:220
5-thio-, 23:206
Aldopentosylpyrimidines, keto derivatives of,
42:232
Aldopyranoses
2,-amino-2-deoxy-, deamination of, 31:77
5-acetamido-5-deoxy-, hindered rotations of
acetyl group, 23: 196-197
acetates, anomerization, 51:6, 9
5-acylamido-5-deoxy-, conformation and
anomeric structures of, 23: 188
3-amino-3-deoxy-, deamination of, 31:77
anomeric equilibrium
ring protons expected to have major effect
on proton relaxation rates, 45: 151
ring substituent effects, 47:48-50
anomerization, 51:6,8
aqueous equilibria of, 42:25-26
NMRspectroscopy,42:19
conformations of, 44:13
analysis of, 26:66
infrared spectroscopy in, 26:54
nuclear magnetic resonance
spectroscopy in, 26:57
in solution, 26534-85
D-, sweetness-structure relationship, 45:248
 SUBJECT INDEX
5-deoxy-5-phosphino-and-5-phosphinyl-,
ORTEP representation, 42: 163
structural analysis of, 42:161-176
2,6-diamino-2,3,4,6-tetradeoxy-, synthesis,
40:4748
orientation, 47:48, 5 1
sweetness, and structure, 45:239-248
I-thio-, conformation of, 26:87
5-thio-, mutarotation of, 24:49
5-thio-, oxidation of sulfur in, 23:2 12
Aldopyranosides
acidic degradation of, 28: 180
alkyl2,3-anhydro-4-deoxy-
configuration, 40:44
ring opening reactions, 40:4447
aIkyl3,4-anhydro-o~-
oxirane-ring opening, 40:57-59
synthesis, 40:56
p-, 48~327
hydrolysis by alkali, 21:137
hydrolysis of, rate constants for, 22:42
methyl
cuprammonia complexes in
conformational analysis, 26:64
infrared spectroscopy and conformational
analysis of, 26:54
methyl 2,3- and 3,4-anhydro-, conformations
of, 26: 124
methyl D-
conformation in solution, 26:84
optical rotation and conformation of,
26:61
methyl 3,4-dideoxy-3-(dimethylamino)-r)~-,
N-oxide, Cope degradation, 40:5 1
valence geometry parameters, 47:72
Aldopyranosuloses, unsaturated, synthesis,
40:6412
Aldopyranosyl fluorides, polyglycoses from,
21:460
Aldopyranosyl halides, conformations of, effect
of halogen on, 26:87
Aldose
amides, preparation of, 31:82, 84, 89
isomerization of, to ketose, with hydride
shift, 46:287
liquid chromatography methods for analysis
of, 46:33
transformations, basic conditions, 46:28 I
Aldoseptanosides, hydrolysis of, rate constants
for, 22:42
21
4ldoses
2-amino-2-deoxy-, deamination and micro
determination or detection of, 31:71
4-acetamido-4-deoxy-, 23: 178
acylated, thioglycosides preparation, 52: 18 1
acyl esters, ammonolysis of, 31539
acyloxonium derivatives, preparation and
rearrangement of, 26: 146
aldehydo-
acetates, preparation of, 32:62
reaction with diazomethane, 32:64
2-5-anhydridq mutarotation of, 25:2 I3
conformation of peracetates of o-ribo. D-
arabino-, o-xylo, o-lyxo-, and L-
galacto-, 26:72
aldonolactone reduction to, 50: 157- I61
and aldosides, cyclic acetals of, 20:2 19-
302
5-(alkylamino)-5-deoxy-,23: 139
amino-, deamination of, 25: 183- 194,
33:114116
2-amino-2-deoxy-
deamination of, 33: 114-1 16
dithioacetals, deamination of, 25: 192
synthesis of, 24:9, 1 12, 265
4-amino-4-deoxy-, 23: 147
6-amino-6-deoxy-, 23: I55
anhydrides of, formation in aqueous solution,
42:35
2,5-anhydro-, 25:182, 185
color reaction for, 25:216
dimethyl acetals, synthesis of, 33: I26
preparation by deamination, 33: I 14
preparation from glycosyl cyanides,
33:131-142
synthetic routes to, 33: 1 15
hemiacetals, 25212
reactivity of, 25:210
2-6-anhydro-, 24:211
3,6-anhydro-, by alkaline degradation,
28:202
anhydro-C-(p-methoxyphenyl), synthesis
and properties of, 27:28&292
anomeric, equilibrium proportions of, 23:3 1
in aqueous solution, 49:25-26
composition, 42:21,3437
liquid chromatography, 42:23-24
branched-and straight-chain, in formose,
29:2 13-2 15
branched-chain sugars, 48:287-288
22 SUBJECT INDEX
Aldoses (continued)
carbon-13 nuclear magnetic resonance
spectroscopy, 41:4546
chemical shifts, 41:45
catabolism by yeasts, 32:2 10, 2 1&2 17
catalytic oxidation of hemiacetal groups,
33537
chemical-ionization mass spectra of, 29:83
chiral centers, multiple sets, 52:73-74
circular dichroism fragment-spectra, 45:82
condensation polymerization of, theory of,
21:469
cyclic acetals, 34: 179-24 1
analysis of, 34:209
reactivity, 39:71-156
cyclic forms, anomeric configuration, 52:74
definition, 5 2 5 0
dehydration in acidic solutions, 28: 174-1 86
in alkaline solution, 28: 193-207
2-deoxy-, 24:262,264
dehydration in acid solution, 28:182-186
polarographic reduction of, 29: 130
synthesis of, 24: 111,39: 147
deoxy-
aldehydo-, acetates, preparation of,
32:63
dithioacetals in preparation of, 32:61
mercaptalation of, 32:23
melting points and optical rotations of,
26:279-296
deoxyhalogeno-, mercaptalation of, 32:27
3-deoxy-3-hydrazino-, 23: 161
4-deoxy-4-hydrazino-, 23: 161
5-deoxy-5-hydrazino-. 23: 159
dialkyl dithioacetals, selective esterification
of, 33:41
dithioacetals
hydrolysis of, 32:62
mass spectra of, 29:71-73
D series, 21:9, 11
esters, rearrangement in liquid hydrogen
fluoride, 26: 176
o-fructose-derived, biosynthesis, 44:287-299
gel chromatography of, 2 5 3 1
hemiacetal formation in, 42: 137
heptoses, 48:285-287
hexoses, 48:281-285
hydrogen bonding in, 2 5 5 7
mass spectra of, 2l:66
multiple configurational prefixes, 52:73
2-0-methyl-
alkaline degradation of, 28:201-202
dehydration of, 28: I8 I
oxidation of, 31:6
tritiated, mechanism of, 27:153-155
oxirane derivatives, 25: 109-179
pentoses, 48:281
peroxidation, 51:ll-12
polarography of, 29: 126
rate constants, equilibrium constants and
entropy of activation of, 29: 139
reaction with thiols, 21:19
D-ribose-derived, in bacterial
polysaccharides, biosynthesis,
44:299-300
o-sedoheptulose-derived, in bacterial
polysaccharides, biosynthesis,
44: 300-3 0 1
selective oxidation with mercuric acetate,
33: 100
separation from ketoses, 32:24
synthesis of, 24: 1 1 1
systematic names, 52:72-73
1-t, preparation of, 27:129
1-thio-, mutarotation of, 2 4 5 0
6-thio-, 23:226
trivial names and structures, 5254, 72
Aldosides
cyclic acetals, 34: 179-24 1
reactivity, 39:71-156
methyl, carbon-13 nuclear magnetic
resonance spectroscopy, 41:46-47
chemical shifts, 41:46-47
preparation of, 3 3 5 5
Aldosterone, P-D-glucopyranosiduronicacid
conjugate, isolation, 36:95
Aldosuloses
deoxy-, dehydration of, 28: 171
1-(dialkyl dithioacetals), preparation from
aldose dialkyl dithioacetals, 32:82
dithioacetals, physical constants of, and
peracetates, 32: 114-1 15
mercaptalation of, 32:24
nomenclature, 52:79-80
synthesis of, 42:261
Aldos-2-uloses, preparation, 37:87
Aldos-3-uloses, polarography of, 29: 145-147,
149
Aldos-5-uloses, 24:258
Aldosulosonic acids, dehydration of, 28: 192
 SUBJECT INDEX
Aldosylamines, N-acyl-, formation of,
31:121-124
Aldosylamino acids, 47:263
Aldosyl halides, solvolysis of, 31:4
Aldotetrofuranosides, oxidation of glycol
groups in, 21 :132
Aldotetroses, 42: 16,49:26
4-acetamido-4-deoxy-, 23: 178
composition in aqueous solution, 42:5 1
3-C-(hydroxymethyl-~-glycero-, see
Apiose
composition in solution, 42:36-37
dehydration in acidic solutions, 28: I75
high-temperature transformation,
46~275-284
polarography of, 29: 129
Aldotrioses, high-temperature transformation,
46~275-284
Aldotriouronic acids
from acidic xylans, 36:237-238
from dextrans, 30:408
synthesis of, 34: 162
Aldulosonic acids
analytical high-performance liquid
chromatography, 46:34
preparation by electrooxidation of
aldosuloses, 29: 121
Alduronate ions, complex-formation, 47:3 1
Alduronic acids, 47:3 1-35
binding strength, 47:33-34
decarboxylation, 46:306
dithioacetals, physical constants of, and their
peracetates, 32: 1 16-1 18
egg-box model, 47:33
high-temperature transformation
acidic conditions, 46:284291
basic conditions, 46:291-295
polysaccharides containing, 47: 177
quinquedentate complex, 47:3435
tridentate complexation, 47:3 1
Alectoria sarmentosa. polysaccharide, 4 1:76
Alectoria sulcata, polysacccharide, 41:76
Alfalfa
analysis by gas-liquid chromatography,
28:45
pectinesterase, see Pectinesterases
Algae
a,-a-trehalose in, 30:230,234
brown
cellulosic cell-well, 41:108
23
guanosine 5 -(D-mannopyranosyluronic
acid pyrophosphate)in, 32:9
cellulose biosynthesis, cytological studies,
41:119-122
cellulose-containing cell-wall synthesis,
41:108
floridoside, 37:3 1&3 16
gas-liquid chromatography of green, 28:47
green, in C-isotope photosynthesis study,
32:6
marine, metabolism of, 32:5
polysaccharides of, 32:45
mass spectrometry of polysaccharides from,
29:66
microfibril orientation, 41: 123-125
polysaccharides
biosynthesis in, 42:323-327,332-333
in cell-walls of, 26:300
of marine, 35:s-9
red, guanosine 5-pyrophosphate esters of L-
galactose and o-mannose in, 32:9
Algaprenol, structure, 44:346
Algin, antitumor activity of, 32:257
Alginate, 47:32
from A . esculenta stipes, circular dichroism,
45: 108-109
alternating sequences, circular dichroism,
45: 107-1 08
chelation of Ca to, circular dichroism,
45: 105- 106
circular dichroism, 45: 105
complexes, 53:411412
composition and block-structure, circular
dichroism, 45: 107
Alginic acid, 24:296,46:307, 52:353-356
acetylated, conformation of, 29:332
preparation of, 29:330
Ascophyllum nodosum, 44: 191, 194- I95
Azotobacter vinelandii, 44: 193
p-eliminative degradation of, 29:25&252
biosynthesis of, 26:406,32: 11
crystallography of, 22:479480
Fucus vesiculosus, 44: 191
gas--liquid chromatography of, 28:89
Laminaria digitata, 44: 194
methyl ester, and pectinesterase activity,
33:329
N-substituted amides, preparation of,
29:347
oligomers, liquid chromatography, 46:40
24 SUBJECT INDEX
Alginic acid (continued)
oligosaccharides, carbon- 13 nuclear
magnetic resonance spectra, 38:94
periodate oxidation of, 31:201
preparation, properties, and uses,
36~298-299
structure, 35:7-8, 10
enzymic analysis, 44: 191-195
sulfate, gelatinization of, 29:336
sulfation of, 29:335
4,5-( 1 ,2-ol-~-Glucofurano)imidazolidine-2-
thione, 1-methyl-, crystal structure
bibligraphy, 32:360
Aliphatic hydrocarbons, 53:352-353
Alkali
effect on
aldosides, 21:137
glycoproteins, 2 5 4 2 8 4 3 1
reaction with sugars, 25:341-345
Alkali-lability, dextrins, 47:293, 295
Alkali metals
alcoholates
carbohydrate complexes with, 21:260
of carbohydrates, structure of, 21:265
alkoxides, reaction with carbonydrates,
21:258
amides, reaction with carbohydrates in liquid
ammonia, 21:269
carbohydrate complexes, 21:209-271
electrophoresis, 21:23 1
preparation of, 21:216-220
solvation of, 21:226
stability of, 21:227
stoichiometry of, 21:222
structure of, 21:236
halides, halogenation of carbohydrates by,
22:178
hydroxides, Carbohydrate complexes,
21~238,243-245,246,255,256
reaction with carbohydrates in liquid
ammonia, 21:269
salts, effect on specific rotations, 21:229, 230
Alkaline degradation, of polysaccharides,
13:289-329
Alkanes, sugar substrates, 40: 109
Alkanolamines, as solvents for sugars, 27:99
Alkenes
activated, reactions with carbohydrates,
33:6648
a-nitro-, alkoxylation of, 24: 130, 132
photoaddition to 1,3-dioxolanes, 39:80,94
Alkenic precursors, for sugar syntheses,
40:+30
Alkenylations, 53: 180-1 86
Alkoxide ion, effect on ammonolysis of
carbohydrate acyl esters, 31: 100
Alkoxyalkyl radicals, fragmentation and
rearrangement by radiation, 37: 14-15
Alkoxycarbonyl function, reduction of, 29:286
Alkoxylation, of a-nitroalkenes, 24: 130, 132
Alkoxyl group
displacement of sulfonyloxy groups by,
24: 193
participation in sugar reactions, 22: 112
(A1koxymethylene)dimethyliminiumhalides,
reactions with alcohols, 28:254
Alkylating agents
preparation of, 29:2,7
specificity, cyclic acetals in study of, 34:208
Alkylation
of 1,6-anhydrohexopyranoses,34534
of nucleotides, 22:382
0-Alkylation
anomenc, 50:23-25
carbohydrate, chemical shifts, 38:20
y-Alkylbutanolactones, synthesis, 50: 183-1 84
y-Alkyl-a$-butenolides, synthesis,
50~183-184
Alkyl chlorides, preparation of, 28:246,254
AIkyl ethers, 1,4:3,6-dianhydrohexitoIs,
49: 135-145
Alkyl fluorides, preparation of, 28:258
Alkyl halides
carbonylation of, 23:61
radiation and reactions with a-hydroxyalkyl
radicals, 37:22
reduction by organotin hydrides, 28:303
4,6-Alkylidene acetal, 51:216
Alkyl iodides, preparation of, 28:281
Alkylthio group
acetolysis of, in dithioacetals, 32:69
participation in sugar reactions, 22: 159
replacement in dithioacetals by action of
mineral and Lewis acids, 32:60-70
by halogen groups, 32:70-75
Allal
4,6-O-benzylidene-
2-C-methyl-~-,24:201, 25139
2-D-, 25: 139
D-, 24:201
 SUBJECT INDEX
iodo (methyoxy1)ation of, 24:203
preparation
3-deoxy-3-C-(iodomethyl)-o-,
and methanolysis of, 28:305
3-O-methyl-~-,24:202,225
3-0-methyl-2-S-methyl-2-thio-o-,
24:225
S-benzyl-4,6-O-benzylidene-3-O-methyl-2-
thio-o-, 24:225
Allantoic antigen, gas-liquid chromatography
of chick, 28:47
AIlaric acid, 2,5-anhydro-o-, preparation of,
33:119
Allitol
1,-amino-I-deoxy-o-, deamination of,
31:60
2-acetamido-l,2-dideoxy-l-nitro-o-, 24: 133
l-amino-2,5-anhydro-l-deoxy-~-, 25209
1-amino-2,6-anhydro- 1-deoxy-D-,
deamination of, 31:52
anhydndation of, 25233
1,5-anhydro-
D-, 25237
L-, 25~237
1,4-anhydr0-6-chloro-6-deoxy-~~-,
preparation of, 33:85
3,5-anhydro-l-deoxy-l,l-di-C-(p-
methoxypheny1)-o-, preparation of,
33:125
2,5-anhydro-3,4,6-lri-O-, benzoyl-D-,
preparation and oxidation of,
33: 123-124
crystallography of, 25:60,30:450
2,3:4,5-dianhydro-o~-,synthesis, 40:26
reaction with fuming hydrochloric acid,
33:85
3,4,6-tri-O-acety1-2,5-anhydro-~-,
preparation of, 33:123
Alliumporum, cell-wall studies on, 42:300
Allofuranose
1,6-anhydro-
p-0-
acetonation of, 34: 155
preparation of, 34:153, 157
synthesis, 39: 163
2-thio-p-~-
acetalation of, 34:90-9 1
per-0- substituted, 34:77
preparation of, 34:86
properties and complexes of, 34:55
p-toluenesulfonylation of, 34:82
25
3-C-rnethyl-P-o-, acetalation of, 3 4 9 1
2-deoxy-2-fluoro-P-o-, specific rotation
of, 34:135
4-deoxy-4-iodo-2-0-p-tolylsulfonyl-~-~-,
preparation of, 34: 132
DL-, preparation of, 34:49
2,3,4-tri-O-p-tolylsulfonyl-~-o-,
preparation of, 34530
2,5-anhydro-~-,preparation of, 33: 1 I8
3-C-(cyanomethyl)-3-deoxy-1,2:5,6-di-O-
isopropylidene-a-o-, preparation of,
27:262
3-d, 1,2:5,6-di-O-isopropyIidene-a-~-,
nuclear magnetic resonance
spectroscopy of, 27: 147
3-deoxy-
3-C-(hydroxymethyl)- 1,2:5,6-di-0-
isopropylidene-a-o-, preparation of,
27:243
1,2:5,6-di-O-isopropylidene-3-C-
(methoxycarbon ylmethyl)-a-D-,
preparation of, 27:262
1,2:5,6-di-O-isopropylidene-3-C-methyl-
WD-, preparation of, 27:241
1,2:5,6-di-O-isopropylidene-3-C-
(nitromethyl)-a-o-, preparation of,
27:243
I ,2:5,6-di-O-isopropylidene-3-
thiocyanato-a-o-, 44: 143
4-fluoro-3-iodo- 1,-2:5,6-di-O-
isopropylidene-a+-, preparation,
38:242
3-hydrazino- 1,2:5,6-diisopropylidene-a-~-
, 23:162, 234
3-hydrazino- I ,2:5,6-di-O-isopropylidene-
a-D-, reaction with iodine in
chloroform, 28:279
I ,2-O-isopropylidene-3-thiocyanato-a-~-,
44: 143
3-deuterio- I ,2:5,6-di-O-isopropylidene-a-~-,
preparation of, 28:303
1,6:2,3-dianhydro-P-o-,preparation of,
34: 107, 1 13
1,6:3,4-dianhydro-P-o-.preparation of,
34:107, 111, 113
1,6:2,3- dianhydro-4-O-benzyl-P-o-, as
synthetic intermediate, 34: 121
5.6-di-O-acetyl-3-deoxy-1,243-
isopropylidene-3-thicyanaato-a-~-,
44: 143
26 SUBJECT INDEX
Allofuranose (continued)
2,3:5,6-di-O-ethyIidene-a-o-,
diastereoisomers, 34: 197
1,2:5,6-di-O-isopropylidene-
Ci-D-
acetal migration in, 34:205
carbon- 13 nuclear magnetic resonance
spectroscopy, 41:53
conformation of, 34:201-202
formation of, 34: 183
hydrolysis of, 34:203
isomerization, 39:26
methanolysis of, 34:205-206
reaction with cyanuric chloride, 28:259
reaction with diethylaminosulfur
trifluoride, 38:227
selective catalytic oxidation of, 33:91
3-O-(methyh~fony~)-o-, displacement
reactions of, 24: 15 1
3-O-p-tolylsulfonyl-o-, displacement
reactions of, 24: 15 I
2,3:5,6-di-O-isopropylidene-o-
preparation of, 34: 183
selective oxidation with silver carbonate-
on-Celite, 33:97
1,2:3,4-di-O-isopropyIidene-3-O-nitro-~i-~-,Allofuranuronic acid, 3-amino-3-deoxy- 1,2-0-
photolysis, 38: 176
methyl 2,3-0- isopropyhdene-p-D-
formation by acetal migration, 34:205
hydrolysis of, 34:204
3-O-acetyl-l,2:5,6-di-O-isopropylidene-cu-~-, Allonic acid
hydrolysis of, 34:203
3,-O-benzyl- 1,2;5,6-di-O-isopropylidene-~i-
D-, hydrolysis of, 34:202
1,2-O-ethylidene-
(Y-D-, preparation of isomers, 34: 190
D-, conformation of, 34:201
phenyk-o-, 1,6-anhydnde formation from,
34:29
phenyl-p-o-, alkaline cleavage of, 34:29
tri-O-acetyl-l,6-anhydro-p-~-, reaction with
trifluoromethanesulfonic acid, 34:88
Allofuranoside
methyl 5-amino-5,6-dideoxy-2,3-0-
isopropylidene-Pa-, deamination of,
31:56
methyl 6-deoxy- 2,3-0-isopropylidene-
p-D-,24: 171
preparation of, 29:4
synthesis, 39: 167
D-, 21:178
5-0-p-tolysulfonyl-p-D-
inversion of, 29:4-5
reactivity of, 24:155
methyl 5,6-dideoxy-5-iodo-2,3-0-
isopropylidene-P-D-, preparation of,
28:242
and iodine displacement in, 28:282
methyl 5,6-di-O-acetyl-2,3-0-
isopropyhdene-DL-, synthesis, 40: 108
methyl 2,3:5,6-di-O-isopropylidene-p-~-,
formation by acetal migration, 34:205
methyl 5 - 0 4 p-bromophenylsulfony1)-6-
deoxy-2,3-0-isopropylidene-p-~-,
solvolysis of, 24: 195
Allofuranosiduronic acid
methyl 5-0-acetyl-2,3-0-isopropylidene-p-
DL-,methyl ester, synthesis, 40:108
methyl 2,3-0-isopropylidene-, methyl ester,
synthesis, 40:75-76
methyl 2,3,5-tri-O-acetyl-P-~~-, methyl
ester, synthesis, 40: 108
Allofuranosyl bromide, 2,3:5,6-di-0-
isopropyhdene-p-o-, reaction with base,
39: I47
isopropylidene-a-o-, preparation of,
33:233
Allolactose, 2-acetamido-2-deoxy-, 24:9
Allomyces rnacrogynus, glycogen, 41:69
5-amino-
5-deoxy-o~-,23: 139
5,6-dideoxy-~~-, synthesis, 40:112
2-amino-3-deoxy-o-, deamination and
oxidation of, 33: 1 19
2,5-anhydro-3,4,6-tri-O-henzoyl-~-, 25209
Allono- 1,4-lactone, 2,3:5,6-di-O-
isopropylidene-o-, oxidation, 38:32 1
Allononitrile, 2,5-anhydro-3,4,6-tri-U-benzoyl.
p-o-, 25:209
Allopyranose
Ci-D-, 45:74
3-amino- 1,6-anhydro-3-deoxy-2-thio-P-~-,
34: 1
1,6-anhydro-
p-D-.sweetness-structure relationship,
45:271
2-deoxy-2-fluoro-p-o-, preparation,
38:246
 SUBJECT INDEX
2-deoxy-2-fluoro-3-C-methyl-~-~-
preparation, 38:246
2,4-dideoxy-2,4-difluoro-P-o- preparation,
38:246
2,3,4-tri-O-benzyl-P-o-, polymerization,
39:182, 187, 194
carba-a-or-, 48:32
carba-P-m-, 48:33
D-, orientation of hydroxyl groups for, in
4 C , ( ~conformation,
) 45:75
2-deoxy-2-fluoro-o-. preparation, 38:2 16
1,6:2,3-dianhydro-
D-,
4-O-benzyl-P-u-, 48: 163
1,6:3,4-dianhydro-o-, 25: I13
2,4-dideoxy-2,4-difluoro-o-, preparation,
38:246
hydrochloride, preparation of, 34: I36
4,6-O-isopropyIidene-o-, synthesis. 39:73
penta-0-benzoyl-P-D-, 22: 124,24: 16 I
preparation of, 34: 122
1,2.6-tri-O-acetyl-3-chloro-3-deoxy-4-O-
(2,3,4,6-tetra-O-acetyh-~-
glucopyranosy1)-P-o-, synthesis, 39:233
3,4,6-tr-O-acetyI- 1,2-O-(R)-ethyIidene-a-o-,
crystal structure, 43:236-237
Allopyranoside
a-o-allopyranosyl CX-D-, calcium chloride
pentahydrate, crystal structure
bibliography, 38:45 1 4 5 2
D-
methyl 6-azido-3,6-dideoxy-3-fluoro-P-
'IC-NMR data for, 46:171
'H-and I9F-NMR data for, 46: 1 I9
methyl 3-deoxy-3-fluoro-
P anomer, 'H- and I9F-NMR data for,
46:90
4,6-O-isopropylidene-P-, 'H-and "IF-
NMR data for, 46:90
6-O-pivaloyl-P-, 'H-and 19F-NMR data
for, 46:90
6-O-trityl-P-, 'H- and "F-NMR data
for, 46:90
methyl 3-deoxy-3-fluoro-P-
'IC-NMR data for, 46:162
6-O-pivaloyl-P-,"C-NMR data for,
46: 162
3,6-dideoxy-3,6-difluoro-p-o-
methyl
'IC-NMR data for, 46: 175
27
'H- and '"F-NMRdata for, 46: 149
methyl 2.4-di-O-bensoyl-, 'H-and I9F-
n.1n.r data for, 46: 149
phenyl
I3C-NMR data for, 46: 175
'H- and "F-NMR data for, 46: 150
p-nitrophenyl. 'H- and "IF-NMR data for,
46: 150
methyl 2, 3-anhydro-a-D-,derivatives,
25: 146
methyl 4,6-U-benzylidene-2,3-dideoxy-2,3-
epimino-a-o, 25352, 356
methyl 2-acetamido-
3-(benzylaniino)-4,6-O-benzylidene-2,3-
dideoxy-a-o-, preparation of, 29:8
2-deoxy-3-O-(methylsulfony)-~~-~-,
infrared spectrum, 23:255
4,6-O-benzylidene-2-deoxy-3-O-
(methylsulfonyl)-a-o-, infrared
spectrum, 23:255
methyl 3-acetamido-
3,6-dideoxy-a-o-, acetylation of,
33:3&3 1
2,4-di-O-acetyI-3,6-dideoxy-a-~-,
selective deacylation, 39:30
methyl 3-amino-
2-anilino-4.6-O-henzylidene-2,3-dideoxy-
a-D-, preparation of, 29:8
3-deoxy-P-~-,deamination of, 31:43
methyl 5-amino-
5,6-dideoxy-2,3-O-isopropylidene-P-~-,
23: 178
5-N-benzoyl-5-deoxy-~~-, synthesis,
40: 100-1 0 1
methyl 2,3-anhydro-
4,6-O-benzylidene-a-o-, 25: 114,
117-118, 141, 188
(Y-D-, methyl 3,6-anhydro-ol-o-
glucopyranoside from, 24:46
6-deoxy-4-0-(2,3.4-tri-O-acetyl-6-deoxy-
a-o-glucopyranosyl)-P-o-, synthesis,
39:236
4,6-O-benzylidene-a-o-
chlorination and migration of acetal
group, 39: 1 17
0x0 reaction with, 23: 107
reaction with (ch1oromethylene)-
dimethyliminium chloride, 28:278
with sodium iodide, sodium acetate and
acetic acid. 28:292
28 SUBJECT INDEX
Allopyranoside (continued)
reaction with 2-lithio-l,3-dithiane,
32:37
4-0-(2,3,4-tri-0-acetyl-6-0-tntyl-a-o-
glucopuranosyl)-6-0-tri tyl-P-o-,
synthesis, 39:236
methyl 3-chloro-3-deoxy-
p-0-
preparation of, 28:301
reaction with sulfuryl chloride, 33:75
2,4,6-tri-0-methyl-P-o-, preparation of,
28:257
methyl 2-deoxy-, 4,6-di- O-p-tolysulfonyl-a-
U-, 23~271
methyl 6-deoxy-
p-U-
catalytic oxidation of, 33:90
2,4-phenylboronate, oxidation, 3 5 5 7
preparation, 3 5 4 8
p-UL-,synthesis, 40:69
2,3-0-isopropylidene-P-~-, 24: 189
methyl 3,6-dichloro-
3,6-dideoxy-
p-0-, preparation of, 28:301
p-D-,preparation of, 33:75, 81
4-0-(4,6-dichloro-4,6-dideoxy-a-~-
galactopyranosy1)- p-D,preparation
of, 33232
4-0-(4,6-dichloro-4,6-dideoxy-a-o-
galactopyranosy1)-P-o-, triacetate,
synthesis, 39:232,234
4-0-(6-chloro-6-deoxy-a-~-
glucopyransoyl)-3,6-di-deoxy-~-u-
preparation of, 33:81
synthesis, and tetraacetate, 39:234
methyl 2,6-dichloro-2,6-dideoxy-,3.4-0-
isopropylidene-a-u-, synthesis,
39:117
methyl 5,6-dideoxy-, 5-dimethylamino-2,3-
0-isopropylidene-P-L-, 23: 178
methyl 4,6-di-U-acety1-2,3-anhydro-a-u-,
0x0 reaction with, 23:108
methyl 2,3:4,6-di-O-benzylidene-a-u-,
reaction with N-bromosuccinimide,
39:106-107
methyl 1,3:4,6-di-O-benzylidene-p-u-,
reaction with butyllithium, 39: 144
methyl 4,6-di-O-methy1-2,3-0-(0-
nitrobenzy1idene)-p-o-, irradiation,
39:89
methyl 2-0-acetyl-3,6-dichloro-3,6-dideoxy-
4-0-
(2,3-di-O-acetyl-4,6-di-chloro-4,6-
dideoxy-a-o-galactopyranosy1)- p-u-
mass spectrum, 39:260
proton nuclear magnetic resonance
spectroscopy, 39:25 1
(2,3,4-tri-0-acetyl-6-chloro-6-deoxy-a-o-
glucopyranosy1)-P-o-, proton nuclear
magnetic resonance spectroscopy,
39:252
methyl 4,6-O-benzylidene-
a-U-
conformation of, 34: 199
hydrolysis of, 34:202
3-chloro-3-deoxy-~-o-,33:74
preparation of, 28:301
reaction with sodium azide, 28:286
with sodium benzoate in
tetrahydrofuran, 28:293
CY-D-, benzoylation with benzoyl
chlondetriethylamine, 33:22
with N-benzoylimidazole, 33:42
2,3-dideoxy-2,3-C-methylene-a-~- and+
u-, preparation of, 28:306
2,3-dideoxy-2,3-epimino-a-o-, 23:278
reaction with nitrous acid, 31:66
2,3-di-deoxy-2,3-[N-
(triphenylphosphonio)epimino]-a-~-,
p-toluenesulfonate monohydrate,
crystal structure bibliography, 38:481
2-0-p-tolylsulfonyl-cy-o-, 23:258
methyl 3-0-benzyl-2-0-methyl-6-0-p-
tolylsulfonyl-CY-D-, 23:240
methyl 3-0-methyl-2,6-di-0-p-tolylsulfonyl-
a-u-, 23:240
methyl 2,3,4,6-tetra-
chloro-2,3,4,6-tetradeoxy-p-o-,
preparation of, 28:235
0-acetyl-P-oL-, synthesis, 40:7 1
methyl 3,4,6-trichloro-3,4,6-trideoxy-
a-D-,hydrogenation over Raney nickel,
28:302
p-o-, 2-(chlorosulfate), preparation of,
33:74
methyl 2,3,6-tri-U-benzoyl-4-0-(2,3,4,6-
tetra-0-henzoyl-a-o-galactopyranosy1)-
p-o-, synthesis, 39:230-23 1
a-o-AlIopyranosyl a-o-allopyranose, 47: 18
a-u-Allopyranosyl a-u-allopyranoside, 47:25
 SUBJECT INDEX 29

Allopyranosyl fluoride acetonation of, 34: 183

D-, 3-azido-4,6-0-benzylidene-3-deoxy-f3-, derivatives, table, 34:2 18-220
I3C-NMR data for, 46: 170 reaction with acetaldehyde, 34: 183-
'H- and I9F-NMR data for, 46: 1 17 184
2,3,4,6-tetra-U-acetyyl-~-,'H- and I9F-NMR biosynthesis, 44:296-298
data for, 46:82 from D-glucose derivatives, 22:117,29:8
Allopyranuronic acid, 1,2,3,4-tetra-O-acetyI-f3- gas-liquid chromatography of,28:49
DL-,methyl ester, synthesis, 40:108 halogen derivatives of, 22:2 17
Allosamine, 3-0-benzoyl- I -O-benzyh-, nonselective spin-lattice relaxation rates,
22:137 45: 148
Allose proton spin-lattice relaxation rates,
2-acetamido-2-deoxy-~-,composition in 45: 150
aqueous solution, 42:47,67 2-deoxy-
3-acetamIdo-3-deoxy-o-, diethyl; D-, synthesis of, 27:4
dithioacetal, oxidation of, 32:8S-86 2-flUOrO-D-. 22~206
2-amino-2-deoxy-~-,22: 130,24: 1 I2 3-deoxy-
3-amino- 3-C-nitrornethyl-o-, composition in
3-deoxy-o-, diethyl dithioacetal, aqueous solution, 4 2 5 7
preparation of, 32:22 3-hydrazino-o-, 23: 162
3-deoxy- 1,2:5,6-di-O-isopropylidene-o-, 6-deoxy-
22:llO D-, 21:173. 178, 180
2,Sanhydro- 2,3-di-O-methyl-o-, 21:173, 179
6-0-benzoyl-3,4-0-isopropylidene-o- 2-O-methyl-~-,21: 173
NN'-diphenylimidazolidine derivative, synthesis of, 23:269
33:135 3-0-methyl-o-. 21:173
preparation of, 33:136 3-O-methyl-~-,synthesis of, 23:269
3-O-benzyl-6-0-(methylsulfonyl)- 2,6-diamino-2,6-dideoxy-o-, 24: 147
aldehydo-D-,dimethyl acetal, 2,3:5,6-di-O-ethylidene-o-, preparation of,
preparation of, 33: 127 34: 184
3,4-&sopr~pyhdene-~~- 1,2:5,6-di-O-isopropylidene-, (Y-D-, reaction
preparation of, 33: 163 with triphenylphosphine-carbon
synthesis, 40:75 tetrachloride, 28:247
3,4,6-tri-O-benzoyI-o-, preparation of, 1,2:5,6-di-O-isopropylidene-, D-, selective
33:136 hydrolysis, 39: I5
of N,N'-diphenylimidazolidine L-
derivative, 33:123, 135 derivatives, table, 34:218-220
3,4,6-tri-O-benzyl-~-,preparation of, polarography of, 29: 127
33:136 sweetness-structure relationship,
3,6-anhydro- 45258
D-, composition in aqueous solution, liquid chromatography methods for analysis
4 2 3 I , 58-59 of, 46:33
4,5-O-isopropylidene-o-, dimethyl acetal, 3-O-methyl-~-,composition in aqueous
25:207 solution, 4 2 4 4
1,6-anhydro-o-, preparation of, 34:36-37 4,5,6-tri-O-benzoyl-
2,3-anhydro-o-, composition in aqueous 2,3-di-Sethyl-2,3-dithio-o-
solution, 4259-60 diethyl dithioacetal, crystal structure
composition bibliography, 38:482483
in aqueous solution, 42:26, 28, 3 1,63 diethyl dithioacetal, demercaptalation
in nonaqueous solvent, 42:68 of, 32:63
D-, 48:282 preparation of, 32:32
30 SUBJECT INDEX
Allose (continued)
3-S-ethyl-2-S-mehtyl-2,3-dithio-o-,
dimethyl dithioacetal, preparation of,
32:32
Alloseptanoside, methyl 2,3:4,5-di-0-
isopropylidene-a-o-, crystal structure
bibliography, 32:369
Alloside
methyl 4,6-0-benzyIidene-2,3-epimino-o-,
22: 143
methyl 5-deoxy-o-, 22: 121
methyl 3,6-dichloro-3,6- dideoxy-P-o-,
formation of, 33:75
2-U-acetyl- I ,h-anhydro-P-o~-,synthesis,
40:55
Allosucrose, 51:150
Alloxan, polarography of, 29: 170
Alluronic acid, DL,crystalline, 39:4
Allyl alcohol, DL-threonic acid synthesis, 40:6
Allyl 4-O-benzoyl-a-~-rhamnopyranoside, 2,3-
dihutylstannylene derivative, 51:214
Allyl 6-deoxy-3-C-methyI-aI-~-lyxo-
hexopyranosid-4-ulose, 51:2 15-216
Allyl 2,3-di-O-benzoy1-6-0-
(4-methoxybenzyl)-, a-o-ghcopyranoside,
51:216-217
(4-methoxyphenyl)-, (3-o-ghcopyranoside,
5 1 ~ 17-2
2 I8
Allyl glycosides
a-L-,51:2 15-2 16
substituent, protection and regeneration,
51:2 12-2 13
syntheses, 51:2 13-2 14
Allyl group, as protecting group, 39:49
Allyl 2-O-methyl-a-~-fucopyranoside,
51~213-214
Allyloxycarbonyl group, N-terminal, with tert-
butyl ester, 50:285-286
Allyl perchlorate, in anhydridization of
hexoses, 34:46
Allyl radical, formation by water elimination by
radiation, 37:13-14
Almond
emukin, a-o-mannosidase from, 28:424,438
glycopeptide N-glycosylase, 44:2 16
Aloin, 25243
Alpha-I-acid glycoprotein, hydrolysis, with
trifluoroacetic acid, 46:268
Alpha amylase, 53:409
in fruit climacteric, 42:364
in plant cell-wall punfication, 42:273,294
Altemansucrase, L. Mesenteroides alternan
synthesis, 51:148
Alternative chair conformation, 46:7
Altritol
1-amino-l -deoxy-D-, deamination of, 31:60
1,5-anhydro-~-,25328
2,5-anhydro- 1,6-di-O-(triphenylmethyl)-o~-,
monohydrate, 43:334
3,6-anhydro-~~-
catalytic oxidation of, 2 9 6 2 1
crystallography of, 2 5 6 0
D-, anhydndation of, 25:233
2,3.4,5,6-penta-O-acetyI-1-deoxy- 1-nitro+-,
21:304
tetracetyl-l,5-anhydro-3-deoxy-3-C-
(hydroxymethy1)-o-, 23:98
A1trofuranose
1,6-anhydro-P-~-,preparation of, 34: 153,
156
1,2:5,6-di-O-isopropylidene-~-,
conformation of, 34:201
Altrofuranoside
methyl P-L-, preparation of, 31:31
methyl 3,6-diamino-3,6-dideoxy-P-~-,
preparation of, 33:233
methyl 2,3-di-U-bensyl-6-0-trityl-~-, 24: 171
methyl 3-O-benzoyl-6-deoxy-2,5-di-0-
methyl-a+-, 24: 165
Altropyranose
a-D-,4 5 7 4
conformation in aqueous solution, 26534
pentaacetate, conformation of, 26:87
3-amino-
1,6-anhydro-3-deoxy-P-o-, preparation of,
34:122, 126
3-deoxy-P-o~-carba-,synthesis, 48:59,
61
2-amino-1,6-anhydro-2-deoxy-~-~-,
preparation of, 34: 122
1,6-anhydro-
2-azido-2-deoxy-P-o-, preparation of,
34: 122
3-azido-3-deoxy-P-o-, preparation of,
34: 122
p-0-
conformation of, 34:61
per-0-substituted, 34:77
3.4-phenylboronate, 34:93
preparation of, 34:89, 116
 SUBJtXT INDEX 31

D- 3-amino-2.3,6-trideoxy-2-fluoro-6-
complexes, 34:54 halogeno-a-. derivatives
formation of, 34:47 IH- and I9F-NMR data for, 46: 123
3-deoxy-3-fluoro-P-o-, preparation of, N-containing synthetic precursors, 'H-
34:133 and "F-NMR data for, 46: 123
3-deoxy-3-iodo-2-0- 3-benzamido-4-O-ben~oyl-6-bromo-, "C-
(methylthio)carbonyl-P-D-, crystal NMR data for, 46: 170
structure, 43:220-22 1 benzyl3-benzamido-2,3,6-tndeoxy-2-
3-deoxy-3-nitro-P-~-,preparation of. fluoro-a-, 'H-and "F-NMR data for,
34:105, 126 46: 123
3,4-dideoxy-3,4-epimino-P-~-, preparation benzyl2,3-dideoxy-2-tluoro-a-
and properties of, 34: 124- 125, 3-azido-6-O-(methylsu1fonyl)-. 'H- and
130-131 I9F-NMR data for. 46: 1 18
2-0-benzoyl-3-0-p-tolylsulfonyl-~-~-, 3-benzamido-, 'H- and I9F-NMR data
preparation of, 34231 for, 46: 1 18
3,4-0-isopropylidene-P-~-, as synthetic 3-benzamido-6-0-mesyl-, 'H- and "F-
intermediate, 34:90 NMR data for, 46: 1 I8
2-O-(methyhlfonyl)-P-~-,reaction with 3-benzamido-6-O-tosyl-, IH- and IYF-
potassium fluoride, 38:220-22 1 NMR data for, 46: 1 I8
3-S-benzy1-3-thio-o-, preparation of, benzyl2-fluoro-a-, 3-benzamido-2,3,6-
34: I36 tr~deoxy-,~~C-NMR data for. 46: 170
2,3,4-tri-0-benZyl-P-D-, polymerization, benzyl 2-fluoro-2,3,6-tndeoxy-6-1odo-a-
39:182, 187 3-azido-, 'H- and "F-NMR data for,
anhydro-4-~-benzyl-3-deoxy-3-fluoro-~-~-, 46: 123
2-0-acetyl-1,6-, 'H- and 19F-NMRdata 3-benzdmido-, 'H- and '"F-NMR data
for, 46: 1 14 for, 46: I23
D- methyl 3-benzamido-2,3-dideoxy-2-
orientation of hydroxyl groups for, in fluoro-a-
4 C , ( ~conformation,
) 45:75 4,6-di-O-benzoyl-, 'H- and "F-NMR
pentaacetate, conformation of, 26: I02 data for, 46: 1 I8
1,6:3,4-dianhydro-P-~-,25:113.48: 163- 4,6-0-acetyl-, 'H-and "F-NMR data
164 for, 46: I 18
preparation of, 34: 108, 1 13 4,6-0-benzyhdene-, 'H- and "F-NMR
1,2:3,4-di-O-isopropylidene-P-~-, hydrolysis data for, 46: 1 18
of, 34:204 methyl 4-O-benzoyl-6-bromo-2.3,6-
penta-0-acetyl-a-o-, crystal structure trideoxy-2-fluoro-a-
bibliography, 34:360 3-benzamido-, 'H- and I9F-NMR data
tri-0-acetyl- 1,6-anhydro-P-o-, reaction with for, 46: I23
trifluoromethanesulfonic acid. 34:87 3-(trifluoroacetamido)-, IH- and "F-
Altropyranose pentaacetate. carba- NMR data for, 46: 123
a-DL-, synthesis, 48:28-29 methyl 4,6-0-benzyliden-2,3-di-deoxy-2-
u-D-,synthesis, 48:44 fluoro-cx-
a-L-, synthesis, 48:46 3-(diallylamino)-, 'H- and "F-NMR
Altropyranoside data for, 46: 1 18
D- 3-(trifluoroacetamido)-, 'H- and I9F-
3-amino-2,3-dideoxy-2-fluoro-a-, NMRdata for, 46: 1 18
derivatives methyl 2.3.6-trideoxy-2-fluoro-a-
'H- and I9F-NMRdata for, 46: I 17- I I8 3-amlno-
N-containing, synthetic precursors, ' H- "C-NMR data for, 46: 170
and "F-NMR data for, 46: I I 7- I I8 'H- and "F-NMR data for, 46:123
32 SUBJECT INDEX
Altropyranoside (continued)
3-benzamido-4-0-benzoyl-
I3C-NMR data for, 46: 171
'H- and I9F-NMRdata for, 46: 124
3-(trifluoroacetamido)-
I3C-NMR data for, 46: 170
IH- and 19F-NMRdata for, 46: 124
4,6-0-benzylidene-2,3-dideoxy-2-fluoro-
a-
benzyl 3-azido-, 'H- and 19F-NMR data
for, 46:117
benzyl3-benzamido-, 46: 118
methyl 3-amino-, IH- and I9F-NMR
data for, 46: 117
2,3-dideoxy-2-fluoro-3-tosylamino-a-~-,
48: 169
methyl
3-acetamido-2-azido-2,3-dideoxy-,4 6-di-
~-(methylsulfonyl)-a-D-,
displacement reactions of, 24: 162
3-acetamido-2,4-di-O-acetyl-3,6-dideoxy-
a-~- selective
, deacylation, 39:29
3,4-anhydro-a-u-, 25: 145
3,4-anhydro-6-0-trityl-a-u-, cleavage of
oxirane ring in, 25: 125
methyl-a-D-, 23: 107
methyl a-u-
crystal structure bibliography, 30:45 1,
34:352
2,3-di-O-benzy1-4,6-dideoxy-4-
thiocyanato-, 44: 143
4,6-0-benzylidene-2,3-dideoxy-3-
(dimethylamino)-2-thiocyanato-,
44: 143
synthesis, 44:134
4,6-0-benzylidne-3-deoxy-3-thiocyanato-,
44: 143
reaction with sulfuryl chloride, 33:75
methyl a-DL-,synthesis, 40:70
methyl 2-amino-
4, 6-0-benzylidene-2-deoxy-a-D-,
deamination of, 25: 188
2-deoxy-P-o-, deamination of, 31:40
4,6-0-benzylidene-2-deoxy-a-~-,
deamination of, 31:41, 57
methyl 3-amino-, 3-deoxy-P-o-, 22:202
deamination of, 31:40
methyl 5-amino-, 5-N-benzoyl-5-deoxy-~~-,
synthesis, 40:lOl
methyl 2-azido-3,4-0-benzylidene-
6-chloro-2,6-dideoxy-a-~-
preparation of, mechanism of, 28:252
reaction with N-bromosuccinimide,
26: 166,39: 102
2-deoxy-a-o-, reaction with
(chloromethylene)dimethyliminium
chloride, 28:252
2-deoxy-3-O-(methylsulfonyl)-cr-~-,
displacement reactions of, 24: 163
methyl 3-benzamido-4,-6-di-O-benzoyl-2,3-
dideoxy-2-fluoro-a-u-, preparation,
38:240
methyl u-, conformation in solution, 26:84
methyl 2-deoxy-2-fluoro-o-, synthesis,
38:24 1
methyl 2,6-dichloro-2,6-dideoxy-3,4-0-
isopropylidene-a-o-, crystal structure
bibliography, 31:350
methyl 2,6-dideoxy-2,6-imino-N-
(phenysulfony1)-a-o, preparation of,
28:290
methyl 4,6-di-O-acetyl-a-o~-,synthesis,
40:70-71
methyl 2-0-acetyl-
3,4-anhydro-6-O-trityl-a-~-,cleavage of
oxirane ring in, 25: 125
4-0-benzoyl-3,6-dibromo-3,6-dideoxy-a-
D, preparation of, 28:268
4,6-0-benzylidene-3-bromo-3-deoxy-a-~,
preparation of, and reaction with N-
bromosuccinimide, 28:268
methyl 2-0-benzoyl-
3-bromo-3,6-dideoxy-a-~-,synthesis,
39: 106
4,6-0-benzylidene-3-bromo-3-deoxy-u-,
synthesis, 39: 112
methyl 4-0-benzoyl-
6-bromo-2,6-dideoxy-2-
(phenysu1fonamido)-a+-, reaction
with methanolic sodium methoxide,
28:290
6-bromo-2,6-dideoxy-2-(p-
toluenesulfonarnido)-3-0-p-
t ~ l y l ~ ~ l f ~ n y23:267
l-~~-~-,
2-S-benzoyl-6-bromo-6-deoxy-2-thio-a-~,
reaction with methanolic sodium
methoxide, 28:290
2,3,6-tribromo-2,3,6-trideoxy-a-~,
preparation of, 28:268
methyl 3,4-0-benzylidene-
 SUBJECT INDEX
a-o-, 23: 107
benzoylation with benzoyl
chloride-triethylamine, 33:22
with benzoyl cyanide, 33:45
with N-benzoylimidazole, 33:42
conformation of, 26: I 15.34: I0 9
2,3-dinitrate, denitration of, 23:266
hydrolysis of, 34:202
selective acylation of, 33:21
2-cbloro-2-deoxy-3-O-formyl-a-t~,
preparation of, 28:278
2-deoxy-2-C-methyl-a-~,24:202
2-deoxy-2-halogen-a-o, acetal migrations
in, 28:292
2-deoxy-2-iodo-a-o-, 24:20 I , 203
isomerization, 39:27
preparation of, 28:292
reaction with
(chloromethylene)dimethyliniinium
chloride, 28:253
2-deoxy 2-(phenylsulfonamido)- (Y-D,
reaction with N-bromosuccinimide,
28:290
2,3-dibrorno-2,3-dideoxy-a-o-, 24:235
preparation of, and reaction with N-
bromosuccinimide, 28:267
reaction with potassium tert-butoxide,
28:293
2,6-dichloro-2,6-dideoxy-cu-o-
hydrogenation of, 28:303
preparation of, 28:278
reaction with N-bromosuccinimide,
26:166,39:102
2-O-(methykulfonyl)-a-~-3-nitrate,
infrared spectrum, 23:256
2-O-(p-bromophenylsulfonyl)-3-cyano-3-
deoxy-a-o-
conformation of, 26: 1 15
crystal structure bibliography, 30:455
2-O-p-tolylsulfonyl-a-~-, infrared
spectrum, 23:256
methyl 3,4-O-isopropylidene-, a-D-,
formation by acetal migration,
34:205
methyl 4,6-O-isopropylidene-a-1-
acetal migration in, 34:205
isomerization, 39:27
preparation of. 34: 192
methyl 3,4-O-(R) benzylidene-
2-chloro-2-deoxy-6-O-p-tolylsulfonyl-a-~,
33
reduction with lithium aluminum
hydride, 28:292
2-deoxy-2-halogeno-au-o-,preparation of,
28:292
2-deox y-2-iodo-6-0-p-tolysulfonyl-a-D.
reaction with lithium aluminum
hydride, 28:292
AI tropyranosides
3-azido-2-fluoro-a-~-,48: 145
3-benzamido-2,3-dideoxy-2-fluoro-a-~-,
48: 166
Altropyranosyl chloride
4-O-~-n-galactopyranosyl-aloo, 26: 194
4-0-P-o-glucopyranosyl-a-i1-, heptaacetate.
26: 195
tetra-0-acetyl-a-o-, acetoxonium salts,
26:161
Altropyranosyl fluorides
D-, 2,3,4,6-tetra-O-acetyyl-
a anomer,13C-NMR data for, 46: 160
p anomer,13C-NMR data for, 46: 160
2-deoxy-2-fluoro-~-,preparation, 38:2 15
3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-~-o-,
48: I 7 5
Altrose
3-acetamido-3-deoxy-o-. diethyl dithioacetal,
oxidation of, 3253-86
acyloxonium rearrangement of, 26: 159
2-amino-2-deoxy-~-,24: I 12
3,4-anhydro-n-, composition in aqueous
solution, 42:60
1,6-anhydro-2-O-benzoyl-P-~
p-toluenesulfonylation of, 33:22
sulfonylation of, 23:252
I ,6-anhydro-2-O-benzoyl-3-O-p-
tolylsulfonyl-p-o-, 23:252
3,6-bis( acetamido)-3,6-dideoxy-11-,diethyl
dithioacetal, hydrogenolysis by Raney
nickel. 32:77
composition
in aqueous solution, 42:26, 63
in nonqueous solvents, 42:68
D-
gas-liquid chromatography of,28:49
halogen derivatives of, 22:218
nonselective spin-lattice relaxation rates,
45:148
proton spin-lattice relaxation rates, 45: 150
4-S-acetyl-6-deoxy-4-thio-, synthesis,
44: 132
34 SUBJECT INDEX
Altrose (continued)
6-deox y-
D-, 21:173, 176
2,5-di-U-methyl-~-,24: 165
L-, biosynthesis, 44:29&298
3-O-methyl-~-,21:173
4-thio-o-, composition in aqueous
solution, 42:53
derivatives, Table, 34:221
2,4-diamino-2,4,6-trideoxy-~-, 23: 155
2,3-di-O-rnethyl-o-, composition
in aqueous solution, 42:4344
in nonqueous solvent, 42:61
DL-,synthesis, 40:93
group of compounds related to, 1:37-76
L-, 48~282
sweetness-structure relationship, 45:258
liquid chromatography, 42:23-24
methods for analysis of, 46:33
Altroside
2-deoxy-2-fluoro-o-, 48: 166
methyl 2-bromo-2-deoxy-a-~-,hydrolysis
rate of, 22:208
methyl 2-chlor0-2-deoxy-a-o-, hydrolysis
rate of, 22:208
methyl D-, halogen derivatives of, 22:2 19
Altnuonic acid, 2-amino-2-deoxy-~-,
biosynthesis, 44:296298
Aluminate complexes, 53:325-326
Aluminum chloride-phosphorus pentachloride,
rearrangements of saccharides in,
26: I 9 6 195
Alveolar glycoprotein glycopeptides, structure,
37:181
Amadori compounds, 22:266,269,272,
299-302
2,3-enolization in weak acids, 46:320
formation of, 46:307-308
reaction with dicarbonyl compounds,
22:288
Amadori rearrangement, 10:169-205,22:267,
269,23:122,211,220,24:6,448,25:335,
337-338,46:311
formation of 3-deoxyhexo-2-dose by way
of, 46:3 11
of glycosylamines and their uronic acids,
36:12&121
mechanism of, 46:308-309
Ambutyrosin, see Butirosin
Amicetoside, methyl, 21:195
Ames test
caramel, 47:267
melanoidins, 47:269
Amicetin, 21:195
structure of, 42:229
Amicetose, 21:195, 197,50:158-159
DL-, synthesis, 40:24
L-, synthesis, 40: 129
Amicetoside
methyl a-,preparation of, 28:283
methyl a-L-,synthesis, 40: 117
methyl p-D-, preparation of, 28:294
Amidases, splitting of N-(~-aspart-4-oyl)
glycosylamine amide linkages, 43: 179
Amidation, in neoglycoprotein preparation,
37:23&238
Amide derivatives, circular dichroism,
4594-102
Amides
bacterial polysaccharides, 48:3 11-3 13
carbohydrate, reaction with nitrous acid,
31:6&70
nomenclature, 52: 104-105
protection as, 46: 194
as solvents for sugars, 27: 1 12
Amidination, in neoglycoprotein preparation,
37:24&248
Aminal, formation of, 42: 133
Amination
in neoglycoprotein preparation, 37:242-245
of polysaccharides, 29:342
Amines, 53:313-374
aliphatic, as solvents for sugars, 27: 112
catalytic effect, on formation of products
from Maillard reaction, 46:3 18-321
deamination of, 31: 16
lactone group reaction with, 50: 151-153
in polarographic determination of
carbohydrates, 29: 150
reaction with nitro sugars, 24:136
p-Aminoacetophenone, effect on f.a.b.
sensitivity, 45:32
Amino acids
a-,dextrinization in presence of, 47:315
of a-amylases, 23:308
of asparagus-pea lectin, 35:284
of p-amylases, 23:332
of Bauhinia purpurea alba lectin, 35305
bitterness, and hydrophobicity of side chains,
4 5 3 19
 SUBJECT INDEX
carbohydrate linkages, structural analysis.
wet methods traditionally used, 43:6-7
carbon atoms, chemical shifts effect on
anomeric configuration of attached,
monosaccharide on, 43:34
pH-dependence, 43:26
of castor-bean lectin, 35:272
catalytic
effect on formation of products from
Maillard reaction, 46:3 18-32 1
sequence homologies around, 48:38 1
C-glycosyl a-,synthesis of, 33: 158
of concanavalin A, 35: 162
D-
centers of electron-rich density, 45:232
superpositioned over same receptor site,
45:236
sweetness, 45:214,231
taste of, 45:207-208
zwitterions, favored conformations,
45:232
derivatives with uridine 5-pyrophosphate N-
acetylmuramic acid esters, 28:328
of discoidin, 35:309
in o-mannanases, 32:307
of eel-serum lectin, 35:28 1
enzymic reactions and, 23:296
ester-and amide-linked, 48:3 10-3 1 I
in glycoproteins, 25:417,33:7
of horseshoe-crab lectin, 35:306
identification of, in glycoproteins, 25:429
L-
superpositioned over same receptor site,
45:236
sweetness, 45:2 14, 23 1
taste of, 45:207-208
in L-arabinanases, 32:288
of lectins, 35:335,337
oflentil lectin, 35:191-193
of lima-bean lectin, 35:247
in mucus glycoproteins, 47:349
N-(benzyloxycarbony1)-, reaction with D-
glucose, 33:45
optically active, as precursors for sugars.
40: 117-1 19
of Osage-orange lectin, 35:267
of pea lectins, 35: 197
of peanut lectin, 35:258
PG-I
composition, 49:248
35
NH,-terminal sequences, 49:253
PG-I1
composition, 49:244247
NH,-terminal sequences, 49:252
of phosphorylase, 23:345
of potato lectin, 35:2 11
in protein components of glycoenzymes,
27:3 15-3 18
reactions with sugars, 47:223
of red kidney-bean lectin, 35:292-293
of ricin, 35:27 1
sequence analysis, proteoglycans,
49:254255
sequences
of concanavalin A, 35: 152
of glycopeptides in glycoenzymes,
27:319-323,333
in glycoproteins, 25:425425
of snail lectin, 35:240
of soybean lectin, 35:234
of sun-hemp lectin, 35:306
sweet and bitter, fixation in rectangular
coordinates, 45:3 1 4 3 17
synthesis from aldonolactones, 50: 195-
20 1
trimethylsilylation of, 28:28
of Ulex europeus lectin, 35:289
of wheat-germ lectin, 35:2 15
Aminoacridine, 5-iodocytidylyl-(3,5)-
guanosine:9-, 24 hydrate, crystal structure
bibliography, 38:527
Amino alcohols, deamination of radicals by
radiation, 37: 11-12
2-Aminobenzoic acid, cyclodextrin inclusion
complexes with, 46:222-224
4-Aminobenzoic acid, cyclodextrin inclusion
complexes with, 46:222-224
p-Aminobenzoic hydrazide, for enhancing
detectability of carbohydrates, 46:67
Amino carba-hexopyranose, physical
properties, 48:60
Amino carba-sugars, synthesis, 48:66-67
Amino compounds
carbohydrate transformation in presence of,
46~307-323
paper electrophoresis, 36:6
Amino-containing sugars, Onoderas work on,
46:3
Aminocyclitols, glycoside hydrolase inhibition,
48:347-348
36 SUBJECT INDEX
Aminodeoxyhexofuranoses, fluorinated, H-
and I9F-NMR data for, 46: 127-128
Aminodeoxyhexofuranosides, fluorinated, 'H-
and IYF-NMRdata for, 46: 127-128
Aminodeoxyhexopyranosyl fluorides
'H- and I9F-NMR data for, 46: 117
N-containing, synthetic precursors, 'H-and
I9F-NMR data for, 46:117
Aminodeoxypentopyranosides,fluorinated, IH-
and IYF-NMRdata for, 46:128
Aminodideoxy-6-fluoro sugars, 'H- and 19F-
NMR data for, 46: 120-122
Aminodideoxyhexoses, 48:290-292
Aminodideoxy-3(0r 4)-flUOrO sugars
'H- and IYF-NMRdata for, 46: 118
N-containing synthetic precursors, 'H- and
"F-NMR data for, 46: 119
(Aminoethoxy)vinylglycine (AVG), effect on
fruit ripening, 42:363-364
N-(2-aminoethyl)aldonamides,50: 152
Aminoethyl groups, nitrosation of hydroxyethyl
groups from, 31:71
Aminoglycoside antibiotics, resistance
mechanism, 48: I 1
Amino groups
in cyclic monosaccharide formation, 23: 1 17
determination of, in polysaccharides, 29:343
oligosaccharides containing, I3C-NMR data
for, 42:209-2 10
participation in sugar reactions, 22: 15 1
protecting groups for, 36:150-152
Aminohexosidases, in carbohydrate
degradations, 38:413
Amino ketonucleosides, synthesis of, 42:257
Aminolactones, intramolecular reaction, lactam
preparation, 50: 154-155
Aminolysis
of o-glucofuranosidurono-6,3-lactones and
o-g~ucofuranurono-6,3-~actones, 33:2 1 3
of sucrose, 27:99
3-Aminonitrobenzene, derivatives, sweetness,
45:226-227
Amino nucleosides, synthesis of, 42:245,257
Amino sugars, 21:17,24:9,47:19, 48:290-292,
see also Sugars
amino groups of, protection of, 46: 192-194
analysis, structural, 38:396
biological activity of, 42:135-137
composition in aqueous solution, 42:42,
46-52,67
definition, 52:5 I
2-deoxy, hydrogenolysis of acetals,
39: I27
difluorinated, 'H- and IYF-NMRdata for,
46:157
I9F labelling, 38:251
fluorinated, L3C-n.m.rdata for, 46: 170
fluorinated unsaturated, 'H- and IyF-NMR
data for, 46:126-127
mass spectra of, 21:67, 93
Maurice Stacey's work, 5 2 1 5
N-acyl substituents, 47: 179
N-containing, synthetic precursors, I3C-
NMR data for, 46: 170
nomenclature, 52:84-86
nucleosides of, 42:230
polysaccharide derivatives, 52: 166
preparation of, 24: 109
radiolysis, 37:49-5 1
reaction with
P-dicarbonyl compounds, 45: 13-14
isothiocyanic acid derivatives, 45: 14-1 5
methanol, 47:202
(1+4)-linked, circular dichroism, 45: I 17
in solution, 49:29-30,34
synthesis of, 29:3
Amino-2,3.6-trideoxy-2-fluorohexopyranoses,
'H- and I9F-NMR data for, 46: 125-126
Amino-2,3,6-trideoxy-2-
fluorohexopyranosides, 'H- and I9F-NMR
data for, 46: 125-126
Amino-2,3,6-trideoxy-2-fluorohexopyranosyl
halides, 'H- and I'F-NMR data for,
46: 125-126
Amipurimycin
natural occurrence of, 42:77
structure of, 42:77
Amitrole, as plant-growth substance, 21:399
Ammonia
lactone group reaction with, 50: 151-153
liquid
metallation of sugars in, 27:92
as solvent for carbohydrates, 27:91
reactions of carbohydrates with alkali
metals, alkali metal amides, and
alkaline-earth metals, 21 :269
methylation of glucans in liquid, 30: 12
reactions with
a,P-unsaturated acids, 27:262-264
acyl esters of carbohydrates, 31:81-134
 SUBJECT INDEX
of carbonyl compounds with aqueous,
25~324-327,344
of sugars with aqueous, 2 5 3 I 1-349
nitroalkenes and nitroalditols, 24: 133, 135
Ammoniacal copper(I1) solution, in
conformational analysis, 26:64, 84
Ammonium cerium(1V) nitrate, reaction with
dithioacetals, 32:61
Ammonium hydrogencarbonate, reactions with
1-hydroxy-o-glycosamines, 50:282-283
Ammonium salts, 53:322-326
Ammonium thiocyanate, addition to matrix for
f.a.b.-mass spectrometry, 4 9 2 8
Ammonolysis
of acetylated nitriles, mechanism of, 31: 1 10
of carbohydrate acyl esters, 31:81-134
of o-glucofuranosidurono-6,3-lactonesand
o-glucof~~anurono-6,3-lactones.
33:2 13-214
and heterocyclic formations, 31:89, 124-1 25
mechanism of, 31:llO-125
selective deacylation, 39:30-33
solvent effect on, 31:99-102
of sucrose in liquid ammonia, 27:93
Amobarhital, cyclodextrin inclusion complcxes
with, 46:223-224
Amosamine, 23: 154, 24: 159
5-AMP, see Adenosine, 5-monophosphate
Amphomycin, inhibition of protein
glycosylation, 40:342-343
Amygdalin, 21:22
catabolism by yeasts, 32:201
structure, 39:359
Amylan, 21:446
P-Amylase in hydrolysis of starch, 36:12
Amylases, 50: 1 I , 16
alpha-, 25436, 44:252, 254, 257
activation energies of, 23:3 I2
amino acids of, 23:308 Amylodextrin
bacterial and fungal, 23:322
carbohydrate content of, 27:306-307
carbohydrate-peptide linkage in, 25:442
in Characterization of amylaceous
polysaccharides, 30:328,33 I Amyloglucosidase, 50: 16-1 7
chromatography and sedimentation of, Amyloids, 24:373, 44:151
27:311, 313
higher-plant, 23:3 15
in hydrolysis of starch, 36:3 1 Amylolysis
kinetics of action of, 23:289, 324
mammalian, 23:3 19
37
mechanism of degradation by, 23:328
Michaelis constants of, 23:326
preparation, properties, and specificity of,
30:285-287
properties of, 23:309,31 I
proteinxarbohydrate linkages in. 27:323
purification
by affinity chromatography, 39:443
by chromatography, 23:283
sources of, 23:305
specificity and action pattern of, 23:3 13
struchire of. 23:307
action pattern of, 30:272
beta-, 44:255
active sites of, 23:334
amino acid composition of, 23:33 1-332
and glucosidase-transferase in
characterization of amylaceous
polysaccharides, 30:329, 33 1
kinetics of action of, 23:289,341
mechanism of action of, 23:342
preparation, activity, and properties of.
30:285,287-291
properties of. 23:333,336
and pullulanase, in characterization of
amylaceous polysaccharides, 30:328,
33 I
purification by chromatography, 23:283
sources of, 23:329
specificity and action pattern of, 23:337
structure of, 23:331
certain alpha, 5:229-268
determination of, 29:401
hngal yeast, carbohydrate content of,
27:307
macerans, glycoside synthesis, 39:429
Pseudoinonus stutzeri, preparation and
activity of, 30:301
a-, constitution of, 2 5 6
Nageli, crystal structure bibliography,
33:393
selective esterification of, 33:38
methylation of, 30: 12
xyloglucan and, 42:287
P-
of glycogen, 3 0 5
38 SUBJECT INDEX
Amylolysis (continued)
mechanism of, of amylopectin and
glycogen, 30:289-290
a-, cofactors in, 30:286
Amylolytic index, dextrins, 47:320-32 1
Amylomaltase, action on maltose, 25:33
Amylopectin, 46:295
alpha-amylase action on, 23:317, 324
alumina and, 53:325
beta-amylase action on, 23:340
binding capacity, 53:280
biosynthesis, transglycosylation reaction,
44:256
carbon-13 nuclear magnetic resonance
spectra of P-limit dextrins, 38:37,
3940
circular dichroism, 4 9 8 9
composition, 53:296
conformation and tautomers, vibrational
spectra used to analyze, 44:26
coumarin with, 53:373
crystallography of, 22:478
decoiling, 53:349
degradation
by a-amylase, 30:286-287
by P-amylase, 30:288
products, 47:310
determination of, in starch, 32:6
fine structure of, 30309-326
gel chromatography of, 25:42
high-temperature transformation of,
46:296-297
-iodine interaction, 53:277-278
monoglycerides and, 53:396-399
0-vinyl-, structure of, 29:326
phosphorylase action on, 23:352,355
photodegradation, 51:293-295
potato, structure, enzymic analysis, 44:253
properties, after high-energy electron
irradiation, 51:265-266
protozoal, 35: 11
pyridine with, 53:373-374
pyrolysis of, 22:489
rate of dextrinization, 47:286,288
reaction with concanavalin A, 35:169-171
relative activities of hydroxyl groups in,
33:63
solvents for, 27: 108
in starch, 53:268-269
Staudinger index and viscosity, 51:257
structure, 36:16-17,53:348
enzymic analysis, 44:253
properties relationships, vibrational
spectroscopic study, 44538
synthesis of, 25:8,34:6
thermal stability of, 22:498
volatile products From pyrolysis of, 22:505
Amylopectin phosphate, preparation of,
29:334
Amylopectin sulfate, preparation of, 29:335
Amylopection acetals, preparation of, 29:339
Amylo-( 1-+6)-glucosidase, 23:362
and phosphorylase, mechanism of action of,
30:312, 328,331
Amylose, 25:8,46:295,51:104,52:340-349
A-, crystal structure bibliography, 40:383
alcohol effects, 53:360-361,363
alkaline hydrothermolysis of, 46:296
alumina and, 53:325
amination of, 29:342
amylolysis of, 23:3 16
6-azido-6-deoxy-, derivatives, preparation of,
28:286
B-, crystal structure bibliography, 33:393,
40~383-384
backbone motion, 51:121
bacterial and fungal a-amylase action on,
23:322
P-amylase action on, 23:338
binding capacity, 53:279-280
carbanilated derivatives, circular dichroism,
45:120-121
carbon- I3
nuclear magnetic resonance spectra,
38:37-39
signals, 38:23
carboxyamides, 53:374
carboxymethyl ethers, preparation of,
29:319
6-chloro-6-deoxy-
preparation of, 28:256,29:348,33:82
reaction with sodium aide, 28:286
circular dichroism, 4585-89
composition, 53:296
conformation and tautomers, vibrational
spectra used to analyze, 44:26
coumarin with, 53:373
crystallography of, 22:468
crystal structure bibliography, 36:3 19
decoiling, 53:349
 SUBJECT INDEX
degradation by a-amylase, 30:286-287
by P-amylase, 30:289
of oxidized, by glucoarnylase, 30:266
6-deoxy-, 21: 174
6-iodo-, preparation of, 29:348
derivatives, 52:347-349
determination of, in starch, 32:6
dextrinization of maize, 22:493
dextrins from, structure of, 22:493
diffraction patterns, 53:359
enzymic degradation of, 23:299, 302
experimental multifield relaxation data,
51:120-121
fatty acids with, 53:371-372
tine structure of, 30:305-309
fractionation, 53:297
fungal, 41:68
as fungal component, 23:369
y-ray irradiation, 51:293-295
hydrogen bonding, Raman and infrared
spectral study of, 44:29
hydrolysis, 53:282-283
hydroxymethyl group conformation, 51: I23
iodine complex, laser-Raman spectroscopy,
44534
-iodine interaction, 53:276-277
KOH-amylose complex, 52:346-347
laser-Raman spectroscopy, 44: 82
maltodextrins from, 23:3 18
mammalian a-amylase action on, 23:319
mass of water-soluble products as function
of, 51:268
6-O-acetylation, 39:63
0-(carboxymethy1)-, structure of, 29:32 1
0-o-glucopyranosyl-, carbon- 13 nuclear
magnetic resonance spectra, 38: 104
0-(2-hydroxyethyl)-, degree of substitution
in, 29:317
6-0-trityl-, oxidation with dimethyl
sulfoxide-acetic anhydride, 33:93
0-vinyl-, preparation and structure of,
29:326
periodate oxidation of, 31:201
phosphorylase action on, 23:352-353
photodegradation, 51:293-295
properties, after high-energy electron
irradiation, 51:265-266
pyridine with, 53:373
pyrolysis of, 22:489, 500,47:340
rate of dextrinization, 47:286, 288
39
reaction with methanesulfonyl chloride in
N,N-dimethylformamide, 33:82
relative activities of hydroxyl groups in,
33:63
SDS with, 53:375-376
selective esterification of, 33:38
selective tritylation of, 3 3 5 2
separation, 53:297
solvents for, 27: 108
in starch, 53:268-269,271
Staudinger index and viscosity, 51:257
structure, 36: 1&17,53:346
of B, 22:470
of V, 22:473
enzymic analysis, 44:252-256
properties relationships, vibrational
spectroscopic study, 44:88
and proton magnetic resonance
spectroscopy of, 27:39
sulfonylation of, 23:242
synthesis of, 23:304,34:6
thermal stability of, 22:498
triacetate, X-ray diffraction diagram of,
22:437
triesters, gas-liquid chromatography of,
28:54
trimethylsilylation of, 28:3 1
2,3,6-tri-O-acetyI-, proton magnetic
resonance spectroscopy of, 27:39
tri-0-ethyl-
chloroform complex, crystal structure
bibliography, 40:385
crystal structure bibliography, 40:386
dichloromethane complex, crystal
structure bibliography, 40:385
nitromethane complex, crystal structure
bibliography, 40:385
tri-@methyl-, crystal structure bibliography,
36:319
V-
anhydrous, crystal structure bibliography,
33:39 I
crystal structure bibliography, 33:390
crystal structure bibliography, 35:378
vibrational spectra, isotopic substitution
studies, 44:55
volatile products from pyrolysis of, 22:505
A-Amylose, 52:340-342,407408
B-Amylose, 52:342-344,409
V-Amylose, 52:345-346,410
40 SUBJECT INDEX
Amylose acetals, preparation of, 29:339
Amylose acetate
enzymic hydrolysis of, 29:332
and hexanoate, physicochemical properties
and conformation, 29:33 1
Amylose benzoate, physicochemical properties
of, 29:333
Amylose-1 -butanol complex
circular dichroism, 4 5 8 7
crystal structure bibliography, 33:391,
40:384
Amylose butyrate, hexanoate, pentanoate, and
propionate, preparation of, 29:330
Amylose carbanilate, physicochemical
properties, 29:344
Amylose-dimethyl sulfoxide complex, crystal
structure bibliography, 33:39 1-393
Amylose-ethylenediamine complex, crystal
structure bibliography, 33:392
Amylose-halogenated hydrocarbon complex,
crystal structure bibliography, 33:391
Amylose Ih, 0-acetyl-, crystal structure
bibliography, 33:394
Amylose-1 -naphthol complex, V-, crystal
structure bibliography, 33:392
Amylose phosphate, preparation of, 29:334
Amylose-potassium bromide complex, crystal
structure bibliography, 33:392
Amylose sulfate
preparation of, 29:335
structure of, 29:336
Amylose triacetate, circular dichroism,
45:121-122
Amylose xanthate, circular dichroism, 45: 122
Amylostatin (XG), synthesis, 48232
Anabaenaflosuyuue, extracellular
polysaccharide, hydrolysis of, 46:253, 260
Anabolic sphingolipidosis-type GM3,
ganglioside deficiency disease, 40:266
Anaerobic fermentation, by yeasts, 32: 144
Analgesics, N-(4-ethoxyphenyl)-~-gulonamide, I ,4-Anhydroaldopyranoses
and N-(4-methoxyphenyl)-~-gulonamide,
38:300
Analysis, see specific substances; spect$c types 1,6-Anhydroaldopyranoses
Anesthetics, effect on ganglioside degradation,
40:273
on protein glycosylation, 40:345
Angelica lactone
as chiral starting compound, 50: 184
reaction with isoprene, 50: 188-1 89
Angelicin, 8-[2-(p-~-
glucopyranosyloxy)isopropyl]-8,9-
dihydro-9-hydroxy-, monohydrate, crystal
structure bibliography, 38:473475
Angiosperms, cell-wall
composition of, 26:300, 302
formation in, 42:268-269
Anguilla anguilla serum lectin, see Eel, serum
lectin
Angustmycin A, 21:174,24:250,252
structure of, 29:295
Angustose, 21:174-176
Anhydrides
1,6-, ofaldohexoses, 34:23-177
2,5-, of sugars, and related compounds,
25: 18 1-228
acetals, intramolecular, 52: 118-120
of alditols, 25:229-283
of aldoses, 25: 109-1 79
difructose, 2253-277
ofhexitols, 5:191-228
of pentitols, 5191-228
Anhydridization
internal of 1-deoxy- 1-nitroalditols, 24: 1 19
during starch pyrolysis, 22:487
Anhydroalditols, 1 5 , sweetness-structure
relationship, 45:261
1,5-AnhydroaIdofuranoses,synthesis,
39: 164-169
I ,6-Anhydroaldofuranoses
polymerization, 39: 179-1 97
synthesis, 39:161-164
1,6-Anhydroaldopyrananu,characterizations
and applications, 39: 197-204
1,2-Anhydroaldopyranoses
polymerization, 39:207-209
synthesis, 39:171-172
1,3-Anhydroaldopyranoses
polymerization, 39:207
synthesis, 39:169-171
polymerization, 39:204-206
synthesis, 39:164-169
polymerization, 39: 179-197
synthesis, 39:161-164
Anhydroaldoses
copolymerization, mechanism, 39: 176-1 79
nomcnclaturc, 39: 160
polymerization, mechanism, 39: 173-176
 SUBJECT INDEX
synthesis, 39:160-173
1,4-.4nhydroerythritol sodium perchlorate.
crystal structure, 43:335-336
2,5-.4nhydrogalactitol, 47: 16
Anhydroglucose, liquid chromatography.
46:53-54
Anhydrohexofuranoid compounds, tastc
properties, 45:270
Anhydrohexofuranose derivatives,
difluorinated, 'El- and I9F-NMR data for,
46: 151-152
1.5-Anhydrohexopyranose.derivatives.
fluorinated, 'H-and "F-NMR data for,
46:113
1,6-Anhydrohexopyranose,derivatives
fluorinated, 'H- and "F-NMR data for,
46: 114
radical-medicated brominations, 4Y:5 1-54
Anhydrohexopyranose derivatives,
difluorinated, IH- and "F-NMR data for,
46: 151-152
3,6-Anhydrohexose,derivatives, fluorinated,
IH- and I9F-NMR data for, 46: I I5
Anhydroketoses, synthesis, 39: 160- I73
Anhydronucleosides, 22:350,362,25:405
1,5-Anhydropentofuranosederivatives, radical-
medicated brominations, 49:54
Anhydro sugars, 22:4
1.2-, 21:467
1,6-, formation of, 28:20
acetates and methyl ethers, gas-liquid
chromatography of, 28: 148
addition polymerization of, 21:477
boronates, properties, 35:79
cleavage of, 22:187-188, 191
degradation of 2 5 , mechanism of,
28:165-166
2-deoxy sugars from, 21:150
3-deoxy sugars from, 21:159
epoxy, 0x0 reaction with, 23:102
formation by mutarotation reaction. 24:46
formation of, 22:202
gas-liquid chromatography of, 28:87-X9
mass spectra of, 21:81,93
mass spectrometry of, 29:74
0x0 reaction with, 23: 105
paper chromatography, phenylboronic acid
in, 3 9 6 0
per(triniethy1silyl) ethers, gas-liquid
chromatography of, 28:147-148
41
polymerization, 39:158-160, 173-212
preparation of'2,5-, 28:287
pyranose derivatives, carbon- 13 nuclear
magnetic resonance spectroscopy, 41:5 1
reduction of to w-deoxy sugars, 21:176
from sugar sulfonates, 23:279
sweetness-structure relationship, 45269-274
synthesis, 39: 157-173
Aniline
effect on f.a.b. sensitivity, 4 5 3 2
4,4'-sulfonyldi-, antimalarial and
antituberculosis agent, 29:2
Anilinium perchlorate, cyclodextrin inclusion
complexes with, 46:222, 224
Animals
conjugates of D-glUcUrOnic acid originating
in, 9:185-246
tissues, polysaccharides from, 24:293
Anisic acid, I-ester with D-glucuronic acid,
36: 104. 106. 108
Anisomycin, SO: 198
Anisoyloxy group
p - , participation in sugar reactions, 22: 1 I7
reactivity of. in acyloxonium salt formation,
26:131
Anna muricalu L., polysaccharide from seeds
of, 24:374
Anno, K., 46:9
ilnnonaceae. galactomannans from,
31:253-254
Anomeric effect, see also Isomers
(ap,up) confonnation, 47: 1 13-1 14
(up.og) conformation, 47: I 13-1 14
carbohydrate reactivity, 47: 1 16
antibonding orbital, 47: 120
ground and transition states, 47: 1 I 8
lone-pair orbital interactions, 47: 1 19
reaction-path energy, 47: I 16-1 18
conformation and, 23:29,26:87,95.99,
103-109, 123-124
definitions, 47:58
delocalization interactions, 47: 109-1 I4
scaling with electrostatic interactions,
47:114-115
electrostatic interactions, 47: 107-109
scaling with delocalizatioii interactions,
47:11&115
energy difference between up and sc
orientations, 47:l 14
energy of, 47:53-59
42 SUBJECT INDEX
Anomeric effect (continued)
measures, 47:58
A parameter, 4753, 57
2-substituted oxanes, 4 7 5 - 5 6
methoxyl, hydroxyl, and aziridinyl groups,
solvent effects, 47:6849
molecular-orbital calculations, 47:75-103
ab initio methods, 47:75
anomeric energy effect, 47:93-97
bond length and angle coupling to
torsional angles, 4798-101
conformational energies, see
Conformational energy
electron distribution and lone pairs,
47: 101-1 03
molecular geometry optimization,
47:75-76
solvent effect, 47:88-93
nature of, 47106-107
overview, 47:4647
potential-function calculations, 47: 103-106
reverse, 26: 108,47:52-53, 59
solvation-energy terms, 47: 115
valence geometry parameters, 47:71-75
aldopyranosides, 47:72-73
bond length and angle patterns, 47:71-72
C-0-C bond, 47:73-74
o-xylopyranosyl fluorides, 47:73
Anomeric energy, from MO calculations,
47:93-96
solvent dependence, 47:93-94
transition from DE to DG, 47:9495
Anomeric equilibria, 47:48-53
aldopyranose orientation, 47:48, 5 1
anomeric effects, 47:52-53
C-4 substituent electronegativity, 47:66
C-5 susbtituent effects, 47:66
D2 effect, 47:66
exo-anomeric effect, 47:48-52
wand P-D-glucopyranose derivatives,
47:4849
reverse anomeric effects, 4752-53
ring substituent effects, 47:48, 50
substituted oxanes and cyclohexanes, 4 7 5 4
Anomeric oxygen-exchange reactions, see also
Trichloroacetimidate, method
glycoside synthesis, 50:21-117
0-alkylation, 50:23-25
Anomerization
and acetolysis, 31:197-199
during acetolysis, 22:16, 18
activation energies of, 2 4 5 1
aldopyranoses, 51:6, 8
acetates, 51:6, 9
of glycosidic linkages during acetolysis of
polysaccharides, 24:399
mechanism of, 24:45
mutarotation and, 23:13
in situ, attachment of cw-~-fucosylunits,
50:280-281
of sugars acetates, by way of cyclic
carbonium ion, 24:43
Anomers, determination by nuclear magnetic
resonance, 23:43
by optical rotation and infrared spectra,
23:41
by oxidation with bromine, 23:42
2-Anthracenesulfonate, inclusion complex with
gamma cyclodextrin, 46:210
Anthracens, complex with dichloromethane and
tetracyanoethylene, structure of, 2555
Anthracycline antibiotics, complexation with
heparin, 43: 117
Anthranilic acid, reaction with nitro olefins,
24: 136
Anthrone
I 0-(a-o-glucopyranosy1)- 1,8-dihydroxy-3-
(hydroxymethy1)-, 25:243
reagent, for plant cell-wall residues, 42:275
test, in sugar analysis, 28:220-222
Anti-2-acetamido-2-deoxy-o-hexoses,
myeloma immunoglobulins, 31:345-346
Antibiotics, 25:243
24010, effect on protein glycosylation,
40:339, 341
A355 12B, branched-sugar in, 42:78
A-396-1, discovery of, 30:112
structure of, 30: 134
aminocyclitol, 38:285
biosynthesis, 3581, 102-122
preparation of, 34:263
aminoglycoside
biochemical mechanism of resistance to,
30:164, 183-225
chemical modifications of, 30: 164-182
1-N-acyl and I -N-acyl-deoxy derivatives,
activity of, 30: 1 7 4 178
structures and syntheses of, 30: 11 1-1 82
aminoglycosidic, synthesis, 39:95
aminopolydeoxy sugars, synthesis, 40: 106
 SUBJECT INDEX
anhydrooctitols from, 25:249
anthracycline, 35:9 1-96
BB-K8, preparation and activity of, 30: 174
biosynthesis of sugar components,
35:81-126
branched-chain sugars from, 42:54-56,
69-77
Bu-1709 E, andE,, discovery of, 30:112,
132
carbohydrate, uronic acids, preparation,
36:6748
chemistry of the amino sugars derived from,
18:259-308
component syntheses, 40:46
crystal structures of, 25:SO-86
diastereoisorneric pyrimidine, 46:28
effect on enzymic synthesis and degradation
of carbohydrates, 34:8
inhibition of protein glycosylation, 40:32 1,
339-344
from ketonucleosides, 42261
mactolide, glycosidic, 35:81
mass spectrometry of, 29:82,96, 105
NK-1001, synthesis of, 30:160
nucleoside, biosynthesis, 35: 122-1 26
nucleoside type, 42230
polysaccharide derivatives, 29:387
SS-56-C, discovery of, 30:112
structure of, 30: 134
stabilizers for, anhydroalditols for, 25:268
synthesis, 42:23@231
Mukaiyama condensation method,
48:106-107
Antibodies
activity, of lectins, 35: 147
anti-glycosyl, affinity chromatography,
39:437441
chromatography in isolation of, 31:323
determination, 35: 129
humoral, to polysaccharide vaccines.
41 :189-1 9 1
lipid A, 50:259-260
preparation of purified, cellulose derivative
for, 29:326
sialic acid analysis, 40: 175-1 76
Anticancer agents
adenine and 6-thiopurine derivatives as, 29:7
4-amino-5-pentofuranosylpyrazolo[3.4-
dlpyrimidines as potential, 33: 186
fluoro sugars, 48:222-23 1
43
isohexides, 49: 165-166
nucleoside analogs as potential, 26: 14
puromycin analogs, 29:4
research, Japan, 48:9-10
Anticarbohydrate antibodies
N-acetyl-P-o-glucosamine, 53:230-23 1
1-P, 53:252-253
analysis, 53:255-256, 258
analytical methods, 53:203-209
BSA, 53:223-224
characterization, 53:20 1-203
fucose, 53:223-224
galactose, 53:218-219
galacturonic acid, 53:227,229
GlcA-Rha, 53:236,238-240
glucoamylase. 53:247-249
glucose, 53:214-215,217
I-P, 53:251-252
glucuronic acid, 53:225-226
gum arabic, 53:242-246
immunization, 53:2 12-2 13
isomaltose myeloma protein, 53:240-242
lactose, 53:231-233,235-236
a-o-mannose, 53:23 1-233.235-236
preparation, 53:209-2 12
rhamnose, 53:229-230
Shigella,fle.meri I ipopolysaccharides.
53:254
1-thio-a-o-mannose, 53:220-223
tumor, 53:249-2 5 0
utility, 53:255-256
xanthan, 53:24&247
xylose, 53:22&227
yeast rnannan, 53:25&255
Anticholinergic drugs, preparation of, 27:209,
219
Anticoagulants
dicumarol, discovery, 39: I
sulfated polysaccharides as, 29:336
Antidepressants
L-gulonic benzylhydrazide, 38:300
L-gulonic (2-hydroxyethy1)hydrazide. 38:300
Anti-dextrans, as murine immunoglobulins,
31:337-342
Antiepileptic agents
denegit, 28:9
D-glucosylamineuronic acid conjugate,
36: I26
Antifreeze glycoprotein, from fish, I3C-NMR
structural analysis, 43:4344
44 SUBJECT INDEX
Anti-fructans, as anticarbohydrate niyeloma
immunoglobulins, 31:326
Antigen-antibody interactions, 31:320-323
Antigenic determinant, Lewis a bloodgroup,
preparation of, 34:268
Antigenicity, glycoprotein, effect of sugar side-
chains, 40:352,355-356
0-Antigen of bacterial polysaccharides,
biosynthesis of, 42:324
Antigens
bacterial, immunology, 39:3 11-3 12
blood-group immunology, 39:3 13-3 16,
50:333-337
3,6-dideoxyhexoses in artificial, 21: I89
gas-liquid chromatography of, 28:47,64
interaction with homogeneous
immunoglobulins, 31:32 1-3 23
lectins and blood-group, 35: 129
neoglycoproteins, 37:241,259-267
plant, immunology, 39:3 12
polysaccharide, interaction with
homogeneous, murine myeloma
immunoglobulins, 31:3 13-346
structure and biosynthesis of blood-group,
32:lO
Antileukemic activity of ketonucleosides,
42:231
Antimalarial agents, history, 29:2
Antimetabolites, 23: 116
acyclic nucleoside analogues as, 32:73
Antimicrobial agents, fluoro sugars,
48:222-23 1
Antimony pentachloride, reaction with
levoglucosan triacetate, 34:89
Antimycin A, synthesis of, 42:129
Antiperiplanar, lone-pair hypothesis,
47: 119-1 20
Anti-pneumococal C polysaccharides, as
myeloma immunoglobulins, 3 1:342-345
Antipyretics, N-(4-ethoxyphenyl)-~-gulonamide
and N-(4-methoxyphenyl)-~-gulonamide,
38:300
Anti-( 1+6)-P-~-galactans, as anti-poly-
saccharide myeloma immunoglobulins,
31:328-337
Anti-recognition effect, sialic acids,
40:220-229
Antispasmolytic agent, Vasopenton, 28:9
Antistatic agents, anhydrohexitols, 25:267
Antithrombin, 43: 118
complexes with coagulation proteinases,
43~119-122
heparin binding, 43:75-79
Antituberculosis agents, sulfones as, 29:2
Antitumor activity
of apiose-containing nucleosides, 3 1: 183
I -(2-~hloroethyl)-3-~-maltosyl- 1-
nitrosourea, 39:243
of 2,4-dihydroxy- I -P-o-ribofuranosyl-
benzene, 33: 160
o f formycin and formycin B, 33: 1 12
of ketonucleosides, 42:262-264
lentinan, 38:5 1
mode of
action of, 32:262-274
polysaccharides, 32:264-274
of noncytotoxic polysaccharides,
32:235-275
o f oxazinomycin, 33:112
structure and, of polysaccharides,
32~258-262
Antitumor agents, see Anticancer agents
Antiulcer agent, dextrins as, 47:333-334
Antiviral agents
of apiose-containing nucleosides, 31: 183
o-arabinosyladenine as, 29:7
of ketonucleosides, 42:263
of pyrazomycin, pyrazomycin B, and
oxazinomycin, 33: 112
Ants, swarming to formose, 29:221,224-225
A parameter, 47:54
Apigenin
biosynthesis of glycoside of, 26:441
7-o-ghcoside, as plant-growth substance,
21:410
glucoapiosyl-, from Digitalis purpurea,
31:175
7-O-(apiosylglucosyl)-, from parsley,
31:143
from Petroselinum crispurn, 31: 143
Apiin
biosynthesis of, 26:442
o-apiose from, 31:138
effect on growth of plants, 31: 148
4-O-methyl-, preparation of, 31: 183
in parsley plant, 31: 140-141
structure of, 31:142
synthesis of, 31:173
Apiin synthetase, activity of, 31: 173-176
Apiitol, D-, metabolism of, 31:153
 SUBJECT INDEX
D-Apiitol dehydrogenase, in apiose metabolism.
31: 153
Apiobiose, from apiogalacturonans, 31 :152,
188
Apiogalacturonans. 44: I85
in plant cell-wall, structure, 42:28 I
from zosterine, and from plant cell-wdlk.
31:lSl
Apionic acid, formation of, 31:137
Apiose, 4:57-74
chemistry and biochemistry of, 42:76
composition in aqueous solution, 42:54-55
D(+)-, in plant tissue, 30:6
D-, 46: 14
biochemistry and chemistry of.
31:13.5-184
biosynthesis in vivo, 31: I 5 4 I62
cyclic phosphate, formation of. 3 I :164
history, 31 :135
metabolism of, 31:153-154
methylation of, 31: 183
nomenclature and structure of, 31 :I37
occurrence of, 31:136
innature, 31:138-140
osazones, preparation of, 31: I 83
polysaccharides containing, 31: 150-
1.52
synthesis (chemical) of, 31: 176
transglycosylation reactions of,
31: 172-173
in plant cell wall polymers, 42280-281
synthesis, 35:lOO-101, 12.5.41:9
3-deoxy, synthesis of, 31:149
DL-, synthesis, 31:176,40:2, 13-14, 81, 84
L-, synthesis, 31:180-182, 40:115, 4 2 8 0
natural occurrence of, 42:69,76
nucleosides, immunosuppressive activity of.
4 2 1 3 1-132
1,2-0-isopropylidene-a-, carbon- I3 nuclear
magnetic resonance spectroscopy,
41:64
poly-, in plant cell walls, 42: I3 1
structure of. 4 2 7 0
synthesis of, 22:286,42:78, 80, 104. 107,
113-1 14
Apiose-containing compounds
characterization of, of low molecular weight,
31: 140-I50
polysaccharides, plants containing,
31:1.5~1.52
45
Apiose-containing plants, 31: 139, 145
D-Apiose reductase, in apiose metabolism,
31:153
Apioside, methyl tri-0-methyl-o-, isomers,
preparation of, 31 :I83
L-Apiosyladenine
deamination of, 31:153
effect on Escherirhia roli and
Staphylococcus aurei~r,31 :153
Apiosyl nucleoside. synthesis of, 31: I84
Apium graveolens, apiose-containing
flavonoids from, 31:146
Apple
cell-wall studies on, 42:280
during ripening, 4 2 3 1.5, 369
development physiology of, 42:340-341,
343,371-376,378,380
Apramycin
discovery of. 30: I I2
isolation and structure of, 30: 139
Apramycin hydriodide, monohydrate.
ethanolate, 43:372
Apricot, development physiology of, 42:341
Apterin, crystal structure bibliography,
38:473-475
Apurinic acid
alkaline degradation of, 28:203
formation by DNA radiolysis, 37:58
polymer, 22322
Apyrimidinic acid, alkaline degradation of,
28:203
Aquapak. 25: 15
Aqueous solutions
Fourier-transform infrared spectroscopy,
44:61
laser-Raman spectroscopy, 44:73-75
vibrational spectroscopic studies, 44:85-86
Aquo cytidine 5-(cadmium phosphate), crystal
structure, 43:359-360
Arabic acid, Barry degradation of, 31:203
Arabinal
wand L-, diacetates, reaction with lead
tetrafluoride, 25: 196
3,4-diacetyl-~-,0x0 reaction with, 2359,
89-90
di-0-acetyl-D-
bromofluorination, 38:237
halogen addition to, 28:26 1
reaction with benzotriazole and 5.6-
diinethyl derivative, 24:2 I7
46 SUBJECT INDEX
Arabinal (continued)
reaction with hydrogen chloride or
hydrogen bromide, 28:264
di-0-benzoyl-o-, reactions with hydrogen
halides, 28:265
Arabinan, 42:383,44:183
citrus, 41:7
definition, 36:217
enzyme for, 42:385-386
L-
as a-L-arabinofuranosidase substrate,
42 :3 90-3 9 1
as endo-L-arabinanase substrate, 42:394
peanut, 41:7
per-0-methylated, carbon-13 nuclear
magnetic resonance spectra, 38:71, 101
in plant cell-walls, 42:375, 44:359
interconnections, 42:305
structure, 42:281-282,286
Arabinan arabinanohydrolases, (l+5)(1+3)-
WL-, L-arabinanases nomenclature, 32:279
Arabinanases
endo-( 1+5)-a-~-
occurrence of, 42:392
in plant cell-wall fractionation, 42:277,
282,394
properties of, 42:393-394
purification of, 42:392-393
substrates and activity of, 42:385
L-, 32:278-292
amino acid composition of, 32:288
assay of, 32:283-284
definition, and nomenclature of, 32279
homogeneity of, 32:285
mode of action of, 32:290-292
molecular weight of, 32:287
occurrence of, 32:280-283
physicochemical properties of,
32:285-290
separation and purification of, 32:284
unit of activity, 32:284
Arabinitol
2,3:4,5,-di-O-cyclohexylidene-l-deoxy- 1-C-
heptyl-L-, preparation, 27:24 1
1-amino-l -deoxy-D-, deamination of,
31:6&62
2-amino-2-deoxy-~-,deamination of,
25:192,31:63
2,Sanhydro-
D-,25:234
1,4-di-O-(rnethylsulfonyl)-~-, 29207
1,4-anhydro-~-,25: 198,233
triacetate, isomerization of, 25:258
1,4-anhydro-~-,25:233
2,5-anhydro-~-,25:200,234
1,5-anhydrotri-~-benzoy~-o-, rearrangement
in hydrogen fluoride, 26: 174
1,l-bis(acetamido)-
1-deoxy-D-, preparation of, 31232
1-deoxy-L-, preparation of, 31:84
1-deoxy-~-O-c~-~-ga~actopyranosy~-~-,
preparation of, 31:98
1-deOXy-3-O-P-D-glUCOpy~inOSy1-D-,
preparation of, 31:97
1,5-dideoxy-~-,preparation of, 31:82
I, 1-bis@enzamido)-
1-deoxy-o-, preparation of, 31:99
1,5-dideoxy-, preparation, 39:31
5-0-benzoyl-1 -deoxy-D-, preparation of,
31:99
D-
degradation of, mechanism of, 28: 165
enzymic production from o-glucose,
32:219
manufacture by yeasts from sugars,
32: 128
selective oxidation with mercuric acetate,
33:99
utilization by yeasts, 32: 147
1-deoxy-
1-C-heptyl-L-, preparation of, 27:241
2-C-phenyl-o-, crystal structure
bibliography, 38:44 1 4 4 2
2-deoxy-2-deuterio-o-, synthesis of, 27:
131
1,5-dideoxy-~-,preparation of, 32:76
1,5-dideoxy-~-,phenylboronate, structure,
3543
DL-
conformation of, 26:69
crystallography of, 25:59,31:364
synthesis, 40:27
infrared spectrum, 45:294
L-
anhydridation, of, 25:23 1
gas-liquid chromatography of, 28:57, 67
utilization by yeasts, 32:147
liquid chromatography methods for analysis
of, 46:33
1,3-O-benzylidene-
 SUBJECT INDEX
D- and+-, selective oxidation with
dimethyl sulfoxide-
dicyclohexylcarbodimide, 3 3 9 3
tri-O-(methyhlfonyI)-o-, solvolysis of,
25:207
2-0-methyl-~-,22: 1 I5
penta-0-acetyl-DL-, rearrangement i n
hydrogen fluoride, 26: 176
-yl)-I-thio-
(1R)-I-S-ethyl-I-(5-fluorouracil-l
D-
conformation of, 32:75
crystal structure bibliography, 38:493
(IR)-2,3,4,5-tetra-O-acetyl- 1 -
( I ,6-dihydro-6-thioxopurin-9-yl)- 1-S-
ethyl- 1-thio-D-
conformation of, 32:74
crystal structure bibliography, 37:436
S-ethyl-l-(5-fluorouracil-l-yl)- 1-thio-D-,
ethanolate, crystal structure
bibliography, 38:499-500
1-S-ethyl-l -thio-D-, oxidation with
Acetobacter suhoxydans. 33: 100
sweetness-structure relationship, 45295
tri-0-acetyi- 1,4-anhydro-o-, rearrangement
in hydrogen fluoride, 26: 174
2,3,4-tri-O-benzyI-
D-, sulfonylation of, 24: 175
1,5-di-0-p-tolysulfonyl-o-, solvolysis of,
24: 196
L-Arabino-D-galactans, in cell-wall
development, 26:348
Arabinofuranosyl-6-hydroxycytosine,6.2'-
anhydro-1-P-D- 1 +-, crystal structure,
43:275
Arabinofuranose
4-a-carba-P-~-,48:22-23
5-acetamido-5-deoxy-L-, 23: 170
1-carboxamido-5-0-benzoyl-01-~-, crystal
structure bibliography, 37:390
5-chloro-5-deoxy- I ,2-0-isopropylidene-3-0-
(methylsulfonyl)-4-thio-P-~-.crystal
structure bibliography, 34:356
conformation of, 34:201
2-deoxy-2-fluoro-o-, 48: 133-134
1,3-di-O-acetyl-5-0-benzoyl-01-, 'Wand
I9F-NMR data for, 46: 1 10
1,3-di-O-acetyl-S-O-benzyl-, 'M-and I9F-
NMR data for, 46: I 10
1,3-di-O-benzoyl-5-0-benzyl-, IH-and
I9F-NMR data for, 46: 110
47
1-0-acetyl-5-0-benzoyI-3-O-formyl-01-,
'H- and "F-n.m.r data for, 46: 1 10
5-0-benzyl-, IH-and I9F-n.m.r data for,
46:llO
5-phosphate, sodium salt, 'H-and I9F-
NMR data for, 46: 109
I ,3,5-tri-O-benzoyl-a-, 'H-and I'F-NMR
data for, 46: 1 10
1,3,S-tri-O-benzyl-01-,'H-and I9F-NMR
data for, 46: 1 I0
1,2-di-O-acetyl-5-O-benzoyl-2-deoxy-2-
fluoro-3-O-formyl-o-, preparation,
38:246
5-0-cr-~-galactopyranosy~-a- and-P-D,
preparation of, 31:98
L-arabinofuranosyl-L-, 24:360
3-0-acetyl-
1,S-anhydro-2-O-benzoyl-P-~-, synthesis,
39: 172
5-deoxy-5-iodo- 1,2-0-isopropylidene-P-
L-, reaction with silver fluoride,
28:291
1,2,5-orthobenzyl-P-~-,crystal structure,
43:345
0-a-L-arabinopyranosyl-(1+ 5 ) - 0 - ~ -
arabinofuranosyl-( 1 - + 5 ) - ~24:360
,
5-0-P-D-xylopyranosyl-L-, 24:354,360
5-0-benzoyl-. 2-deoxy-2-fluoro-3-0-formyl-
D-, formyl group removal, 39:36
I-0-benzoyl-. a - ~and++-,
- acyl migration
in, 33: 103
5-0-benzoyl-2-deoxy-2-fluoro-3-O-formyl-
D-, preparation, 38:245
1,2-0-isopropylidene-3,5-di-0-p-
tolysulfonyl-L-, displacement reactions
of, 24: 15 1
I ,3,5-tri-O-benzoyI-P-~-
acyl migration in, 33: 104
rearrangement in hydrogen fluoride,
26:181-182
1,3,5-tri-0-(p-nitrobenzoyl)-P-D-, acyl
migration in, 33: 104
Arabinofuranosidase, a-L-,44:159, 163,
185-1 86,247
Arabinofuranoside
OI-L-
from Aspergillus niger, 42:386
assay of, 42:388
effect on cell-wall glycoprotein,
42:380-381
48 SUBJECT INDEX
Arahinofuranoside (continued)
occurrence of, 42:386-387
pH optima of, 42:387-388
properties of, 42:389-392
purification of, 42:389
substrates and activity of, 42:385
alkyl2, 5-anhydro-
a-L-, 25200
hemiacetals, 25:2 12
p-0; hemiacetals, 25212
D-
1,2-di-O-acetyl-5-0-benzoyl-2-deoxy-2-
fluoro-3-0-formyl-
(Y anomer, 'H- and I9F-NMR data for,
46:141
j3 anomer, IH- and I9F-NMR data for,
46: 142
methyl 2-deoxy-2-fluoro-a-
3,5-di-O-benzyl-, 'H- and IYF-NMR
data for, 46: 111
IH- and IYF-NMRdata for, 46: 11 1
5-0-henzyl-, IH- and IYF-NMRdata for,
46:111
methyl 2,5-di-0-benzoyl-3-deoxy-3-
fluoro-a-, 'H- and I9F-NMR data for,
46:112
ethyl 2, 5-anhydro-a-~-,hydrolysis of,
25212
ethyl 2-acetamido-2-deoxy- 1-thio-p-L-,
21:116
ethyl a-L-,formation from dithioacetal,
32:68
ethyl 3-amino-3-deoxy-o~-,24:229
ethyl 1,5-dithio-P-~-,formation from
dithioacetal, 32:67
ethyl 5-S-ethyl- 1,5-dithio-a, p-L-,
preparation of, 32:50
ethyl 1-thio-p-o-, 21:116
preparation from dithioacetal, 32:67
methyl 4-acetamido-4-deoxy-
D-, synthesis, 41:9
L-, synthesis, 41:9
methyl a-D-,21:103,23:280
conformation of, 21:96
methyl a-L-, conformation of, 21:lOO
methyl 2-amino-2-deoxy-a-o-. deamination
of, 31:57
methyl 2,5-anhydro-a-~-,24: 176
methyl 3-azido-2,5-bis(benzamido)-2,3,5-
trideoxy-p-o-, 23: 174
methyl p-D-,23:280
conformation of, 21:98
preparation of, 34:278-279
methyl 2-O-(methylsulfonyl)-o-, 23:260
methyl 5-0-p-tolysulfonyl-a-~-,
displacement reaction of, 24: 176
methyl 3-S-benzyl-2-chloro-2-deoxy-3-
thio-5-0-p-tolylsu~fony~-~-o-, 22:
193
methyl tri-0-
acetyl-a-o-, rearrangement in hydrogen
fluoride, 26: 18 1
benzoyl-a-o-, rearrangement in hydrogen
fluoride, 26: I81
methyl-a,P-L-, mass spectrum of, 21:63
phenyl a-L-,as enzyme substrate, 42:384,
390
p-nitrophenyl a-L-,as enzyme substrate,
42:384,390
Arabinohranosyl
2,2'-anhydro-
1-p-0-
2,4-diamino-5-fluoropyrimidinium
chloride, crystal structure
bibliography, 38:527
5-dimethylmercapto-6-oxocytosine
chloride, crystal structure,
43: 288-289
I -P-L-,2-hydroxy-4-pyridone, crystal
structure bibliography, 38:439-440
5-chloro-l-3,5-di-0-acetyl-P-~-, 6-
oxocytosine, crystal structure,
43~292-293
8,2'-anhydro-9-P-o-, 8-hydroxyadenine,
trihydrate, crystal structure, 43:285-
286
Arabinohranosyladenine
9-a-o-,crystal structure, 43:288
8,2'-anhydro-8-mercapto-9-P-o-, 5'-
monophosphate, trihydrate, crystal
structure, 43:287
~ - P - D -8,2'-an-hydro-8-mercapto-,5'-
,
phosphate, polymerization, 36: 170
Arabinohranosylamine
N-acetyl-5-0-a-~-galactopyranosyl-a-~-,
preparation of, 31:98
N-acetyl-3-0-~-~-galactopyranosyl-~-,
preparation of, 31:98
N-acetyl-3-O-~-~-glucopyranosyl-~-,
preparation of, 31:97
 SUBJECT INDEX
Arabinofuranosyl bromide
2-deoxy-2-fluoro-a-o-
3,5-di-O-benzoyl-, 'H-and I9F-NMR data
for, 46: 138
3-O-acetyl-5-O-benzoyl-, 'H-and "F-
NMR data for, 46: 138
3,5-di-O-acyl-2-bromo-2-deoxy-a-t)-,
methanolysis of. 34:28 1
3,s-di-0-benzoyl-
a-L-, reaction with methanol or with
1,2,3,4-tetra-O-acetyl-P-~-
glucopyranose, 34:280
2-O-nitro-a-~-,reaction with methanol or
with 1,2,3,4-tetra-O-acetyl-P-~-
glucopyranose, 34:280
2-O-(p-nitrobenzoyl)-a-~-,reaction with
methanol or with 1,2,3,4-tetra-O-
acetyl-P-D-glucopyranose, 34:280
2-O-acetyl-3,5-di-O-benzoyl-a-1.-. reaction
with methanol or with 1,2,3,4-tetra-O-
acetyl-P-D-glucopyranose,34:280
2,3,5-tri-O-benzoyl-c~-r.-,reaction with
methanol or with I ,2,3,4-tetra-O-acetyI-
P-o-glucopyranose, 34:280
9-P-o-Arabinofuranosyl-8-
(butylamino)adenine, crystal structure,
43:294
Arabinofuranosyl chloride
2,3,5-tri-O-benzoyl-P-~-, benzoxonium salt,
rearrangement, of, 26:155
2,3,5-tri-O-benzoyl-a-o-, reaction with
diethyl sodiomalonate, 33: 152
Arabinofuranosyl cyanide
2,3,5-tri-O-benzoyl-ol-o-, preparation of,
33:139
2,3,5-tri-O-benzoyl-p-~-, preparation of.
33: 140
Arabinofuranosylcytosine
2,2'-anhydro- I -P-u-, 43:275
3', 5'-bisphosphate, monohydrate. crystal
structure, 43:280-28 1
6,2'-anhydro- 1 -P-D-, crystal structure
bibliography, 37:410
1 -P-D-Arabinofuranosylcytosine 5 I-
monophosphate, trihydrate, crystal
structure, 43:281-282
Arabinofuranosyl fluoride
3,5-di-O-benzoyl-2-O-methyl-, I3C- and "F-
NMR data for, 46: 106
per-O-benzoyl-2-bromo-2-deoxy-a-n-.
49
synthesis, 38:203
2,3,5-tri-O-benzoyI-a-n-, NMR data for,
46:106, 168
2,3,5-tri-O-benzyl-, 'H- and I9F-NMR data
for, 46: 107
2,3,5-tri-O-benzyl-a-~-.'~C-NMR data for,
46: 168
2,3,5-tri-O-benzyl-P-~-,"C-NMR data for,
46: 168
9-~-~-Arabinofuranosyl-8-morpho~~noadenine,
dihydrate, crystal structure, 43:327-328
Arabinofuranosyloxy-r-proline,a-and p-L-,
I3C-NMR chemical-shift data, 43:4546
I -P-~-Arabinofuranosyl-6-oxyuracil, 6,2'-
anhydro-,5'-phosphate, polymerization,
36: 170
Arabinofuranosyl-2-thiouraci1,2,2'-anhydro-1-
p-D-, crystal structure. 43:309
1 -P-D-Arabinofuranosylcytosine, crystal
structure, 43:359
I -P-D-Arabinofuranosyluracil. crystal structure,
43:358-359
1-P-o-Arabinofuranosyl-6-uracilcarboxylic
acid, 6',2'-lactone, crystal structure,
43:314-315
Arabinogalacatorhamnogalacturonan,44: 182
Arabinogalactan, 24:341,44: 182
in bamboo shoots, 36:243
carbon-I 3 nuclear magnetic resonance
spectra. 38:71,97
gel chromatography of, 2541
hydrolysis ofoxidized, 31: 194
interaction with concanavalin A, 35: 179
L-, as a-L-arabinofuranosiddse substrate,
42:390
larch, Barry degradation of, 31:203
methylation of tritylated, 30: 12
in plant cell-walls, 42:283-285, 287
interconnections, 42:303-304, 307, 309,
31 1
structure, 42:284-285
soybean, 44: I84
structure
enzymic analysis, 44:247
of green coffee bean, 26: 16
Arabinoglucoxylan, antitumor activity of,
32:255-256
Arabinoglucuronoxylan, 42:288
antitumor activity of. 32:255-256
enzymic analysis, 44: 161
50 SUBJECT INDEX

Arabinoglucuronoxylan (continued) 1,2,3,4-tetraacetate, 22: 16

oligosaccharides from enzymic hydrolyzates
from, 32:346
o-Arabino- I ,4-lactone, crystal structure, 43:206
Arabinomannan
gas-liquid chromatography of, 28:53
interaction with concanavalin A, 35: 179
o-Arabinonate ion, conformation of, 26:69
Arabinonic anilide, 24: 1 15
Arabinono- 1,4-lactone, 5-deoxy-DL-,synthesis,
40: 19
Arabinono-l,5-lactone, 4-C-[ 1(S)-methylethyll-
2,3-O-methylene-~-
natural occurrence of, 42:73
structure of, 42:71
synthesis of, 42:126
Arabinononitrile
2,3,4,5-tetra-O-acetyl-
D-, reaction with ammonia, 31233
L-, degradation and ammonolysis of,
31:112
reaction with ammonia, 31:82
2,3,4,5-tetra-O-benzoyI-~-, ammonolysis of,
effect of solvent on, 31: 100
Arabinooxylan, L-, as a-L-,as a - ~ -
arabinofuranosidase substrate, 42:390-39 1
Arabinopyranose
3,4,-O-isopropylidene-~-, selective oxidation
with silver carbonate-on-Celite, 33:97
a-, conformation in solution, 26:85
5-acetamido-5-deoxy-
D-, 23:173
L-, 23: 170
a-D-, 45:74
conformation of, 25: 103
methyl-a+, polymerization, 39:204
methyl-L-, synthesis and polymerization
of, 21:488
a-L-
calcium chloride tetrahydrate, crystal
structure bibliography, 38:420
taste properties, 45:242
5-amin0-5-deoxy-o-, 23: 130
p-0-
conformation, 25: 102
in solution, 26:85
crystallography of, 2 5 5 9
sweetness-structure relationship, 45:249,
25 1
taste properties, 45:242
1,2,3,4-tetra-O-(trideuterioacetyl)-
interproton distances, 45: 167
proton spin-lattice relaxation, 45: 158,
166
p-DL-
crystal structure, 43:206-207
oxygen atoms, 47: 102
5-[(benzyloxycarbonyl) aminol-5-deoxy-p-
L-, 23: 190
p-L-
crystal structure, 25:59,38:418419,
43:207
ester of uridine 5'-pyrophosphate, enzymic
preparation of, 28:343
isolation of, 28:325
sweetness, 45:2 18-2 19
structure relationship, 45:24 1
taste properties, 45:242
D-, 1,3,4-tri-O-acetyl-2-deoxy-2-fluoro-~-
"C-NMR data for, 46: 167
'H- and I9F-NMR data for, 46: 104
2-deoxy-2,2-difluoro-o-, preparation,
38: 196, 23 1
3-deoxy-3-fluoro-P-, 'H- and I9F-NMR data
for, 46: 105
2,4-di-O-benzoyl-o-, 26: 179
1,2:3,4-di-O-benzylidene-p-o-, reaction with
triphenylmethyl borofluoride, 39: 112
1,2:3,4-di-O-isopropyIidene-, p-L-,
conformation of, 26: 119,226
1,2:3,4-di-O-isopropyIidene-, D-, preparation
of, 34: 188
0-a-o-galactopyranosyl-( b 3 ) - L-, in plant
tissues, 37:3 10
1-0-benzoyl-a-L-and-P-L, acyl migration in,
33:103
1,2-O-isopropylidene-P-~-,3,4-
phenylboronate, preparation, 35:39
3,4-O-isopropylidene-~-, preparation of,
34:188
1,2,3,4-tetra-O-acetyI-
a-D-,43:371
crystal structure bibliography, 32:368
a-L-, reaction with ethanethiol, 32:34
p-D-.43:371
crystal structure bibliography, 32:368
1,2,3,4-tetra-O-acetyl-, 5-
[(benzyioxycarbonyl) amino]-5-deoxy-
p-L-,23~191
 SUBJECT INDEX
conformation of, 26238
tetra-0-acetyl-
(Y-D-, rearrangement in hydrogen fluoride,
26:176
p-D-,conformation of, 26:93
p-L-,anomeric and conformational
equilibria, 26:lOl
tetra-0-benzoyl-
p-D-, rearrangement in hydrogen fluoride,
26:177
p-L-, rearrangement in hydrogen fluoride,
26:176
1-thio-a-L-, tetraacetate, proton magnetic
resonance spectroscopy of, 27:2 1-22
1,2,4-tri-O-acetyl-a-o-, 26: 155
tri-O-benzoyl-2-0-methyl-a, p-D-,
rearrangement in hydrogen fluoride,
26: 183
2,3,4-tri-O-methyl-~-,polarography of,
29: 142
Arabinopyranoside, 53:98
3,4,-O-isopropylidene-~-, selective oxidation
with silver carbonate-on-Celite, 33:97
benzyl p-D-, catalytic oxidation of. 33538
benzyl p-L-, selective esterification of, 33:25 methyl 3,4-dichloro-3,4-dideoxy-a-L-,
benzyl 1,5-dithio-a, p-L-, preparation of,
32:34
benzyl2-O-benzyl-3,-4-0-benzylidene-@-~-,
endo- and exo-, hydrogenolysis
regioselectivity, 39: 131
benzyl 3,4-O-benzylidene-P-~-,endo- and
exo-, hydrogenolysis regioselectivity,
39:131
D-
methyl 4-0-allyl-2-amino-2,3-dideoxy-3-
fluoro-p-, IH- and I9F-NMR data for,
46:128
trifluoromethyl3,4-di-O-acetyl-P-, 'H-
and 19F-NMRdata for, 46:104
2,4-di-O-methyl-~-,synthesis of, 33:25
L-, methyl 4-deoxy-4-fluoro-
a anomer
I3C-NMR data for, 46:168
'H- and I9F-NMR data for, 46: I06
p anomer
13C-NMRdata for, 46:168
'H- and I9F-NMR data for, 46: 106
methyl 3
4-anhydro-a-~-,25~152
4-anhydro-p-~-,25: 150
51
nuclear magnetic resonance spectrum,
25:171
methyl a- and p-D-,conformation in
solution, 26:84
methyl 4-acetamido-4-deoxy-p-~-, 23: 184
methyl a-D-, 23:280
acetolysis and anomerization of, 22: 16
methyl a-DL-, synthesis, 40:69
methyl a-L-
crystal structure bibliography, 38:427
reaction with sulfuryl chloride, 28:237,
33:75
methyl 3,4-anhydro-a-o-, conformation of,
26: 125
methyl 4-azido-4-deoxy-P-~-,23: 184
methyl-p-o-, 2,3,4-triacetate,acetolysis of,
22:16
methyl p-L-,23:276
crystal structure bibliography, 38:427-428
formation from dithioacetal, 32:68
reaction with sulfuryl chloride, 33:75
selective esterification of, 33:25
methyl 2-C-(aminomethyl)-p-~-,
deamination of, 31:53
preparation of, 33:75
methyl 2,3-di-O-benzoyl-4-0-
(methylsulfony1)-p-L-, displacement
reactions of, 24:160
y-tolylsylfonyl-P-L-, displacement
reactions of, 24: 160
methyl 2,4-di-0-benzyl-3-bromo-3-deoxy-P-
D-, synthesis, 39: 1 1 1
methyl 2-0-acetyl-3,4-anhydro-o-, 25: 154
methyl 2-0-benzoyl-
3, 4-di-O-p-tolysulfonyI-~-~-,
displacement reactions of, 24: I61
P-L-, p-toluene-sulfonylation of, 33:25
p-L-. sulfonylation of, 23:249
3,4-O-benzylidene-P-o-, reaction with N-
bromosuccinimide, 39:lOl
with triphenylmethyl fluoroborate,
39:llO
4,6-O-benzylidene-P-~-,reaction with N-
bromosuccinimide, 26: 165
3,4-0-benzylidene-p-i-, diastereoisomers,
hydrolysis, 39: 19
3-O-p-tolylsulfonyl-p-~-, 23:249
methyl 3,4-0-benzylidene-P-~-,
configuration of, 34: 196
52 SUBJECT INDEX
Arabinopyranoside (continued)
methyl 3.4-O-endo-ethylidene-fb~-
irradiation, 39:93
synthesis, 39:79
methyl 3,4-0-ethylidene-P-~-.
photochemical reaction mechanism with
excited acetone, 38: 143
preparation of, 34: 190
methyl 3,5-U-(ethyl orthoacetyl)-P-L-,
acetoxonium fluoroborate, 26: 168
methyl 3,4-O-isopropylidene-
p-L-,23~276
reaction with N-(2-chloro-l, 1.2-
trifluoroethyl)diethylamine,28:258
2-0-methyl p-D-, reaction with
butyllithium, 39: 142
2-0-methyl-P-~-,sulfonylation of,
23:238
2-O-p-tolysulfonyl-P-o-, displacement
reactions of, 24:152
methyl 4-O-methyl-u-~~-, preparation of,
28:296
methyl 2-0-methyl-p-~-,benzoylation of,
33:25
methyl 2-U-(methylsulfonyl)- p-D-, 23:260
methyl 2-0-p-tolylsulfonyl-~-~-, 23:260
methyl tri-0-methyl-P-D-, mass spectrum of,
21:60
methyl 2,3,4-tri-O-methyl-
p-L-,mass spectrum of, 21:48
D-, mass spectrum of, 23:202
methyl tri-0-(methylsulfony1)-a+(and p-
L)-, displacement reactions of, 24: 161
2-O-methyl-o-, from 3-0-methyl-D-glucose
by oxidation, 33:98
p-nitrophenyl a-L-,as U-L-
arabinohranosidase substrate, 42:390
trifluoromethyl 3,4-di-O-acetyl-2-deoxy-2-
fluoro-p-D-, preparation, 38:233
Arabinopyranosylamine, N-acetyl-u-L-,
configuration of, 31:104
Arabinopyranosyl azide, tn-0-acetyl-u-o-,
crystal structure bibliography, 32363
Arabinopyranosyl chloride, 4-chloro-4-deoxy-
~-,2,3,-di(chlorosulfate), preparation of,
28:235
Arabinopyranosyl fluoride
2-bromo-2-deoxy-
a-D-,crystal structure of, 25:74
P-D-, 24:204
D-
2-deoxy-
2-bromo-P-, 'H- and I9F-NMR data for,
46:135
3,4-di-O-acetyl-2-bromo-u-, 'H- and
"F-NMR data for, 46:135
3,4-di-O-acety1-2-iodo-a-, IH- and I9F-
NMR data for, 46:135
3,4-di-O-acetyl-2-deoxy-2-fluoro-P-, 'H-
and "F-NMR data for, 46: 155
3,4-di-0-acetyl-2-O-methyl-p-, 'H- and
I9F-NMR data for, 46: 101
3,4-di-0-benzoyl-2-0-methyl-, 'H- and
"F-NMR data for, 46:lOI-102
3,4-0-acetoxonium-2-0-methyl-, 'H- and
"F-NMR data for, 46:lOl
3.4-0-benzoxonium-2-0-methyl-, 'H- and
I9F-NMR data for, 46:lOl
3(or 4)-0-benzoyl-2-O-methyl-~-,'H- and
'"F-NMR data for, 46:102
2,3,4-tri-O-acetyl-,'H- and 19F-NMR data
for, 46: 101
2,3,4-tri-O-acetyl-P-, I3C-NMR data for,
46: I67
2,3,4-tri-0-benzoyl-~-, 'H- and "F-NMR
data for, 46: 101
3-deoxy-3-fluoro-
p-D-,preparation, 38:213
D-, preparation, 38:213
2-deoxy-2-fluoro-o-, preparation, 38:2 14,
245
di-O-acetyl-2-bromo-2-deoxy-p-~-,
preparation, 38:235
3,4-di-0-acetyl-2-deoxy-2-fluoro-p-~-,
preparation, 38:233
3,4-di-0-benzoyl-2-0-methyl-o-, anomers,
synthesis, 38:201
tri-O-acetyl-p-~-,proton magnetic resonance
spectroscopy of, 27:82
tri-0-benzoyl-
U-D-, 26: 177
p-D-.26: 179
Arabinopyranosyl isothiocyanate, 2,3,4-tri-0-
acetyl-a-o-, 44:141
I3C NMR, 44:141
formation of amino acid diastereoisomers
using, 44: 1 17
infrared spectrum, 44: 141
Arabinopyranosylmethane,bis(ethylsulfony1)-
U-D-, triacetate, nuclear magnetic
 SUBJECT INDEX 53

resonance spectrum of, 25253 in nonaqueous solvents, 42:68

Arabinopyranosyloxy-L-proline,a-and (%I.-, D-
13C-NMR chemical-shift data, 43:45 46 from 2-amino-2-deoxy-o-glucose
Arabinose radiolysis, 37:49
5-acetamido-5-deoxy- radiation chemistry, 37:33
D-,23: I69 derivatives, Table, 34:211
L-, 23: 169 dialkyl dithioacetal. reaction with p -
diethyl dithioacetal, oxidation of, 32:85 toluenesulfonyl chloride, 25: 199
ring isomers, ir spectra, 44:25 diethyl dithioacetal tetraacetate, mass
synthesis, 41:9 spectrum of, 21:85
aldehyde- diethyl dithioacetal
D-, hexaacetate, 22: 16 chemical shifts ofproton resonances of,
halogen derivatives, 22:214 32:90
I.-, tetraacetate, aldehydrol formation, irradiation, 39:94
42:3 1 dimethyl dithioacetal, oxidation by
2-amino-2-deoxy-~-,synthesis of, 2 4 9 Acetohacter suhoxydans, 32532
2,3(2,5-and 3,5)-di-O-methyl-, from diphenyl dithioacetals, conformation of,
mesquite gum, 24:350 26:72
2,s-anhydro- dithioacetal
a-i.-,dimethyl acetal, 25:212 reaction with sulfonyl chloride, 32:48
D-, 25:202 selective esterification of, 33:40-41
dimethyl acetal, 25:2 1 1 phosphorylation of, 33:47
3,4-dideoxy-3,3-epimino-r.-, diarotization enantiomeric carba-sugars from, 48:4244
of, 32:57 enzymic isomerization, 36:46
L- high-temperature transformation. acidic
2-furaldehyde from, 25:222 conditions, 46:276-277
dehydration of, 28: 166 mutarotation in pyridine, 28:39
3,4-O-isopropylidene-aldehydo-o-, nonselective spin-lattice relaxation rates,
mutarotation of, 25:214 45: 148
3,4-O-isopropylidene-o-, 25:209 5-phosphate isomerase, metabolism of 3-
hydrolysis of, 2521 1 deoxy-~-n~anno-2-octulosonic acid,
1,4-anhydro-2,3-di-O-methyl-a-1.-, synthesis. 38~378-379
39: 165 polarography of, 29: 126
S-azido-S-deoxy-2,3- preparation by oxidation of dithioacetals,
di-0-isopropylidene-o-, diethyl 32:83-84
dithioacetal, reaction with p - proton spin-lattice relaxation rates, 45: 152
toluenesulfonyl chloride, 32:5 1 solubility in methanol. 27:97
O-isopropylidene-4-O-(methylsulfonyl)-u- utilization by yeasts, 32: 147
, azidolysis of, 3 2 5 1 5-deoxy-
p-D-, mutarotation of, 23:23 D-,21:177
P-DL-,crystal structure bibliography. 31:363 1.-, 21:176-178
5-(benzyloxycarbonyl)amino-5-deoxy-~-, 2,3-O-isopropylideiie-o-,diethyl
composition in solution, 42:49- 50 dithioacetal, reaction with p -
p-L- toluenesulfonyl chloride, 32:5 1
circular dichroism, predicted and fragment 1,2-O-isopropylidene-~-, 23:273
spectra, 45534 2-deoxy-5-O-(p-nitrobenzoyl)-2-
crystal structure bibliography, 31 :363 (trifluoroacetamid0)-o-,diethyl
mutarotation of, 23:23 dithioacetal, reaction with bromine in
composition methanol, 32:70
in aqueous solution, 42:26,43,64 determination of enantiomrric form, 46:66
54 SUBJECT INDEX
Arabinose (continued)
2,3:4,5-di-O-benzylidene-
diethyl dithioacetal, selective
D-,
hydrolysis, 39:22
L-, diethyl dithioacetal
preparation of, 32:53
selective hydrolysis, 39:22
1,2:3,4-di-O-isopropyIidene-, D- or-L-,
dithioacetals, preparation of, 32:53
1,2:3,4-di-O-isopropylidene-
aldehydo-, reaction with 2-lithio- 1,3-
dithiane, 32:38
aldehydo-L-, in D-apiose synthesis, 31: 178
p-D-,reaction with butyllithium, 39: 142
p-L-
conformation of, 26: 119,226
hydrolysis of, 34:204
D-
dialkyl dithioacetals, selective
hydrolysis, 39:22
diethyl dithioacetal, reaction with bases,
32:58
reaction with mercury(I1) chloride,
32:64
diphenyl dithioacetal, reaction with
based, 39: 147
diphenyl dithioacetal, reaction with
bases, 32:57
L-, mass spectrum of, 21:76
2,3-di-O-methyl-
D-
composition in aqueous solution,
42:43-44
composition in nonaqueous solvent,
42:61
L-, composition in aqueous solution, 42:43
DL-,synthesis, 40:8-10, 73,91
ester with adenosine 5-pyrophosphate,
occurrence of, 28:3 15
in fungi cell-walls, 23:4 13
gel chromatography of, 25:3 1
1-O-(indole-3-acetyl)-, 21:391
a-L-,circular dichroism, predicted and
fragment spectra, 45:84
L-
in Acacia gums, 24:346
butylboronates, hydrolysis, 35:5 1
preparation, 3 5 4 3
calcium chloride complex, mutarotation
of, 23:35
catalytic oxidation of, 33:87
dithioacetal, selective methylation of,
3366
reaction with sulfuryl chloride, 33:76
selective oxidation with silver
carbonate-on-Celite, 33:97
derivatives, table, 34:211
1,2:3,4-diacetaI, selective hydrolysis,
39:16
dimethyl acetal, synthesis, 39:8
dibenzyl dithioacetal, reaction with
mercury(I1) chloride in methanol,
32:68
diethyl dithioacetal, methylation of, 32:47
diphenyl dithioacetals, conformation of,
26:72
dithioacetals, reaction with sulfonyl
chloride, 32:48
enantiomeric carba-sugars from, 48:4 1 4 2
enzymic phosphorylation of, 32:9
gas-liquid chromatography of, 28:46
glycoenzyme constituent, 27:302,307,
32 1
solubility in liquid ammonia, 27:91
in glycoproteins, 25:413
linkage to hydroxy-L-proline, 43:45
in living tissue, 42:383
methyl ethers, periodate oxidation and
gas-liquid chromatography of, 30:34
separation of, 30: 18
mutarotation and gas-liquid
chromatography of, 28:40
(p-bromophenyl)hydrazone, crystal
structure bibliography, 31:367
pemicotinate, ammonolysis of, 31:89
phenylboronates, hydrolysis, 35:50-5 1
preparation, 35:43
in plant cell-wall hydrolyzates, liquid
chromatography analysis, 46:55
in plant cell-wall polymers, 42:281-283
polarography of, 29:127
preparation of, 32:22
protein linkage with, 25:418
reaction with
I-hexanethiol, 32:22
sulfuryl chloride, 28:238
syn-oxime, crystal structure, 43:336
uridine 5-pyrophosphateester, in mung
bean, 32:9
utilization by yeasts, 32:227
 SUBJECT INDEX
L-anti-oxime, crystal structure, 43:336
liquid chromatography of, 46:33, 52-53
3-O-a-~-galactopyranosyI-~-, 24:354, 372
0-a-o-galactopyranosyl-( 1+3)-0-01-~-
arabinofuranosyl ( I+~)-L-,24:372
3-O-u-D-XylOpyranOSy1-L, 24:370
from golden-apple gum by acid by
hydrolysis, 31: I88
O-a-o-xylopyranosyl(1-+3)-0-a-~-
arabinofuranosyl-( 1+3)-~-, 24:370
3-O-a-~-arabinofuranosyl-~-, 24:354,360
3-O-P-o-galactopyranosyl-~-,24:355, 376
3-O-P-~-glucopyranosyl-o-,preparation of,
31:97
O-P-D-XylOpyranOSyl-( 145)-0-a-~-
arabinofuranosyl-( I + ~ ) - L - , 24: 354
5-O-bemzoyI-o-, diethyl dithioacetal, partial
demercaptalation of, 3 2 6 7
2,3-U-bemzylidene-~-,diethyl dithioacetal,
oxidation of, 32:80
4-O-benzoyl-5-deoxy-5-iodo-2,3-0-
isopropylidene-r-, diethyl dithioacetal,
preparation of, 28:242
5-O-benzoyl-2,3-O-isopropylidene-i
-,
diethyl dithioacetal, reaction with
methyltriphenoxyphosphonium iodide,
28:242
3-O-P-~-arabinopyranosyl-~-
from golden-apple gum by acid
hydrolysis, 31: 188
from larch arabinogalactan by acid
hydrolysis, 31: 188
0-(D-glucopyranosyluronicacid)-( I-6)-O-
o-galactopyranosyl-( 1+3)-~-,24:358
4,5-O-isopropylidene-~-,
dibenzyl dithioacetal, oxidation of, 32:8 1
dithioacetals, preparation of, 32:54
5-O-methyl-~-,composition in aqueous
solution, 42:45
2-O-(methylsulfonyl)-o-, 23:260
5-O-p-tolylsulfonyl-, D-, dithioacetals,
reaction with lithium aluminum hydride.
3252
5-O-p-tolylsulfonyl-, L-
dibenzyl dithioacetal, reaction with
sodium iodide, 32:34
diethyl dithioacetal, ethylthio group
migration in hydrolysis of, 32:34
5-0-trityl-~-,diethyl dithioacetal,
preparation of, 32:46
55
in pectic polysaccharides, 42:277-278
removal from plant cell-wall during ripening,
42:375-376
5-S-ethyl-S-thio-, D-, diethyl dithioacetal,
hydrogenolysis by Raney nickel, 32:76
5-S-ethyl-5-thio-, L-, diethyl dithioacetal,
partial hydrolysis of, 32:67
5-S-methyI-5-thio-r-, ethyl methyl
dithioacetal, identification by mass
spectrometry, 32:94
2,3,4,5-tetra-O-acetyl-
aldehydo-L-
ammonolysis of, 31:84
preparation of. 32:62
D-, diethyl dithioacetal, nuclear magnetic
resonance spectra of. 3 2 8 8
ultraviolet photolysis of, 32378
4-thio-o-, composition in aqueous solution,
4253
5-thio-~-,23:213
2,3,4-tr-O-acetyl-
L-, diethyl dithioacetal, reaction with
ethanethiol, 32:34, 36
5-S-ethyl-5-thio-~-,diethyl dithioacetal,
preparation of, 32:34
5-S-methyl-5-thio-i.-. ethyl dithioacetal,
preparation of, 32:34
1,3,5-tri-O-acetyl-2-chloro-2-deoxy-~-,
aromatization of, 28:305
2,3,5-tri-~-benzyi-4-~-p-to~yIsu~fony~-o-,
dibenzyl acetal, preparation of, 32:5 1
2,3,5-tri-o-benzoyl-o-
dibenzyl acetyl, reaction with p -
toluenesulfonyl chloride, 3 2 5 1
diethyl dithioacetal
methylation of, 32:47
reaction failure with p-toluenesulfonyl
chloride, 3 2 5 1
2,3,5-tr-O-methyl-
D-, composition in aqueous solution,
42:46
I.-, dehydration of, 28: 181
UDP-L-. in polysaccharide biosynthesis,
42322
2-O-~-xylopyranosyl-~-, 46:305
Arabinose-5-14c-, L-, synthesis, 41:9
Arabinose-2-d, preparation of, 27: I33
Arabinose-5,5-d2, L-, nuclear magnetic
resonance spectroscopy of, 27: 148
Arabinose diacetamide, preparation of, 31:82
56 SUBJECT INDEX
D-Arabinose isomerase, isomerizations, of D-
arabinose and L-fucose, 36:46
Arabinose 5-phosphate
composition in aqueous solutions, 42:46
2-deoxy-2-fluoro-o-, 48:208
L-Arabinosidase, 42:383-394
a-,fruit ripening and, 42:375-376
classification of, 42384
exo-a-, in plant cell wall fractionation,
42:282
Arabinoside
methyl p-D-, catalytic oxidation of, 33:89
methyl p-L-,23:276
selective periodate oxidation of, 33:95
Arabinosyl cytidine hydrochloride, 2,2'-
anhydro-p-D-, 43:280-28 1
Arabinosyl fluoride
p-L-,hydrolysis rate of, 22:208
2-bromo-2-deoxy-p-~-,hydrolysis rate of,
22208
Arabinosyl groups, in xylans, 36:233-235, 241
Arabinosyloxy-L-proline-richglycoprotein in
plant cell wall, 42:309
Arabinoxylans, 24:369
aggregate formation by, 42:307
analogy with galactomannans, 31:268
antitumor activity of, 32:255-256
in cell walls of barley and wheat, 36:242
corn cob, enzymic analysis, 44: 160
enzymic analysis, 44: 160-1 6 1
enzymic degradation of, 31:276
hydrolysis of oxidized, 3 1:194
interconnections of, 4 2 3 14
isolation, 36:228, 23 1
oat spelt, enzymic analysis, 44: 163
oligosaccharides from enzymic hydrolyzates
from, 32346
soybean, enzymic analysis, 44: I62
structure of, 31:270
wheat bran, enzymic analysis, 44: I63
wheat flour, 36235
enzymic analysis, 44: 159, 163
Arabinoxyloglucan, enzymic analysis
Nicotiana tabucum. 44: 153
tora bean, 44: 154
Arabinoxylo-oligosaccharides, from xylans,
32347-349
Arabinuronic acid, D-, decarboxylation of,
28: 187
Arabionic acid, L-, strontium salt pentahydrate,
crystal structure bibliography, 31:363
Ara-C, crystal structure bibliography, 31:360
Arachis hypogaea lectin, see Peanut lectin
Aralkylthio group, participation in sugar
reactions, 22: 159
Arbusov reaction, 22: 182
Arbutin
catabolism by yeasts, 32:20 I
structure, 39:358
utilization by yeasts and associations of
abilities, 32:223
Arbuzov reaction, fluorinated carbohydrate
synthesis, 38:244
Arcanose
D-, synthesis of, 4278-79
natural occurrence of, 4 2 7 2
structure of, 4270, 78
Archaebacteria, thermacidophilic, branched
nonitol from, 42:76
L-Arginine L-ascorbate, crystal structure,
43:208-209
Aristeromycin, 50: 196
4-a-carba-, 48:23
crystal structure of, and hydrobromide, 25:85
hydrobromide, crystal structure bibliography,
31:371
Armed-disarmed concept, 52: 189-1 93
Armilluria mellea, polysaccharide, 41: 103
Amdt-Eistert reaction, 42: 110
Arabmonic acid, D-, preparation of, 29: 119
Aromatic compounds, biosynthesis of, from D-
glucose, 15:23 5-270
Aromatic hydrocarbons, 53:352-353
Aromatization, of 1,3,5-tri-O-acetyl-2-chloro-2-
deoxy-o-arabinose, 28:305
Arrhenius acids, 53:3 13-3 14
Arrhenius equation, 2 4 5 1
Arsenic compounds
of nucleosides, attempted preparation of,
28:253
tribromide, reactions with uridines, 28:253
trichloride, reactions with uridines, 28:253
trihalides, reaction with nucleosides in N,N-
dimethylformamide, 33:82
Arsenolysis, of glycogen, 23:355, 357
Arthrobacter
di-o-fructose dianhydrides and, 52:213-214
polysaccharides, 41:80
preparation, properties, and uses,
36999-300
 SUBJECT INDEX
Arthropods
a,&-trehalose in, 30:23 I , 234
glycolipids, see Glycolipids
Ariindo donux, cell-wall studies on, 42:292
Aryl cyanates, chlorination with hydrochloric
acid and, of carbohydrates, 28:257
1.2-tiuns Aryl glycohranosides, synthesis,
48:111
1,2-tvans Aryl glycopyranosides, synthesis,
48:111
Aryl glycosides, photoinduced cleavage of,
46: 182-1 83
Aryl halides, radiation and reactions with a-
hydroxyalkyl radicals, 37:22
Aryl migration, in p-nitrophenyl CY-D-
glucopyranoside. 33: 109
Aryloxypropanolamines, P-blocker side-chain,
49: I62
Aryl-thiocarbamide, taste properties, 45:3 I I
Asafoetida gum, 24:351
Ascaris S U U M ,trehalose biosynthesis in. 30:239
Ascarylose, 21:188, 190,50:171-172
degradation of, 28:3 I7
ester of cytidine pyrophosphate, isolation of,
28:316
Ascomycetes, polysaccharides of, 233367
Ascorbic acid, 53:296
5,6,-O-isopropylidene-r.-, selective
phosphorylation of, 33:48
and analogs, gas-liquid chromatography of,
28:76
analogs of, 2:79-106
constitution of, 22:4
D-, synthesis, 37:88, 123
D-firabif?o-, see Isoascorbic acid, D-
decarboxylation of, 28: 186
dehydro-L-
dimer, crystal structure bibliography,
30:452
polarography of, 29:168-170
o-phenylenediamine condensation
products, 29: I54
6-deoxy-6-fluoro-~-,48: 142
history, 35:5-6
L-
biosynthesis and structure of, 29:236
calcium salt dihydrate, crystal structure
bibliography, 32:354355
carbon-I3 nuclear magnetic resonaiice
spectroscopy, 41:64
57
synthesis, history, 41:2,7
cryslal structures of, 31:364, 37:83
labelled, commercially available,
37: 154-1 55
labelled, synthesis, 37: I5 1-1 55
nomenclature. 37:82
properties. 37:83-84
radiation-induced, free-radical
reactions, 37:65-66
sodium salt, crystal structure
bibliography, 31:364
and sodium salt, 25:91
L-. hydrogen bonding in, 25:57
structure, and spectral properties,
37:80-83
synthesis, 37:79-155
from o-glucitol, 37: 1 12-1 15, 149
by direct fermentation. 37:150-15 I
from 1.-sorbose, 37: 105- I 12
~-threo-2-pentosulose-cyanide,
37:86-89
from 1.-threose, 37: 149-1 50
from pectin, 37:147
Reichstein-Grussner, 37:89- I05
by way of D-galacturonic acid,
37: 146-1 48
by way of D-glucuronic acid,
37: 1 15-1 1 Y
by way of v-threo-2,5-hexodiulosonic
acid, 37: 137-140, 145-146
by way of ~-xy/o-5-hexulosonicacid,
37: 126-1 37
by way of L-gulonic acid, 37: I 19- 125
decarboxylation of, in acid solution,
46:289-290
dehydration of, 28: 188
dehydration of, mechanism of, 28: I92
trimethylsilylation of, 28:26
as growth regulator, 21:391
polarography of, 29: 168
selective phosphorylation of, 33:48
synthesis of, 26:198,248,33:219, 232,
38:2Y2, 3 14
liquid chromatography, 46:35-36
2-0-sulfato-i-, barium salt dihydrate, crystal
structure bibliography, 32:354
synthesis, Helferichs work on, 45:4
44
i--urrihino-, preparation of, 27: 134
I.-xylo-. preparation of, 27: 134
58 SUBJECT INDEX
Ascorbic acid (continued)
ultraviolet absorbances of, 46:65
[l-'4C]Ascorbic acid, L-, preparation, 37: 154
[2,3,4,5,6-'4C]Ascorbicacid, L-, preparation,
37: 154
[4-3H]Ascorbic acid, L-, preparation,
37:152-153
[5-2H]Ascorbicacid, L-, preparation, 37: 152
[5-'4C]Ascorbic acid, L-, preparation, 37: 154
[6-3H]Ascorbic acid, L-, preparation,
37: 151-152
[6-'4C]Ascorbic acid, preparation, 37: 154
Ascorbigen, 21:392
Ascoric acid, 3-U-
[(bismorpholino)phosphinyl]-5,6-U-
isopropylidene-L-, crystal structure,
43:249
Asialo a,-acid glycoprotein, 'H-NMR
spectroscopy
glycoprotein (compound 8), 41:219,237,
-240
glycoprotein (compound 9), 41:2 19,
239-242
glycoprotein (compound 13), 41:219,239,
248-25 1
glycoprotein (compound 48), 41:306,
3 19-32 1
glycoproteins (compounds 49,50, and 51),
41:306,31&315,321-324
Asialo ceruloplasmin, glycoprotein (compound
48), 'H-NMR spectroscopy, 41:306,
309-321
Asialo-fetuin glycopeptide fraction C, 44:240
Asialo-orosomucoid, 44:233
binding to liver membranes, 37:273-274
Asparagine
2-acetamido-2-deoxy-~-~-glucosyl-~-,
linkage with N-glycopeptides,
50~278-283
anomeric azides as precursors,
50:27&280
1-hydroxy-D-glycosaminesreactions with
ammonium hydrogencarbonate,
50:282-283
I-isocyanates as precursors, 50:281-282
in situ anomerization,50:280-281
D-, superpositionedover same receptor site,
45236
L-
carbohydrate chains linked to, in
glycoproteins,26:460
in glycoproteinlinkages, 25418,420
0-glycosyl derivatives, synthetic,
43: 135-20 1
superpositionedover same receptor site,
45:236
4-N-(2-acetamido-2-deoxy-p-o-
glucopyranosy1)-
I3C-NMR spectrum, 43:lO-11
L-, 43:4
Asparaginylglucosaminuria,oligosaccharides
and glycoasparaginesfrom urine,
structure, 37:198
Asparagus-pea lectin
carbohydrate-binding specificity,
35285-288
composition, 35284
isolation, 35:138
purification, 35283
Aspartame
possible conformations, 45:308-309
and interaction with receptor site, 45309
stabilizing properties of caramel, 4 7 2 3 1
sweetness, 45306-307
AH, B system in, 45:22 1
relative, 43332
structure relationship, 45245
Aspartamidoglycan,from ovalbumin,
28:440-442
L-Aspartate-oxoglutarate aminotransferasein
fruit climacteric, 42:365
L-Aspartic acid, in glycoproteins,25: 149,421
from sheep and ox, 33:7
Asparticin, inhibitor of protein glycosylation,
40:342
L-Aspartoyl-aminomalonicacid, esters, taste
properties, 45:307-308,310
L-Aspartoyl-D-alaninamides,taste properties,
45:306
a-L-,Aspartoyl-D-alanine isopropyl ester, taste
properties, 45:307
N-(L-Aspartoy1)-1,l-diaminoalkanes, taste
properties, 45:306
L-Aspartoyl-t-phenylalanine methyl ester, see
Aspartame
Aspartylglucosaminuria,'H-NMR
spectroscopy
glycoprotein (compound 3), 41:219,
225-226
glycoprotein (compound 55), 41:333-337
 SUBJECT INDEX
glycoprotein (compound 56), 41:333,
336338
glycoprotein (compound 57), 41:333, 335.
337-33 8
glycoprotein (compound 58). 41:333.
337-3 39
glycoprotein (compound 59), 41:333, 337,
340-342
glycoprotein (compound 60), 41:333, 337,
340-343
'H-NMR spectroscopy, glycoprotein
(compound I), 41:219-224
Aspen, cell wall studies on, 42281
Aspergillusjlavus, polysaccharides, 41 :95
Aspergillus firmigatus
di-D-fructose dianhydrides and, 52:2 13-2 14
polysaccharides, 41 :95
Aspergillus nidulans
cordycepin from, 31:149
polysaccharide, 41:69-70,95, 101
Aspergillus niger, 53:2 1 1
a-r-arabinofuranosidase from, 42384,
386-387,390-392
galactomannan, 41:94
heteropolysaccharide, 41:70, 94. 10 I
glucoamylase, 50:1&18
transglycosylation processes. 52: 10
Aspergillus otyzae
exo-enzyme, 44: 154, 156
trehalase from, 30:251-252
Aspergillus terreus, polysaccharides, 4 I :95
Asperlin
in benzene solution, configuration and
conformation, 45: 160-161
proton spin-lattice relaxation rates, 45: 141
Aspidosperma australe, 46: 13
Astraglin, as plant-growth substance, 21 :412
ATP regeneration, sugar phosphates,
49:208-2 10
Atrazine, as herbicide, 21:406
Atrolactic acid. asymmetric synthesis of,
27: 193,200
Atropine-like drugs, preparation of, 27:2 13,
219
Atropisomerism, 2 4 5
Aureobasidium pullulans
heteropolysaccharide, 41 :96
polysaccharide, 41:72,41:75
pullulan, preparation, properties, and uses,
36:3 1cL3 12
59
4 uricularia auriculajudae, polysacccharide,
41:75,97
Autohydrolysis, of polysaccharides, 24:338
Automation, and crystal-structure
determination, 30:446
Autoradiography
biosynthesis sites and. 26:469
of cell-wall polysacchandes, 26:34 1, 344
histochemical detection and localization of
sugars in tissue by, 27: 18 I
Auxins, 21:378
in fruit ripening, 42:341-345,348-35 I , 355
plant cell-wall growth, 26:346
respiration and metabolism in plants, 21:387
on starch in plants, 21:386
on sugar cane, 21:424
Auxogluc, 45:202-205,218
Avena coleoptile, cell wall studies on,
42267--268,300, 349, 352
Avidin, carbohydrate linkage in, 25:420
Avocado
development physiology of, 42:341, 343,
363,369,371-372,379-380
sugars, gas-liquid chromatography of, 28:49
Axenose
natural occurrence of, 4 2 7 2
structure of, 42:70
synthesis of, 42: I I9
Axial bonds. 26:52
Axinella po1.vpoides lectins, isolation and
properties, 35:3 16
2-Azaadenosine, hemihydrate, crystal structure,
43:279
8-Azaadenosine. crystal structure bibliography,
323381
monohydrate, 38:486
6-Azacytidme
crystal structure bibliography, 32:372
selective tritylation of, 33:51
2',3,'5'-tri-O-formyl-, methanolysis,
selective, 39:37
Azaoxabicyclo compounds, hydrogenolysis,
39: 134-1 35
6-Azapseudouridine, synthesis, 40:80
6-Azathymidine, crystal structure bibliogaphy,
38506-507
8-Azatubercidin, monohydrate, crystal structure
bibliography, 3 8 5 1 1-512
6-Azauraci1, 5-o-pentitol-l-yl-, preparation of
isomeric, 33: 176
60 SUBJECT INDEX
6-Azauridine
crystal structure bibliography, 31:355
5-niethy1, 5-phosphate, 22:373
5-phosphate, 22373
monohydrate, crystal structure
bibliography, 31:359
trihydrate, crystal structure, 43:273-274
selective tritylation of, 33:5 1
2,3,5-tri-O-formyl-,methanolysis,
selective, 39:37
Azepine, sugar derivatives, 25:404
Azides
anomeric as precursors, 50:278-280
I ,4:3,6-dianhydrohexitols,49: 154
irradiation of carbohydrate, 38: 176-178,
180-1 84
sugar, aziridine sugars from, 25:354
Azido ketonucleosides, synthesis of, 42:257
2-(2-Azidophenyl)ethyl
alcohol, 46:200
photocyclization of, 46:201
Azido-pheylselenylation, 53: 16 1-1 67
Azidosphingosine, derivatives, glycosylation
with trichloroacetimidates, 50:41,
45-48
Azines
of o-fructose, 22:280, 303
irradiation of carbohydrate, 38: I86
Aziridirie ring
fonnation in sugar reactions, 22: 143, 146,
151
saccharides containing, 25:352-356
stability of, 34: 13I
Aziridines
glucosidase inhibition, 48:37 1-373
preparation of, 27:257,264
reaction with nitrous acid, 31:66
Aziridinium chloride, N,N-diethyl-, and
reactivities of hydroxyl groups toward,
33:57
Aziridino ketonucleosides, synthesis of, 42:
257
Aziridinyl groups, anomeric effects, solvent
effects, 47:68-69
Azoospermia, o-fructose level in, 34:304
Azo-proteins, preparation and properties,
37:230
Azotohacter indicum, see Belierinckia indicu
Azulenes, C-glycosylation in preparation of,
33: 159
B
Bacillosamine, 23: 155
Bacillus circuluns, trehalase from, 30:25 1
Bacillus licheniformis peptidoglycan, crystal
structure bibliography, 40:399
Bacillus maceruns, 46:212, 2 15-217
cyclodextrin transglycosylase, 46:207
Bacillus potvniyxa, polysaccharide, 36:300
Bacillus .subtitis
a-1.-arabinofuranosidase from, 42387-388
endo-L-arabinanase in, 42392-393
L-arabinanases from, 42:384, 391
teichoic acid from, 21:350, 354
Bucillus thrtringiensis, exotoxin from,
preparation of, 34: 170
Bacitracin
effect on peptidoglycan biosynthesis,
26:43 1
inhibition of protein glycosylation,
40:325-326
Bacteria, see also specific species
a+-trehalose in, 30:230,234
amphiphiles, 44:277
cell-walls
extension in, 42:51
lipopolysaccharides of gram-negative,
26:409424
peptidoglycan in, 26:424432
synthesis. 44:342
dextran-synthesizing, 30:373
gas-liquid chromatograpliic analysis for,
28:XI
glucansucrases, 51: 138-139
glycolipides of acid-fast, 16:207-238
gram-negative
extracts, gas-liquid chromatography of,
28:59
lacking lipopolysaccharides, 50:262-263
infection, immune response of capsular
polysaccharides, 41: 186-191
lipopolysaccharides, 44:277
0-specific chains, biosynthesis,
44:3 12-3 I9
block mechanism, 44:3 12-3 18
monomeric mechanism, 44:3 18-3 19
structure, enzymic analysis, 44:230-23 1
mass spectrometry of polysaccharides from,
29:66
nucleosides and nucleotides of, 15:201-234
 SUBJECT INDEX
peptidogl ycans
carbohydrate chains. assembly.
44:330-333
structure, enzymic analysis, 44: 195- I98
polysaccharides, 2:203-233,3:311 336
acetyl-substituted, 48:304-306
acyl groups, 48:306-3 1 1
alditol phosphates, 48:3 16-3 17
amides, 48:311-313
biosynthesis in, 42:323-327,443278-279.
48:318
glycosyl esters of nucleotides and
polyprenyl glycosyl phosphates in.
44:279-286
of polymeric chains for, activation of
monosaccharides for, 44:302 303
biosynthetic classification, 4 4 3 3 4 335
branched-chain monosaccharides.
biosynthesis, 44:299
branched-chain sugars, 48:287-288
capsular, 44:277
1 -carboxyethy1 ethers, 48:303-304
chains
composed of oligosaccharide repeating
units, biosynthesis, 44:278-339
groups, 44:277
monosaccharide components.
biosynthesis, 44:286-302
complex, structural aiid sequencc analysis
of, 46:57
diamino sugars, 48:292
disaccharide fragments, 44:307
having most common monosaccharides
at nonreducing end, 44:307-308
isomeric, composed of most common
monosaccharides, 44:308-300
enzymic synthesis, from modified
percursors, 44:335-339
ether and acetal substituents, 48:290-306
exocellular, 44:277
biosynthesis
block mechanism, 44:32&323
monomeric mechanism, 44523-326
by unidentified mechanism of chain
assembly, 44:326-327
structure, 44:376
extracellular, 44:277
Acinohucter. enzymic analysis, 44:230
Agrobacterizmt, enzymic analysis.
44:225-226
61
Alroligenr.v. enzymic analysis.
44:225-226
Klebsidlu
enzymic analysis, 44:2 17-225
phage hydrolysis. oligosaccharides.
released by. 44:218-224
liquid chromatography fractionation,
46:49
phage-induced hydrolysis, 44:228-
230
R h i ~ o b i ~enzymic
~i. analysis,
44225-229
f.a.b.-mass spectrometry, 45365-66
furanose monosaccharides. biosynthesis,
44:298-299
glycerol phosphate substituents, 48:3 15
glyculosonic acids. 48:295-298
glycuronic acids, 48:293-295
of Gram-negative. 15:27 1-340
of Gram-positive cell walls, biosynthesis
block mechanism, 44:327-328
monomeric mechanism, 443328-329
unidentified mechanism of chain
assembly, 44:329-330
heptoses, 48:285-287
hexose components, see also Hexoses
of configurations other than glut-n.
gtrlocto, and monrzo. biosynthesis,
44:295-298
hexoses. 48:281-285
inter-monomeric linkages in, 44:305-
309
linkage region, 44:278
methyl ethers, 48:300-302
monoamino sugars. 48:290-292
monosaccharides
modifications of functional groups in,
44: 302-3 05
structurally related to ri-fructose.
biosynthesis, 44:298-299
structures, 44:302-303
non-sugar aglycons, 48:299-300
0-specific lipopolysaccharides,
biosynthesis. 44:290-293
pentoses. 48:281
biosynthesis, 44:298
phosphoric esters, 48:313-3 17
polymeric chains
assembly, 44:309-335
mechanisms. 44:31&312
62 SUBJECT INDEX
Bacteria (continued)
structure, and mechanism of assembly
44:333-335
reducing terminal linkage, 48:3 15
structure, enzymic analysis, 44:217-23 1
sulfated, 48:3 13-3 14
synthesis, 51: 135-138
teichoic acids, 48:315-316
serological identification of pathogenic,
39:437
sialic acid occurrence, 40: 134
surface structures of Grampositive, 21:324
themiophilic, 46:211
trehalase from, 30:247
virulence
capsular polysaccharide activity, 41: 189
role of capsular polysaccharides,
41:202-206
Bacteriostatic activity, of apiosyl nucleosides.
31:184
Baeyer, Adolf von. 45: 1
Baeyer-Villiger reaction, 34:98
Baiyunoside, synthesis, 48: 107
Baker, Bemard Randall, obituary, 29: 1-10
Bamboo
arabinogalactan, 36:243, 26 1
cell-wall studies on, 42:268
polysaccharide from, antitumor activity of,
32:253-255
xylans, 36:234
Bamford-Stevens reaction, 34:98
Bamosamine, 24: 159
Banana
developmental physiology of, 42:363, 369,
379
pectinesterase, see Pectinesterases
Bandeirueu simplicifolia
I lectin
carbohydrate-binding specificity,
35:264-266
purification and properties, 35:262
I1 lectin
carbohydrate-binding specificity, 35:206
isolation, properties, and structure,
35:206-208
lectin isolation, 35: 137, 138
Band 3 lactosaminoglycans
f.a.b. mapping, 45:3841
f.a.b.-mass spectrometry, 45:35, 59
Barbaloin, 25:243
Barban, as herdicide, 21 :404
Barbituric acid
5-(2,3-~-isopropylidene-5-~-trityl-P-~-
ribofuranosy1)-, sodium salt, preparation
of, 33: 179
tho-, reaction with cleavage products of
pectic substances, 33:368, 380
Barium o-ribose 5-phosphate pentahydrate,
crystal structure bibliography, 31:363
Barium ion, effect on reducing sugars in
solution, 42:33
Barium 2-O-sulfato-~-ascorbate,dihydrate,
crystal structure bibliography, 32:354
Barium oxide, complex with sucrose, 21:213
Barium salts, 53:31S
Barley
cell-walls
arabinoxylans, 36:242-244
studies on, 42:271,293-294, 314-315
glucan, carbon-13 nuclear magnetic
resonance spectra, 38:49-50
hemicellulose-cellulose ratio, 36:253
lectin, isolation and properties, 35:3 14
xylans, 36:235
Barry degradation, 24:342, 345
of carbohydrates, 35:9
of polysaccharides, 31:202-203
Base-catalyzed rearrangement, bromodeoxy
aldonolactones, 50: 175-1 79
Bases, 53:313-314
catalysis of mutarotation of sugars by, 24: 14
effect on reducing sugars in solution, 42:34
ketonucleoside stability in, 42:247-248
reactions with dithioacetals, 32:5740
Basidiomycetes, polysaccharides of, 23:367
Bauerlein, Karl, 45:3
Bauhinia purpureu alba lectin
carbohydrate-binding specificity, 35:305
composition and purification, 35:305
isolation, 35: 138
Baumycins, 48: 10
BB-KI (antibiotic), preparation and
antibacterial activity of, 30: 174
SP-Carda-8( 14), 20(22)-dienolide
3b-O-(2-deoxy-a-~arabino-hexopyranosy1)-
,21:280,302
3P-bydroxy-, 21:279
SP-Carda- 14,20(22)-dienoIide
3P-O-(a-~-rhamnopyranosyl)-,21 :289
3P-hydroxy-, 21 :279
 SUBJECT INDEX
SP-Card-20(22)-enolide
I9-O-(a-~-mannopyranosyl)-3~,5, I4P-
trihydroxy-, 21:294
3b-0-(a-o-rhamnopyranosy1)-
5,14P-dihydroxy- 19-0x0-, 21:290
14P-dihydroxy-19-0x0-, 21 :290,296
14@-hydroxy-,21:296
3b-O-(a-~-rnannopyranosyl)-S, 14P-
dihydroxy-19-0x0-, 21:292
3P,12P,14P-trihydroxy-, see Digoxigenin
3b-O-(P-~-ghcopyranosyl)-5146. 19-
trihydroxy-, 21:288
3P. 14P-dihydroxy-, 21:273
3P, 19-di-O-(a-r-rhamnopyranosyl)-
5,14P-dihydroxy-, 21:294
3P,5,14P,lY-tetrahydroxy-, see
Strophanthidol
3P,5,14P-trihydroxy-, see Periplogenin
Ig-oxo-, see Strophanthidin
3~-(2-deoxy-~-~-~vxo-hexopyranosy~)oxy-
14P-hydroxy-, synthesis of, 27:4
3h-O-(2-deoxy-P-o-ribo-hexopyranosyl)-
,14P-hydroxy-, 21:306
3b-0-(2,6-dideoxy-a-o ribo-hexopyranosy1)-
14P-hydroxy-, 21:299,301,3 12
3b-O-(2,6-dideoxy-P-o-ribo-hexopyranosy1)-
14P-hydroxy-, 21:299, 301,30X
3b-0-(2,6-dideoxy-3-O-methyl-P-o-riho-
hexopyranosyl)-5,14~-oihydroxy- 19-
0x0-, 21:293
14P-hydroxy-3-oxo-,21:306
Beans
cell-wall studies on, 42:271,288, 301, 328,
35 1
cyclic AMP in, 42367
lectins and toxic properties, 35: 130
Beech
cell-wall studies on, 42282-283
glucuronoxylans, spectral analysis and
identification, 44:24
polysaccharides, 24:376-377
Beef ganglioside, circular dichroism, 45: I I2
Beer, analysis by gas-liquid chromatography,
28:46
Beers Law, 45:76
Beetles, repellents for, 24:7
Beets, see Sugar beets
Beijerinckia indica, polysaccharide,
preparation, properties, and uses,
36:297-298
63
P-Eliminative degradation, see Degradation
Bell, David James, obituary, 3O:l-8
Bengal Rose. 53:384
Benzaldehyde
compounds with alditols, 21: 19
reaction with glycerol, 34: 181
Benzamide, N-cyclopropyl-4-(decyloxy)-3,5-
dimethoxy-, synthesis as antiepileptic
agent, 28:9
Benzamido youp, participation in sugar
reactions, 22: 134
Benzene, 53:27 I
a-wand P-o-glucopyranosyl-, tetraacetates.
25240
azeotropic removal of water. 51:248,
250-2s I
o-galactopyranosyl-, preparation of, 33: 158
o-glucopyranosyl-, preparation of, 33: 158
2,4-dihydroxy-1 -P-o-nbofuranosyl-,
antitumor action of, 33: 160
2,s-dihydroxy- 1 -o-ribofuranosyl-,
preparation of, 33:159-160
2,4-dimethoxy-1-(2,3,5-tri-O-benzoyI-o-
ribofuranosy1)-, preparation of,
33: 1 59-160
2,s-dimethoxy- I -(2,3,5-tri-O-benzoyl-o-
rihofuranosy1)-, preparation of,
33: 159-1 60
o-mannopyranosyl-, tetraacetate, 25:24 1
o-xylopyranosyl-, preparation of, 33: 158
fluoro-. complex with amylose, crystal
structure bibliography, 33:39 1
1-fluoro-2,4-dinitro-, reaction with amino
group in dithioacetals, 32:SS
2-[(3-hydroxy-4-methoxyphenyl)ethyl]-,
sweetness, 45:285
iodo-, dichloride, reaction with tri-0-acetyl-
o-glucal, 28:263
1-nitro-4-P-~-rihofuranosyl-,synthesis of,
33: 144
2,3,4,6-tetra-0-aCetyl-P-D-glUCOpyranDSyl-,
preparation of, 33:142, IS8
2,4,6-trimethoxy- 1-
P-o-ribofuranosyi-, preparation of. 33: 160
(2,3,S-tri-O-benzoyl-P-o-ribofuranosyl)-,
preparation of, 33: 159
Benzeneboronic acid
effect of o-fructose on, 22:287
reaction with sulfonic esters of
carbohydrates, 23:267
64 SUBJECT INDEX
Benzeneselenyl triflate, 53:191-192
Benzenesulfenyl chloride, mercaplalation with,
32:26
Benzenesulfonamide, N.N-dibronio-,
brominations, 39: 1 19
Benzenesulfonyl chloride
2,4,6-triisopropyl-
esterification of nucleotides by, 33: 13
intemiediate in nucleotide formation,
36:157, 171
sulfonylation with, 33:34
2.4.6-trimethyl-, selective esteriiication with,
33: 14
Benzenethiol
in dithioacetal preparation, 32: I , 17
o-amino-, reaction with aldoses, 32:20
Benzilic acid, rearrangement, 25:3,44
in alkaline degradation, 28:205
in dehydration of sugars, 28: 171
in lactic acid of formation, 28: 197
in saccharinic acid formation, 28: 194
Benzimidazoles
2-(aldo-polyhydroxyaIkyI)-,6: 175-203
carbohydrate derivatives, polarography of,
29:154, 160
2-chloro- 1 -p-D-ribofuranosyl-, crystal
structure bibliography, 31:358
o-glucuronic acid conjugates, synthesis,
36: 129
sugar derivatives, 25:373
2-Benzimidazolethio, 1-P-D-ribofuranosyl-,
monohydrate, crystal structure
bibliography, 31:358
I ,2-Benzisothiazolin-3-one 1 ,]-dioxide, see
Saccharin
Benzoate ion, cyclodextrin inclusion complexes
with, 46:221
Benzoates, p-chloro-, in conformation analysis,
26:63-64
Benzoic acid
4-butoxy-3,5-dimethoxy-,2-( 1-
pyrro1idinyl)ethyl ester, as spasmolytic
agent, 28:9
2-chloro-, as herbicide, 21:408
3-chloro-, as herbidcide, 21:408
4-chloro-, as herbicide, 21:408
cyclodextrin inclusion complexes with,
46:221,234
2,6-di-terf-buty-4-(hydroxymethyl)-, I -ester
with o-glucuronic acid, 36: 104
esters
of n-glucuronic acid, 36: 104, 106, 108
of diethylaminoethyl polysaccharide
ethers, 29:325
of sugar dithioacetals, preparation of,
32:45
as herbicide, 21:408
2-hydroxy-, see Salicylic acid
3-hydroxy-, as herbicide, 21:408
4-hydroxy-, as herbicide, 21:408
m(and p)-amino-, reaction with nitro olefins,
24: I36
methyl ester, transesterification of methyl a-
o-ghcopyranoside with, 33:44
p-nitro-, esters of sugar dithioacetals,
preparation of, 32:45
2,3,5-tniodo-
effect on abscission and ripening, 21:429
as herbicide, 21:407
2,3,6-trichloro-effect on sugarcane, 21:427
2,4.6-trimethyl-, esters, hydrolysis, 39:34
Benzoic chloride, p-phenylazo-, esterification
with, effect of hydrogen-bonding on.
33: 15
Benzoin, esters of, photocyclization of, 46:201
Benzonitrile, 2,6-dichloro-, inhibitor of
cellulose biosynthesis, 41:144
Benzoquinones, formation, 46:294
Benzothiazole, derivatives, preparation of,
32:20
Benzotriazole
S,b-dirnethyl-, reaction with glycals, 24:2 17
2-(3,4-di-O-acetyl-2-deoxy-P- r-erythro-
pentopyranosyl)-5.6-dimethyl-, crystal
structure bibliography, 37:427
2-(4-O-acetyl-2,3-dideoxy-P-~-glycero-pent-
2-enopyranosyl)-5,6-dichloro-,crystal
structure bibliography, 34:371
reaction with glycals, 24:217
Benzoxonium ions
reaction with nucleophiles, 39:l 13, 151-152
rearrangement, 39: I0 1-1 02
Benzoxonium salts, 26: 130
Benzoylacetic acid cyclodextrin inclusion
complexes with, 46:223-224
Benzoylation
of 1,6-anhydrohexopyranoses,34:82
of carbohydrate boronates, 35:53
in excess of pyridine, 50: 164
of glycosides. 23:249
 SUBJECT INDEX 65

selective, of maltose derivatives, 39:225-227 Bergmann. E., 45:9

Benzoyl chloride, reaction with amino group in
dithioacetals, 32:55
Benzoyl cyanide, selective benzoylation with.
33:45
Benzoylformyl group, in nucleosidc chemistry,
39:41
Benzoyl groups in syntheses with dithioacetals.
32:66
Benzoyloxy group
participation in sugar reactions, 22: I 17
reactivity of. in acyloxonium slat fomiation.
26:131
Benzoyl-phenylmethanol (benzoin) esters. as
protecting group, 46:200-201
3-Benzoylpropanoyl group, in nucleoside
chemistry, 39:41
3-Benzoylpropionyl group, as protective group
in nucleosides and sugars, 33:248
Benzoylribitol, 1,5-anhydro-2,3,4-tri-0-.crystal
structure, 43:258
Benzoylxylitol, 1,5-anhydro-2,3,4-tri-0-, 4753
crystal structure, 43:258
Benzyl alcohol, a-methyl-, R and S isomers,
preparation of, 27: 197
Benzylation, 53:61
of 1,6-anhydrohexopyranoses,34:85
Benzyl ethers
acetolysis of, of acetals, 22: 15
in carbohydrate synthesis, 31:4
photochemical cleavage of, in presence o f
bromine, 46:182-183
of sugars, 12:137-156
Benzyl glycosides, preparative liquid
chromatography, 46:60
Benzyl groups
protecting groups, 36: 147-149
in synthesis of methylated sugars, 30:4
Benzylidenation
of D-ribose, 34: 184
of D-xylose, 34: 186
with gem-dihalides and base, 34: I89
Benzyloxycarbonyl chloride
reaction with amino group in dithioacetals,
3255
in selective esterification, 33:23
Benzyloxy group, effect on sugar reactions,
22:114
Benzylthiocarbonyl chloride, selective
acylation with, 33:20
Beta amylase, 47:298
catalysis of P-maltosyl fluoride hydrolysis,
48:358-359
Betueorcus awhinosuc,eus, dextran from
sucrose by, 32:5
Betaines, formation in Wittig reaction.
27:290-292
Betaprenol, structure, 44:346
Betulaprenol, structure, 44:346
Beverages. polarographic determination of 2-
furaldehyde in, 29: 167
Bibliography
crystal structures
of carbohydrates, nucleosides. and
nucleotides. 30:445466,
31 :347-37 I , 32:353-384,
34:345-378,37:373436,
38:417-529
of polysaccharides, 33:387404,
35:377-385,36:3 15-332,
40:381-399
of Edmund L. Hirst and colleagues
publications, 35: 17-29
of Edward John Bournes published works,
34: 13-22
Emil Hardegger publications, 38:& I 1
John Kenyon Netherton Jones publications,
41:ll-26
Bicyclic precursors, sugar synthesis, 40:74-80
Bicyclic systems, carbohydrate, sulfonylation
of, 23:250
Bicyclo[2.2. Ilheptane, carbohydrates
containing ring, 24: 176
Bile-acid glucosiduronates, synthesis and
occurrence, 36:95
Bilirubin
in biosynthesis of saccharides, 26:440
conjugates with o-glucuronic acids, 36: 105,
116-119
structure, 36: 1 16
Binder, dextrins as, 47:324-325
Bioactive products, from marine
microorganisms, 48: 14
Biochanin-A, from lanceolarin, 31: 147
Biochemical reductions. at the expense of
sugars, 4:75-117
Biochemistry. see al.so specific substances
of a-o-gahctosidic linkages in plant
kingdom, 37:283-372
66 SUBJECT INDEX
Biochemistry (continued)
ofapiose, 31:135-184
p-o-fructofuranose in, 22:230
o-fructose derivatives in, 22:289
energetics, 30:7
hydrogen movement within the cell and
incorporation into cell components,
27:177
incorporation of labeled monosaccharides
into polysaccharides, 27: 179
mechanistic, hydrogen-labeled sugars in
study Of, 27~155-176
of monosaccharides having sulfur or nitrogen
in ring, 23:212
pathway of enzymic transformations in
tritiated compounds, 27: 176
of plant galactomannans, 35341-376
of resistance to aminoglycoside antibiotics,
30: 164, 183-225
stereochemistry and, 21:34
Bio-Gel P, 25:15,20,23
Biogenesis, of cellulose and plant cell-walls,
26:297-349
Bio-Glas, 25: 15
Biological activity
of fluorinated carbohydrates, 38:28 1-284
of gulonic acids and gulono- 1,4-lactones,
38:320
of herbicides, chemical structure, physical
properties and, 21:408
Biological assays, see spec@ substances:
specific tern
Biological fluids, gas-liquid chromatographic
analysis of, 28:80
Biological functions, sialic acids, 40:2 I &
232
Biologically active compounds, configuration
and purity of, 27:205-22 1
Biomass
conversion processes, carbohydrates in,
analysis of, 46:52-54
polysaccharides in, 46:306
Biopolymer CS, see Scleroglucan
Biosynthesis
of ap-trehalose, mechanism of,
30:236-245
of antibiotic sugar components, 3 5 8 1-126
of apiose in vivo,31: 154-162
of aromatic compounds from D-ghCOSe,
15:235-270
of cellulose, 26:319-326,32:11-12,
41: 105-1 53
structural considerations, 41: 110-1 16
of dextrans, 30:418433
of enzymes, adenosine cyclic 3',5'-
phosphate in, 30:224
guanosine 5'-tetraphosphate in, 30:225
of galactomannans, 31:255-256
of glycans, 37:182-189, 218-221
of glycoenzymes and glycoproteins, 27:303,
308,328-337
of glycoproteins, 25:467472
of glycosphingolipids, 40:24&268
enzyme preparation and enzyme assay,
40:245-247
of hyaluronic acid, 12:299-319
of immunoglobulins, genetic control of,
31:317
lipid-linked oligosaccharides, 40:288-32 I
of L-streptidine, 27: I77
of microbial exopolysaccharides,
36:286-289
of the monosaccharides, 11: 185-262
of nucleotides, 27:336
of plant galactomannans, 35352-356
of polysaccharides, 33:296
of raffinose family oligosaccharides,
37:351-360
of saccharides, from glycopyranosyl ester of
nucleotides, 18:309-356
pyrophosphates, 26:35 1 4 8 3
of sialic acids, 40: 170-194
sites of, 26:466471
of sucrose, 32:7
ofteichoic acids, 21:372
of I-thio-P-o-glucosiduronicacids, 36:
103
of UDP-o-apiose by decarboxylation,
31 :162-169
Biotin
absolute configuration of, 27:212
dethio-, synthesis and absolute configuration
of, 27:2 12
and isomers, 29:2
4,4'-Bipyridinium bis(methy1 sulfate,l,l '-
dimethyl-, effect on sugarcane, 21:422
Birch xylan, see Xylan
BIRD pulse, 51:19.23
Birefringence of gels, 24:305
Birotation, term, 23: 12
 SUBJECT INDEX
Bis(acetamid0) sugars, circular dichroism.
45:98
N , N -Bis (2-minoethyl) ethylenedianiine, as
matrix for f.a.b.-mass spectrometry. 45:26
Bis( 1.4-anhydroerythritol) sodium iodide.
crystal structure bibliography, 37:374
Bis(P-D-fructopyranose) calcium chloride
trihydrate, crystal structure bibliography,
32:359
Bis(2-chloroethyl)methylamine,in cellulose
cross-linking, 3 3 6 3
Bis(cyc1ohexaaniylose) lithium triiodide
complex, crystal structure bibliography,
34:372
Bis(cycloma1tohexaose)
cadmium polyiodide, hexacosahydrate.
crystal structure, 43:267
lithium triiodide iodine, octahydrate. crystal Blasticidin S, 24:226, 238
structure, 43:267-268
Bis( 1,4:3,6-dianhydro-~-mannitolo)-30-crown- biosynthesis of, 35:12&125,42:230, 262
10,49:107-108
Bis(2,4-dinitrophenyIhydrazone),49: I 56
Bis-nomaytasinoid, 50: I95
Bis(2,3-O-sodioinosine S'-monophosphate)
(diethylenetriamine) copper( II),
decahydrate, crystal structure
bibliography, 38:523-524
Bisoxirane
affinity chromatography adsorbent supports,
39:431432
agarose activation for affinity
chromatography, 39:415
Bistable (two-state) jump model, 51: 120
3'5,'-Bis(thymidylyl)
difluoromethylphosphonate, synthesis and
biological activity, 48:266
Bitterness, see also Sweetness
AH,B concept for. 45:3 12-3 I8
anomeric hydroxyl group essential for.
45240-241
biochemistry, 4 5 3 10-325
bitter-sensitive protein
equilibrium constants of binding of bitter
compounds, 45:3 I 1
from porcine tongue, 45:3 1 1
taste threshold of bitterness, for various
compounds, 45:3 I I
bitter-sweet molecules
binding to receptor, 45:322-324
polarization on taste receptors, 45:324
67
receptor locations, 45:320-322
topographical overlap of interaction
patterns on taste receptors,
45:323-325
and configuration of anomeric center.
45:239
initial chemistry, 45:3 1 1
and lipophilicity, 45:243, 3 18-320
and nitro groups, 45:3 10
role of structure in, 45:200
structural parameters for, schematic
representation. 45:3 15-3 17
Bivalent substitution prefixes, 52: 143- 145
Bivalves, glycolipids, see Glycolipids
Black-locust lectin, see Rohiniu yseudoaccaciu
lectin
Blasticidin H. biosynthesis of, 42:262
antibiotic, 33:200
crystal structure of, 21:84
structure of, 42:229
Blastmycinone
(+)-, 50~184
natural occurrence of, 42:73
structure of, 42:71,78
synthesis of, 42: 129
Blustocludiella emersonii. glycogen. 41 :69
Blustomjws dermatiditis
galactomannan, 41 :93
polysaccharide, 41:70
Blastymycinolactol isomers, synthesis of,
42: 129
Bleomycin
migration of carbainoyl groups and antibiotic
activity, 33: 102
research, Japan, 48:9-10
Bleomycin A,, '?C-NMR structural analysis,
43:4748
Blix sulfatide, 24:405,407
Blood
a-D-mannosidase in human, 28:403
D-fructose
in fetal, 30:s
metabolism in. 34:298
D-glucitol determination in. by gas-liquid
chromatography, 28:57
gas-liquid chromatography of, 28:4547. 81
supply. effect of antitumor bacterial
polysaccharide on, 32:264
68 SUBJECT INDEX
Blood-group determinants
biosynthesis of, 26:472475
blood group O,Le(a-b-), 4 9 5 6
glycosides related to, W N M R data for,
42:217-219
human, p-elimination and degradation of,
31:214
Lewis a, preparation of, 34:268
MN
dispIay,4.5:171, 191, 194-195, 197
by glycophorin A, 45: 175
functional groups with crucial role in,
4.5: I94
oligosaccharides, liquid chromatography
separation, 46:43
polysaccharides of, 4:37-55
Ss, 45: 173
display, 45:171
sweetness relationships, 45:320-325
Blueberry, development physiology of, 42:341
Blue Dextran 2000, structure of, 29:352
Bluensidine
aglycon of bluensomycin, 30: 1 14
biosynthesis, 35: 105, 107
Bluensomycin
biosynthesis, 35: 102
discovery of, 30:112, 114
structure of, 30:114, 35:102-103
Blue staining residue, dextrins, 47:283
Boar spermatozoa, forrnose utilization by,
29:2 18
Bognar, Rezso, 49:3-9
academic career, 49:4
antibiotic research, 49:5-6
C-nucleoside synthesis, 49:8
glycosylamine research, 49:6-7
honors, 49:8
reaction of a,a-dihalo ethers, 49:7-8
research on flavonoid compounds and
carbohydrates, 4 9 5
Boivinose, 21: 186
Boltzmann distribution, in nuclear magnetic
resonance spectroscopy, 27:44
Boltzmann factor, 51:30
Bonds
angles, coupling to torsional angles,
47:96-101
axial and equatorial, 26:52
length, coupling to torsional angles,
47:96-I01
Boranediyl, nomenclature, 35:36
Borate complexes
of cyclitols, aqueous equilibria of, 42:25
effects
on acetylation of alditols, 28:34
on trifluoroacetylation of sugars, 28:36
Borates, effect on mutarotation of sugars, 23:35
Boric acid, 53:293
carbohydrate complexation with, infrared
and Raman spectroscopic study of,
44:30
catalysis of polymerization by, 21:466
for determining configuration of
carbohydrates, 4: 189-2 I0
effect on mutarotation of sugars, 23:35
reaction with o-glucose, 35:3 1
Borinates, see Sodium diphenylborinates
2,3-Bomanedione, mutarotation of, 23: 13
Bomesitol, from quebrachitol, and
rearrangement in acetic acid-sulfuric acid,
26:191
Borohydrides
as reducing agents for o-fructose, 22:283
reduction, of acetals, 34: 192
Boronates
in aqueous solutions, 3548-52
carbohydrate, 35:5, 31-80
esterification, 35:53
etherification, 3 5 5 5
hydrolysis, 3550-52
mass spectrometry, 35:65-70
nomenclature, 35:36
nuclear magnetic resonance spectroscopy,
3570
nucleophilic displacement reactions,
3.5:55-57
oxidation, 3 9 5 7
preparation and structure, 35:4345
properties, 35:72-80
removal of boronate group, 3 5 5 2
in separation of carbohydrates, 3557-58
stability, 3 5 3 5 , 53-55
structure, 35:33,4148
synthesis, 3 5 3 7 4 1
Boron compounds, in synthesis of deoxy
sugars, 21:168-169. 181
Boronic acids
in biochemistry, 3 5 3 2
in column chromatography, 3563-65
in gas-liquid chromatography, 35:65
 SIJDJECT INDEX
interactions with carbohydrates in aqueouh
solutions, 35:48-52
Boronic esters, of diols from periodate
oxidation of polysaccharides, mass
spectrometry of, 30:43
Boron tribromide
1,6-anhydrohexopyranose cleavage by, 34:68
for cleavage of glycoside sulfonic esters.
23:259
Boron trichloride
1,6-anhydrohexopyranose cleavage by, 34:68
for cleavage of glycoside sulfonic esters,
23:259
in demethylation of methyl ethers of sugars,
34:8
reaction with anhydro carbohydrate
derivatives, 28:280
Boron trifluoride, debenzylation with. 31:4
Boron trifluoride etherate
1,6-anhydrohexopyranose cleavage by. 34:66
as catalyst in acetalation, 34: 186
Borylene, nomenclature, 3 9 3 6
Botany, carbohydrate chemistry and. 21:378
Botrytis cinerea
a-L-arabinofuranosidase from, 42:387
fermentation of D-fructose and D - ~ I U C ~by,
S~
32: IS3
Botryti.s/uhue, a-L-arabinofuranosidase of.
42387
Bourne, Edward John, obituary, 34: I 22
Bourquelot, Emile, obituary of, 18:l X
Bovine a-lacatabumin, crystal structure 01:
25:98
Bovine brain monosialoganglioside, mass
spectrometry of, 29:89
Bovine mannosidosis urine, structure of
oligosaccharide, 37: 182
Bovine-milk lactotransferrin glycan. st ruclure,
37: 176
Bovine nasal cartilage, carbon-I3 nuclear
magnetic resonance spectra and structure,
38:36, 78-81
Bovine serum antigens, 53:223-224
Brachiopods, glycolipids, see Glycolipids
Braggs law, 52:3 14
Branched-chain sugars, 48:287-288
composition in aqueous solution, 42:43,
54-58
configuration determination of, 42: 132- I34
natural occurrence of, 42:72-73
69
nucleosides of, 42: 13 1-132,230,244-246
in antibiotic synthesis, 42:261
in solution, 49:30-~3I
synthesis of, 42:69-134
addition to C-alkylidene glycosides,
429-95
by addition to unsaturated sugars,
42:97-103
by aldol addition, 42: 104-105
cyclitols, 42: 129- I3 I
by cyclization of dialdehydes with
nitroalkanes, 42: 107-109
forrnyl- and hydroxymethyl-branched,
42: 128-129
methyl-branched, 42: 1 18-128
by nucleophilic addition to glycosiduloses,
42:78-91
by nucleophilic reactions of sugar
oxiranes, 42:95-97
by photochemical addition, 42: 105-107
by rearrangement reactions, 42: 109- I I3
two main groups of, 42:77-78
Branched models, mucin structure, 47:353-356
Brussicu ulbu, polysaccharide from seed of,
24:374
Bratton-Marshall assay, 52:299
Braun, Julius von. 45: 1
Bredinin monohydrate (4-carbamoyl- I -P-n-
ribofuranosyliniidazolium-S-olate),crystal
structure bibliography, 34:364
Brewsters rules, of optical rotation and
conformation, 26:63
Bridged-ring systems, of carbohydrate sulfonic
esters, displacement reactions, of. 24: IS3
Brigls anhydride, 25: 164, 53: 1 SO- I52
Brigls synthesis. 39: I7 I
levoglucosan synthesis from, 34:29,48
0x0 reaction with, 23: 105
polymerization of, 21:490, 39:207-208
synthesis, 39: 161
Brigls chloride
methyl a-o-glucopyranoside from, 34:256
selective deacylation. 39:35
Brigls compound, structure of, 3230-3 I
British gums, see Dextrins
Brome grass. cell-wall studies on, 42:271, 287,
291,300
Bromelain
a-o-mannosidase as structural reagent for,
from pineapple stem. 28:444
70 SUBJECT INDEX
Bromelain (continued)
glycoenzymes, 27:309
pineapple
carbohydrate components of, 27:325
purification of, 27:310
stem, 25:436,44:232
Bromination, see also Radical-mediated
brominations
of nucleotides, 22:377
of sugars, with N-bromosuccinimide, 28:249
of hi-0-acetyl-D-glucal, 24:203
of unsaturated sugars. 27:241, 249
Bromine, reaction with cyclic acetals, 39: 1 18
Brominolysis, of 2-deoxy-2-iodopyranoses,
25: 194
Bromoadenosine, 1,N-Dibenzoyl-2,3,5-tri-O-
benzoyl-4-, synthesis, 49:65
p-Bromobenzenesulfonate, in displacement
reactions of carbohydrates, 24: 140
Bromobenzoates, circular dichroism
d i p , 45:123-124
tri-p-, 45:123-124
Bromoconduritols, 48:376-377
Bromodeoxyaldonolactones
base-catalyzed rearrangement, 50: 175-179
hydrogenolysis, 50: 173-174
preparation of aminodeoxy aldonic acids and
sugars, 50: 135
1-Bromo-o-glycosyl cyanides, synthesis, 49:58
Bromofluorination, of glycals, 38:234235
Bromoform, complex with amylose, crystal
structure bibliography, 33:39 1
Bromo(methoxyl)ation, of glycals, 24:203
(Bromomethylene)dimethyliminiumbromide.
in synthesis of bromodeoxy sugars, 28:250
Bronchitis patient, mucus glycoproteins,
47:36&36 1
Brffnstedacids, reaction with 0-
(glycosyl)trichloroacetimidates,50:30-32
Bronsted relationship, between catalytic
activity and dissociation constants, 24: 19
Brown-Brewster-Shechter rule, for m-dioxane
ring formation, 26:2 10
Browning, see Caramelization
Brucellu abortus, inhibitors for, 2 2 2 1 1
Brucine, L-gulonate, preparation, 38:299
Brucine HCL, taste properties, 4 5 3 1 I
Bu- 1709-E ,
from butirosins, 30: 132
discovery of, 30:112
B~l709-E~
from butirosins, 30: I32
discovery of, 30:l 12
Bufadienolides, 46: 13
synthetic, 21 :273-321
Bufo, 46: 13
Building industry, galactomannans in, 31:3 11
Burdock root, polysaccharide from, antitumor
activity of, 32:253
Butadiene, diepoxy-. sulfonylation of, 23:239
I ,3-Butadiene
1-alkoxy-, carbohydrate substrates, 40:3&38
1,4-dimethoxy-, sugar substrate, 40:49
trans. trans- 1,4-diacetoxy-, sugar substrate,
40:49
1,3-Butadienyl ethers, sugar, cycloaddition,
40: 123-128
Butanal
4-hydroxy, as hemiacetal in solution, 4 2 3 0
reaction with hexitols, 39:26
Butane, tetra-0-acetyl-a-o-glucopyranosyl-,
25:241
Butaneboronates
carbohydrate, in gas-liquid chromatography,
28:38, 5 1
gas-liquid chromatography of
monosaccharide, 28: 120
1,3-Butanediol, 2,4-difluoro-
preparation, 38:237-238
synthesis, 40: 104
Butanedione, 46:32 1
formation of 2,5-dimethylhydroquinone
from, 46:294-295
from hydrothemiolyzed cellulose,
46:304-305
4-Butanelactam, 2-enamino-N,N-bis[(p-
methyoxycarbonyl) phenyl]-4-(~-galacro-
pentaacetoxypenty1)-, 23: 166
I-Butanethiol, reaction with sucrose, 3 2 2 9
1,2,4-ButanetrioI, tripivalate, acyloxonium
rearrangement of, 26: 143
Butanoic acid, 2-etbyl-,l-ester with p-D-
glucuronic acid, 36: 104
Butanol, 4-methoxy-. solubility of sucrose in,
27:87,89
I-Butanol, 53:361
complex with amylose, crystal structure
bibliography, 33:391
complex with sodiocellulose. crystal
structure bibliography, 33:395
 SUBJECT INDEX
cyclodextrin inclusion complexes with,
46~222-224
reactions with carbohydrates and sodium
hydroxide, 21 :257
2-Butanol,2-phenyl-, asymmetric synthesis of.
27: 193-194
Butanone, 53:367
1 -hydroxy-2-, formation, 46:294
3-hydroxy-2-, 46:321
4-Hydroxy-2-, formation, 46:294
Butanoyl chloride, 2-acetoxy-2-methyl-,
reaction with diol groups, 33:83-84
2-Butena1, see Crotonaldehyde
1-Butene, 4-acetoxy-3-(acetoxymethyl)- 1 -
ethoxy, m-apiose synthesis, 40: 13
Butenoic acid
cis-2-, see Isocrotonic acid
trans-2-, see Crotonic acid
3-Butenoic acid, precursor for sugar synthesis,
40:6
Ei-Butenolides, synthetic uses, 50: 190-1 0 I
y-Butenolides, synthetic uses, 50: 182- 190
double bond reaction, SO: 187-188
2-Butenyl group, as protective group, 39:51
1-Buten-3-yne, 1 methoxy-, precursor for sugar
synthesis, 40: 11-12
Butirosin A
inactivated, 30: 197
isolation and structure of, 30: 131- I32
I -N-acyl derivatives, 30: 174
synthesis and structure of, 30: 196
Butirosin B
3,4-dideoxy-, minimum inhibitory
concentrations of, 30:221
synthesis and activity against resistant
bacteria, 30: 176
isolation and structure of, 30: 131-1 32
minimum inhibitory concentrations of,
30:221
synthesis of, 30:112. 163-164
and derivatives, 30: 176
and structure of, 30: 196
Butirosins, discovery of, 30: 1 12
Butyl alcohol, solubility of sucrose in, 27:89,
98
tert-Butyl alcohol
complex with amylose, crystal structure
bibliography, 33:391
as solvent in ammonolysis of benzoyl
groups, 31: 102
71
5-Butylbarbituric acid, cyclodextrin inclusion
complexes with, 46:223-224
rert-Butyldimethylsilyl group, 0-protecting
group, 39:64, 66-67
Butyllithium, reaction with
cyclic acetals, 34:49,409
1,3-dioxolanes, 39: 138- 148
2-Butyne-l,4-diol, substrate for carbohydrate
synthesis, 40:27-29
2-Butyn-4-01, 1.1 -diethoxy-, precursor for sugar
synthesis, 40:7
Butyraldehyde, 2,4-dihydroxy-3-
(hydroxymethy1)-, synthesis, 40: 13-14
Butyric acid, amylose ester, preparation of,
29:330
C
C-2, deoxygenation effects on enzyme-
substrate affinity, 4 8 5 6 I
Cabrera, Blas, 45: 10
Cadmium carbonate, in Koenigs-Knorr
reaction, 34:253
Cadmium(11) cytidine 5-nionophosphate,
monohydrate, crystal structure
bibliography, 38:505
Cadmium ion. effect on a-1)-mannosidase
activity, 28:426,428,430,433
Caffeine, taste properties, 45:3 1 1
Calcitonin M, amino-acid sequence in, 25:
425
Calcium a-o-galacturonate, tetrahydrate,
crystal structure bibliography, 32:380
Calcium a-1,-isosaccharinate, crystal structure
bibliography, 31:364
Calcium alginate. 47:33
Calcium and calcium ion
effect on reducing sugars in solution, 42:33
function in cell walls, 42:305, 346, 369
Calcium P-i)-uruhino-hexulosonate trihydrate,
crystal structure bibliography, 37:376
Calcium bis(2-amino-2,3,4-trideoxy-l.-g/~cero-
pentrate), crystal structure. 43:205-206
Calcium bromide-cu-D-glucopyranuronate
trihydrate. crystal structure bibliography,
34:347
Calcium chloride, 53:323-324
complex with lactose and methanol, 21:215
effect on
72 SUBJECT INDEX
Calcium chloride (continued)
equilibrium rotation of-o-g1,vcrro-o-gulo-
heptose, 21:231
mutarotation of sugars, 23:34
sugar solubility in methanol, 27:95
Calcium chondroitin 4-sulfate, 52:38 1-382,
425426
Calcium cyclamate, relative sweetness, 45:
332
Calcium o-glucarate tetrahydrate, crystal
structure bibliography, 37:375
Calcium di-DL-glycerate, dihydrate, crystal
structure, 43:204
Calcium-di-L-glutamate, crystal structure,
43:205-206
Calcium o-phosphoglycerate trihydrate, crystal
structure, bibliography, 30:447
Calcium o-xybhexosulosonate dihydrate,
crystal structure bibliography, 31:364
Calcium hyaluronate, 52:376377
crystal structure bibliography, 35:383
Calcium hydroxide, as catalyst in formose
reaction, 29:183-199
Calcium ion
chelation, proton shielding by, 47: 129
exchange of Gd3+,and Mn2+for, 47: 136
interaction with N-acetyl-a-o-neuraminic
acid, 47: 160
Calcium ionophores, inhibitors of cellulose
biosynthesis, 41:144
Calcium L-arabinonate pentahydrate, crystal
structure bibliography, 31:363
Calcium L-ascorbate, crystal structure,
37~83-84
dihydrate, 32:354-355,43:337
Calcium pectate, 52:353
Calcium sodium a-o-galactopyranuronate
hexahydrate, crystal structure
bibliography, 34:347
Calcium sodium a-o-galacturonate,
hexahydrate, crystal structure
bibliography, 32:380,37:377
Calcium thymidylate, hexahydrate, crystal
structure bibliography, 31:370
Calcium welan, structure, 52:432434
Calcofluor White, 41:117, 131
Caldariomycin, derivative, crystal structure of,
25:74
Calf thyroglobulin unit A glycan, structure,
37: 175
Callose, 23:384,44:273
in cell walls, 26:345, 349
effect on cellulose biosynthesis, 41:128-129
synthesis of, 26:324-325, 32:11
Calorimetry, mutarotation measurement by,
23:5 1
Cambridge Crystallographic Data Bank
refcodes, 43:204, 377421
Camphor derivatives, mutarotation of, 23: 12
(+)-I 0-Camphorsulfonic acid, aqueous
solution, calibration 0fc.d. instruments
with, 45:77
Canadensolide, synthesis of, 42:95
Canarose, L-, 21: 186
Cunavulia ensiformis, see Jack bean
Cancer
antigens, antitumor activity of, 32:270
chemotherapy
deoxy sugars in, 21: 145, 158
research, 29:2,6
glycoconjugates role, 37:159, 161
therapy
lectins in, 35: 130
spongoadenosine in, 31:4
tissue, a-o-mannosidase activity in, 28:404
Cundidu ulbicans
glycogens, 41:69
phosphonomannan, 41:86
polysaccharide, 41 :74
Cundidu bogoriensis, polysaccharides, 41:98
Cundidu intermedia, lactose utilization by,
32: 183
Cundidu lzjJolyticn, galactomannan, 41:92
Cundidu purupsilosis. polysaccharide, 41 :74
Cundirfu spp. mannans, 41:82
Cundidu sielluioideu, phosphonomannan,
41:86
Cundidu utilis
chitin, 41:103
polysaccharide, 41:77
thiamine synthesis, 52:291
Cane sugar, see Sugar cane
Cannabinol, D8-tetrahydro-, C-glycosylation in
preparation of, 33: 159
Cannabis, constituents, 29:2
Canna starch, structure of, 32:5
Cannizzaro reaction
in formose formation, 29:176, 180, 192,
199-205,213-216
with pyruvaldehyde, 28:200
 SUBJECT INDEX
Carugana ahorescens lectins, purification.
composition. and properties of, 352 13
Caramel, see also Caramelan; Caramelen:
Caramelin; Melanoidins
acceptable daily intake, 47:233
as adhesive and binder, 47:232
ammonia
carcinogenicity, 47:268
processes, 47:228-229
standardization, 47:208
analysis, 47:235-237
background, 47:204-205
bad, 47:229
Bakers types, 47:231
biological screening, 47:267-270
for brandy, 47:23 1
for brewing, 47:23 1
i3C-c.p./m.a.s.NMR, 47:24&245
chemical nature, 47:237-267, 52:222- 223
acid-catalyzed reversion, 47:252
aqueous sucrose solution pH, 47:239
carboxylic acid or Schiff base paths,
47:263
caustic caramel, 47:253
degree of polymerization, 47:244
diketosamine decomposition, 47:264-266
electronegative, 47:215
electropositive, 47:2 14
formation of heterocyclic low-molecular-
weight products, 47:266-267
intramolecular cis eliminations, 47:248
isoelectric points, 47:2 14, 227
isoelectric properties, 47:23 1
metal salt effects, 47:252-253
mutagenicity, 47:267-269
mutarotation, 47:249
oxaheterocycle formation, 47:247-248
from plain sugars, 47:237
reductones, 47:249-250
thermal stability, 47:238
volatile and nonvolatile fractions.
47:238-239
clastogenic effect, 47:268
colloidal particles in. 47:227
colorants
analytical characteristics, 47:206, 209-2 13
range of shades, 47:232
for soft drinks, 47:231
standardization, 47:205-206, 208
sugar colors, 47:214
73
composition, in presence of acid catalysts,
47:252
cosmetic use. 47:23 1-232
definition, 47:205
detection, 47:234-236
dry, 47:227-228
gas-liquid chromatography, 47:233-236
killing heat, 47:228
manufacturing, 47:218-225. 228
inhibitor use, 47:224
light and browning, 47:225
melanoidin formation. 47:223-224
from molasses, 47:22 I
nonconventional sources, 47:222
in presence of ammonia, 47:22&225
y-radiation effect, 47:225
reducing properties, 47:218,220
from saccharides, 47:223
from sucrose and its products, 47:2 19-22 1
water loss, 47:218-219
pharmaceutical industry, 47:23 1
physical properties, 47:214-218
aroma, 47:2 18
composition, 47:2 I5
firmness. 47:222 223
flavor. 47:2 18
hygroscopicity, 47:223
pH, 47:21&217
from Pictet-Andrianoff vacuum process,
4 7 2 16-21 7
solubility, 47:217
plastic resins colored with. 47:232
presence of proteins, 47:230
quaternized by metal ions, 47:232
size-exclusion chromatography, 47:235
spectral analysis and identification, 44:24
storage, 47:229
thin-layer chromatography, 47:236
tinctorial strength. 47:2 18, 23 1
types, 47:20&208
applications, 47:233
test form, 47:206, 208
ultrafiltration, 47:229
undesirable properties, 47:229
in urine, 47:269
uses, 47:230-233
viscosity control, 47:227
world production, 47:233
Caramelan
analytical characteristics. 47:24 I , 243
74 SUBJECT INDEX
Caramelan (continued)
infrared absorption spectra, 47:241-242
from intermolecular polymerizations,
47~248-249
physical properties, 47:2 I6
ultraviolet absorption spectra, 47:241,243
Caramelen
analytical characteristics, 47:241, 243
chemical nature, 47:241, 244
infrared absorption spectra, 47:241-242
physical properties, 47:216
ultraviolet absorption spectra, 47:241,
243-244
Caramelin
chemical nature, 47:244
infrared absorption spectra, 47:241-242
physical properties, 47:2 16
Caramelization, 46:307, 324
acidic medium or acid catalysts, 47:250-
252
under alkaline conditions, 47:253-255
background, 47:204-205
by-products, 47:267
concepts, 47:226-227
condensation, 47:245
degradation reactions, 47:245
degree of, 47:2 18
of o-glucose, 34:46
kinetics, 47:226
during manufacturing of table sugar,
47:221-222
polymerization, 47:245
in presence of ammonia, amino acids,
peptides, and proteins, 47:255
products of, 47:238-240
solution versus solid state, 47:239-240
sucrose, 47:2 19-220
Carbamates
as herbicides, 21:403
of polysaccharides, 29:344
Carbamazepine, o-glucosylamineuronic acid
conjugate, 36: 126
Carbamic acid
N-methyl-, 1-naphthyl ester, effect on
abscission and ripening, 21:429
N,N-dimethyldithio-
I -thio-P-o-glucopyranoside, 21 :404
zinc salt, fungicide-herbicide, 21:404
NN-dipropylthio-, S-ethyl ester, as herbicide,
21:403
N-phenyl-, esterification of carbohydrate
boronates by, 35:54
Carbamoyl group, reversed anomeric effect,
47:65
Carbanilates, as herbicides, 21 :403
Carbanilation, of polysaccharides, 29:344
Carbanilic acid
3-chloro-
4-chloro-2-butynyl ester, as herbicide,
2 1:404
isopropyl ester, as herbicides, 21:403
isopropyl ester, as herbicide, 21 :404
Carbanions
condensation reactions with carbohydrates,
33: 145-1 53
detection, 38:391
Carba-sugars, see also Enantiomeric carba-
sugars; Racemic carba-sugars
60c-~arba-~-fructopyranoses, 48:49-52
amino, synthesis, 48:6&67
biological activity of, 42:132
biological effects, 48:8&89
chemistry, 4 8 2 - 9 0
definition of, 42: I 16
mono- and dicarba-disaccharides, 48:67-73
physical constants, 48:37
taste properties, 45292-293
Carbazole test. in sugar analysis, 28:222
Carbene, dichloro-, reaction with alcohols,
28:260
Carbenoxolone, metabolism, 36: 109
Carbocyclic compounds, from dehydration
reactions of carbohydrates, 28: 174, 191
Carbodiiniides
affinity chromatography adsorbent supports.
39:434435
N-N-dicyclohexyl-
activating agent in phosphorylation,
22:332
effect on solubility of sugars in methyl
sulfoxide, 27: 109
intermediate in nucleotide formation,
36: 157
in synthesis of glycosyl esters of
nucleoside pyrophosphates, 28:353
reaction with glycuronans, 29:347
in synthesis of glycosyl esters of nucleoside
5-pyrophosphats,28:353
Carbodiimidium iodide, N-N -dicyclohexyl-N-
methyl-, reactions with alcohols, 28:260
 SUBJECT INDEX
Carbohydrases, endo and exo actions of,
29:340
Carbohydrate. chains
proton nuclear magnetic resonance
spectroscopy of glycoprotein-related,
4 1:2 10-3 74
structural reporter groups, 41:212
Carbohydrate-alkali metal alcoholate
complexes, 21:260
Carbohydrate amines, deamination of, and
related compounds, 31:9-79
Carbohydrate-amino acid linkages, see ~ S < J
Glycosyl linkage
structures, 43:4-6
types, 43:4-6
Carbohydrate anomers, separation of, 46:
70-7 1
Carbohydrate-binding specificity, of lectins,
35:139-145,331-333
Carbohydrate chemistry, Wittig reaction in,
27:227-299
Carbohydrate esters, photochemical reactions,
38: 136-142
Carbohydrate-metal base complexes, 2 1 :237
Carbohydrate-metal salt complexes
electrophoresis, 21:23 1
optical rotations of, 21:228
preparation of, 21:2 16-220
proof of existence of, 21 :2 1 1
solvation of, 21:226
stability of. 21:227
stoichiometry of, 21:222
structure of, 21:236
Carbohydrate-peptide linkage, of
glycoproteins, 2 5 4 6 7 4 7 2
Carbohydrate polymers, compositional analysis
of, 46:5457
Carbohydrate-protein compounds, in urine
(human), 24:435452
Carbohydrate-protein linkages, 2 9 4 17-43')
amino acid and carbohydrate residues,
50~277-278
proteoglycans, 49:242-243
structural analysis, 43:6
type, distinguished by I3C-NMR
spectroscopy, 43: 10
unusual, 43:4449
model compounds, 43:4547
Carbohydrates, see also Food, carbohydrates
acetals. photochemistry, 38: 142-147
75
action of hydrogen peroxide on, 19:149-
179
acyclic, selective esterification of
dithioacetals of. 33:4041
selective methylation of, 33:65-66
acyl esters, reaction with ammonia,
31:81-134
affinity chromatography adsorbents for
macromolecular substances,
39:405-447
anomeric carbon atom, 47: 102
anomeric region, 44: I I , I9
anti. see Anti-carbohydrate antibodies
application of trifluoroacetic anhydride in
chemistry of, 16:59-84
applications of reductive desulfurization by
Raney nickel, in the field of, 5: 1-28
asymmetric carbon atom source, 27:205
benzyl ethers in synthesis of, 31:4
boronates, see Boronates
branched-chain. by fomiose reaction,
29:209-2 16
butaneboronates, in gas-liquid
chromatography. 28: 3 8
carbonates of. 15:91-158
catabolism in yeasts, central pathways of,
32: 160-1 6 I
charge requirements, 47: 128
CH,OH group. determination of rotational
isomerism, 44:53
'T-labelled, preparation of, 32:8
complex carbohydrates
biosynthesis, in plants, 44:358-377
regulation mechanisms, 44:376-378
f.a.b.-mass spectrometry, 4559-62
complexes with alkali metals and alkaline-
earth metals, 21:209-271
as components of cardiac glycosides.
1:147-173
conformation
and interactions of, vibrational
spectroscopic study, 44:87-88
vibrational spectra used to analyzc.
44:25-26
constitution of, 15: 11-51
in con) syrup. 36:29
crystalline, radiation-induced, free-radical
reactions, 37:67-74
crystal structure
analysis of, 19:7-22
76 SUBJECT INDEX
Carbohydrates (continued)
bibliography, 30:445466,31:347-354,
359,363-369,32:353-372,380-381,
34~345-378,37:37&408,434,
38:417-185,526
and derivatives, 25:53-107
gel chromatography of, 25: 13-5 1
glycoprotein components, 25:4094 14
definition, 52:49-50
degradation, 19:181-218
by p-elimination, 29:229-303
dehydration reactions of, 28: 161-224
derivatives, anomeric and aglycon C,H
bonds, carbon-proton coupling
constants, 51:33, 35
determination of configuration of, with boric
acid, 4: 189-2 10
deuterated, interpretation of spectra of,
44:53-55
dicarbonyl, 17:223-299
dithioacetals, photolysis, 38: 150-153
effect of plant-growth substances on,
21:377430
electrochemistry of, and derivatives,
29: 107-1 71
electrophoretic migration of, 21:234-235
enzyme specificity in the domain of, 5:49-78
errata for 1970-1978, 43:374375
excited derivatives, photochemical reactions,
38:125-131, 135
fingerprint region, 44: 1 I , 17, 19
fluorinated, 38: 195-285
biological applications, 38:28 1-284
chemical shifts, 38:256-260
i9F-labelled,38:285
"F-nuclear magnetic resonance
spectroscopy, 38:256-281,285
infrared spectra, 38:280
mass spectrometry, 38:253-255,285
X-ray crystallography, 38:280, 285
formazan reaction, in research on,
13: 105-167
free-radical reactions, by radiation, 37:7-77
FriedelLCrafts and Grignard processes
applied to, 6:251-289
functional groups, 47: 127
gas-liquid chromatography of, 28: 1 1-1 60,
30:9-110
derivatives of, 19:95-147
in glycoenzymes, 27:302,306, 321-327
halogenated, 22: 177-227
biological activities of, 22:209
effect of halogen on, 22:207
enzymes and carrier specificity of, 22:209
oxidation rates of, 22:208
halogen oxidation of simple, 3: 129-184
high-o-mannose, f.a.b.-mass spectrometry,
45:63
hydrogen bonding, 44: 15-16
Raman and infrared spectral study of,
44~28-30
vibrational spectroscopic study, 44:87
1,2-hydroxyl groups, protecting group,
Helferich's work on, 45:5
index for 1935-1980,43:377405
infrared spectroscopy of, 12: 13-33,
19:2349
correlated to specific chemical structures,
44: 10
at low temperatures, 44:27-28
interaction with boronic acids in aqueous
solutions, 35:48-52
lanthanide shift-reagents and proton
magnetic resonance spectroscopy of,
29:25
large-scale production of, 29:221-226
lipids and, 53:400
mass spectrometry in structural analysis of
natural, 29:41-105
mechanisms of replacement reactions in
chemistry of, 9: 1-57
medical uses, 52:lO
metabolism of, 2: 1 19-1 60, 3:229-250,33:4
molecular structure, vibrational
spectroscopic study, 44536-87
nitrogen-containing, 24:9
nomenclature, 52:43
N-reacetylation, after methanolysis, 46:256
nuclear relaxation times, measurement of,
27:59
orientation, infrared dichroism study,
44:26-27
orthoesters of, 1:77-127
paper electrophoresis of, 1 8 6 - 9 7
periodate oxidation of, 11:1-11
the dialdehydes from, 16:105-158
pennethylated, degradation and structural
analysis, 3fk396-107
phenol derivatives, in higher plants,
20:371-108
 SIJBJECT INDEX
phosphates, mass spectrometry of boronates,
35:69
photochemistry of, 18:9-59,38: 105- 193,
46: 180
physiochemical properties of, 15: I 1-5 I
polarography
of dehydration products, 29: I64 16X
of derivatives, 29: 149-162
of oxidation and degradation products,
29: 162- I64
determination of, 29: 167
oxidizable products of, 29: 168- I7 1
protein-bound, biological significance,
40:287-379
proton magnetic resonance spectroscopy of,
27:7-83
proton nuclear magnetic resonance
spectroscopy. 29: I 1-13
radiation chemistry of, 16:13-58
radioactive labelled, self-decomposition.
37:76
reaction with sulfuryl chloride, 33:250. 259
reactivity, see Anomeric effect
and related compounds, action of hydrogen
peroxide on. 19: 149-1 79
paper chromatography of, 9:303 353
relative reactivities of hydroxyl groups in,
8:144,33:11-109
reserve, dextrans as, in cariogenic plaques.
30:437,439
selective catalytic oxidation of, 33:Xh-lOO
employing platinum catalysts. 17: 169-
22 I
selective chlorination, 39:23 1-235
selective halogenation of, 33:72-80
selective removal of protecting groups,
39:13-70
separation
on cation-exchange columns, niechanisms,
46:26
by use of boronates, 35:57-58
sequence, liquid chromatography methods
for determining, 46:57-58
size requirements, 47: 127
in the soil, 16:335-355
solubility in liquid ammonia, 2 7 9 1
in solution, 51:63-127
dynamic modeling, 51:74-82
internal motion, 51 :77-78
overall motion, 51:74-77
77
segmental motion, 51378-82
molecules whose relaxation behavior has
been treated qualitatively, 51 :8488,
90-9 1
qualitative motional description, 51:83,
89-105
monosaccharides, 51:83, 89-97
oligosaccharides, complex glycosides,
and derivatives, 51:97-102
polysaccharides, 51: 102-105
quantitative motional description,
51: 105-124
monosaccharides, 51: 105-1 14
oligosaccharides, 51:114-117
polysaccharides, 51:117-124
solvents (non-aqueous) for, 27:85- 125
stereochemistry of cyclic derivatives of.
10:l-53.36:4
structural analysis of, 44: I I
methylation techniques, 38:389 4 1 6
structure
and atomic coordinates. 44: 13-1 5
factors in, 44:11-16
liquid chromatography methods for
determining, 46:57 -58
properties relationships, 44:88-89
sulfonic esters of, 8: 107-2 15, 23:233-280,
24: 139-1 97
sulfonylation of, 28:255
by sulfonyl halides, 23:236
symmetry operation, 44: 12
in synthesis and configurational assignments
of optically active non-carbohydrate
compounds, 27:191-225
synthesis of optically active, 40: I 12-129
from chiral precursors, 40: 1 15-1 19
from natural products, 40: 1 19--I23
by resolution of racemates, 40: 1 13-1 15
stereo-differentiating, 40: 123- I29
tautomers, vibrational spectra
analysis of intensities of, 44:35-36
used to analyze, 44:25-26
thiocarbonates of, 1 5 9 1 - I 58
tin-containing inteimediates, see Organotin
trityl ethers of, 3:79-111
unsaturated
carbon-13 nuclear magnetic resonance
spectroscopy, 41:58
photochemical cycloaddition with
carbonyl compounds, 38: 106-108
78 SUBJECT INDEX
Carbohydrates (continued)
photochemical radical-addition
reactions, 38:109-115
vibrational spectra, 44: 17
frequency region of below 700 cm-,
44:17,21-22
frequency region of 950-700 cm-I, 44: 17,
19-2 I , 4 3 4 5
frequency region of 1200-950 cm-I, 44: 17,
19
frequency region of 1500-l200 cm-,
44:17-19,4346
frequency region of 3600-2800 cm-I,
44: 17-1 8
volatile derivatives for gas-liquid
chromatography, 28:23-38
zone electrophoresis of, 12:81-115
Carbon
adsorbent, in corn syrup technology, 36:27
anomeric, in carbohydrates, 47: I02
2-isotope, in photosynthesis study, 32:6
electron-nuclear relaxation methods,
47: 136-1 37
isotope I3C, identification in sugars by use of
deuterium, 27: 149
participation in sugar reactions, 22: 170
ring oxygen replacement by, 52:141-143
Carbon- 13
effect on f.a.b. spectra, 45:29
H coupling
single-bond, 38: 17
three-bond, 38: 17-1 9
nuclear magnetic resonance spectroscopy,
42:18-19,62
for branched-chain sugars, 42: 133
capsular polysaccharides, 41: 159-1 64
chemical-shifts
acyclic monosaccharides, 41:59
alditols and acetates, 41:59-60
aldonic acids, 41:63
aldonolactones, 41:63
aldoses, 41:4546
aminoanhydrodeoxyalditols,41:6 1
aminodeoxyalditols, 41:61
aminodeoxy pyranoses, 41:54
anhydroalditols, 41:60-6 1
anhydropyranose derivatives, 41:5 1
benzylidene and isopropylidene
monosaccharide derivatives, 41:53
biologically significant
monosaccharides, 41 :64-65
deoxyhalo pyranoses, 41:54
deoxy sugars, 41:55
glycosides of aromatic aglycons,
41:4849
ketoses and methyl glycosides, 41:48
methyl aldosides, 41:46-47
methyl anhydro-o-glycosides, 41:57
methyl deoxypyranosides, 41:56-57
monosaccharides, 41:28, 3 1
complexation, 41:43
0-substituted monosaccharide
derivatives, 41:52-53
peracetylated pyranoses and furanoses,
41:49
tetra-0-acetyl(benzoy1)-o-
glycopyranosyl derivatives, 41 :50
thio-o-pyranoses, 41:54
unsaturated carbohydrates, 4 1 3 8
uronic acids, 41:62
uronolactones, 41:62
monosaccharides, 41:27-65
conformational analysis, 41:43
effect of paramagnetic reagents, 41:38
for identification, 41:3940
protonation shifts, 41:39
relaxation rates, 41:43
for structure determination, 41:4042
for oligosaccharides, 42: 193-225
quantitative data, 41:32-33
resolution enhancement, 41 :33-34
of sialic acids, 40:169
signals
monosaccharide, comperison with
model compounds, 41:34-35
correlation with proton spectra,
41:3&37
isotopic substitution, 41:35-36
relaxation rates, 41:37-38
monosaccharide, identification,
38: 19-22
oligosaccharide and polysaccharide,
identification, 38:22-25
signal-to-noise ratio, 41:30
solvents, 41:29-30
spectroscopy
aldopyranans, 39: 198,200
of 1,6-anhydrohexopyranoses,34:61
3-deoxy-o-manno-2-octu~osonicacid,
38:359-36 1
 SlJBJtCT INDEX
maltose and derivatives. 39:254-258
polysaccharides, 38: 13-1 04
quantitation, 3 8 2 - 3 7
parameters, configurationally dependent.
38: 15-1 9
Carbonates
of carbohydrates, 15:91-158
of dithioacetals, preparation of, 32:48
of polysaccharides, 29:344
preparation and properties of rrm-cyclic
acetals in, 34:208
Carbon-carbon bond-forming reactions, .\ee
Enzymic methods
Carbon dioxide
evolution from cellulose on heating.
23:428429
production in pyrolysis of starch.
22:507-508,510,512-514
Carbon-fluroine bond
anomeric, 47:73
energy, 48:92
"Carbon-hydrogen coupling constants, vicinal.
47:70
Carbon-hydrogen vectors
angles formed with principal axes, 51:76
random proton motion, 51:66
Carbonitrile, 2-cyclopentene- I-, ( In. 40,51)-I -
(~-~-g~ucopyranosy~oxy)-4.5,-dihydroxy-.
crystal structure bibliography, 30:466
Carbonium ion, 25: 183
anomerization by way of a cyclic, 24:43
in @-amylaseaction, 23:343
in cellulose thermal degradation. 23:463
in deamination and in solvolysis. 31: I I - 14,
39
in phosphorylase action, 23:357
Carbonization, of cellulose on heating, 23:435
''Carbon-labeled, trimethylsilylation of, 28:32
metabolism by bacteria, gas-liquid
chromatography and. 28:47
trimethylsilylation of, 28:23-33
unsaturated, alkaline degradation of.
28:203-205
reactions of, 28:260
reactions with nitryl iodide, 28:29
Carbon monoxide
elimination reactions by radiation. 37: 14,
34
evolution from cellulose on heating.
23:428429
79
production in pyrolysis of starch, 22507,
510,512-514
"Carbon-NMK spectroscopy, 4 3 : 2 4 , 7
biochemical implications, 43: 10
chemical shifts, 46:77
13C-NMR-"JFcoupling constants. 46:77-78
dianhydride components of glycosyl di-n-
fnictose dianhydrides, 52:256-257
1,4:3.6-dianhydrohexitols,49:109-1 I I
dihexulose dianhydrides, 52:245-246
drawbacks. 4 3 : 3 4
fructose components
di-o-fructose dianhydride derivatives,
52:262
per-0-acetylated di-o-fructose dianhydride
derivatives, 52:263
per-0-acetyl glycosyl dl-D-fructose
dianhydride derivatives, 52:258
of glycoproteins. 43: 1 4 9
glycosyl di-o-fructose dianhydride
derivatives. 52:259
of heparin, 43:65-66
1J ("C, "F). 46:77-78
W ( I 3 C ,'"F), 46378
3J(IzC, I9F), 46:78
4J("C, "F). 46:78
of 3-0-o-galactopyranosyl-and 3-0-D-
xylopyranosyl-1.-serines.43: I80
per-0-acetyl dihexulose dianhydrides,
52:247
reporter-group regions. 43:8
for structural analysis of oligosaccharides of
glycoprotiens. 432-10
of synthetic 0-glycosyl derivatives, 43: 180
Carbon nucleophiles, for oxirane aldoses.
25: I25
Carbon oxygen bond
anomeric. shortening, 47:71
exo-anonieric effect, 47:70
Carbon-oxygen-carbon bond, exo-anomeric
effect. 47:73--74
Carbon- proton coupling constants, 51: 15-57
conformational dependence, 51 :29-57
multiple-bond couplings, 51 :20-23
one-hound couplings, 51:18-20, 3 1 4 5
angular dependence. 51:4144
anomeric and aglycon C,H bonds
acetylated monosaccharide derivatives,
51:36
carbohydrate derivatives, 51 :33
80 SUBJECT INDEX
Carbon-proton coupling constants (continued)
monosaccharide derivatives, 51 :32-33
oligo- and polysaccharide derivatives,
51:34-35
rigid carbohydrate derivatives, 51:35
application to oligosaccharides, 51:45
calculated FPT-INDO results, 51:3941
model systems, 51:38-39
solvent effects, 51:4445
relationship with structure, 51:16
solvent effect, theory, 51:29
three-bond couplings. 51:46-57
C-C-C-H segment of bonded atoms,
51 t.53-57
C-0-C-H arrays of bonded atoms,
51:47-51
C-S-C-H arrays of bonded atoms,
51 z.5 1-53
two-bond couplings, 51 : 4 5 4 6
Carbon radical stabilization factors, radical-
mediated brominations, 49:70-7 1
Carbon-sulfur bonds, hydrogenolysis of,
32~75-79
Carbon tetrachloride-triphenylphosphine,
reactions with alcohols and carbohydrates,
28:246
Carbon tetrahalides, with tertiary phosphines,
selective halogenations with, 33:79
Carbonyl-amine reaction, formation of N-
substituted aldosylamine by, 46:308
Carbonylation, of alkyl halides, 2 3 5 1
Carbonyl compounds
hydrated, of reducing sugars in solution,
42: 30-32
photochemical cycloaddition with
unsaturated carbohydrates, 38: 106-108
photosensitive protecting groups,
46: 195-202
reaction with ammonia, 2 5 3 2 4 3 2 7 , 344
Carbonyl groups
determination in oxidized polysaccharides,
29:340
formation from cellulose on heating, 23:426,
428,435
reactions involving, of sugars, 25:2 12
Carboxaldehyde, S-methylpyrrole-2-, formation
of, 46:312
Carboxamide, 5-amino- I-P-D-
ribofuranosylimidazole-4-
crystal structure, 43:282-283
5 '-phosphate, monohydrate, crystal structure,
43:283
Carboxyamides, 53:374
Carboxy(decarboxamido)vancomycin, hydrate,
43:373
1 -Carboxyethy1 ethers, 48:303-304
Carboxylate groups, at active site, 48:379
Carboxyl derivatives, circular dichroism,
45:102-111
Carboxyl groups, formation from cellulose on
heating, 23:426427,435
Carboxylic acids, 53:296,367-372
5-amino-l -cyclohexylimidazole-4-, 52299
a-substituted, configuration of, 21:33
carbohydrate, mass spectrometry of,
29~79-81
as catalysts for mutarotation, 24:27, 34
detection of, amylose-iodine reaction in,
29:401
( I ,3,5/2,4)-2,3-diacetoxy-4,5-
dibromocyclohexane-I-, 48:32
1,4:3,6-dianhydrohexitolsesters, 49: 125-
130
free, photochemical release of, from a 2-
nitrobenzyl-substituted
poly(vinylalcohol), 46: 199
2-oxazoline-4-, ci~-5-(hydroxymethyl)-2-
phenyl-, mutarotation of, 23: 13
polyhydroxy, p-eliminative degradation of,
29:234-237
protection of, 46: 198-202
1-pyrroline-2-, 4-hydroxy-5-(o-urubino-
tetritol-1 -yl)-, 40: 141
Carboxylic esters, 53:372-373
Carboxymethyl ether, of cellulose, 9:285-302
Carboxypeptidase Y, 44:370
Carcinoembryonic antigens, 53:250
Carcinogenesis, chemical, by N-hydroxylation
ofamines, 36:131
Carcinoscorpin, sialic acid analysis, 40: 175
Cardenolides
furanoid, 21:309
mercuric cyanide in synthesis of, 21:278
molecular weight determination, 21:274
physiological activity of, 21:311, 314
synthesis of, 27:3
l-2-cis-, 23:267
synthetic, 21:273-321
properties of, 21:3 19-321
Cardiac glycosides, synthetic, 21:273-32 1
 SUBJECT INDEX
Cardiotonic activity, 21:274
of cardenolides, 2 1 3 1 I , 314
Carob galactomannan, structure, 35:349
Carob gum, structure, 35:349
Carob tree, galactomannan from, history,
31:244
Carrabiitol, mass spectrum of, 29:89
Carrabiose, dimethyl acetal, 243280
L-Carrageenan, 24:281,285,288-289
K-Carrageenanase. 44:25 1
Carrageenans, 52:366-368,418419
)L-, 24:282
hydrolysis of methylated, 31:191
L-
carbon-I 3 nuclear magnetic resonance
spectra, 38:77-79
circular dichroism, 45:93-94
crystal structure bibliography, 33:404
interactions with galactomannans.
31:285-291
K-
carbon-I 3 nuclear magnetic resonance
spectra, 38:77-78
crystal structure bibliography, 33:404
oligomers, liquid chromatography, 46:40
A-, 24:283-284
mechanism of gelation, 24:3 14
methylation of, 30: I 1
structure, 24:279-290
enzymic analysis. 44:25 1-252
Carrobonic acid 4-sulfate, preparation of,
31:191
Carrot
cell-wall studies on, 42:336, 354
development physiology of, 42:343
Can-Pursell-Meiboom-Gill sequence. 51 :72
Cartilage, glycosaminoglycans. analysis. 4 6 5 6
Casein, gas-liquid chromatography of. 28:X3
Casoron, see Benzonitrile, 2,h-dichloro-
Castanospermine, P-o-ghcosidase inhibition,
48:342-344
Castaprenol, structure, 4 4 3 4 6
Castor-bean lectin, see also Ricin
carbohydrate-binding specificity,
35:273-276
interaction with cellular structures, 3 5 3 17
isolation, purification, and properties of,
35:137, 270,272
Catabolism
of a+-trehalose, 30:245-254
81
of alditols by yeasts. 32:210-219
of 2-deoxy-o-glucose by yeasts, 32: 177.
181-183
of o-fructose by yeasts, 32: I73
of o-galactose by yeasts, 32: 174-1 77
of o-glucose by ycasts, 32: 159-1 73
of o-mannose by yeasts. 32: 173
of glycans, 37: 189-1 99.222-223
of glycosides by yeasts, 32: 183-2 10
of glycosphingolipid. 40:268-286
enzyme preparation and enzyme assay,
40:269-271
protein activators. 40:28 1-286
of mw-inositol by yeasts. 3 2 2 19-22 1
of pentoses by yeasts, 32:2 10-2 19
of starch and glycogen, enzymes in.
30:285--302
of sugars by yeasts, 32: 127
Catalase, in fruit climacteric, 42:364
Catalysis
Bronsted relationship between dissociation
constants and, 24: 19
of hydroxyl ion and sugar anions, 24:24
of mutarotation of sugars by acids and bases.
24: 14
of polymerization of sugars
by boric acid. 21:466
by hydrogen chloride. 21:462
by ion-exchange resins, 21:464
substrate distortion, glucosidase inhibition,
48:382
of water molecule, 24:22
Catalysts
acetalation, 39:80
acid in hydrolysis of glycosides, 22:25
bifunctional, in mutarotation, 24:27. 34
in cyclic acetal preparation from ketoses,
26: I99
for diazomethane methylations, 33:68-70
effect on reaction of sugars and ammonia,
25:320 323.328
for formose
preparation, 29: 175
reaction, 29: I8 I . 183
for glycofuranoside forniation, 21: 104
platinum, ni selective catalytic oxidation of
carbohydrates. 17: 169-22 1
for polymerization, 39: 183-1 84
for anhydroaldoses, 39: 174
of I .6-anhydrohexopyranoses, 34:70. 74
82 SUBJECT INDEX
Catalysts (continued)
of sugars, 21:452
for selective oxidation of carbohydrates,
33: 86-92
Catalytic coefficients
for anions of weak acids, 24: 18
evaluation of, 24: I6
of mutarotation reactions, 24:47
ratios for mutarotation of sugars. 24:30
for weak acids, 24: 17
Catalytic efficiency, glycoside hydrolases,
48~323-325
Cataracts, 1,4:3,6-dianhydro-o-gIucitolin
treatment of, 25269
Catechol, 46:295
as enzyme inhibitor, 46:326
Cathepsin, isolation of carbohydrates from, on
analytical-scale columns, 46:60
Cathepsin B, glycopeptides, liquid
chromatography separation, 46:48
Cathepsin C, 44:2 17
Cathepsin-D, glycopeptides, liquid
chromatography separation, 46:48
Cation-exchange columns
metal cation-carbohydrate complexes
applications, 47:3640
methyl aldofuranosides, retention volumes,
47:20
CEA, see Carcinoembryonic antigens
Celery, see Apium graveolens
Celesticetin, chemical-ionization mass spectra
Of, 29:82-83
Celestoraminol, N-acetyl-3, 4-0-isopropyl-
idene, glucitol in treatment of, 25269
P-Cellabiose octaacetate, reaction with
piperidine, 39:30
Cellan, 21:445
Cell cultures, plant cell-wall studies using,
42:272
Cell death, programmed, 40:368
Cell differentiation, effect of glycosylation
inhibition, 40:36&369
Cell division in plant growth, 42:266
Cell elongation in plant growth, 42:266-267
Cell expansion in fruit ripening. 42:348-349
Cell growth, ganglioside effect, 40:23 1
Cell membrane
contact inhibition, role in antitumor activity,
32:272-274
glycoproteins, 44:232
Cell mutants
effect on biosynthesis of lipid-linked
oligosaccharides, 40:3 12-3 14
effect on protein glycosylation, 40:347
Cellobial, 2-acetoxyhexa-O-acetyl-, alkaline
degradation of, 28:205
Cellobiitol
I , 1-bis(acetamido), I-deoxy-,
octa-0-methyl-, preparation of, 31:94
and peracetate, preparation of, 31:92
nonaacetate, degradation by oxidation with
chromium trioxide, 31:230
6-0-benzoyl-, ammonolysis, 39:32
sweetness-structure relationship, 45:275-
276
Cellobiohydrolase, ( l-t4)-P-o-glucan,
Trichoderma viride, 44: 149
Cellobionic acid, hydrolysis of, rate of, 22:78
Cellobiononitrile, octa-0-acetyl-
ammonolysis of, 31:97
reaction with ammonia, 31:92
Cellohiosan
2-acetamido-2-deoxy-, preparation of
peracetate, 34: 160
synthesis of, 34:159-161
6-thio-, synthesis of, 34: 170
Cellobiose, 21:30,24:373, 375
(Y-
2,3,6,2',3,'4',6'-hepta-O-acetyl-,
preparation, 39:30
octaacetate, 22:22
acceptor products, 51: 152
aerobic respiration by yeasts on, 32:144
alkaline degradation, product pattern, 46:302
aqueous, versus solid, laser-Raman
spectroscopy, 44:75
P-
crystal structure bibliography, 31:367
hydrogen bonding, Raman and infrared
spectral study of, 44:29
mutarotation of, 23:23
octa-0-acetyl-, crystal structure
bibliography, 37:406
proton spin-lattice relaxation, 45: 160
benzoylation of, 33:36
carba-. synthesis, 48:68-70
and cellulose structure, 35:5
configuration of, 2555
crystal structure of, 25:75, 77
dehydration of, 28: 169
 SUBJECT INDEX
gas-liquid chromatographic separation of.
28:70,74
hydrogen bonds in, 25:99
hydrolysis of, 46:299
rate constants and activation energies for,
22:68
rate of, 22:78
liquid chromatography methods for analysis
of, 46:33
nonselective spin-lattice relaxation rates.
45: 149
6-0-benzoyl-
ammonolysis, 39:3 I
preparation of, 31:9S
octaacetate, 22:20
rearrangement in aluminum chloride-
phosphorus pentachloride, 26: 195
in hydrogen fluoride, 26: I88
octa-0-acetyl-. reaction with ammonia.
31:92
octa-0-benzoyl-, ammonolysis of. 3 I :9h
perbenzoate, ammonolysis of, 31 :95
pyrolysis of, 34:4S
radiation and radical-induced scission,
37:51-55
structure of, 22:446,39:358
sweetness, comparison to o-glucose.
452477248
synthesis of, 26:325,374
utilization by yeasts, 32:146, 201
and associations of abilities, 32:222
vibrational spectra
frequency calculations, 44:49-SO
isotopic substitution studies, 44:M
volatile products from pyrolysis of, 22:508
Wohl degradation of, 26:8
Cellobiose hexaacetate, I ,6-anhydro-P-
allowed rotational orientation of glucosidic
bond, 45:160-161
nonselective relaxation rates of H-I '.
45:143-145
proton spin-lattice relaxation, 45: 154, I S9
P-Cellobiose octabenzoate, ammonolysis.
39:3 1
Cellobioside
P-, methyl, '3C-signals,38:23
benzyl, selective chlorination with
methanesulfonyl chloride, 33:82
P-Cellobioside methanolate, methyl, crystal
structure bibliography, 30:4S4
83
Cellobiosylamine
N-acetyl-. preparation of, and anomer,
31:92
preparation of, 31:92
Cellobiouronic acid
conjugate, imniunogenicity. 41: 197
determinant group in polysaccharide
immunology. 41 : 176. I80
hydrolysis of, 46:299
Cellobiulose
composition in aqueous solution, 42:65
liquid chromatography methods for analysis
of. 46:33
Cellobiuronic acid, hydrolysis of. rate con-
stants and activation energies for. 22:68
Cellodextrins, enzymic synthesis of, 26:324
Cello-oligosaccharides
liquid Chromatography. 46:39
peak-area analyses, 46:64
preparative, 4 6 6 0
structure of, 26: I6
Cellotetraose
crystal structure of, p-%25:77
pyrolysis of, 34:45
Cellotetraose hemihydrate, 52:33 1
Cellotriose
acetolysis and acid hydrolysis of, 31: 199
P-, undecaacetate. crystal structure
bibliography, 38:483485
pyrolysis of. 34:45
synthesis of. 26:325
Cells, see ulso specific hpes
interaction with lectins, 35:3 17-333
leaf-mesophyll, from perennial ryegrass.
Composition. 36:259-262
stem-parenchyma, hemicellulose
composition, 36:262
transformed, tibronectin content, 40:3 75-376
virus-transformed, glycosphingolipid
biosynthesis, 40:266
Cells intact cellulose synthetase activity, and
transmembrane electrical potential,
41: 147-1 50
Cell-surface glycoproteins, glycosylation
inhibition effect, 40:374-375
Cellular chemistry, 26:297
Cellulase. 23:376,44: IS I . 273
mode of action, analysis of, 46:54
on plant cell-walls, 42:35 1-352
preparation of, 30:348
84 SUBJECT INDEX
Cellulose, 52:326, 329--332, 53:412413
OL-, 26:308,41:138
2,3,6.-tri-O-acetyI-. proton magnetic
resonance spectroscopy of, 27:39
acetate, circular dichroism, 45: I2 1
acetobrominolysis of, 22:23
acetolysis of, 2 2 2 2
acid-catalyzed hydrolysis of, mechanism of,
46:298-299
acid hydrolysis of, 46:297-298
affinity chromatography adsorbent, 39:407,
412413
6-aldehydo-, preparation of, 29:333
algal
cell-walls, biosynthesis, 42325-327
crystal structure bibliography, 33:395
alkali, crystal structure bibliography, 40:388
alkaline degradation of, products, 46:304
alkaline peeling of, 46:301-303
alkaline stability and gas-liquid
chromatography of, 28%
alternate unit cells, 52:329-330
amination of, 29:342
3-amino-3-deoxy-6-0-trityl-, preparation of,
29:341-342
antitumor activity of, 32:261
biosynthesis of, 26:3 19-326, 386-391, 32:8,
40:311,41:105-153,44:360-362
chemical inhibitors, 41: 143-144
cytological studies, 41: 116-123
genetic mutations, 41:143-144
hypothetical model, 41: 151
lipid intermediates involvement,
41: 132-135
nucleotide precursors, 26:323-326
organisms, 41:107-110
in plants. 32: 11-12
site, 41:116-123
structural considerations, 41:110-116
C-(aminomethyl)-, preparation of, 29:342
carbon- 13
nuclear magnetic resonance spectra,
38:48
signals, 38:23
carbon-I4,26:15,320-321
carboxymethyl-, 9:285-302
review, 36:ll
cellulose I
crystal structure bibliography, 33:396,
36:323-324
formation by recrystallization, 26:334
green algae, crystal structure bibliography,
35:38 1
normal coordinate analysis, 44:46
in plant cell-walls, 26:300
structure of, 25:80,26:309,328, 41:113
tri-0-acetyl-, crystal structure
bibliography, 40:388
vibrational spectra
atomic displacements for frequencies of.
44:46-51
calculated frequencies and computed
potential-energy distribution of,
44:4649
cellulose 11
crystal structure bibliography,
35:379-380,36:320-322,40:387
structure of, 25:78,26:328,41:113
tri-0-acetyl-, crystal structure
bibliography, 40:389
cellulose 111
crystal structure bibliography, 35:380,
36:322,40:387
structure, 41:113
cellulose IV, 41:113
crystal structure bibliography, O387
chain packing, 40:382
chemistry of, and derivatives. 2 3 5
circular dichroism, 45:89, 120-121
conformation, 24:272, 2651, 31 8.328,
31:281
and tautomers, vibrational spectra used to
analyze, 44:25
constitution of, 25:6
cross-linked, 33:63
with divinyl sulfone, 33:68
preparation and use of, 29:353, 355
crystal structure of, 22:439, 25:80
bibliography. 36:320,323
HI,,, 40:387
single crystals. 33:395
fine structure, 30:347
and micellar theory, 26:308-312
degradation of, 22:20
degree of polymerization of native,
41:114-116
derivatives, 52332
2,3-dicarboxy-, preparation of, 29:340
2,3-di-O-acetyl-, preparation of, 29:330
esters of, with organic acids, 1:309-327
 SUBJEC'T INDEX
ethers of, 2:279-294
flash pyrolysis of, 23:456
fungal, 23:376, 41:72
gas-liquid chromatographic structure
analysis of methylated trimethyls~lyl
ethers of, 30:28
heterogeneous hydrolysis of, 26:3 I2
high-temperature transformation of: alkaline
conditions, 46:30&305
hydrogen bonding
parallel sheets, 52:329
Raman and infrared spectral study of,
44:29
hydrolysis of, 2285, 28:21
derivatives, 22:58
hydrothermolysis of, 46:299-300
ignition behavior of, 23:452
isothermal pyrolysis of, 23:457
laser-Raman spectroscopy, 44:82-83
levoglucosan from, 34:3840
liquid chromatography analysis, 46:39
mechanism of pyrolysis and volatilimtion of,
23:437
of secondary reactions in pyrolysis of:
23:459
methylation of, 3 3 5 3 , 56
analysis, 30:20
in liquid ammonia, 27:91
microcrystalline, for thin-layer
chromatography, 26: 15
molecular constitution of, 3: 185-22R
morphology and biogenesis of, 26:297-
349
native, crystal structure bibliography.
33:396,40:386
non-crystalline, 41: 1 17
non-fermentable oligosaccharides, liquid
chromatography methods for, 46:52
O-(2-aminoethyl)-, preparation of, 29:323
0-(carboxymethy1)-, 24:327
antitumor activity of, 32:253, 261
azide, for insolubilization of enzymes,
29:371
carbon-13 nuclear magnetic resonance
spectra, 38:98, 101-102
effect on cellulose biosynthesis, 41: I I8
hydrolysis of, 29:321
with multivalent cations, 24:330
0-(2-hydroxyethyI)-, preparation of,
29:315
85
physicocheriiical properties of, 29:3 15,
320
preparation and structure of, 24271
sodium salt, 24:328
0-(2-cyanoethylj-, acetate, in films. 29:330
0-(2-diethylarninoethyl)-
benzoylated and naphthoylated, 29:325,
333
in chromatography, 29:322-323
O-(2-diethylaminoethyl)-, in ion exchange
Chromatography, 24:335
O-ethyl-
gas-liquid chromatographic analysis of,
30:36
0-(2-hydroxyethyl)-. hydrodynamic
properties of, 29:3 1 8
0-(2-ethylaminoethyl j-, preparation of.
29:323
U-guanidinoethyl-, preparation and
properties of, 29:327
U-(2-hydroxyalkyl)-, physicochemical
properties of, 29:3 18
0-(2-hydroxyethyl)-
carbon- I3 nuclear magnetic resonance
spectra, 38:98, 101-102
degree of substitution and
physicochemical properties of,
29:3 17
enzymic hydrolysis of, 29:3 19
physicocheniical properties of, 29:3 I5
0-(2-hydroxypropyl)-
degree of substitution in, determination,
29:3 16-3 17
structure of. 29:3 15
0-(m-aminobenzyloxymethy1)-, preparation
of, 29:328
2-U-methyl-, thermal degradation of, 34:
44
O-methyl-
antitumor activity of, 32:254.261
effect on immune tumor response.
32:266
carbon- I3 nuclear magnetic resonance
spectra, 38:98, 100- I0 1
gelation of, 24:33 1
preparation of structure of, 24:271
structures and conformations of, 29:314
O-(N-(N-[3-( dihydroxybory1)-
phenyl]succinamoyl) aminoethyl j-,
preparation and uses of. 29:324,329
86 SUBJECT INDEX
Cellulose (continued)
0-[3-( p-aminophenoxy)-2-hydroxypropyl]-,
29:328
0-p-tolylsulfonyl-, crystal structure
bibliography, 35:380
orientational measurements in, 44:27
0-sulfoethyl-, preparation and properties of,
29:327
0-sulfomethyl-, preparation and properties
of, 29:327
oxidation, 37: 1 19
with dimethyl sulfoxide-acetic anhydride,
33:93
with dinitrogen tetraoxide, 29:346
in plants
cell-walls, 26:300,42:274, 294-297
biosynthesis, 42:3 17-320,332-337
creep of, 42:356-357
interconnections, 42:302-303, 306-307,
312, 314315,338,355
primary cell-walls, 42:268
structure, 42:295-297,3 17
tissue, gas-liquid chromatographic
determination, 28:60
polymer grafting, by radiation, 37:74
polymerization in hydrogen fluoride, 21:445
pyrolysis of, 22:511, 34:3843, 152
cotton, 23:432
mechanism of, 34:43-45
thermoanalytical techniques in, 22:488
pyrolyzate, analysis of, 23:459
ratio to hemicellulose in grasses, 36:253-255
reaction with alkali metal alkoxides,
21:257-258
regenerated, crystal structure bibliography,
35:379
relative crystallininty of, 5:103-126
relative reactivities of hydroxyl groups in,
33:60-63
secondary reaction products of pyrolysis of,
23:454455
selective etherification with acqlamide,
3367
with methyl vinyl sulfone, 33:67
selective methylation with diazomethane,
33:68
sodio-, crystal structure bibliography,
35:379,36:322
solubility in anhydrous hydrogen fluoride,
27:93
solubilization by thiocyanates, 27:95
solvents for, 27: 1 13
some reactions of, 19:219-246
stopping reaction involving, 46:302-303
strength of, effect of heating on, 23:430-
43 1
structure of, 19:219-246, 35:5, 36:315-316,
46:297,52:405
enzymic analysis, 44: 150-1 5 I
new research on, 22:443
from Posidonia austrulis, 30:6
and proton magnetic resonance
spectroscopy of, 27:39
synthesis
orientation model and, 26:333
in vitro, 26:322, 333
thermal degradation of, 23:423, 425
analysis, 23:446
thermal stability of, 22:498
treatment with HF,48:97
triazine derivatives, preparation of, 29:349
tributanoyl-, crystal structure bibliography,
36:325
trimethylsilylation of, 28:3 1
trinitrate, crystal structure bibliography,
36:324
tri-0-acetyl-
complex with nitromethane, crystal
structure bibliography, 33:397
crystal structure bibliography, 36:325
tripropanoyl-, crystal structure bibliography,
36:325
Vulonia, crystal structure bibliography,
33:396
Vulonia ventricosa, structure, 44:26
of wood, polysaccharides associated with,
10~283-333
X-ray studies on, 22:424
Cellulose acetate
carbon-I3 nuclear magnetic resonance
spectra, 38:97
and ethers and esters, 29:330
physicochemical properties of, 29:33 1
thermal degradation of, 29:332
Cellulose acetate nitrate, preparation of, 29:334
Cellulose acetate phosphate, preparation of,
29:334
Cellulose acetate phthalate, dissolution of,
29:331, 333
Cellulose anhydrides, preparation of, 29:343
 SlJBJE.('T INDEX
Cellulose bromoacetate
for insolubilization of enzymes, 29:37 I
preparation and effect on enzymes. 29337
Cellulose carbanilate, physicocheinical
properties, 29:344
Cellulose carbonates, preparation o t 29:344
Cellulose esters, conformational changes.
51 :103-104
Cellulose furoates, 29:338
Cellulose heptanoate propionate,
physicochemical properties of, 29:33 1
5,6-Cellulosene, preparation of, 29:346, 350
Cellulose nitrate
ignition of, 26: 15
physicochemical properties of, 29:333
Cellulose-A"-dimethyl- 1,3-propancdiamine
complex, crystal structure bibliography,
40:388
Cellulose oligosaccharides, conformation and
tautomers, vibrational spectra used to
analyze, 44:25
Cellulose phosphate, preparation of, 29:334
Cellulose precursors
biosynthesis, 41:125-132
high-molecular-weight, 41: 135-142
radioactive compounds, 41: 152
a-Celluloses, research on. 309
Cellulose sorption, 53:384
Cellulose sulfate, 24:322
gelatinization of, 29:336
preparation of, 24:271. 29:335
structure of, 24:271
Cellulose synthetase, 26:390
activity. effect of transmembrane electrical
potential, 41: 147
lability, factors affecting, 41: 145
Cellulose 3-thenoates, preparation of, 29:338
Cellulose 2,2,2-trichloroacetimidate.
preparation of, 29:349
Cellulose trinitrate, crystal structure
bibliography, 40:389
Cellulose xanthates, preparation and use of,
29~346
Cellulosic materials
flameproofing of, 23:465
kinetics and rate of thermal degradation of,
23:442443
pyrolysis
combustion of and, 23:419474
rate of, 23:444445
87
secondary reactions and combustion of,
23:44n
thermal degradation of, 23:424
thermograms of, 23:447.471
transformation and carbonization of, 23:434
volatile products ofirradiated. 23:458
yellowing of, by aging, 46:324-325
Cellulosic waste. levoglucosan from, 34:40
Cellulosine, 46:2 I 1
Cell wall. .see Plants, cell-walls
Centose, in honey. 25297
Centrihgation, in glycoenzynie
characterization, 27:3 12, 3 14
Centrosenitr plumuri. polysaccharide from.
31:253
Cephalochordates. sialic acids occurrence,
40: 137
Cephalopods. glycolipids, see Glycolipids
Cephalosporin. hydrazone with I -gulonic
phenylhydrazide. preparation, 38:300
Ceramide
in biosynthesis of gangliosides. 26:442450
di-o-galactosyl-. biosynthesis of, 26:450
diglycosyl sulfates, 24:406
glycosylation by trichloroacetimidates,
50:49-5 1
inonoglycosyl sulfates, 24:403
monosaccharides, 24:305.400
attachments, 40:238
oligosaccharides. 24:395,400
pentasaccharides. fucose-containing.
characterization. 45:55-56
Cwutocystis hrurmea. polysaccharides, 41 :9 1
Cerutocyms fimhriatti, polysaccharides. 41 :9 1
Cerutocystis olivocea, polysaccharides. 41 :72
C'eratoc.vsti.7 ,ritwadmtr. polysaccharides, 41 :9 I
Cerarocystis .stenoc~'ru~
amylose, 41:69
galactomannan, 41:93
polysaccharide, 41 :69
rhamnomannan, 41:90
Ceratocwtis ulmi, rhamnomannan, 41 :89
Cereals, see ul.to Grasses
P-r-glucans, 363246-248
cultavars. 36:2 19
y-ray irradiation. 51:290-291
hemicellulose-cellulose ratio. 36:253
hemicelluloses. 36:2 15-264
hemicellulosic composition and milling
properties, 36:250
88 SUBJECT INDEX

Cereals (continued) DL.-, synthesis, 40:22

irradiated, biological studies, 51:29 1-292 Chalcoside
Cerebronic acid, 24:396-397,410 methyl, 23:75, 273
Cerebrosan, 23:389 methyl DL-, synthesis, 40:46
Cerebroside, 24:383, 395,44:437438 Chartreusin, 39:302
biosynthesis of, 26:449 11-fucose, 21: 172,39:281
in coelenterates, 44:41 1 Chebulinic acid, 21:27
discovery, 40:235 Cheiroside, 39:302
gas-liquid chromatography of, 28:54 Chelates, of o-fructose, 22:286
laser-Raman spectroscopy, 44:84 Chelation
mannose-containing, from freshwater in carbohydrate-metal base complexes,
bivalves, 44:420 21:237
in sponges, 44:410 in cell-wall structure, 42:305, 346
in starfish, 44:429 Chemical-enzymic synthesis, 44:335
Cerebrosulfatides, 24:403 Chemical ionization mass spectrometry
Cerium salts, 53:327 maltose derivatives, 39:261-263
Cerulenin, inhibition of protein glycosylation, of methylated alditol acetates, 38:401
40:324 of methylated monosaccharides, 38:402
Ceruloplasmin of plant cell-wall components, 42276
carbohydrate linkage n, 25420 Chemical processes, carbohydrate
glycopeptides, liquid chromatography transformation in, 46:323-236
separation, 46:48 Chemical reactions, vibrational spectra in study
heterogeneity in, 25:39 of, 44:30-3 1
human-plasmin, glycoprotein (compound Chemical shifts
53), 'H-NMR spectroscopy, 41:306, in fluorinated carbohydrates, 38:25&260
327-3 30 polysaccharide, 38: 15-1 6
isolation of carbohydrates from, on Chemistry,
analytical-scale columns, 46:60 of amino sugars, 14:213-281
oligosaccharides, liquid chromatography of 2-amino sugars, 7:247-288
separation, 46:4243 of anhydro sugars, 237-77
sialylated oligosaccharides, fractionation. of carbohydrates
46:46 physical, 15: 1 1-5 1
2-C-ErythrofUranosylfurans, 45: 14 of starch, 11:335-385
Cesium iodide, for calibration of mass marker radiation, 16: 13-58
and data system in f.a.b.-mass of carbohydrates, applications of
spectrometry, 45:37 trifluoroacetic anhydride in, 16:59-84
Cetruriu richardsonii polysaccharide, 41 :75-76 crystal-structure analysis in, 19:7-22
C-Glycosides, 25:239 infrared spectroscopy and, 19:2349
C-Glycosyl aromatic compounds, mass some implications of theories relating to
spectrometry of, 29:8 I the mechanisms of replacement
Chaconine, 24:7 reactions in, 9: 1-57
Chacotriose, 24:7 of cyclitols, 3:45-77
Chain folding, polymorphism and. in chitin, containing four of five hydroxyl groups,
22455 20: 1 1-65
Chalcomycin, 21: 173, 179 of 2-deoxy sugars, 8:45-105
Chalcose, 21:191-192,23:75,273 of heparin, 10:335-368
D- of mucopolysaccharides and mucoproteins,
preparation of, 28:300 2:161-201
synthesis, 10 cherry gum, structure, of the nucleic acids, 1: 193-245
41:7-8 of osazones, 20:139-181
 SUBJECT INDEX
of osotriazoles, 18:99-12 1
of pectic materials, 2235-25 1
ofribose, 6:135-174
stereo-, of cyclic derivatives of
carbohydrates, 10: 1-53
of streptomycin, 3:337-384
structural, of the hemicelluloses, 14:429--
468
of polysaccharides, 15:53-89
of thio sugars, 18:123-199
Chemotaxonomy ,25:39
of Leguminoseae, 31:258
Chemotherapeutic agents, o-glucosyl-
amineuronic acids, 36: 123
Cherry, development physiology of, 42:34 1
Cherry gum, structure, 41:7-8
Chick pea, see Cicer nnetiriuni
Chill injury of fruits, 42:339
Chinovin, 6-deoxy-o-glucose from, 2 I : 173
Chinovose. 21: I7
Chirality
aromatic, in conformational analysis,
26:63-64
conformational nomenclature and, 26:76
Chiral precursors, for sugar syntheses,
40:115-123
Chiral synthesis, use in branched-sugar
synthesis, 42:95
Chiroptical properties, I ,4:3,6-
dianhydrohexitols, 49:99-100
Chitaric acid, preparation of, 31: 18
Chitaric acid, dehydration of, 28: I66
Chitin, 15:371-393, 52333-334.405
a-
crystal structure bibliography, 33399,
35381, 36:32&327.40:392-393
structure of, 2 2 4 5 0
X-ray data for, 22454
p-, crystal structure bibliography, 33:399.
35:381. 40:393
biosynthesis of, 26:399,44:373-375
carboxymethyl ethers, 29:3 19
circular dichroism, 45:lOO-101
crystallography of. 22:449
deamination of, 31:235
diatom, crystal structure bibliography.
33:399
esters, ethers and sodio derivatives. 29:343
Fourier-transform infrared spectroscopy,
44:63
89
fungal, 23:376, 386,401,41:72, 103
gel chromatography of hydrolysis products
of, 2 5 5 5
in glycoproteins, 25:415
hydrolyses, neutral, N-acetylated analogs
from. liquid chromatography, 46:41
laser-Raman spectroscopy, 44:83
oligosaccharides
degree of polymerization of, 28:83. 85
liquid chromatography, 46:3940
orientational measurements in. 44:27
in plant cell-walls, 26:302
polymorphism in, 22:450,455
regenerated. crystal structure bibliography,
40:393
solvolysis, 47: 171-1 72
structure. enzymic analysis, 44: I98
sulfation of, 29:336
treatment with HF, 48:98-99
in yeast cell-wall, 32:139
Chitinase, 44: 198
Chitin synthase, 44:374-375
Chitobiose
a-, di-N-acetyl-, monohydrate, crystal
structure bibliography, 34:372
p-, di-N-acetyl-, trihydrate, crystal structure
bibliography, 34:372
circular dichroism, 45:lOl
derivatives, glycosylation, 50:81, 89
di-N-acetyl-. crystallography of, 25:93
as donor, 50:8 I 89
N , N-diacetyl-, monohydrate, crystal
structure bibliography, 38:466467
P-Chitobiosyl fluoride, di-N-acetyl-
biological activity, 38:282
synthesis. 38:203
Chitohexaose, circular dichroism, 45: 101
Chitonic acid
dehydration of, 28: 166
preparation of, 3 1 :I8
Chitosamine, synthesis of. 25:6
Chitosan, 22:450, 23:401
complex with agaropectin, 29:398
crystal structure bibliography, 35:382
depolymerization and deamination in
structure determination of, 31:73
fungal, 41:103
oxidation with nitrogen tetraoxide, 29:347
S-sulfation of nitrogen atoms of, 29:343
structure, enzymic analysis, 44: 198
90 SUBJECT INDEX
Chitose, 25: 18 1, 185
degradation mechanism of, 28: 164-1 65
dimethyl acetal and, 25:212
mutarotation of, 25:213
preparation of, 31:18, 33:115
properties of, and derivatives, 31: 19
reaction with phenylhydrazine, 25:212
structure of, 31:9
and derivatives, 31:19-21
Chitotetraose, circular dichroism, 45: 101
Chitotriose
P-tri-N-acetyl-, crystallography of, 25:93
gel chromatography of lysozyme products
with, 25:35
Chloral, 53:365-366
levoglucosan cleavage by, 34:65
as solvent for sugars, 27: 107
Chloral hydrate in plant cell-wall purification,
42:273
Chloralose, preparation from levoglucosan,
34:65
Chloramphenicol
acetyl bansferase, in E. coli carrying R
factor, 30: 184
cyclic analog, synthesis of, 33: 144
'
Chlorella p.yrenoidosa, 'C-isotope
photosynthesis study, 3 2 6
Chlorination
of nucleotides, 22:378
selective, of carbohydrates, 39:23 1-235
of tri-0-acetyl-o-glucal, 24:203
Chlorinolysis, of glycosidic bond, 34:47
Chloroacetylation, of carbohydrate boronates,
35:54
Chloroacetyl group
as blocking group, 39:35
in nucleoside chemistry, 39:4243
3-Chlorobenzoylacetic acid, cyclodextrin
inclusion complexes with, 46:223-224
Chlorocresols, 53:364365
Chlorodeoxysucroses, AH,B, g systems of,
45:268
3-Chloro-4-enouronate, reactions with AgF,
48: 102- I03
Chlorofluorination, of glycols, 38:237
Chloroform
complex with tri-0-ethylamylose, crystal
structure bibliography, 40:385
effect on conformation, 26:86
as solvent for sugars, 27: 105
sugar composition in, 4260-6 1
sweetness, AH,B system in, 45:22 I
Chloroformates, carbohydrate, decomposition
of, 22:198
A"-[Chloromercuri(II)] guanosine, crystal
structure bibliography, 38:5 10
Chloro(methoxyl)ation, of glycals, 24:203
Chloromethoxymethane
back-donation of lone-pair orbital,
47:109-110
dipole-dipole interactions, 47:82, 84
torsional potential, 47:82-83
(Chloromethy1ene)dimethyliminiumchloride,
in synthesis of chlorodeoxy sugars,
28:250,278
2-Chlorooxane
(Y form preference in solvents, 47:92
conformational equilibria, 47:85
Chloroperoxidase
carbohydrate components of, 27:326
glycoenzyme, 27:309
purification of, 27:3 10
3-Chlorophenyl acetate, cyclodextrin inclusion
complexes with, 46:223-224
Chlorosulfonic acid, reaction with sucrose,
33:252
Chloro(terpyridyl)platinum(II) adenosine 5 '-
monophosphate, hydrate, 43:373
Choanephora curcurbitarum, chitin and
chitosan, 41:103
Cholanic acid, p-elimination and degradation
of, 31:215
Cholera toxin, biological response, 40:230-
23 1
Cholestane, Sa,6P-dibromo-, mutarotation of,
23:13
Cholesterol
conjugate with P-o-glucopyranosiduronic
acid, preparation and characterization,
36:94
with methyl 2,3,4-tri-O-acetyl-a-~-
galactopyranosiduronate, 36:93
glucosidation of, 34:248
25-hydroxy-, inhibition of protein
glycosylation, 40:323-324
proton nuclear magnetic resonance spectrum,
effect of lanthanide chelate-complex on,
29: 16
Chole~terol-4-'~C, thesis, 27:2
Choline, acetyl-a- and-P-methyl-,
 SUBJECT INDEX
enantiomeric, preparation and effect on
nervous systems, 27:210
Choline chloride, radiation-induced radical-
chain reaction, 37: 12
Cholinergic drugs, structure-activity
relationships, 27:208-209
Cholla gum, 24:353
Chondroitin
circular dichroism, 45: 115-1 16
disaccharides, liquid chromatography.
46:37
hydrolysis of carboxyl-reduced deacety lated,
31:196
sulfate
structure of, 26: 16
in urine, 24:443
4-sulfate
biosynthesis of. 26:435
proton magnetic resonance spectroscopy
of, 27:41,43
repeating units of, 26:432
6-sulfate, 24:291
biosynthesis of, 26:436
proton magnetic resonance spectroscopy
of, 27:41,43
repeating units of, 26:432
Chondroitin ABC lyase, 44: 199, 205
Chondroitin AC lyase. 44: 148,205-207
Chondroitinase AC, 44:2 16
Chondroitin B lyase, 44:205
Choiidroitin sulfate, 52:378-382, 4 2 4 4 2 6
as activator of enzymes in trehalose
biosynthesis, 30:243
composition, analysis, 46:55
f.a.b.-mass spectrometry, 45:69-70
hydrazinolysis and deamination of. 3 1:78
oligosaccharides from sulfation patterns,
46:49
structure of, 31:75
and sequence analysis of, 46:57
Chondroitin 4-sulfate
circular dichroism, 45: 117
crystal structure bibliography, 33:400,
40:394
disaccharide repeating units, 43:53-55
Fourier-transform infrared spectroscopy,
44:61
glycosidic linkage, 43:53
hexosamine, 43:53,55
major uronic acid, 43:53, 55
91
sodium salt, crystal structure bibliography,
40:395
Chondroitin 6-sulfate
circular dichroism, 45:l 15-1 17
conformational inversion, 46:7
crystal structure bibliography, 33:399400
disaccharide repeating units, 43:53-55
glycosidic linkage, 43:53
hexosamine. 43:53, 55
major uronic acid, 43:53, 55
Chondroitin sulfate ABC lyase. 44:216
Chondroitin sulfates, 25439
4-and 6-
gel chromatography of ohgosaccharides
from, 25:34
in glycoproteins, 2 5 4 1 7
p-eliminative degradation of, 29:239. 241
carbohydrate chains in, 2 5 4 6 0 4 6 2
carbon-I 3 nuclear magnetic resonance
spectra, 38:74-76, 80
gas-liquid chromatography of hydrolyzates,
28:78
gel chromatography of, 2 5 4 6
molecular weight of chains in, 25:45 1
structure, enzymic analysis, 44: 198-203
sulfation of, 29:336
Chondromucoprotein, 25:435436,439
Chondrosamine, synthesis of, 22:4
Chondrose, preparation of, 31:25
Chondrosine
monohydrate, crystal structure bibliography,
34258
structure, 38:3 I I
Cliondro-4-sulfatase, 44:200
Chondro-6-sulfatase, 44:200
Chordu Wmpuni
response to taste stimuli. protein- modifying
agents that inhibit, 4 5 3 3 5
taste units in, 4 5 3 3 9
Chromatograms, of formose sugars and reduced
formose. 29:207-208.224
Chromatography, 22:6, 25:9
and action pattern of enzymes, 30:271
affinity, see Affinity chromatography
of 1,6-anhydrohexofuranoses.34: 155
of 1,6-anhydrohexopyranoses,34:62
of 2,5-anydrides of sugars. 25: 182
column, see Column chromatography
of cyclic acetals, 34: 180
ofdeoxy sugars. 21:197-199
92 SUBJECT INDEX

Chromatography (continued) in purification of

of D-fmctose, 22~239 L-arabinanases, 32:284
anhydrides, 22:261 of o-galactanases, 32:294
in enzyme purification, 23:283 of D-mannanases, 32:306
extrusive column and thin-layer, of acylated of o-xylanases, 32:329
sugars, 26: 15 oligonucleotides, 36: 195-204
gas, of volatile products from starch and relative reactivities of hydroxyl groups,
pyrolysis, 22:502-503 33:12, 56
gas-liquid, see Gas-liquid chromatography separation of 2'-and 3'-phosphates of
gel, 25:14 adenosine by, 22:349
of carbohydrates, 25: 13-5 1 of sphingosines, 24:390
principles and definitions, 25: I6 and structural integrity of synthetic
in purification of methylated polynucleotides, 36:204-206
polysaccharides, 30: 16 of sugar
separation by, 25: 17 and ammonia reaction products, 25:328
theory of, 25:16-30 solutions, 27: 123
glycoenzyme purification by, 27:3 10 of sulfonic esters of carbohydrates, 23:253
of halogenated sugars, 22:200 thin-layer
high-performance liquid, of aldonic acids, of aldonic acids, 38:3 18
38:319 of cyclic acetals, 26:233-235
history, 35:6 of sialic acids, 40: 162-164
of honey, 25:290-293,295 two-dimensional, interspersed with enzymic
of hydrolyzate of methylated maizestarch reaction, 30:275
dextrin, 22:492 of urine protein-carbohydrate compounds,
ion-exchange 24:44 1,444
of aldonic acids, 38:3 19 vapor-phase, conformation equilibria
cellulose and dextran ethers for, 29:327 measurement by, 24:58
2-diethylaminoethyl ethers of Chromium trioxide
polysaccharides in, 29:322-323 1,6-anhydrohexopyranose oxidation by,
polysaccharide sulfates in, 29:336 34:lOl
and paper, in isolation of glycosyl esters of cyclic acetal oxidation, 39:82-85
nucleoside pyrophosphates, 28:3 10 in degradation of oligosaccharides and
of sialic acids, 40: 150 polysaccharides by oxidation,
liquid, of degradation products of 31~229-232
polysaccharides, 31:239 selective oxidation of carbohydrates with,
of methylated sugars, 30:5 33:98
molecular-weight determination of enzymes, Chromobacterium violaceurn. lipid A, 50:242
23:287 Chromomycin, 21:184-185
0-(carboxymethyl) cellulose in, 29:32 1 Chromomycin A,, 23:262
of oligonucleotides, polynucleotides, and Chromomycin A,, 23:262
ribonucleic acids, 29:333 Chromone, 3,8-dihydroxy-2-methyl-, from
of oligosaccharide, physicochemical uronic acids or pentoses, 28: 190
analysis, 50:3 12-3 13 ChromoseA,21:184185, 187,23:271
paper, see Paper chromatography Chromose B, 21: I85
partition on cellulose, of sialic acids, 40: I5 1 natural occurrence of, 42:72
in pectinesterase purification, 33:338-343 structure of, 42:70,78
of pentoses, 30:7 Chromose C, 21:185-186,308
of polysaccharides, 24:335,338 Chromose D, 21:185, 187,23:271
gels and networks, 24:268 Chronic myelogenous leukemia cells
preparative column, of cyclic acetals, 26:233 glycosphingolipids, 45:55
 SUBJECT INDEX
lactosaminogl ycans
f.a.b.-mass spectrum, 45:39-40
sialylated fucosylated, f.a.b.-mass
spectrometry, 45:59
0-linked oligosaccharides, f.a.b.-mass
spectrometry, 4S:64
Chrysanthemumdicarboxylic acids, synthesis
of, 42:97
Chrysoeriol
biosynthesis of glycoside of, 26:442
from Petroselinum crispum, 3 1:I43 I44
~
a-Chymotrypsin, selective deacylation agent,
39:43
Cibachron Blue, for dyeing amylose, cellulose, Citrus pectinesterase, see Pectinesterases
and starch, 29:351
Cicer arietinum, apiose-containing compound
from, 31:147
Cichorium intJJbZUL, D-fructose from, 22:232
Cinchonine, L-gulonate, preparation, 38:299
Cinerulose A, synthesis, 40:65
Cinnamate, 2,3:4,5-di-O-methylene-~-mannitolCladinoside, methyl a-D-,
I ,h-di-trans-, crystal structure,
43:259-260
Cinnamic acid
I-ester of a- and P-D-glucopyranuronic acid. Cladosporium wernekii. galactomannan, 41 :93
36:106
fruns-, as plant-growth substance. 2 1 :409
trans-p-hydroxy-, esters, in xylans. 36:242
Cinnoline, 3-(~-arahino-tetrahydroxybutyl)-.
22:266, 25:396
Circular dichroism, 45:73-124
artifacts, 45:78
in conformational analysis, 26:63
difference spectra, 45:80-81
fragment-spectra, 4 5 8 1-83
gulono-l.4-lactones, 38:297
instrumentation, 4S:73, 76-78
calibration, 45:77-78
principles, 45:73,76
of reducing sugars in solution, 42:2 1
of sialic acids, 40: 170
spectra
aldopyranans, 39: 197,201
of 1,4:3,6-dianhydrohexitolnitrates,
25254
of dithioacetals, 32:98
of glycosiduronic acids, 36:88-90
measurement, 4576-78
noise in, 45:78
predicted, 45:83-84
93
of substituted carbohydrates, 45:92-124
of unsubstituted carbohydrates, 45:78-92
cis-1,2-Cyclohexanedicarboxylicanhydride,
reaction with cellulose, 29:338
Citeromyce.smutritensis. mannan, 41 :82
Citrate lyase in fruit climacteric, 42:365
(+)-Citreoviral. SO: 193-194
Citric acid, fluoro-, as inhibitor of aconitase,
22:210
Citrosamine. deamination and structure of,
31:76
Citrus fruits, development physiology in,
42:363
Cladinose
a-i--,2 5 8 3
D-, synthesis of, 42:78-79
I.-, synthesis, 35:82, 41:9
natural occurrence of, 42:72
structure of. 42:70, 78
23:272
Cladosporium herhanrm
galactomannan, 41 :94
polysaccharide, 41:70
Claisen condensation, fluorination of
carbohydrates, 38:237
Claviceps,/u.~~formis. polysaccharide. 41 :75
Clindamycin, preparation of, 28:266
from linocmycin, and 7-bromo and 7-iodo
analogs. 28:247
Cloning, effect of tunicamycin, 40:376
Clostridial infections, sialidase role, 40:2 14,
219
Clostridial sialidase, 4 0 ~2 7 2
Clostridium ,/elsineum
a-L-arabinofuranosidase of, 42:388
var. sikokianum, endo-L-arabinanase in,
42:392
Clostridium multzfermentans. 1yase and
pectinesterase from, 33:330-33 I
Clusianose
occurrence. 37:3 18-320
structure, 37:3 19
C-Methyl groups. proton magnetic resonance
spectroscopy of. 27:29
CMP-3-deoxyoctulosonate: 3-
deoxyoctulosylono-lipid A, metabolism of
3-deoxy-~-manno-2-octu~osonic acid.
38:38&386
94 SUBJECT INDEX

CMP-N-acetyl-neuraminate D- Coleoptiles, plant cell-wall studies using,

galactosylglycoprotein transferase, 44:246 42272-273
CMP-N-acetylneuraminic acid Colitose, 21:188, 190
biosynthesis, 40: 186-1 88 ester with guanosine 5'-pyrophosphate,
hydrolase, 40:211 28:32 1
CMP- sialates, enzymic synthesis, 40: 186-1 88 periodate-thiobarbitic acid assay,
CNT, 50:196-197 38:335-336
Coagulation cascade, 43: 117-1 18 Collagen, 43: 136
Coal mining, galactomannans in, 31:3 1 1 biosynthesis of, 27:331
Coatings glycosylation effects, 40:36&366
dextrins as, 47:325 bovine nasal-cartilage, 38:79
levoglucosan esters, 34:76 carbohydrate-peptide linkage in, 25:419,
Cobalt carbonyls, as catalysts in 0x0 process, 436,438,442443,468
2360 fibrils, proteoglycans role in organization,
Cobalt compounds, carbohydrate, preparation, 49:258-259
3556 heterogeneity in, 25:447
Cobalt hydrotetracarbonyl, 0x0 reaction and, as urinary proteinxarbohydrate compound
23:83 source, 24:450
Cobalt(1I) cytidine 5'-monophosphate, Colominic acid, 25:463
monohydrate, crystal structure synthesis of, 26:409
bibliography, 38:505-506 Colony-stimulating factor, 40:377
Cobalt(II1) Color
bis(acetylacetonate)(nitro)(deoxyadeno- coloration scales, 53:376,378
sine), heptahydrate, crystal structure formation in sugar solutions, 26: 14
bibliography, 38528 of sugar products, 9:247-284
Cobalt ion, effect on a-o-mannosidase activity, Colorimetric analysis, of sialic acids,
28:426,428,433 40: 153-160
Coccidioides immitis, polysccharide, 41 :103 Colostrum
Cocksfoot (N-acetylneuraminy1)lactose from cow,
hemicellu1ose:cellulose ratio, 36:253 24:8
xylans, 36:235 sialic oligosaccharides from, gel
Cocrystallization chromatography, 2 5 3 5
of anomers, 25:7 1-77 Column chromatography
of proteins with inhibitor molecules, 25:93 boronic acids in, 35:63-65
Codex Alimentarius Commissioh Draft, on of sugars and their derivatives, 1 0 5 - 9 4
honey, 25:287-288 Combrefum leonense, polysaccharide from gum
Coelenterates, glycolipid content, see of, 24:375, 377
Glycolipids Combustion
Coenzyme B,,, degradation of, 24:261 of cellulosic materials, 23:419474
Coffee beans, a-o-galactosidase from, 35:363 flaming, levoglucosan in, 34:26
Coformycin history of, 23:419
analogs, 46:28 significance of, 23:421
sesquihydrate, crystal structure bibliography, Comenic acid, preparation, 37: 138, 143
32:383,37:422 Compactin, inhibition of protein glycosylation,
Coglucosidase, activator, 40:283 40~323-324
(+)-trans-Cognac lactone, 50: I86 Concanavalin A, 21507
Colanic acid, pyruvic acid in, 30:284 acetylation and succmylation, 35:162
Colchicines, N-deacetyl-N-(per-O-acetyl-o- affinity chromatography, 39:444
glucopyranosyl thiocarbamoy1)- amino acids, 35:161-162
(methylthio), synthesis, 44: 102-103 amino acid sequence, 35: I52
 SCJBJECT INDEX
carbohydrate-binding specificity,
35:142-143, 157-164, 179-190, 204
complex formation, 35: 163, 168, 178
crystal structure, 35: 152
dextran interaction, and dextran structure,
30:405
hemagglutinating activity, 35:20 1
insolubilized, as affinity chromatography
material, 29:385
interaction with amylopectin, 35: 169- 171
with cellular structures, 3 5 3 17
with dextrans, 35:166, 171-173
with o-fructans, 35: 175
with glycogen, 35:169-1 7 I
with glycoproteins, 35: 177-1 79
with mannans, 35: 173-1 75
with polysaccharides. 35: 166-1 69, I79
with teichoic acids, 35: 175-177
isolation, 351 36, 138
of jack bean, physical and chemical
characterization, 35: 150-157
mono-, di-, and tetra-valent, preparation and
biological activities, 35: 164-1 65
preparation and properties, 35: 150L I5 I
structure, 351 53-155
Concentration, effect on gel chromatography.
2919
Condensation, caramel, 47:245
Conductivity (electrical), effect of
carbohydrate-complex salt fomiatioii on,
21:213
Conduritol epoxides
glycoside hydrolase inhibition, 48:364-37 I
kinetic constants, 48:366
reaction with glycosidases, 48:368-369
Conduritols, conformational and
configurational analysis of, 243265
Configuration
of anhydroalditols, 25264
anomeric
determination of, 29:332
effect on hydrolysis of pyranosides,
22:4344
of biologically important non-carbohydrate
compounds, proof of, 27:205-22 I
of branched sugars, 42: 132-1 34
of carbohydrates, determination of.
4: 189-2 I0
carbohydrate use in asymmetric synthesis
and proofof. 27:191-204
95
of carbon atoms, effect on hydrolysis rates
for glycosides, 2252
conformation and, of alditols, 26:70. 73
of cyclic acetals, nuclear magnetic resonance
spectroscopy and, 34: 195-198
of cyclitols. 3:45-77
determination of, of carbohydrate amides,
31:102-110
effect on acyl migration, 33:102
on selective catalytic oxidation, 33:90
on selective esterification of
carbohydrates, 33:35
on selective oxidation of cyclic glycols,
33:94
of higher-carbon sugar alcohols, 1: 1-36
of inositols. effect on relative reactivities of
hydroxyl groups, 33:65
mass spectrometry and, of carbohydrates,
29:43
of monoses, 21:8, 13, 15
of 1,-eq'thvo-pentulose derivatives by proton
magnetic resonance spectroscopy,
26:22 I
of a-substituted carboxylic acids, 21:33
of sucrose, 4: 1-35
of tartaric acids, 21:32
of unsaturated sugars, 24:265
Conformation
of agarose, 24:279
of aldopentofuranosides, 21:99
of aminodeoxy 1,6-anhydrohexopyranoses,
34:127
of 1,6-anhydrohexofuranoses,34:24, 153
of 1,6-aiihydrohexopyranoses,34:24, 5 I
and proton magnetic resonance
spectroscopy, 34:5&61
capsular polysaccharides, and serological
specificity, 41: 178-1 82
of carbohydrates, 30:447
hydrogen bonding effect on. 25:56
of carrageenans, 24:284
of cellulose, 24:272
changes during polymerization of anhydro
sugars, 39: 192-194
crystallography and, 25:101-104
of cyclic acetals, nuclear magnetic resonance
spectroscopy and, 34: 195-1 98
definition. 26:5 I
determination of, 26:53-68
of dithioacetals, 32:90-92, 99
96 SUBJECT INDEX
Conformation (continued)
effect on
acetoxonium rearrangements, 26: I55
on acyloxonium rearrangements, 26: 144
cleavage of anhydro sugars, 22: I89
on ring formation in sugar reactions,
22:171
gel chromatography, 25:3 I
on oxirane ring, 25: 113, 123
selective catalytic oxidation, 33:89
on selective esterification, 33: 15
on selective oxidation of cyclic glycols,
33:93-94
envelope, 26: 109
equilibria, 24:57,26:89
of cyclic acetals, 34: 198-202
extended-chain, of cellulose, 26:328
factors affecting, 23:23,28
folded-chain, of microfibrils, 26:3 12, 3 17,
328
free energy and equilibria, 26:99-103
of o-fructose and acetals, 26:2 I8
of galactomannans, 31:279,281
of gel-forming polysaccbarides, 24:270
of glycans, 37:2062 12
of glycoenzymes, 27:327
of glycofuranosides, 21:96
of glycosuloses, 34: 100
in halogenated carbohydrate formation,
22: 189, 194,207
of hexopyranosuloses, 34:96
of hexopyranuronates, 29:25&259
of L-idopyranuronates, 29:266
instability factors, 26:98
macromolecules, effect of sialyl residues,
40:2 18-2 19
nomenclature, 26:76-81, 109
of polysaccharides
gels and networks, 24:267-332
X-ray diffraction and, 22:43 1
protein, effect of sugar side-chains, 40:353
proton magnetic resonance spectra of cyclic
acetals and, 26:222
of pyranoid sugars, 26:74
representation and terminology, 26:75-81
sickle, 26:72
sofa, 26: 122
of L-sorbose and acetals, 26:213
of sugars, 26:49-125
symbols for, 23:27
term, 23:26
of unsaturated sugars, 24:265
Conformational analysis, 47:4547
of o-g~ucofuranosidurono-6,3-lactones,
33:205-2 10
of polysaccharides, 33:388
review, 3 6 : 3 4
Confomiational energy
anomeric effect, 47:77-88
acyclic model compounds, 47:77-81
cyclic model compounds, 47:83-88
dimethoxymethane, 47:78-79
methanediol, 47:78-79
methoxymethanol, 47:78-79
ROCH,X, 47:79-80
RSCH,X, 47:80-8 1
saccharides, 47: 88
torsional potentials, 47:82-85
map, dimethoxymethane, 47:76-78
Conformational free energies in auqeous
solutions of aldopyranoses, 42:26
Congo Red, 53:384
Coniferyl alcohol polymer in lignin, 42:269
Coniophora cerebella. a-L-arabinofuranosidase
of, 42:387
Coniothyrium diplodiella, pectinesterase from,
33:333
Conjugates, of o-glucuronic acid, 9: 185-246
Constitution, of carbohydrates, 15:11-51
Convallatoxin
6-hydroxy-, 21:292
preparation and cardiotonic activity of,
27:4
synthesis of, 21:278,282,285
Convolvulaceae, galactomannans from,
31:253-254
Convolvulin, o-fucose, 21: 172,39:28 I
Convolvulus awensis, cell-wall enzymes in,
42:301
Coordination spheres, metal ions, 47: 128
Cope degradation, 40:5&5 1,53
Copolymerization
of anhydroaldoses, 39: 176-179
of 1,6-anhydro sugars, reactivity ratios,
39: 188-194
Copper bis@henanthrolinej, for enhancing
detectability of carbohydrates, 46:67
Copper(II), effect on cis-inositol I3C-NMR,
47: 142-143
Copper(l1) (glycylglycinato) cytidine, di-
 SUBJECT INDEX
hydrate, crystal structure bibliography.
38:SOO-SO 1
Copper( 11) guanosine 5-monophosphate,
tetrahydrate, crystal structure
bibliography, 38508-5 10
Copper(I1) guanosine 3-monophosphate I , IO-
phenanthroline, crystal structure
bibliography, 38:529
Copper(l1) iminodipyridine adenosine 5 -
monophosphate, crystal structure
bibliography, 38:528
Copper(I1) inosine 5-phosphate (2,2-
bipyridyl)( H,O), nitrate, monohydrate.
crystal structure bibliography, 38:527
Copper(l1) uridine 5-phosphate (2,2-
dipyridylamine)(H,O),, pentahydrate,
crystal structure bibliography, 38:528
Copper ions
complex-formation, 47:2 1
effect on a-wmannosidase acitivity, 28:426,
428,433
Copper salts, effect on conformation of sugars,
23:37
Coprinus mucrorhizus, polysaccharide.
41 :7 1-73
Corchsularose, 21 :145
Cordycepin, 21:157
biosynthesis, 35: 123
from Cordyceps milituris. 31: 149
crystal structure, 43:3 17-3 I8
3 -(dihydroxyphosphinyl-,methyl)-,
ethanolate, crystal structure
bibliography, 30:462
stnicture of, 29:5
synthesis of, 29:289,33:85
of analog of, 33:142, 188
Cordycepose, 21: 157, 159
structure of, 31:149
Coriofuranose, I ,2,4,5,7-penta-O-
(trimethylsily1)-c*-,and trimethylsilyl
glycosides, 28:25
Coriose
in aqueous solution, 42: 16,41
crystal structure bibliography. 30:45 1
1,2,4,5,6,7-hexa-0-(triemthyIsilyl)-keto-,
28:25
trimethylsilylation of, 28:25
Com
cell-wall studies on, 42:268, 285, 292-294,
300,314,332
97
dextrinization and properties. 47:320-32 I
dextrins from, 47:3 17-3 I8
glycogen and starch from sweet, stnichire of,
325
hull, xylans. 36:236
production, 36:20
roots, polysaccharides, 36:245-246
wet-milling and separation processes.
36:23-24
Comforth reaction, 38:329
3-deoxy-r~-manno-octulosonicacid synthesis,
38:365- 369
Corn starch. see ulso Starch
bulk density, 51:248,250
composition, 36: I6
dextrinization, 47:289
hydrolyzates. composition, 36:35
separation after irradiation, 51:271-274
sorption-desorption hysteresis, 51:248-249
Corn syrup
carbohydrates, 36:29
gas-liquid chromatographic analysis of,
28:46,48, 68
high-D-fructose, technology, 36:SO-55
oligosaccharides, liquid chromatography
analysis, 46:39
technology. acid catalysis, 36:22-29
modem, 36:35-39
transportation and uses, 36:29
Coronary vasodilators. dianhydrohexitol di-
nitrates as, 25:268
Corticium rolfsii. a-L-arabinofuranosidase
from, 42:387, 389,390-391
C,ororticztrn, gum, 36:305
Corynomycolic acid. trehalose ester, in
mycobacteria. 30:235
Cosmetics
dextrins in, 47:329
1,4:3,6-dianhydrohexitolsapplications,
49: I68
galactomannans, 31:3 11, 35:342
Cotton boll
biosynthesis in. 26: 15
enzymes from, in cellulose synthesis, 26:324
Cotton effect, 23:127, 24: 134, 25:375,26:13
in conformational analysis, 26:6344
and octant rule, 34: 104
and optical rotatory dispersion spectra and
circular dichroism of dithioacetals.
32:W
98 SUBJECT INDEX

Cotton fiber for 5-phosphonylaldopyranoses,42: 163-164

cellulose biosynthesis, 41 :109147-1 48 Cresol, as solvent for mutarotation of D-
precursors, 41:126, 139, 141 glucose, 27: 104
cell-wall studies on, 42:268 Cross-linking,of polysaccharides, 29:353-358
gas-liquid chromatographicanalysis of, Crotalaria juncea lectin, isolation, purification,
28:62 and properties of, 35:306
liquid chromatographyanalysis, 4652 Crotonaldehyde,precursor for sugar syntheses,
Cotyledon, galactomannans,35346, 35&36 1 40:7
Cotylenins, methyl-branched sugars from, Crotonic acid, precursor for sugar synthesis,
42:70,76 40:4-7
Coumaric acid Crustaceans, sialic acids occurrence, 40: 136
o-,as plant-growth substance, 21:409 Cryptate 212, inhibitor of cellulose
p - , as plant-growth substance, 21:409 biosynthesis, 41: 144
attachment to primary-wall polysaccharides, Crypticity, in sugar utilization by yeasts,
42:382 32:149
Coumarin, 53:373 Cryptococcosis,41:97
3-(4-bromobenzamido)-4-hydroxy-8-methyl- Cryptococcus, polysaccharide, 36:301,41:69,
7-[3-0-(5-methyl-2- 97-98
py~rolylcarbonyl)noviiopyranosyloxy]-, Crystalline dextrins, 46:211-213
crystal structure bibliography, 37:406 Crystallinity, 53:303
and derivatives as plant-growth substance, relative, of celluloses, 5: 103-126
21:409 Crystallization
inhibition of protein glycosylation,40:344 dextran effect on, of sucrose, 30:443
inhibitor of cellulose biosynthesis, of D-fructose, 36:55-56
41:143-144 of D-glucose, 36:30,41,43
4,4'-methylenebis-4-hydroxy-, see Crystallography
Dicumarol of adenosine 5'-phosphate, 22:3 12
Coumaryl alcohol polymers in lignin, 42:269 of cellulose, 22:439
Coupling constants, see Carbon-proton of chitin, 22:449
coupling constants of D-fructose, 22:232-233
Courtois, JeanEmile, 49:11-18 of galactomannans,31:280
academic career, 49: 11-12 of mannans, 22:458
archeologicalwork, 49: 17-1 8 and molecular structure of carbohydrates,
glycosidase research, 49: 1 4 1 5 25:58-56,30:445
glycosidases and glycanases from xylophagic of polysaccharides, 22:424
insects, 49:15-16 of thymidine 5'-phosphate, 22:3 12
honors and distinctions,49: 17 X-ray, in conformationalanalysis, 2653
international organizations,49: 1 6 - 1 7 of xylans, 22:458
periodic acid oxidation research, 49:12-13 Crystal structure
plant oligosaccharideresearch, 49:13-14 analysis, of 1,6-anhydrohexopyranoses,
role in Societe de Chimie Biologique, 49: 16 3 4 51
Cram rule, 21:180,24:108, 130,34:105, bibliography
42:151 of carbohydrates, nucleosides, and
in asymmetric synthesis, 27:193,263 nucleotides, 30:445466,
Cranberry, development physiology of, 42:37 1 31~347-371,32:353-384,
Crankshaft motion, 51:8&81 34:345-378,37:373436,
Crayfish, trehalose biosynthesis in, 30:239 38:4 17-529
Cremer-Pople puckering parameters of polysaccharides, 33:387404,
for 4-deoxy-4-phosphinylpentofuranoses, 35:377-385,36:315-332,
42: 183-184 40~38 1-399
 SlJI3JEC'T INDEX
of carbohydrates and derivatives, 25:53
107
of concanavalin A, 35:152
of dianhydrohexitol nitrates, 25:255
of fluorinated carbohydrates, 38:280. 285
of monosaccharides. 25:53-75
C-substance
cell-wall component, 33:296
structure of, 33:320-32 1
CTP:CMP-3-deoxyoctulosonate
cytidylyltransferase, metabolism of 3-
deoxy-r)-ntanno-2-octulosonic acid.
38 :38 1-3 84
Cucumber
development physiology of, 42:34 1-342.
363,370-371
wild, lectin, isolation, 35: 135
Cuprammoni um
complexes, mutarotation measurenient by,
23:52
for enhancing detectability of carbohydrates.
46:67
glycoside complexes. 6: 107-134
Curacin, 46: 14
Curacose
~-,21:172,46:14
occurrence, 39:281
Curamycin, 46: 14
o-fucose derivative from, 21: 172
Curamycose, 46: 14
Curdlan, 52:356-361
circular diehroism, 45:89
fine structure of, 30:369
gelation, Fourier-transfomi infrared
spectroscopy, 44:62-63
helix structure, 52:358, 360
parallel packing arrangement, 52:3511-359
preparation. properties, and uses,
36:307-3 I0
structure, 52:415
Currant, development physiology of, 42:34 I
Cutscum, activator for enzymic hydrolysis of
glycosphingolipids, 40:28 1-285
Cyanainido group, participation in sugar
reactions, 22: 15 1
Cyanoaeetamide, for enhancing detectability of
carbohydrates. 46:67
2-Cyanoethyl group, as protecting group for
phosphate, 36: 153
2-Cyanoethyl phosphate
99
as phosphorylatiiig agent for nucleosides,
22:33 1
selective phosphorylation of nuclcosides
with. 33:49
Cyanogen broinidc, agarose activation. for
affinity chromatography. 39:4 1 4 . 4 3 0 4 3 1
Cyanohydrin synthesis, Fischer. 1: 1-36
3-Cyanophenol. cyclodextrin inclusion
complexes with, 46:22 I
4-Cyanopheno1, cyclodextrin inclusion
complexes with, 46:22 1
3-Cyanophenolatc ion, cyclodextrin inclusion
complexes with, 46:221
4-Cyanophenolate ion. cyclodextrin inclusion
complexes with. 46:22 1
Cyanuric chloride, reactions with alcohols and
carbohydrates. 28:258
Cyclamate
sweetness. 45:23 I
structure relationship. 45297- 303
three-dimensional X-ray analysis of. 45:301
Cyclaniic acid
sweetness. AH.B system in. 45:22 I
third structural feature comprising postulated
glucophore in. 45:234
Cyclic acetals
of the aldoses and aldosides. 20:219-302
as photosensitive protecting groups, 46: 195
Cyclic adenosine monophosphate, 2-
nitrobenzyl and 6-nitroveratryl esters of,
irradiation of. 46:204
Cyclic AMP. i n plant tissues, 42:367
Cyclic derivatibes
of carbohydrates, stereochemistry of.
10: 1-53
definition. 52:50
nomenclature, 52:4849
Cyclic guanosine monophosphate, 2-nitribenzyl
and 6-nitrovcratryl esters of. irradiation of,
46:204
Cyclic model compounds, conformational
energy. 47:83-88
Cyclic polysaccharides, f.a.h.-mass
spectrometry. 45:68-69
C'yclitols, 14: 135-212
acetates, gas-liquid chromatography of,
28: I so
ainino-
antibiotics, synthesis, 35:8 I . 102- 122.
38:285
100 SUBJECT INDEX
Cyclitols (continued)
selective esterifications of, 33:40
aminodeoxy-
gas-liquid chromatography of, 28:87
selective catalytic oxidation of, 33:9 1
2-amino- I ,2-dideoxy-, deamination of, 31:77
chemistry and configuration of, 3:45-77
conformation of, 26:84
containing four or five hydroxyl groups,
chemical and physical studies of,
20:11-65
deoxynitro-, 24: 100
eletrophoresis in metal salt solutions, 21:232
equilibria with borate complexes in aqueous
solutions, 42:25
gas-liquid chromatography of, 28:89-90
induced shifts of proton signals, 47:7
inversion in, 31:4
lanthanide-induced shifts, 47:9-10
natural occurrence of, 42:73,77
nitro-, acylation of, 24: 1 I5
per(trimethylsily1) ethers, gas-liquid
chromatography of, 28: 149-150
as plant-growth substances, 21:4 16
rearrangement in acetic acid-sulfuric acid,
26: 188-191
in liquid hydrogen fluoride, 26: 169-1 73
selective catalytic oxidation of, 33:90
selective esterification of, 33: 14, 38
selective etherification and relative
reactivities of hydroxyl groups in,
33:64-66
sulfonylation of, 23:250
sweetness-structure relationship, 45:24 1,
290-293
synthesisof, 42:115-118, 129-131
trifluoroacetyl derivatives, gas-liquid
chromatography of, 28: 114
Cyclization
of aldohexoses by acids, 34:3437
of 6-C-substituted hexopyanoses, 34:33-34
of hexopyranosyl derivatives containing
reactive substituents, 34:3 1-33
intramolecular and sulfonate displacement,
33: 126-1 3 1
mediated reactions, 53: 1 8 6 1 88
of oligosaccharides, 34: 158
radical, 53:188-191
Cycloaddition, photochemical, carbohydrate,
38:106- 108
Cycloamyloses
carbon-1 3 nuclear magnetic resonance
spectra, 38:37-39
cross-linking of, 29:404
derivatives, 29:402--405
determination by trimethylsilylation, 28:25
gas-liquid chromatographic separation of,
28:70
per(dimethylsily1)ated. gas-liquid
chromatography of, 28: I35
separation as diemthylsilyl derivatives, 28:3 1
Cyclo-Ara-C, hydrochloride, crystal struchire
bibliography, 31:360
Cyclo-Ara-U, crystal structure bibliography,
31:355
Cyclobarbital, cyclodextrin inclusion
complexes with, 46:223-224
Cyclobutanol, formation mechanism from
penta-O-acetyl-keto-r~-sorbose, 38: 128
Cyclobutene, sugar derivative, synthesis of,
27:299
Cyclodextrin
alpha, 46:206
chemical synthesis of, 46:207
conformational change of, during
complex-formation, 46:23G23 1
o-glucosyl units, 46:228
dipole moment, 46:232
inclusion-complexes, enthalpyxntropy
compensation for, 46:224
strained, high-energy conformation,
46:228
beta, 46:206
chemical structure, 46:207
inclusion-complexes, enthalpy-entropy
compensation for, 46:224
numbering of atoms of, 46:207
partially methylated, 46:245
branched, 46:246
cavity, water of, 46:227-228
"C c.p.-in.a.s. shidies of, 46:23 1
chiral discrimination by, 46:247-249
covalent capping of. 46:247
r>-glucosyl residues, 46:2 14
2,6-di-O-methyl derivative, 46:245
discovery of, 46:211-213
enthalpy of association, 46:228
facilitation of association of molecules
through presence of. 46:2 10
formation of, from starch, 46:2 15-2 I7
 <IJHIkCT INDEX
further research in. 46:249
gamma, 46:206
modified, 4632455246
space regulation of cavity by appcndetl
naphthalene moiety, 46:246
substitution with two naphthyl groups.
46:246-247
liquid chromatography separation, 46:44-
45
modified
catalytic properties, 46:244-247
chiral selectivity of, 46:249
complexing ability, 46:245
molecules, covalent linking of two, 46:245
periodate oxidation of, 46:214-2 IS
physical properties of, 46:208
properties, 46:206
reactions catalyzed, 46:244
chiral selectivity. 46248-249
separation, 46:207
structural and sequence analysis of. 46:57
structure of, determination of, 46:2 1.3- 2 I5
tri-0-methyl-a-, 46:245
ulhasonic-relaxation techniques for, 16:230
a-Cyclodextrin hexahydrate, crystal structure,
43:266
Cyclodextrins, 12:189-260
CY-,53:313
crystal structure bibliography, 32:37 I
"C-NMR data for, 42:199
inclusion complexes. 46:205-250
acid-base titration. 46:220
advantage of, 46:208
with azo dyes, 46:235,239
with biphenyl compounds, 4 6 2 3 9
with cinnamates, 46:239
circular dichroism, 46:2 19-220
complex-formation
detection of, 46:219-220
enthalpy-entropy compensation,
46:22 1-225
favorable entropy change in, 4 6 9 3 3
hydrophobic interactions in, 46:233
kinetics of, 46:234-244
in nonaqueous solvents, 46:220
solvation changes on complexar inn.
46:225-226
standard-enthalpy change
accompanying, 46:220-223
standard-entropy change, 46:220-223
101
standard free-energy decrease
associated with. 46:220
thermodynainics of, 46:220-234
confomational change. 46:236,238~
239
cross-polarization, magic-angle-spinning,
I 'C-NMR spectroscopy, 46:2 19
crystal structure analyses, 46:232-233
with crystal violet, 46:24 1
with cyanine dyes, 46:244
discovery of, 46:2 I7
electric-field pulse relaxation, 4 6 2 3 4
fluorescence, 46:219
formation of, 46:210-21 1
kinetics, 46:237-238
'H-nuclear magnetic resonance
spectroscopy, 46:2 18
hydrophobic interactions, 46:226-227
with inorganic aiiions, 46:235-236
isoequilibrium. 46:22 1-225
with long-chain fatty acids, 46240
with Methyl Orange, 46:242-244
nuclear magnetic resonance, 46:220
one-host-one guest complex-foimation,
46:235-239
one-boat-two guests complexation.
46:209-2 10,240-243
mechanisms, 46:2 1 I
with methyl orange. 46:245
with organic dyes, 46:235,240-242
phosphorescence decay. 46:235
properties, 46:2 17-2 18
with Pyronine Y . 46:240
with Roccellin, 46:244
Saenger's theory of formation. 4 6 2 9
single-step, binding mechanism, 46:237
solubility, 46:220
stability, 46:20X-209
dependence on polarizability of guest
molecule, 46:232
stopped-flow kinctic studies. 46:234,
237~-238
temperature. 46:225
temperature-.jump relaxation kinetic
studies. 46:234, 237-238, 240
with Tropaeolin, 46:242, 244
two-dimensional, nucleat Overhauser
effect experiment on, 46:21X 219
two hosts-one guest complex formation,
46:239- 240
102 SUBJECT INDEX
Cyclodextrins (continued)
two hosts-two guest complex-formation,
46:242-244
two-step mechanism, 46:238-239
ultrasonic absorption relaxation, 46:234
ultraviolet-visible absorption. 46:2 19
van der Waals forces in, 46:23 1-233
X-ray crystallography, 46:2 I8
metal binding to, f.a.b.-mass spectrometry,
45:70
Cyclodextrin transglycosylase, 46:207-208
Cycloheptaamylose
carbon-13 signals, 38:23, 38
carboxymethyl and sulfomethyl ethers and
truns-2,3-carbonates, 29:403
coinplex with r-hydroxybenzoic acid, proton
magnetic resonance spectroscopy of,
27:32
crystal structure, 25:79
fragmentation by radiation, 37: 14
heptakis(6-azido-6-deoxy)-,hepta(2,3-
diacetate), preparation, 39:33
inclusion complexes, 29:405
radiation effect on complexes, 37:74
spin-labelled monoester and monophosphate,
29:404
sulfonylation of, 23:236
Cycloheptaamylose peracetate
carbon-I3 nuclear magnetic resonance
spectra, 38:97
preparation of, 29:402
Cyclohexaamylose
6-aniino-6-deoxy-, preparation of, 29:403
6'-azido-h'-deoxy-, amylase reaction, 39:241
6-azido-6-deoxy-, preparation of, 29:403
6-bromo-6-deoxy-, preparation of, 28:303,
29:403
carboxymethyl and sulfomethyl ethers, and
truns-2,3-carbonates, 29:403
6-chloro-6-deoxy-, preparation of, 28:303,
29:403
crystal structure of, 25:79
6-deoxy-, preparation of, 28:303,29:403
6-deoxy-6-iodo-, preparation of, 28:303,
29:403
dodeca-0-methyl-, structure of, 29:402-
403
fragmention by radiation. 37: 14
hexahydrate. crystal structure bibliography,
32:371
hexakis
(6-acetamido-6-deoxy)-, preparation of,
29:403
(6-amino-6-deoxy)-, preparation of,
29:403
(6-azido-6-deoxy)-, preparation, 39:33
(6-azido-6-deoxy)-, preparation of. 29:403
(6-O-p-tolylsulfonyl)-, preparation of,
29:403
inclusion complexes, 29:404
monobenzoate and 2,5-
pyridinedicarboxylate, 29:403
0-(carboxymethy1)-, amide, ether
derivatives, preparation of, 29:322, 327
structure of, 29:323
0-(2-diethylaminoethyl)-.benzoylated,
29:325
toxicity of, 29:323
O-(2-hydroxypropyl)-, in adsorption studies,
29:3 18
potassium acetate complex, crystal structure
of, 25:78
radiation effect on complexes, 37:74
selective p-toluenesulfonylation of, 33:38
selective tritylation of, 3 3 5 2
tetra(6-O-trityl)-, oxidation with dimethyl
sulfoxide-acetic anhydride, 33:92
a-Cyclohexaamylose P-iodoaniline, trihydrate,
crystal structure bibliography, 37:407
Cyclohexaamylose carbon- I3 signals, 38:23,
38
a-Cyclohexaarnylose complexes, crystal
structure bibliography, 37:407
Cyclohexaamylose hexahydrate, crystal
struchire, 43:266
Cyclohexaamylose-iodine tetrahydrate, crystal
structure bibliography, 31:354
a-Cyclohexaamylose krypton hydrate, crystal
structure bibliography, 37:408
a-Cyclohexaamylose methanolate,
pentahydrate. crystal structure
bibliography, 37:407
Cyclohexaamylose octadecabenzoate, selective
deacylation, 39:33
Cyclohexaamylose peracetate
carbon-I3 nuclear magnetic resonance
spectra, 38:97
preparation of, 29:402
a-Cyclohexaamylose-p-iodoaniline, trihydrate.
crystal structure bibliography. 34:362
 SCIBJEC'T INDEX
Cyclohexaamylose-potassium acetate hydrate
complex, crystal structure bibliography.
31:369
Cyclohexaamylose-1 -propanol-4. 8-hydrate.
crystal structure bibliography, 32:37 I
Cyclohexane
conformation of, 2650-5 I , I I8
interconversion of conformers, 26:O I
polyhydroxy-, optical rotation and
conformation of, 26:61
Cyclohexanecarboxaldehyde, 2-hydroxy-,r,,rrn.s
.23:63
Cyclohexanecarboxylic acid, cyclodexttin
inclusion complexes with, 46:22 I
Cyclohexanediols
1,4-, cyclic boronates, preparation, 35:?6
cis- I ,2-
acetylation of, 33:33
diacetate, acetoxonium slat from.
26:13 1-132
reaction with 2-acetoxy 2-
mythylpropanoyl chloride, 33:X4
cis-I ,3-
cyclic boronates, preparation, 35:36
sweetness-structure relationship. 45:27 1
trans, trans-2-carbethoxy-2-nitro-, 24: 106
trans, trans-2-(hydroxymethyl)-2-nitro-,
24: 106
trans, tran.r-2-niethyl-2-nitro, 24: I06
trans, trans-2-nitro-, 24: 106
trans-2-ehtyl-2-nitro-. 24: 106
trans-2-nitro-2-plienyl-, 24: I06
laser-Raman spectroscopy, 44:83
oxidation with lead tetraacetate, 33%
trun.v-, reaction with 2-acetoxy 2-
mythylpropanoyl chloride, 33:X4
Irans- 1,2-, diacetate
cis-acetoxonium salt from, 26: 13 I I32
~
rearrangement in hydrogen fluoride.
26: 115
trans-l,3-, diacetate, acetoxonium salt from.
26: 132
Cyclohexaneglycolic acid, a-phenyl-.
preparation of. 27:201
I .2.4,4/3,6-Cyclohexanehexol (muco-inosiiol),
crystal structure, 43:2 16
Cyclohexane- I ,2,3,4,5/0-pento1347:8, 4 I
Cyclohexanepentols
rearrangement in acetic acid-sulfuric acid,
26:189, 190
I03
sweetness. 45290-293
Cyclohexanes, substituted, anomeric
equilibrium, 47:54
C'yclohexanctetrol, C-( hydroxymethy I)-,
rearrangement in acetic acid-sulfuric acid.
26:191
( 1.2.5/3)-Cyclohexanetetrol~rearrangement in
acetic acid-sulfuric acid. 26: 188
( 1 2 3 3 )-Cyclohexanetetrol, rearrangement in
acetic acid-sulfuric acid, 26: 188
( I ,2/3)-CycIohexanetriol. acyloxontuni
derivatives, 26:137, 138
( 1.3/5)-Cyclohexanetriol.tripivalate,
acyloxonitim rearrangement of, 26: 144
C'yclohexanetriol triacetate. ( 1,3/2,4,6)-4-
bromo-6-(brornomethyl)- 1.2.3-, 48:3 1
Cyclohexanol
acetylation ot. 33:33
2-amino-. deamination of, 25: 184
2-aniino-4-tert-butyI-, deaniination of,
25: 185. 31 :23. 39
cis-2-amino-. deainniation of. 3 1 2 3
cyclodextrin inclusion complexes with,
46:222-224
4-phenyL. esrerification by p-phenyl-
azobenzoyl chloride, effect of
conformation on, 33:15
as solvent in reduction of o-glucose. 2 7 9 9
Cyclohexanone
cis-2, h-bis(acetaniido)-, 24: 1 12
2-(2,3,S-tri-O-benzoyl-~-n-r~bofuranosyl)-,
preparation of. 33: 160
Cyclohexene oxide, hydroformylation of.
23:63
5-Cyclohexene- I .2.3,4-tetroI. selective catalytic
oxidation ofstereoisomers, 33:91
Cyclohexenones, from dehydration reactions of
carbohydrates, 28: 174
Cycloheximide, inhibitor o f galactomannan
degradation, 35:360
h" -Cyclohexyl-a-forniy laminoacetamidine.
52:299-300
Cyclohexylainines
deamination of. 31: 16
2-methoxy-, deamination. of, 31:77
Cyclomaltoheptaose, 46:206
dodecahydrate, 43: 3 3 3, 3 72
laser-Raman spectroscopy. 44:82
nonselectice spin-lattice relaxation rates.
45: 149
104 SUBJECT INDEX
Cyclomaltoheptaose-2,5-diiodobenzoicacid,
hexahydrate, 43:372
Cyclomaltoheptaose-dipropanol
dodecahydrate, 43:334
nonahydrate, 43: 3 34
Cyclomaltoheptaose-ni-methylphenol,
decahydrate, 43:334
Cyclomaltoheptaose4-nitroacetanilide,
hydrate, 43:3?2
Cyclomaltoheptaose-p-iodophenol,
tetracosahydrate, 43:372
Cyclomaltoheptaose-I-propanol.43:372
Cyclomaltoheptaose-sodiumpolyiodide,
octahydrate, 43:334
Cyclomaltohexaose, 46:206,53:3 13
dihydrate, 43:372
laser-Raman spectroscopy, 44:82
Cycloinaltohexaose-bis(m-nitrophenol,
hexahydrate, crystal structure. 43:354
Cyclomaltohexaose-dimethyl sulfoxide,
methanol solvate, dihydrate, crystal
structure, 43:354
Cyclomaltohexaose hexahydrate. crystal
structure, 43:266
Cyclomaltohexaose inclusion complexes,
standard formation enthalpies and
entropies of, 46:221-223
Cyclomaltohexaose-N, N-dimethylfonnamide,
pentahydrate, crystal structure,
43:266267
Cyclomaltohexaose-p- hydroxybenzoic acid,
trihydrate, crystal structure, 433355
Cyclomaltohexaose-p-iodophenol,trihydrate,
crystal structure, 43:354
Cyclomaltohexaose-p-nitrophenol. trihydrate,
crystal structure, 43:354
Cyclomaltohexaose-potassium [sodium]
Methyl Orange, hydrate, crystal structure.
43:355
Cyclomaltohexaose-1-propanol, 43:372
Cyclomaltohexaose-2-pynoldinone,
pentahydrate, crystal structure. 43:267
Cyclomaltohexaose-sodium henzenesulfonate.
decahydrate, crystal structure, 43:355
Cyclonialtohexaose-sodium 1 -propane-
sulfonate, nonahydrate, crystal structure,
43:354
Cyclomaltohexose, circular dichroism, 45:87
Cyclomalto-octaose, 46:206
heptadecahydrate, 43:334
I-propanol complex. hydrate, 43:334
Cyclomalto-oligosaccharides, .see U ~ C J
Cyclodextrins
branched, 46:246
liquid chromatography separation, 46:4445
Cyclooctaamylose, carbon-13 signals, 38:38
Cyclooctaamylose peracetate, carbon- I3
nuclear magnetic resonance spectra, 38:97
Cyclooctadecane, 1,4,7,10,13,16-
hexaoxadibenzo[P, K]-, in Koenigs-Knon
reaction. 34:25 1
Cyclopentaiiediol
cis- 1,2-, diacetate, acetoxonium salt from,
26: I3 1-132
1,2-
cis- and /ram-, reactions with 2-acetoxy-
2methylpropanoyl chloride, 33:84
1,2-dimethyl-,rran.~-,oxidation with lead
tetraacetate, 33:95
trms-, oxidation with lead tetraacetate.
33:95
(I,2,3/4,5)-Cyclopentanepentol, 26: I42
( 1,2,4/3)-Cyclopentanepentol,acyloxoniuni
salts, 26: 140
( I .2,4i3,5)-Cyclopentanepentol, acyloxonium
salts, 26: 140
( 1,2/3,4)-Cyclopentanetetrol, tetra-0-acetyl-,
rearrangement in liquid hydrogen fluoride.
26:171
( 1,3/2,4)-Cyclopentanetetrol,acyloxonium
slats, 26: 139
Cyclopentane-l,2,3,4-tetrol, 2,3-0-
cyclohexylidene-5-nitro-, isomers, 24: 105
(1,2,3/0)-Cyclopentanctriol,preparation of,
26: 137
2-Cyclopeiiten- 1 -one, 2,3-dihydroxy-, see
Reductic acid
Cyclopentenones, fomyation, 46:294
Cyclopenten- 1-ylium perchlorate. 2,3-diphenyl-,
in Koenigs-Knorr reaction, 34:250
Cycloserine, D-, in peptidoglycan hiosynthesis,
26:42?
Cyclosophoroses
liquid chromatography separation, 46:4445
preparative liquid chromatography, 46:60
Cymarin, 21:293
Cymarose, DL-, synthesis (attempted), 40:22-23
Cymaroside
methyl LY-DL-, synthesis, 40:40
methyl UL-, synthesis of, 28:298
 \11131t ( 1 INDEX
Crystalline structures
versus compounds in solution, vibrational
spectra. 44: 14, 16. 2 1
orientation, infrared dichroism study,
44:2&27
Cysteine
DL -. with 1)-galactose, products from.
46:3 17-3 18
1.-, and a-dicarbonyl compounds, reaction
between, 46:3 18
N-acetyl-i -, ketonucleoside reaction %ith,
42:263-264
reaction with aldoses, 32:20
Cystic fibrosis, a-L-fucosidase activity.
39:333-334
Cytidine
a-, crystal structure bibliography,
38:486487
5-(cu-o-glucopyranosyl pyrophosphate).
enzymic synthesis of, 28:338
occurrence and isolation of, 28:3 I 5
structure of, 28:309
5 -(2-amiiio-2-deoxy-a-~-glucopyl.anosyl
pyrophosphate), enzymic syntIie\i\ of;
28:339
2.2-anhydro-, preparation of, 28:253
2,5-anhydro-2, 3-O-isopropylidene-.
24:177, 179
S-(barium phosphate), 8.5 hydrate. ciystal
structure, 43:3 13-3 14
3-(benzyl hydrogenphosphate), hydrolysis of,
21:329
5-bromo-2-deoxy-.2-deoxyguanosnie
complex, crystal structure bibliography.
31:370
[cadmium(Il) 5-monophosphate].
monohydrate. crystal structure
bibliography. 38:505
cadmium 54nonophosphate dihydratc.
crystal structure bibliography, 34:373
3 -(cesium cis-platinumdiammine
phosphate), tetrahydrate. 43:334
(choline 5-diphosphate). monohydrate.
crystal structure bibliography. 34:376
5 -(choline diphosphate). monohydratc,
crystal structure bibliography, 37:435
(choline S-diphosphate), sodium salt
pentahydrate, crystal structure
bibliography, 34:376
5-(choline diphosphate), sodium sali
105
tetrahydrate. crystal structure, 43:367
[cobalt( II)S -monopliosphate]. monohydrate,
crystal structure bibliography.
38:505-506
cobalt 5-monophosphatc monohydrate,
crystal structure bibliography, 34:373
conformation of. 26: I I 0
crystal structure bibliography, 31:364
2:3-cyclic phosphate, 2 2 3 14, 357
3:5-cyclic phosphate, 22:360
hydrolysis, 39:61
2 4.2-deoxy-, proton magnetic resonance
spectroscopy of, 27: 145
2-deoxy-
crystal structure bibliography, 343364
35-cyclic phosphate, hydrolysis. 39:61
3,5-diphosphate. 22:322. 348
hydrochloride, crystal structure
bibliography, 30:458
5 -phosphate monohydrate, crystal
structure bibliography. 30:459
5-methyl
3.5-diphospliate, 22:323
5-phosphate. 22:323
5-O-~~-tolyIsulfonyI-. displacement
reaction of, 24: I77
3-phosphate, 22:343, 345
5-phosphate. formation of. 29:237
selective oxidation with chromium
trioxtde. 3 3 9 9
S -( 6-deoxy-a-o-.r~~/o-he~opyranosyl-4-ulose
pyrophosphate). 28:3 I 8
5 -(3-deoxy-n-munno-octulosonic acid
triphosphate), 28:333
5-(3-deoxyoctulosonic acid phosphate).
28:332
5-(0-glucosyl phosphate), derivative. froin
spores of C!rrilugo uvenae, 28:333
S-(~.6-dideoxy-a-o-~ru/~inu-hexopyranosyl
pyrophosphate), isolation of. 28:3 I6
59 3,6-dideoxy-a-~-eryrhvo-hexopyranosyl-
4-ulosc pyrohosphate), 28:3 18
S-(3,6-ciideowy-a-o-,.iho-he~opyranosyl
pyrophosphate). isolation of. 28:3 16
5-(3.6-dideoxy-cc-o-~~~~~~-liexopyranusyl
pyrophosphate), isolation of, 28:3 16
5-( 3,6-dideoxy-P-~-ururbinu-hexopyranosyl
pyrophosphate), isolation of. 28:3 I 5
5-diphoaphate monohydrate. crystal
struclure bibliography, 34:374
106 SUBJECT INDEX
Cysteine (continued)
5'-(glycerol pyrophosphate), isolation of.
28:334
5'-(glycosyl pyrophosphates), alkaline
hydrolysis of, 28:359
(glycy1glycinato)-, copper(I1) complex.
dihydrate crystal structure bibliography.
38:SOO-50 1
glycylglycinatocopper (11) dihydrate, crystal
structure bibliography, 34:374
guanylyl-(3 ' - t S ' ) -
calcium salt octadecahydrate, crystal
structure bibliography. 37:430
monophosphate calcium salt,
octadecahydrate, crystal structure
bibliography, 34:378
sodium salt nonahydrate, crystal structure
bibliography, 37:429
sodium salt octahydrate, crystal structure
bibliography, 31:361
iodination of, 28:243
keto derivatives of, synthesis. 42:233 -234
5'-(~-rihitolpyrophosphate), biosynthesis
and isolation of, 28:333
manganese 5' -monophosphate 2.5 hydrate,
crystal structure bibliography, 37:434
methyl-2'-O-methyl-, synthesis of, 33:70
N4-acetyl-
crystal structure bibliography, 38:528
selective bromination with N-
bromosuccinimide and triphenyl-
phosphine, 33:78
N6-acetyl-. selective tritylation of, 3 3 5 2
N4-anisoyl-3'-O-(chloroacetyl)-2'-deoxy-5 '-
U-(p-methoxytrity1)-, selective
deacylation, 39:43
N4-benzoyl-2',3,'5,-tri-O-benzoyl-
methanolysis, selective, 39:37
selective deacylation, 39:394O
N6-henzoyl-
5'-0-benzoyl-, acylation of, 33:3 1
selective tritylation of, 3 3 5 2
3"-etheno-, hydrochloride, crystal
structure bibliography, 37:4 19
5'-(N-glycolyneuraminic acid phosphate),
28:332
2',3'-O-isopropylidene-5'-U-p-tolysulfony I-.
displacement reaction of, 24: 177
2'-O-methyl-, crystal structure bibliography,
32:383.38:490-491
2'-O-methyl-, synthesis of, 33:70
3 '-0-(methylsulfony1)-
2,'5'-di-O-trityI-. displacement reaction
of, 24: 180
displacement reaction of, 24:180
2',3'-phosphate, crystal structure
bibliography, 38507-508
2'-phosphate, 22:353
3'-phosphate, 22:353
crystal structure bibliography, 31:369
5'-phosphate, 22:308, 31 I , 325,327
preparation, 35:54
2'-phosphate trihydrate, crystal structure
bibliography, 31:360
proton magnetic resonance spectroscopy of,
27:33, 146
5'-pyrophosphate, glycosyl esters,
occurrence and enzymic synthesis of,
26~355-356
reaction with
(chloromethy1ene)dimethyl iminium
chloride, 28:253
N.N-dimethyI(chIoromethaniminimum)
chloride, 33:83
selective benzylation and methylation of,
33:59
selective bromination with N-bromo-
succininiide and triphenylphosphine,
33:78
selective methylation with diazomethane,
33:70
sulfonylation and halogenation of, 33:83
2-thio-, dihydrate, crystal structure
bibliography, 30:458
4'-thio-a-o-, 23:223
4'-tliio-P-o-, 23:223
5'-(vinelosyl pyrophosphate), 28:317
zinc 5'-monophosphate monohydrate,
crystal structure bibliography, 37:
435
Cytidine 5 '-(copper monophosphate), 2,2'-
dipyridylamine, pentahydrate crystal
structure, 43:298
Cytidine 5'-diphosphate, glycosyl esters,
44:280
Cytidine methosulfate, 3-methyl-.
monohydrate, crystal structure
bibliography, 32377-378
Cytidine S'monophosphate. glycosyl esters,
44:280
 SUBJECT INDEX
Cytidine monophosphate N-acetylneuraminic
acid
enzymic synthesis, 49:2 15-2 16
reaction catalyzed by, 49:2 14-215
Cytidine 5-(N-acetylneuraminic
monophosphate), 44:283
Cytidine platinum ethylenediamine 5 -
phosphate, crystal structure bibliography,
38:527
Cytidine frans-dichloroplatinum(II) (dimet hyl
sulfoxide), crystal structure bibliography,
38:317-318
Cytidine triphosphate, enzymic preparation,
49:211,213
Cytidinium chloride, crystal structure. 43:281
Cytidinium nitrate, crystal structure
bibliography, 37:411
Cytidylic acid, 22:3 13, 323
Cytidylyl-(3+5 )-adenosine-proflavine,
43:335
Cytidylytransferases, 40: 186-1 88
Cytisus sessilifolius lectin
carbohydrate-binding specificity of. 35:209
hemagglutinating activity, 35:208
Cytochrome C, photoreduction, 37:327
Cytochrome C reductase, in fruit climacteric,
42365
Cytokinins in fruit ripening, 42:342-343, 345
Cytolipin H, 24:400401
Cytosamine triacetate, crystal structure
bibliography, 32:379
Cytosine
I -2,3-anhydro-
P-o-xylofuranosyl-, 24: 180
2,5-di-O-trity~-P-~-xylofuranosyl-, 24: 1 80
2,2-anhydro-l-
p-o-arabinofuranosyl-, hydrochloride,
crystal structure bibliography, 31:360
(3,5-di-O-phosphono-@-o-
arabinofuranosy1)-, 22:368
arabinofuranosyl-
1-P-0-
crystal structure bibliography, 31:360
33-diphosphate, 22:369
hydrochloride, crystal structure
bibliography, 31:356
p-0-
2,5-monophosphate,crystal structure
bibliography, 38:485486
platinum ethylenediamine dichloride,
107
crystal structure bibliography. 38:5 18
1 -(P-D-glucopyranosyluronicacid)-.
formation, 35: 124
isolation, 35: 124
5-P-o-ribofuranosyl-,see Pseudocytidine
I -(2-deoxy-2-fluoro-P-~-arabinofuranosy~)-,
synthesis, 48:236
I -(3-deoxy-3-fluoro-P-~-xylofuranosyl)-,
synthesis and biological activity, 48:260
glucuronic acid conjugate, preparation,
36:127, 129
N-acetyl- 1-(3,5-di-O-acetyl-P-o-
arabinofuranosy1)-, 24: I83
1 -N-[2,3,6-trideoxy-4-0-(4,6-dideoxy-4-
dimethy lamino-a-o-glucopyranosy1)-P-
D- eythro-hexopyranosyl]-, triacetate,
crystal structure bibliography, 32:379
(3-O-methyl- 1-P-D-arabinofuranosyl)-,
crystal structure bibliography, 37:435
proton magnetic resonance spectroscopy of
derivatives, 27:28-29, 146
1 -(5-thio-~-xylopyranosyl)-,23:2 I 1
Cytosine nucleosides, preparation of. 42:253
Cytosinine, 24:238
Cytostatic activity
chemical structure and, of carbohydrates,
28:7
of halogenated sugars, 2 2 2 13
Cytostatics, synthesis of, 28:7
Cvtturia hariori, polysaccharide, 41:72, 103
D
Dahlia tubers
D-fructose from, 22231
fructose oligosaccharides from gel
chromatography of, 25:35
Dalapon, as plant-growth substance, 21 :402
Dalbergiu lanceolaria. apiose-containing
flavonoid glucoside from, 31: 147
Damson gum, structure, history, 41:3, 7-8
Dansylhydrazones, liquid chromatography, pre-
column derivatization procedures, 46:68
DANTE pulse. 51:19, 21
Daphnetin-8-yl P-o-ghcopyranoside,
dihydrate, crystal structure, 43:345
DAST reagent, fluorine introduction, see
Fluorine, introduction by DAST reagent
Date, development physiology of, 42:371-372
108 SUBJECT INDEX

Datiscoside bis(p-iodobenzoate), dihydrate, dianhydrohexopyranoses prepared by,

crystal structure, 43:356 34:112
Daunosamine of dithioacetals of amino sugars, 32:32,
D-, synthesis of, 22:132 55-57
4-dexoy-o~-,synthesis, 40: 111 glucosamines, 52:16
synthesis, 39: 140, 142,40: 16 and micro determination, 31:71
Daunosaminide migration of carbon atom in, 31:64
isopropyl N-acetyl-or-oL-, synthesis, 40: 17 nature of reaction, 31:10-18
methyl DL-, synthesis, 40: 17 of nucleotides, 22:376
methyl 3-N-acetykbdeoxy-a-~~-, synthesis, pH effect on, 31:65
40:18 of radicals from amino alcohols by radiation,
Duviesiu lutifolia, apiose-containing compound 37:11-12
from, 31: 148 solvent effect on, 31:16
DCB, see Benzonitrile, 2,6-dichloro- and structure determination, 31:71-79
Deacetylation of sugars, 25: 182
and acid degradation, 38:410411 in synthesis, 31:70
of cellulose acetates, 29:330 3-Deazaadenosine, crystal structure
of glycosiduronic acids, 36:79 bibliography, 37:420
by hydrazinolysis, 31:78 3-Deaza-6-azauridine, crystal structure
hydrolysis, 39: 14-24 bibliography, 38:528
of polysaccharides, 31: 194 3-Deazacytidine, crystal structure bibliography,
Deacylation 38:490
of dithioacetal esters, 32:46 Deazaguanosine 5-phosphate, 7-(3,4-truns-4,5-
enzymic, 39:33-34,36,43 cis-dihydroxy- 1-cycle-penten-3-
and methanolysis of polysaccharide aliphatic ylaminyl)-7-, hydrate, 43:335
carboxylic esters, 29:332 Deazaisotubercidin, picrate, crystal structure
regioselective, 39:40 bibliography, 37:423
selective, 39:2844 3-Deazauridine
in nucleoside derivatives, 39:3644 crystal structure bibliography, 31:356
DEAE-dextran, antitumor activity of, 4-deoxy-, crystal structure bibliography,
32~257-258,273 38:488489
P-oealkoxylation, of pectic substances, 29:245 Debenzylation
Dealkylation, selective, 39:44-53 by acetolysis, 39:45
Deamination of benzyl ethers of 1,6-
of aminoaldonic acids, 33:114-119 anhydrohexopyranoses, 34:74-75
of aminoaldoses, 25:183-194,33:114-119 of glycosiduronic acids, 36:79
of aminocyclohexanols, 25: 184 Deboronation, selective, 39:53-55
of 2-amino-2-deoxyalditols, 25: 191 Deboronation
of 2-amino-2-deoxyaldohexoses,25: 183 of boronates, 3 5 5 2
of 2-amino-2-deoxyaldonic acids, 25: 19 1 selective, 39:53-55
of 2-amino-2-deoxyaldonolactones,25: 189 I , 10-Decanedithiol, in dithioacetal preparation,
of 2-amino-2-deoxyaldose dithioacetals, 32:19
25: 192 Decarboxylation
of aminodeoxy 1,6-anhydrohexopyranoses, enzymic, of glycosyluronic acid
34: I28 pyrophosphate esters, 28:385
of amino sugars by radiolysis, 37:48-5 1 of sugar acids, kinetics of, 28: 186-1 87, 190
of carbohydrate amines and related Deca(ribonucleotide), synthesis, protecting
compounds, 31:9-79 groups, 36: 147
degradation of polysaccharides by, Decasaccharide, in fucosidosis urine, structure,
31:232-237 39:332
 SUBJECT INDEX
4-Decene-3,6-diol, 6-butyl- I ,2-dimethoxy-.
synthesis, 39: 141
Dechlorination, of chlorodeoxy sugars in
presence of triethylamine, 28:302
Decoynine, 21:174, 24:250, 252
biosynthesis, 35: 123
A-2 effect, on conformation, 23:30
Defoliation, 21:429
Deglocosylation, glycoproteins, 47:200
Degradation, see also Bany degradation;
Depolymerization; Fragmentation; Smith
degradation
acid, methylation structural analysis,
38:408410
of acylated nitriles of aldonic acids,
4: 119-15 1
and ammonia reaction with carbohydrate
acyl esters, 31:83
0-eliminative
of alditol methyl ethers and mass
spectrometry, 29:57
of carbohydrates, 29:229-303
and double 0-elimination in activated
vinylog systems, 29:283
in furanuronate derivatives, 29:273-28 1
of heteropolysaccharides, 29:238-252
of hydroxy carboxylic acid derivatives,
29:234-237
principle and types of, 29:233
and structure of natural uronate-sugar
conjugates, 29:254
in unsaturated hexopyranoid systems,
29:282
during methylation of carbohydrates,
30: 14
biochemical, of galactomannans, 35:356-
375
of carbohydrates, 19:181-218
of cellulose, 22:20
decarboxylative enolacetal-forming p-
elimination, 29:301
of 2-deoxy sugars. 21: 147
of dextrans by dextranglucosidase, 30:395
by endoglycosidases, 38:415416
enolacetal-forming p-elimination,
29:255-273
enzymic
p-elimination in, 33:358, 367
of starch and glycogen, 33:4
of dextrans, 30:390-399
109
of glycogen and starch, 3:251-310.
17:407430
of linear polysaccharides. 23:299
of starch, 23:282
by exoglycosidases, 38:412415
of glycosyl esters of nucleoside 5 ' -
pyrophosphates, 28:356
ofhigher sugars to deoxy sugars., 21:153
localization of hydrogen isotopes by
chemical, 27:140
Macdonald-Fischer, of dithioacetals.
32: 82-85
N-deacetylation and acid. 38:410-411
of polysaccharides, 31: 185-240
by acid action, 31:187-200
by p-elimination, 31:212-229
by deamination, 31:232-237
with hydrazine, 31:195
by oxidation with chromium trioxide,
31 :229-232
by periodate oxidation, 31:200-211
preceded by oxidation, 31:220-226
by way of sulfone derivatives, 31:226-229
by Weermann and Lossen rearrangements,
3 1:237-238
Smith, 22:7
of capsular polysaccharide, 33:301
of dextrans, 30:383,389
mass spectrometry of oligosaccharides
from, 30:40
and structural analysis of
polysaccharides, 30:282
of polysaccharides, 28:98-101
of sugars, 28: I63
of teichoic acid, 21:340
thermal
of cellulose and cellulosic materials,
23:423424
of polysaccharides, 34:3845
of starch, 22483-515
Degranol, synthesis and antitumor activity,
28:&7
Degree of methylation, of partially methylated
methyl glycosides, mass spectrometry of,
29:50-51
Degree of polymerization
and action pattern of enzymes, 30:271
in cellulose synthesis, 26:333, 348,
41:114115
determination of, of glucans, 30:284
110 SUBJECT INDEX
Degree of polymerization (continued)
in methylation of pectins, 30: 15
of oligosaccharides, gas-liquid
chromatography of, 28:58, 83, 85
of 4-0-methylmaltopolysaccharidesby
gas-liquid chromatography, 28:47
Degree of substitution
of 0-(carboxymethyl)cellulose, and
physicochemical properties, 29:320
of polysaccharides, 29:308-309,3 13
Dehalogenation
deoxy sugars prepared by, 34: 14 1
reductive, of deoxyhalogeno sugars, 28:299
Dehydration, 53:300-30 1
of aldoses and ketoses in acidic solution,
28: 174-193
in alkaline solution, 28: 193-207
analyses involving, 28:218-224
of carbohydrates, 28: 161-224
polarography of, 29: 164-168
of hexuronic acids, 28: 190
Dehydroacetylation
by a-nitroalkenes, of P-nitroalkyl acetates,
24: 127
of deoxynihoalditol acetates, 24: 127
Dehydroascorbic acid, 2-(p-
bromophenyl)hydrazone, crystal structure
bibliography, 37:386
Dehydrohalogenation, of deoxyhalogeno
sugars, 28:291,294
Dehydro names, aldoketoses, 52:80
Deiodination, by ultraviolet irradiation, 28:304
Dejean-Laupretre-Monnerie model, 51:82, 12 I ,
125
Delignification
of grasses, 36:222-224
and hemicellulose loss, 36:261
Delocalization interactions, see also Lone-pair
orbitals
anomeric effect, 47:109-114
scaling with electrostatic interactions,
47:114115
perturbation calculation, 47: 11 1
stabilization energy, 47: 113
Demercaptalation, of dithioacetals, by
mercury(I1) chloride, 32:61-70
Demethylation
in hydrolysis of methylated polysaccharides,
28:22
of methylated sugars, 39:4445
in methylation analysis of polysaccharides,
30:16
Demissine, as beetle repellent, 24:6
Demycarosylleucomycin A-3 hydrobromide,
ethanol solvate, crystal structure, 43:35 1
Dendroketose
in formose reaction, 29:175
L-
selective metabolism of, 42:77
structure of, 42:77
synthesis of, 42: 128-129
Denegit, antiepileptic agent, 28:9
Denitration
of nitro sugars, 24: 109, 1 1 1
selective, 39:55-58
of sulfonic esters of carbohydrates, 23:266
Dental caries
dextrans and sucrose in formation of,
30:433435
prevention of, 30:44M42
role of dextrans in formation of, 30:435-
439
vaccines, 30:441
Dental plaque
dextrans as structural components of, 30:438
formation of, 30:433435
fungal endodextranase in control of, 30:395
Deoxyadenosine
3-, crystal structure, 43:3 17-3 18
3-amino-3-, crystal structure, 43:322-323
3 -(cyclobutylamino)-3 -,methanolate,
crystal structure, 43:327
5 -Deoxyadenosine-5-ylcobalaminhydrate,
vitamin B,, coenzyme, crystal structure
bibliography, 31:371
Deoxyalditols, 52533
Deoxyaldohexoses, 2-acetamido-2-,
50: 164-165
Deoxyaldonolactams, 5-Amino-5-, glycosidase
inhibition, 48:330-332
1-(2-Deoxy-2,2-difluoro-@-~-erythro-
pentofuranosyl)cytosine, synthesis,
48~239-240
Deoxyfluoro carbohydrates, labeled
biological studies, 48:203-204
synthesis and biological applications, 48:204
Deoxyfluorodeoxy carbonhydrates, labeled,
synthesis, 48: 190-199
D~Oxy-flUO~O-~-D-ga~~CtOpyr~~OS~~-D-
glycopyranosides, 48:211
 SUBJECT INDEX
Deoxyfluoro-a-o-ghcopyranos yi phosphates,
48:205-206
Deoxyfluorohexofuranoses, I3C-n.m.r data for,
46:165-167
Deoxyfluoro starches, 48:222
Deoxyfluoro sucroses, 48:21&2 17
Deoxyfluoro sugars, fluorine- 18-labeled
biological application, 48: 199-203
uses, 48:186-189
9-(3-Deoxy-3-fluoro-~-~-xy~ohranosy~)-
adenosine, synthesis, 48:275-276
5-Deoxyfructose, taste properties, 49252
Deoxyglucopyranosyl trichloroacetiniidates. 2-
azido-2-, reaction with nucleophiles,
50:73-76
6-Deoxyglucose, liquid chromatography
methods for analysis of, 46:33
Deoxyglycosides
hydrolysis of, 2254-55, 60
taste properties, 45259-260
2-Deoxyglycosides, glucosidase inhibit ion,
48: 359-3 62
3-Deoxyglycosones, see Glycosuloses, 3-
deoxy-
3-Deoxyglycosuloses, see Glycosuloses, 3-
deoxy-
3-Deoxyglyculsonic acids, 48:296
Deoxyguanosine, 7-bromoactinomycin D bis2'-
, undecahydrate, crystal structure.
43:368-369
2'-Deoxyguanosine 5'-[nickel(II) phosphate],
trihydrate, 43:334
Deoxyguluronic acid, 2-acetamido-2-.
glycosidic linkage, 47: 185
Deoxyhalosucroses, sweetness-structure
relationship, 45:265-269
3-Deoxyheoxs-2-ulose, formation of, 46:3 I 1
6-Deoxyheptoses, 48:28&287
3-Deoxyheptulosaric acid, 48:298
6-Deoxyhexopyranose, derivatives, fluorinated,
'H- and I9F-n.m.r data for, 46:132-133
Deoxyhexopyranosides, possible AH,B unit
involved in sweet-taste stimulation,
4S:261
2-Deoxyhexoses, 48:282-283
trichloroacetimidates, SO: 110-1 12
Deoxylactams, 5-amino-5-, reversible inhibitors
of glycosidases, 48:327-333
Deoxylividomycin B, 48:229-230
Deoxymannuronic acid, 2-acetamido-2-,
Ill
glycosidic linkage, 47: 183-1 84. 186
Deoxymidine, 5 '-acetamido-3'-O-acetyl-5'-,
chloroform solvate, crystal structure,
433326-327
I-Deoxynojirimycin. 51: 150
glucosidase inhibition, 48:380
3-Deoxynonulosonic acids, 48:297
Deoxy nucleosides, synthesis of, 42:246
2'-Deoxy nucleosides, 53:158-161
3-Deoxyoctulosonate aldolase, metabolism of
3-deoxy-~-manno-2-octulosonicacid,
38:386
3-Deoxyoctulosonate 8-phosphate phosphatase,
metabolism of 3-deoxy-o-manno-2-
octulosonic acid, 38:380-381
3-Deoxyoctulosonate 8-phosphate synthetase,
metabolism of 3-deoxy-o-manno-2-
octulosonic acid, 38:379-380
Deoxy-2-octulosonic acids, liquid
chromatography, 46:3&37
3-Deoxyoctulosylonotransferase, metabolism of
3-deoxy-~-manno-2-octulosonic acid,
38:384386
3-deoxy- 1,2-O-isopropylidene-~-~-threo-
pentodialdose 5-(dibeuzyl dithioacetal),
preparation of, 32:28
mercaptalation of, 32:28
Deoxypentohranose derivatives, fluorinated,
'H-and 19F-n.m.rdata for, 46:138
'
2-Deoxypentopyranosyl fluorides, H-and "F-
n.m.r data for, 46:137
5-Deoxypentoses, 49:27
Deoxyribonuclease
amino acids of, 27:3 15-3 I6
as glycoenzyme, 27:308
Deoxyribonucleic acid, radiation-induced
degradation. 37:59-64, 76, 5 2 1 I
5-Deoxysorbose, taste properties, 45:252
6-Deoxysucrose, 51: 150
Deoxy sugars, 21: 143-207. 23:267
2-
esters, 21:146
synthesis of, 21:147
3-, synthesis of, 21:157
4-, synthesis of, 21:166
5-, synthesis of, 21:167
acid decomposition, 46:252
in aqueous solution, NMR spectroscopy,
42:18
in cardenolides, 21:275
112 SUBJECT INDEX
Deoxy sugars (continued)
chemistry, Maurice Staceys work, 52: 14
chromatography of, 21:197-199
definition, 52:5 1
deoxyalditols, 52233
2,3-dideoxy, 21: 193
2,6-dideoxy, 21: 183
3,6-dideoxy, 21:187
4,6-dideoxy, 21: 190
5,6-dideoxy, 21:192
from higher sugars by degradation, 21: 153
liquid chromatography, 46:3 1,33
mass spectra of, 21:64, 204
names derived from hivial names of sugars,
52:81
nomenclature of, 52:81-83
nuclear magnetic resonance of, 21:202-203
omega
occurrence of, 21 :17 1
synthesis of, 21:175
properties of, and derivatives, 26:279-296
rate constants and equilibrium constants in
polarography of, 29: 143
sweetness-structure relationship, 45:259-
261
synthesis of, 21:18,23:269,271, 274,
53:186-188
from aldonolactones, 50: 170-1 79
base-catalyzed rearrangement of
bromodeoxy aldonolactones,
SO: 175-1 79
bromodeoxyaldono- 1,44actone
hydrogenolysis, SO: 173-1 74
enonolactone catalytic hydrogenation,
50: 170-173
systematic names, 5253-83
trideoxyhexoses, 21: 195
trivial names, 52:8@81
Deoxytrichloroacetimidate, 2-N-phthaloyl-2-,
reaction with nucleophiles, 50:81-83
Deoxyuridine, 5-acetyl-2-, crystal structure,
43:324
Dephosphorylation
selective, 39:5842
of sugar phosphates by radiolysis, 37:4246
Depolymerases
classification of, 33:325
nomenclature of pectic, 33:326
Depolymerization
of cellulose on heating, 23:42&427
enzymic, isolation of products of partial,
30:272
of permethylated carbohydrates, 38:39&398
starch, 47:280
Deprotection, see also Protecting groups
of glycosiduronic acids, 36:77-82
in polynucleotide syntheses, 36: 14 I ,
146-147, 155
selective
enzymic, glycopeptide synthesis, 50:303
N-glycopeptides, 50:283-287
methods, 50:294-298
DEPT, 51:19
Dermatan sulfate, 24:291, 44: 199, 52:382-383
as activator of enzymes in trehalose
biosynthesis, 30:243
p-eliminative degradation of, 29:239,
24 1-242
carbohydrate chains in, 25:46046 1
carbon-13 nuclear magnetic resonance
spectra, 38:73-74, 76
circular dichroism, 45: 1 17
composition, analysis, 46:55
crystal structure bibliography, 33:400
depolymerization and structure of, 31:75
disaccharide repeating units, 43:53-55
in glycoproteins, 25:417
glycosidic linkage, 43:53
hexosamine, 43:53,55
major uronic acid, 43:53,55
molecular conformation, 43: 109, 1 1 1
proton magnetic resonance spectroscopy of,
27:4 1,43
structure
enzymic analysis, 44:205-207
repeating units in, 26:432
in urine, 24:443
Desalting, of solutions of glycosyl esters of
nucleoside pyrophosphates obtained by
chromatography, 28:3 11
Desglucocheirotoxin, 21 :285
Desilylation, of trimethylsilyl derivatives,
28:32
Desmosine, from urine peptide, 24:45 I
Desosamine
p-, 25:83
D-, biosynthesis, 35:84, 122
DL-, synthesis of, 28:299,40:22,46, 106
L-, synthesis, 40: 120
Maurice Staceys work, 52:14-15
 SUBJECT INDEX
Desosaminide
ethyl D-, synthesis, 40:47
methyl DL-, synthesis, 40:46, 107
Destomic acid, in destomycin A and
hygromycin B, 30:133
Destomic lactam, from destomycin A. 30: I33
Destomycin A
discovery of, 30: 1 12
isolation and structure of, 30: 133-134
Desulfation, of sulfated polysaccharides.
29:336
Desulfonylation, of sulfonic esters of
carbohydrates, 23:258
Desulfonyloxylation, of carbohydrate sulfonic
esters, 23:269
Desulfurization
deoxy sugars prepared by, 34: 141
reductive, by Raney nickel, 5 - 2 8
Detergents, as inhibitors for pectinesterase,
33:336
Dethiobiotin, synthesis and absolute
configuration of, 27:212
De(trialkylsilyl)ation, selective, 39:62--70
Detritylation
selective, 39:48
of trityl ethers of dithioacetals, 32:46
Deulofeu, Venancio
academic career, 46: 12
awards and honors, 46: 14
book, 46: 13
doctoral thesis, 46: 1 1
at E. R. Squibb & Sons, 46: 12, 14
editorial work, 46: 14
education, 46: 11
family, 46: 11
publications, 46: 13
research, 46: 11-13
Deuterated dimethyl sulfoxide, solvent for
cambon-13 nuclear magnetic resonance
spectroscopy, 41:29
Deuteration
of anhydrodeoxyalditols, 23:78
effect on proton magnetic resonance spectra,
29: 15
polysaccharide, 38: 19-20
Deuteriochloroform, solvent for carbon-13
nuclear magnetic resonance spectroscopy,
41:29
Deuterium
determination of location of, by nuclear
1I3
magnetic resonance spectroscopy,
27: I43
labeled methylated monosaccharides, mass
spectra of, 21:71
Deuterium oxide
effect on mutarotation of sugars, 24:28, 31
solvent for carbon-13 nuclear magnetic
resonance spectroscopy, 41:29
Deuterium-substitution method, in assignment
of vibrational frequencies. 44:53-55
Deuteromvceres. polysaccharides of, 23:368
Deuterostomes, sialic acids occurrence, 40: I37
Dextran, 47:19,51:104
acetate
circular dichroism, 45: 12 I
determination of acetyl content of.
29:330
aqueous, versus solid, laser-Raman
spectroscopy, 44:75
bacterial, development, 36:27 I
carbanilates, preparation of, 29:344
carbon-I 3 nuclear magnetic resonance
spectra. 38:98-99
of branched-chain. 38:4146
of linear, 38:40
carboxymethyl derivative, circular
dichroism, 45: 122- I23
circular dichroism, 45:89
Fourier-transform infrared-difference
spectroscopy, 44:6 1-62
L. mesenteroides. branch linkage synthesis,
51:159-l62
laser-Raman spectroscopy, 44:82
Leuconostoc. structure, enzymic analysis,
44:258--261
mass spectrometry of, 29:69
periodate oxidation of, 33:95
per-0-benzyl-, carbon- 13 nuclear magnetic
resonance spectra, 38:98-99
phosphate, preparation of, 29:334
preparation, properties, and uses,
36:303-305
proton magnetic resonance spectroscopy of
derivatives of, 27:40
pyrolysis of, 22:496
(1+6)-, structure of, from sucrose, by
Leuconostoc mesenrerioides, 32: 7
relative reactivities of hydroxyl groups in,
33:57,64
solubility in methanol, 27:95
114 SUBJECT INDEX
Dextran (continued)
Streptococcus, structure, enzymic analysis,
44:263-264
structure, 47:285,288-289
crystal structure bibliography, 36:3 19-320
enzymic analysis, 44:258-264
in methanol, 27:95
moisture content and, 47:289-290
and synthesis of, 15:341-369
sulfate, structure of, 29:336
sulfation of, 29:335
synthesis
control, 51: 158-1 59
glucose addition to reducing end,
51:144-145
vibrational spectra, isotopic substitution
studies, 44:54
Dextran-antidextran reactions, antigenic,
30:400
Dextran-antipneumococcal cross-reactions,
30:402404
Dextranases, 44:258
as anticaries agents, 30:440
assay of, with Blue Dextran 2000, 29:352
cross-linked, 29:354
0x0 derivatives, 29:341
trimethylsilylation of, 29:329
and dextran degradation, 30:39 I
induction of, 30:262
preparation, and dextran degradation by,
30:338-342
Dextranxoncanavalin A interaction, and
dextran structure, 30:405
Dextran gels, in chromatography, 25: 14
Dextranglucosidases, 44:258-259
from liver and spleen homogenates, and
hydrolysis of dextrans and glycogens,
30:395
Dextran NRLL 1353-3, acetolysis of, 22:21
Dextran peracetate, carbon- I3 nuclear magnetic
resonance spectra, 38:98-99
Dextrans
acetolysis of, 30:378-379, 386
acid hydrolysis and acetolysis of,
30~377-379,386
affinity chromatography adsorbent, 39:419
antigenicity of, 21:504
antitumor activity of, 32:261
A and B, properties and antitumor activity of,
32:263
bacterial, hydrolysis of oxidized, 31: 194
bacteria synthesizing, 30373
biosynthesis of, 30:418433
mechanism of, 30:427433
branching in, 30:412
branching patterns of, 46:41
constitution of, 2 5 6
definition, 30:371
degradation by acetolysis, 31:197
by hydrolysis, 31: 196
and dental caries, 30:433442
enzymic analysis of, 30:338-342
gas-liquid chromatography of, 28:94
gels
chromatography of, 2518-19,35
formed by water-insoluble, 30:417418
formed by water-soluble, 30:414416
hydrolysis
by dextranglucosidases, 30:395
of methylated, 28:22
immunochemical reactivities of, 30:399404
immunogenicity and molecular size, 41: 182
interaction with concanavalin A, 35: 166,
171-173
with lentil lectins, 35: 194
length of branches in, 30:40&411
levoglucosan from, 34:40
liquid chromatography analysis, 46:39
Maurice Staceys work, 52:X-9
methylation of, 3O:ll-12, 384-386
molecular-weight determination by gel
chromatography, 25:22
in neoglycoprotein preparation, 37:25 1
network structures, 30:413
origin and preparation of, 30:372-376
periodate oxidation of, 30:382-385
proton magnetic resonance spectroscopy of,
30:380-382
pyrolysis of, 34:152
as reserve carbohydrates in cariogenic
plaques, 30:437
role in dental caries development,
30:435439
secondary linkages, 30:411
segment and type structures, 30:412
skeletal chain structures, 30:411
Smith degradation of, 30:383,389
as structural components of dental plaque,
30:438
structure of, 30:376-418
 SUBJECT INDEX
from sucrose, 32:s
water-soluble, a-glucan 3-
glucanohydrolases in, 30:39X
in sugar industry, 30:442-444
sulfone degradation of, 31:229
synthesis, 39: 196
Dextransucrase, 51: 141
catalytic activity of, 30:423427
cleavage of sucrose and formation of a -
(1+6)-glycosidic bond, 51:146-147
in dextran biosynthesis, 30:418419
in D-fructose production, 22232
L. mesenteroides
acceptor reactions, 51: 155-158
branching experiment, 51: 159-1 6 1
dextrm synthesis by, 51: 148-149
preparation and properties of, 30:4 I 9 4 2 3
reaction scheme, 51:163
synthesis, primer-dependent mechanism,
51: 142-143
Dextran sulfates, antitumor activity of, 32:257.
273
Dextran xanthate, circular dichroism, 45: 122
Dextrinization
acid factor, 47:3 18
catalysts, 47:3 18-3 19
chemistry, 47:302-317
acid catalyst role, 47:3 13-3 14
acid hydrolysis, 47:309-3 10
action of water on starch, 47:303
aldehyde yield, 47:316
base catalyst role, 47:3 15
branching and cross-linking, 47:306-308
I T - or H-NMR, 47:313
free-radical mechanism, 47:304-305
hydrolytic scission, 47:304
hydroxyl groups, 47:303
phenol yield, 47:316
in presence of a-amino acids, 47:3 I5
in presence of oxidants, 47:3 16-3 1 7
starch containing fatty acids, 47:303
structural changes, 47:3 12-3 13
tamarind-kernel polysaccharide,
47:3 10-3 12
thennolysis with glycine, 47:3 15-3 I6
transglycosylation, 47:308
condition of, 47:3 18
degree of, 47:286-287
general reaction characteristics of, 22:484
of maize amylose, 22:493
I I5
potato, maize. and rice starch, 47:289,
291 -292
products. specific rotation, 47:301
purpose, 47:286
rate, 47:286, 288
salts as catalysts, 47:319, 321
Dextrins, 22484,492
a-amylase action on @-limit,23:3 I7
alkali-lability, 47:293, 295
amylolytic index. 47:320-321
from amylose, structure of, 22493
as antiulcer agent, 47:333-334
biological activity, 47:333-335
on humans. 47:334
on lower organisms, 47:334-335
@-limit,structure, enzymic analysis,
44:254255
blue staining residue, 47:283
classification, 47:282-284
color and water content, 51:275-276
complexes, 53:411412
critical micelle concentration, 47:301-302
generally-recognized-as-safe, 47:329
historical background. 47:28 1-282
hydrolysis, 47:301
infrared spectra, 47:3 12-3 13
iodine affinity. 47:283-284,297-298
limit, from dextrans, 30:392
from starch and glycogen. 30:286.
289-290
structure of, 30:303
macrodextrins from glycogen, 30:3 14
manufacture, 47:32 1-323
maturation, 47:321-322
methylation analysis, 47:308-309
mutagenicity, 47:3 16
Nageli, structure, enzymic analysis, 44:255
4-befa-,from glycogen and amylopectin,
30:3 I5
organoleptic control, 47:298
preparation of, 22:483
in presence of catalyzing acid, 47:29 1. 293
properties. 47:284--302
atmosphere effects, 47:305
catalyzing acid effects, 47:293-294
modification, 47:301
reaction time and temperature of heating,
47~320-321
reducibility changes, 47:294, 296
regulations, 47:333
1 I6 SUBJECT INDEX
Dextrins (continued)
retrogradative ability, 47:306
roasting, 47:322
the Schardinger, 12: 189-260
solvation, 47:328
sources for manufacture, 47:3 17-32 I
starch, gel chromatography 0,25:42
starch, levoglucosan from, 34:40
structure of, from starch, 22:490
sulfonylation of a-and p-, 23:242
temperature relationship, 47290-29 1
total radioinduced acidity, 51:269
uses, 47:323-333
adhesives, 47:324-325
as binders, 47:32&325
coatings, 47:325
as complexing agent, 47:327-328
in cosmetics, 47:329
as depressant in flotation system,
47:328-329
electroplating brighteners, 47:326
as encapsulating agents, 47:332
in food, 47:329-332
free radical propagation, 47:327
in fuel compositions, 47:326-327
matrices, 47:324-325
in protective colloids, 47:325
replacement by synthetic polymers,
47:324
thickness, 47:323-324
viscosity
changes, 47:294,297
of solutions, 47:283
water-soluble, as function of water content,
51:271
yellow, composition and characteristics,
47:3 14
yield, form, and color, 47:285
Dextrose, commercial production of crystalline,
5: 127-143
3-Dexyaldulosonic acids, in bacterial
polysaccharides, biosynthesis, 44:30 1-
302
Diabetes
glycoprotein in, 25:474
levoglucosan role in, 34:50
Diacetoxonium ion, in fragmentation of
peracetylated glycosides, 29:46
I ,4-Di-0-acetyI-2,3-di-O-methyl-a-~-
rhamnopyranose, 51909
Dialdehydes
cyclization with nitroalkanes in branched-
sugar synthesis, 42:107-109
from the periodate oxidation of
carbohydrates, 16: 105-158
Dialdoses, 52:50,74-75
a,P-unsaturated, Wittig reaction with,
27:25 1
dithioacetals, physical constants of, 32: 115
Dialkylstannylene acetals
regioselectivity, 53:3644
structure, 53:26-32
Dialkyltin dialkoxides
nomenclature, 53: 18
structure, 53:26-32
Dialysis bags, immobilization in, 49: 188
Diamagnetic species, 47: 129-130
Diamino sugars, 48:292
Diamond lattice model, 51:80-81
1,2:5,6-Dianhydrogalactitol, 43:333
1,4:3,6-Dianhydro-o-glucitol
acylation (selective) of, 25:262
biological uses of, 25268
dinitrate, circular dichroism spectrum of,
25:254
infrared spectra of, and nitrates, 25:25 1-252
isomerization of, 25:260
monostearate, surface activity of, 25:255
nuclear magnetic resonance spectra of, and
derivatives, 29254
ring opening of, 25:256
sulfonylation of, 23:246,252
1,4:3,6-Dianhydrohexitols,49:93-I 73
alkyl ethers, 49:135-145
P-blocker side-chain, 49:137
bis-glycidyl ethers, 49: 136
crown ethers, 49:143-144
2,5-di-O-ethylisohexides,49: 141
isohexide etherification, 49: 139
isosorbide 5-nitrate, 49: 142
oxaprostaglandins, 49: 138
pentafluorophenyl ethers, 49: 141-142
analytical behavior, detection, and
determination, 49: 117-1 19
Chemical Abstracts references, 49:94
chemical uses, 49:158-161
cosmetics use, 49: I68
deoxy derivatives
amines, 49: 150-1 52
azides, 49: 154
 SUBJECT INDEX
C-nitro compounds, 49: 155
halogens, 49:149-150
mono- and di-substituted, 49: 146- 149
oxidation products, 49: 155-1 58
phosphanes, 49: 155
thio derivatives, 49: 153
esters
with carboxylic and sulfonic acids.
49:125-130
of nitric acid, 49: 133-1 35
with phosphoric acid, 49: 130-132
ethoxides, 49: 17 1
food applications, 49: 167-168
as herbicides, 49: 170
nomenclature, 49:96-98
bridged systems, 49:97-98
fused systems, 49:98
sugar-derived names, 49:96-97
parent compound preparation, 49: I 19-1 25
2,3:4,5-dianhydro-o-iditol, 49: 124-125
isohexides, 49: 122-124
protonation, 49: 120
(1R)-[l-2H]isomannide,49: 120-122
pharmaceutical uses, 49: 161- 167
antitumor agents, 49:165-166
aryloxypropanolamines, 49: 162
di-0-methylisosorbide, 49: 166
isohexide nicotinic esters, 49: 162
isohexide nitric esters, 49: 161-162
isosorbide dinitrate, 49: 16 1
isosorbide disulfite, 49: 164-165
isosorbide 5-mononitrate, 49: 161
isosorbide sydnonimine derivatives,
49: 163
sornidipine, 49: 163
as plasticizers, 49: 168-169
polymers containing isohexide moieties,
49: 171-173
polyurethanes, polycarbonates and
polyamides, 49: 172-1 73
preparation survey, 49:95
silyl ethers, 49: 145-146
spectroscopic properties, 49:99-114
chiroptical properties, 49:99-100
infrared spectra, 49: 100-102
mass spectra, 49:110, 112-1 14
NMR spectra, 49: 102-1 1 1
structural aspects, 49: 1 1 4 1 17
ultraviolet spectra, 49:99-100
Diastase, in honey, 25:303
117
Diastereoisomerism, of cyclic acetals, nuclear
magnetic resonance spectroscopy and,
34: 195-198
Diastereotopism, proton magnetic resonance
spectra, 27:63
1,5-Diazabicyclo [5.4.0] undec-5-ene, P-
elimination by, 31:240
Diazepine, 1H- l,2-, o-xylo-4,5,6-trihydroxy-I -
methyl-4,5,6.7-tetrahydro-,conformation
of, 26:114
1,2-Diazine, derivatives, from sugar
derivatives, 25:396
1,4-Diazine,derivatives, from sugar
derivatives, 25:396-398
Diazo compounds
carbohydrate, decomposition of, 22: 197
irradiation of carbohydrate, 38: 178-1 79
preparation and reactions of, 31:59
Diazo coupling, neoglycoprotein preparation,
37:229-234
Diazodicarboxylic acid, diethyl ester, reaction
with thymidine, 33:45
Diazomethane
o-nitrophenyl-, selective etherifications with,
33:70
selective methylation of cellulose with,
33:68
Diazomethane reaction, transition states in,
42:89
Diazonium ions, in deamination. 31:11-14, 39
Diazotization, of dithioacetals of amino sugars,
32:56
Di-P-o-fructofuranose 1,2:2,1-dianhydride,
21:462
Di-P-o-ribofuranose I ,5:1 5-dianhydride,
2,3:2,3-di-O-benzylidene-, preparation.
of, 34: 184
Dibekacin, synthesis, 48: 1 1-12
Dibenzyl hydrogenphosphate, reaction with a
and P-trichloroacetimidates, 50:30-32
Dibenzyl phosphorochloridate
as phosphorylating agent for 2-deoxy-
nucleosides, 22:345
for nucleosides, 22:326
phosphorylation of I-deoxy-l -fluoro-L-
glycerol with, 33:50
Dibromomethyl methyl ether, reaction with
cyclic acetals, 39:l 19-121
Dibucaine, effect on protein glycosylation,
40:345
118 SUBJECT INDEX
Dibutylstannylene acetals
alkylation, 53:63,98
benzoylation, 53: 131
as glycosyl acceptors, 53:126-127
near deoxy centers, 53: 103-1 10
nomenclature, 53: 18-19
reactions, 53:32-33
regioselectivity, 53:65-68,95-97
terminal diols, 53:120-121
Dibutyltin oxide, 53:19
Dicarba-disaccharides, synthesis, 48:67-73
Dicarbonyl derivatives, of carbohydrates,
17:223-299
Dicarboxylic anhydride, 4-cyclohexene-cis-
1,2-, reaction with cellulose, 29:338
Dicellobiosylamine, preparation of, 31:92
Dichlobenil, inhibitor of cellulose biosynthesis,
41:144
Dichloro-L-isoidide, 49: 149
Dic hloromethane-anthracene-tetracyano-
ethylene complex, structure of, 2555
Dichloromethylenation, aldonolactones, 50: 145
trans-Dichloroplatinum(II)(dimethyl sulfoxide)
cytidine, crystal structure bibliography,
38:517-518
Dichroism, 53:288-290
Dicotyledonous plants
Albersheim model of cell-wall of,
42: 309-3 14
p-o-glucan from, 42:293
cell-wall bound enzymes in, 42:301
hydroxy-L-proline-rich glycoproteins of,
42:299
primary cell-wall polysaccharides of,
42:275
hemicelluloses, 42:287-292
interconnections of, 42:303-309
pectic polysaccharides, 42:277-287
Dictyostelium discoideum
lectin, isolation and properties, 35:308
trehalase in, 30:239-241, 253
Dictyostelium discoidum, cellulosic cell-wall,
41:108
Dicumarol
discovery, 39: 1
structure, 39:6
8,5'-Didehydroadenosine,monohydrate, crystal
structure, 43:3 1 6 317
Di(3-deoxy-~-glycero-pentulose) 1,2':2,1-
dianhydride, 52:227
1,6,-Dideoxy-l,6-difluoro-galactito1, 'H and
I9F-NMR data for, 46:158
Dideoxydifluorohexopyranoses, 'H and I9F-
NMR data for, 46:149-151
Dideoxydifluorohexopyranosides,'H and I9F-
NMR data for, 46:149-151
9-(2,3-Dideoxy-2-fluoro-~-o-efythro-
pentofuranosyl)adenine, synthesis,
48:269-270
1,2-Dideoxy-3-heptuloses, 49:28
Dideoxyhexoses
3,6-, 48:284-285
2-acetamido-2,6-, glycosidic linkages,
47:188-189
Dideoxyisohexide C-nitro compounds, 49: 155
Dideoxyisohexides, 2,5-diazido-2,5-, 49: 101,
104-10s
hypnotic properties, 49: 165
Dideoxylactones, 50: 172
Dideoxy sugars, see Deoxy sugars
Di-D-fructopyranose 2'. 1 :2,1'-dianhydride,
from o-fmctose in anhydrous hydrogen
fluoride, 27:94
Di-o-fructose dianhydrides, 22:260
acid hydrolysis, 52:232
in chemical synthesis, 52:234
derivatives, 52:260
optical rotations and melting points,
52:261
from higher plants, 52:2 13
industry and, 52:232-233
microorganisms and, 52:2 13-2 16
'H NMR spectra, 52:264
I3C NMR spectra, fructose components,
52:262
nutrition and, 52:233-234
per-0-acetyl derivatives, 'H NMR spectra of
fructose components, 52:265-266
Di-o-fructose-glycine, 22:279
Dielectric constant
effect on solubility of sucrose, 27:90
of solvents, effect on sugar solubility, 27:87
Diels-Alder reaction
adduct, resolution, 48:36,38-39
in C-glycosylations, 33:163
condensation
of alkoxy-1,3-butadienes, in sugar
syntheses, 40:3638,49
and reduction of acrolein, 34:48
in sugar syntheses with furan, 40:74-75
 SUBJECT INDEX
cycloaddition, furan and acrylic acid,
racemic carba-sugars, synthesis,
48:29-36
product, 24: 129
L- I ,6-Diepicastanospetmine, SO: 198- I99
Dietetic foods, hexitols in, gas-liquid
chromatographic estimation of, 28:58
Diethanolamine, see also 2,2'-Iminodiethanol
from aminolysis of sucrose, 27:99
Diethidium 5-iodocytidylyl-(3',5')-guanosine,
27 hydrate, crystal structure bibliography,
38:502-503
Diethidium 5-iodouridylyl-(3 '+5 ')-adenosine,
27 hydrate, crystal structure bibliography,
38:501-502
Diethylamine
(2-chloro-I , 1,2-trifluoroethyI), fluorinating
agent, 38:227-229
N-(2-chloro-l, 1,2-trifluoroethyl)-
fluorinating agent, 38:227-229
reactions with alcohols and carbohydrates,
28:257
Diethy lamine, reducing sugar behavior in.
42:34
Diethylaminosulfur trifluoride, fluorinating
agent, 38:225
Diethyl dithioacetals, circular dichroism.
45: I23
Diethylenetriamine-guanosine-palladium(I1)
bisperchlorate, crystal structure,
43 ~328-329
Diethyl ether, as solvent for sucrose, 27:87
Diethyl-hi-(trimethyIsilyl)amine,
trimethylsilylation with, 28:28
Diferulic acid, esters, in ryegrass cell-walls,
36:260
in xylans, 36:242
Differential scanning calorimetry, I ,4:3,6-
dianhydrohexitols, 49: 119
Differential thermal analysis, starch,
47:299-300
Diffusion, agar, 53:205-206
Diffusion coefficients
of a-amylases, 23:309
of P-amylases, 23:333
of phosphorylases, 23:348
Diffusion-in-a-cone model, 51: 119-120. 126
Diffusion measurement, enzyme molecular-
weight determination by, 23:287
Diffusion model, 51:106
I I9
Difluorinated hex-5-enofuranoses, 'H and I9F-
NMR data for, 46: IS4
2P.6P-Difluoroandrost-4-ene-3,I 7-dione.
48: 165
3,3-Difluoro-3-de( methoxy)sporaricin A,
48:223
Difluorofuranoses, 3,6-anhydro-6,6-, 48: 153
Difluorogalactopyranose, 6-deoxy-6,6-
I ,2:3,4-di-O-isopropylidene-a-~-, IH-and
I9F-NMR data for, 46: I5 1
1,2,3,4-tetra-O-acetyI-i,-,'H-and "F-NMR
data for. 46:150-151
Difluorokanamycin A
4,6-dideoxy-4-epi-4,6-. 48:226
5,6-dideoxy-S-epi-5,6-, 48:225
Difluoromethylenation, aldonolactones.
50: 145- 146
Difluorosucrose. 6,6'-dideoxy-6,6'-. 48:2 16
Difluoro sugars, 2-deoxy-2,2-, synthesis,
48:181 182
Difluorouridiiie, 2',3'-dideoxy-3.'5'-, synthesis
and biological activity, 48:256
Di-P-o-fiuctopyranose 1,2':1 '2-dianhydride,
47: 17,26
Difructose anhydrides, 2:253-277,
52:211-212,240
formation, S2:2 19
Digalactosylceramide, biosynthesis, 40:248
Digalacturonopolygalacturonase,nomenclature,
33:327
m-Digallic acid, 21:25
Digestibility, 53:399400
Digipronin, 39:302
Digitalis pttrpitrra
flavonoid from, 31:145
glucoapiosylapigenin from. 31: 175
Digitalose
occurrence, 39:28 I
steroid glycosides, 39:302
synthesis of. 32:65
Digitoxal, 3,4-di-O-nitrobenzoyI-, 2 1:299
Digitoxigenin, 21:273
a-and P-o-rhamnosides, synthesis of, 27:4
a-r-rhamnopyranoside, preparation of, 27:4
3-U-(or-r-rhamnopyranosy)-, 21279
8,14-anhydro-. structure of, 2 5 5 5
anhydro-, 21:279
3-O-(~-u-glucopyranosyl)-, 21:282,3 12
3-(2-deoxy-a-i) arubino-hexopyranosyl)-.
21:304
120 SUBJECT INDEX
Digitoxigenin (continued)
3-0-( 6-deoxy-a-~-mannopyranosyl)-,
21:279,288
3-(2-deoxy-~-~-urubino-hexopyranosyl)-,
21:304,306
3-(2-deoxy-P-o-ribo-hexopyranosyl)-,
21:308
3-0-(6-deoxy-3-0-methyl-P-o-
glucopyranosy1)-, 21 :287
a-digitoxoside, 21:299, 3 12
Digitoxigenin glycosides
cardiotonic activities of, 21:314
properties of, 21:313, 319
Digitoxose, 21:186,297
p-D-,crystal structure bibliography,
38:425-426
D-, I ,3,4-tris(p-nitrobenzoate), preparation
of, 27:3
ester of uridine 5-pyrophosphate, isolation
of, 28:326
Digitoxoside, 21:299
methyl (Y-D-, 23:271
mono-, preparation and properties of, 27:3
Diglyceride
di-O-D-galactosyl-
biosynthesis, 37:362-366
isolation, 37:323, 325
mono-0-o-galactosyl
biosynthesis, 37:362-366
isolation, 37:323, 325
Diglyme, 24:341
Digoxigenin, 3-~-o-glucopyranosy~-, 21:282
Digoxin, crystal structure, 43:269-27 I
Digritoxigenone, 21:306
gem-Dihalides, in acetal preparation,
34:188-189
Diheteroevulosans, 22:260,52:209-211,240
Dihexulose dianhydrides, 52:207-266
I3C NMR spectra, 52:245-246
conformation, electronic control, 52:224228
conformational rigidity, energetic outcomes,
52:228
hexulopyranose rings, 52:226
historical overview, 52:210-213
H NMR spectra, 52:248-249
intramolecular hydrogen-bonds, 52:227
isomerization, 52:23 1-232
1,2-linked, em-anomeric effect, 52:224-225
listing, 52:240-241
nomenclature, 52:208-2 10
optical rotations and melting points,
52:242-243
protonic activation
with acids other than HF, 52:221
using anhydrous hydrogen fluoride,
52:216-220
from spriodioxanyl pseudo-oligosaccharides,
52:220-221
thermal activation
in presence of acids, 52:22 1
without acids, 52:221
thermodynamic versus kinetic control of
product distributions, 52:228-232
three spiro-linked rings, 52:225-226
Dihydrocerebroside, ethanol solvate, crystal
structure, 43:355
Dihydrochalcone glycosides, taste properties,
45278-285
Dihydrochalcone-receptor complexes,
45:281-282
Dihydrochalcones
4-0-(carboxyalkyl)-, sweetness structure
relationship, 45:245
proposed AH,B,X systems of, 45:283-285
sulfoalkyl
sweetness-structure relationship, 45:245
taste properties, 45:342
taste properties
sulfobutyl, 45342-344
sulfoethyl, 45:342-344
sulfomethyl, 45:342-344
Dihydrocinnamoyl groups, enzymic hydrolysis,
39:4344
o-(+)-Dihydrocoumariloyl group, enzymic
hydrolysis, 39:44
Dihydroisodonal, taste properties, 45:3 12
o-Dihydro-N-(2-~-hydroxyoctadecanoyl)-~-~-
galactosylsphingosine, ethanol solvate,
crystal structure, 43:355
Dihydropyrrolopyrazine, formation of, 46:3 14
Dihydrotrichodonin, taste properties, 45:3 12
Dihydrouridine, 6,5-anhydro-2-deoxy-5-
diazo-5,6-, hemihydrate, 43:373
Dihydrouridine 3 -(potassium phosphate),
hemihydrate, crystal structure, 43:3 14
Dihydroxyacetone, 46:32 1
acetophenones formation, 46:280
aromatics formation in acid solution,
46~279-280
benzofuran formation, 46:280
 SUBJECT INDEX
high-temperature transformation, in alkali
conditions, 46:284
hydroxydimethylpyranopyrandiones
formation, 46:280
3-hydroxy-6-methyl-4H-pyran-4-one
formation, 46:280
pyranones formation, 46:280
reaction of, with amino acids, 46:321
taste-structure relationship, 45:252-253
1,3-Dihydroxyacetone phosphate, reactions
with aldolase, 49: 192
2,3-Dihydroxyacetophenone,46:290
1,2-Dihydroxyacrolein, see Triose-reductone
6,7-Dihydroxyphthalide, 46:290
(2R, 3S,4R)-3,4-Dihydroxyproline,50: 197
Diisoamylborane, reduction of aldonolactones,
50: 160-161
Di-0-isopropylidene-a-DL-carba-
mannopyranose, 48:73
Di-0-isopropylidenecyclohexaneterol,48:40
Di-0-isopropylideneglycofuranosederivatives,
51: 109-1 12
Di-0-isopropylidene-m-validamine,48: 76
Di-0-isopropylidenevalinamine, 48: 76
Diisopropyl phosphorofluoridate, cyclodextrin
inclusion complexes with, 46:222,224
Diketosamines
decomposition, 47:264-266
mechanism for cleavage of, 46:309-3 11
Diketoses, 52:50, 78-79
Dilatometry, mutarotation measurement by,
23:50
3,4-Dimenthoxyphenylethylideneacetal,
51:212
4,7-Dimethanesulfonates, 48:63
3,5-Dimethoxybenzyloxycarbonylgroup,
photochemical removal of, 46: 192
Dimethoxymethane
bond lengths and angles, 47:97-98
conformational energy map, 47:76-78
dipole-dipole interactions, 47:82,84
highest-occupied MO orbitals, 47: 120-121
molecular orbitals, 47: 1 1 1
relative energies, 47:78-79
torsional potentials, 47:82-83
N,N-Dimethyl(a1koxymethaniminimum)
bromide, selective bromination with,
33:78, 81
5-(Dimethylamino)uridine, crystal structure,
43:29 1-292
121
2,5-Dimethyl- 1.4-benzenedio1, from
hydrothermolyzed cellulose, 46:304-305
2,5-Dimethylbenzoquinone
formation, 46:294
from hydrothermolyzed cellulose,
46~304-305
Dimethylbenzyloxycarbonyl groups, 3,5-
dimethoxy-, photochemical removal of,
46: 192
Dimethylcyclopent-2-en- 1-one, 2-hydroxy-3,5-,
formation, 46:294
3,4,3 ,4-Dimethylenedioxybenzoin,
photocyclization of, 46:201
Dimethyl ethers, substituted
bond length and angles, 47:96,98
net charge, 47:102-103
rotational potential constants, 47:82-83, 85
N,N-Dimethylformamide, 53:374
in g.1.c. of sugar trimethyl ethers, 42:22
sugar composition in, 42:60,68
N,N-Dimethylformamide-sul fur trioxide, as
sulfating agent for polysaccharides,
29:335
1,7-Dimethylguanosine iodide, 43:373
N,N-Dimethylhydrazones, 46: 197
photosensitized decomposition of, in
presence of oxygen, 46: 198
N,N-Dimethyl(methaniminimum) halides,
selective halogenations with, 33:79-83
Dimethylnojirimycin, 1-deoxy-NN-,
glucosidase inhibition, 48:339-340
Di-m-(methyl4,6-0-benzylidene-a-~-
glucopyranosid-2,3-diyl)bis[dibutyl-
tin(IV)], crystal structure, 43:271
Dimethyl- 1-pentanol, 3-4, molecular-
connectivity index, correlation with
biological activity, 45:229-230
Dimethylsilylation, of cycloamyloses, 28:3 1
Dimethyl sulfoxide, 53:359-360
amino sugar behavior in, 42:48
in anhydridization, 34:48
complex with amylose, crystal structure
bibliography, 33:391-393
NMR spectroscopy of sugars in, 42:23
periodate oxidation in, 31:201
in selective oxidation of carbohydrates,
33:92-93
sugar composition in, 42:60-61,68
Dimethyl sulfoxide-acetic anhydride
ketonucleoside synthesis, 42:232
122 SUBJECT INDEX
Dimethyl sul foxide-acetic anhydride
(continued)
for oxidation of isolated hydroxyl groups,
34:97
Dimethyl sulfoxideedicyclohexycarbodiimide
method for keto derivatives, 42:232-233,
238
Dimethyl sulfoxide-phosphorus pentaoxide
method for ketonucleoside synthesis,
42:232
Dimethylthiocarbarnates, photochemical
cleavage, 46: 189-1 90
Di(neogarobiose) hydrolase, p-D-,44: 190
2,4-Dinitrobenzenesulfenicesters
photolysis of esters, 46:200
as protecting groups for carboxyl groups,
46:200
Dinitrogen tetraoxide
oxidation of polysaccharides with, 29:346
reaction with glycals, 24:206
as solvent for sugars, 27:94
3,5-Dinitrophenyl phosphoric esters,
photohydrolysis, 46:203
2,4-Dinitrophenylsulfenylgroup, as protecting
group, in nucleoside chemistry, 39:43
Dinucleoside phosphates, synthesis of, 28:287,
3554
Dinucleosides, monophosphates, proton
magnetic resonance spectroscopy of,
27:36
Dinucleotides, monophosphates, proton
magnetic resonance spectroscopy of,
21:36
Diogenine, hydrogenolysis, 39: 122
Di-0-isopropylidene-P-o-fructopyranose,
2,3:4,5-, phosphorylation, Garcia
Gonzalez work on, 4 5 8
gem-Diol, formation in aqueous solution,
42:30,38
Diols
acyclic, 53:129-131, 133
cis-, 53:71,95-100, 103
near deoxy centers, 53: 103-1 10
near doubled bonds, 53: 103-1 10
protection of, 46:188-189
symmetrical, 53:44
terminal, 53:110, 119-124
trans-, 53:44,61-88
Di-0-methylhexopyranosylderivatives,
sweetness, 49263
Di-0-methylisosorbide, 49: 140, 166
2,6-dioxabicyclo[3.1. llheptanes, synthesis,
39: 169-17 1
2,7-Dioxabicyclo[2.2. llheptanes,
polymerization, 39:2 10
synthesis, 39: 164-1 69
2,7-Dioxabicyclo[4.1 .O]heptanes, synthesis,
39: 171-172
2,7-Dioxabicyclo[3.2.O]hept-3-ene,6-methyl-,
substrate for 3-deoxystreptose, 40:83
2,6-Dioxabicyclo[3.3.O]octane,(R,R)-cis-,
49:147-148
2,6-Dioxabicyclo[3.3.O]octane,ring of D-
glucofuranurono-6,3-lactone,33: 191
2,8-Dioxabicyclo[3.2. lloctane, structure for
1,6-anhydro-~-~-aldohexofuranoses,
34:24-25
6,8-Dioxabicyclo[3.2.1 ]octane
2-bromo-, preparation of, 34:48
cis- and trans-Cbromo-, preparation of,
28:296
1,5-dimethyl-, in aggregation pheromones of
westem-pine bark-beetle, 34:26
exo-7-ethyl-5-methyl-, in aggregation
pheromone of westem-pine bark-beetle,
34:26
hydrogenolysis, 39: 133
polymerization, 39:210
preparation of, 28:296
from acrolein, 34:48
structure for 1,6-anhydro-P-~-
aldohexofuranoses, 34:24-25
synthesis, 39:161-164
2,8-Dioxabicyclo[3.2. Iloctanes, synthesis,
39:161-164
6,8-Dioxabicyclo[3.2. I ]oct-2-ene, preparation
of, 28:296
6,8-Dioxabicyclo[3.2.l]oct-3-ene
preparation of, and isomer, 28:296
synthesis, 40:35-36
2,6-Dioxabicylo[3,3,9]octane,framework,
49:97
1,3,2-Dioxaborinane
5-hydroxy-2-phenyl-, nomenclature, 3 5 3 6
nomenclature, 35:36
1,3,2-Dioxaborolane
2-methyl-, preparation, 35:39
nomenclature, 35:36
1,8-Dioxadecalin, photoelectron spectra,
47: 120
 SUBJECT INDEX
p-Dioxane
effect on mutarotation of carbohydratcs.
28:39
as solvent for sugars, 27: 107
1,4-Dioxane,cyclodextrin inclusion complexes
with, 46:222,224
rn-Dioxane ring
Brown-Brewster-Shechter rule for formation
of, 26:2 10
conformation of, 26: 120-1 2 I
stability in cyclic acetals, 26:202
1.3-Dioxan-5-01
cis- and trans-2-phenyl-, esterification with
p-phenylazo-benzoyl chloride, 33: 15
2-phenyl-, preparation of, 34: I81
as solvent for sugars, 27:88-89
Dioxanylium salts, 26: 129
1,3,2-Dioxaphospholene, carbohydrate
substrate, 40:122-123
I ,7-Dioxaspiro[5.5]undecane, 52:224
Dioxastannolane, 2,2-dibutyl- I ,3.2-, structure.
53:27,30-32
1,3,5,2,4-Dioxazadiborepane, 2,4-diphcnyl-,
formation, 3 5 6 7
Dioxolane, benzylidene acetals, 51:223
1,3-Dioxolane
2-(a-cyclohexyl-a-hydroxybenzyl)-4-
(dimethylaminomethyl)-, isomers,
preparation of anticholinergic drug.
27:219
cis-2,4-dimethyl-, nuclear magnetic
resonance spectroscopy reference
compound, 27:209
4-[(dimethylamino)methyl]-2-methyl-,
methiodide, isomers, cholinergic
potency of, 27:208
2-(2-furyl)-4,4,5,5-teramethyl-, substrate for
carbohydrate synthesis, 40:73
4-(hydroxymethyl)-2-methyl-,relative
configurations of, 27:208
4-methano1, as solvent for sugars, 27:88-
89
2-(o-nitrophenyl)-, irradiation, 39:86
photoaddition to alkenes, 39:80, 94
photochemical addition with unsaturated
carbohydrate, 38: 1 18-1 I9
ring
conformation of, 26: 1 17
2,2-dimethyl-, hydrolysis of, 26:204
stability in cyclic acetals, 26:202
123
I ,3-Dioxolane-4-methanol, 2-phenyL. cis- and
truns-. formation of, 34: I81
Dioxolanylium ion. in neighboring-group
reactions, 26: I28
Dioxolanylium salts. preparation of. 26: 129
1.3-Dioxol-2-one
4-bromo-5-( trichloromethyl)-, synthesis,
40:85-86
carbohydrate substrate, 40: 8 4 9 6
4-chloro-5-(trichloromethyl)-
substrate for monosaccharide synthesis,
40:84-96
telomers, 40:85-86
Dipeptide esters. sweetness-struchire
relationship, 45:30&3 10
Dipeptide sweetcners, location of third binding-
site in, 45:234-235
Diphenylamine reagent, for o-fructose
estimation. 22:237
1,2-Diphenylethylene dithioacetals. 46: 196
photochemical decomposition of, in presence
of oxygen, 46: 197
Diphenylphosphoric anhydride, as
phosphorylating agent for (2-
deoxyribofuranosyl)purines, 0-
benzylphosphorus 0.0-,22:328,345
Diphenyl phosphorochloridate
as phosphorylating agent for nucleosides,
223326
selective phosphorylation of trehalose and
kanamycin with, 33:49-SO
Dip1ococcic.Tpneumoniae
gas-liquid chromatography of, 28:47
mass spectrometry of capsular
polysaccharides from. 29:55
type 111 immunoadsorbent, preparation of,
31:323
Dipolar interaction, correlation times, 47: 133
"C-H dipolar interaction, relaxation
parameters, 51:69
Dipoleedipole interaction, energies, 47: I07
Dipole4ipole relaxation, 51:65 -67
Dipole moment
in conformational analysis, 26:65
of D-fructose. 22~237
of solvents, effect on sugar solubility, 27:87
Dipotassiuni a-u-glucosyl phosphate dihydrate.
crystal structure bibliography, 31:364
Dipropyl sulfoxide, as solvent for sugars,
27: 108
124 SUBJECT INDEX
Dipterex, biological activity and structure of,
42: 189
Dipyrido[ 1,2-a:2, 1-clpyrazidinium
dibromide, 1,l -dimethyl-, effect on
sugarcane, 21:422
Diquat, effect on sugarcane, 21:422
Disaccharide alditols, trifluoroacetyl
derivatives, gas-liquid chromatography of,
28:113
Disaccharide glycoside, synthesis Helferichs
work on, 45:3
Disaccharide precursors, synthesis, 40: 128
Disaccharides
acetals, cyclic, 34:209
acetates, gas-liquid chromatography of,
28:70
acetolysis of, 31:197-200
acyl esters, reaction with ammonia, 31:92-
99
amino, per(trimethylsilyl)ated, gas-liquid
chromatography of, 28: 134
aminodeoxy, synthesis of, 33:233-234
ammonolysis
of perbenzoylated, 39:30-32
products from acylated, 31: 132-134
anomeric protons, nonselective spin-lattice
relaxation rates, 45: 149-152
in blood and urine, trifluoroacetic acid in
hydrolysis of, 28: 16
C-C and C-0 bond-lengths in, 44: 14-15
conformational analysis, 44: 14
in dairy products, liquid chromatography
separation, 46:52
definition, 52:148
dithioacetals, physical constants of, and their
peracetates, 32: I 16
enzymic synthesis of, 5:2948
fragmentation by radiation, 37: 14
with free hemiacetal group, 52: 149-150
hydrogen bonding, 44: 15-16
hydrolysis of, rate constants and activation
entropies for, 22:76
and kinetic parameters for, 22:75
interaction with concanavalin A, 35: 184
with lectins, 35: 142
ionic, high-performance liquid
chromatography, 46:33-37
large-scale preparative liquid
chromatography, 46:62
laser-Raman spectroscopy, 44:75-8 1
mass spectrometry of
permethylated, 29:84
trimethylsilyl derivatives, 30:39
mercaptalation of, 32:28
neutral, analytical high-performance liquid
chromatography, 46:32
occurrence in plant kingdom, 37:309-3 10
peracetylated, gas-liquid chromatography of,
28: 133
permethylated, mass spectrometry of,
30:42
1-phenylflavazole acetates, mass
spectrometry of, 29: 100
preparative liquid chromatography, 46:60
proton spin-lattice relaxation rates, 45: 152
radiolysis and radical-induced scission,
37:5 I , 53-55
reaction with sulfuryl chloride, 33:76
reducing, sweetness, comparison to
monosaccharides, 45246-247
(1+2)-linked, sweetness-structure
relationship, 45277-290
selective esterification of, 33:35
solubility in liquid ammonia, 27:91
structure, 35x5
crystal structure of, 2575-77
sulfates
esters with uridine 5-pyrophosphate, in
hen oviduct, 28:330
liquid chromatography, 46:37
synthesis of, 24:115, 132,34:160-161,
40: 123-129
trehalose, 18:201-225
tritiated, preparation and position of tritium,
27: 188
trivial names, 52: 150- 15 1
utilization by yeasts, 39:347404
vicinal carbon-proton coupling constants,
51:52-53
without free hemiacetal group, 52: 148-
149
Dische test, 52: 13
for 2-deoxy-o-euythro-pentose, 28:224
Discoidin, preparation, composition, and
properties of, 39309
Diselenide
bis(5-deoxy- 1,2-O-isopropylidene-a-o-
xylofuranose-5-yl) 5,5-, 23:232
bis(methy1 5-deoxy-o-xylofuranoside-5-yl)
5,5-, 23:232
 SUBJECT INDEX 125

Disialosyllactosylceramide, biosynthesis, gas-liquid chromatography of, 30:33

40:225,254,262 mass spectra of sugar, 29:71-73
Disilazane, hexamethyl-, trimethylsilylation of sugar, 26: 13
sugars with, 28:23 thioglycosides preparation, 52: 181
Disinfection, 53:297-298 Dithiocarbamoyl group, participation in sugar
Disodium phosphate, 2 '-deoxyuridine-5 '-. reactions, 22: 146, 164
pentahydrate, crystal structure. 43:3 10 1,3-Dithiolane-4-methanol. derivatives.
Disodium (pT'pT*), crystal structure preparation of, 32:20
bibliography, 31:361 Diumycin, inhibition of protein glycosylation,
Disodium thymidylyL(5 ' 4 3 ')-5 '-thymidylate 40:343-344
dodecahydrate, crystal structure Diuretics, 1,4:3,6-dianhydro-~-glucitol as,
bibliography, 31:36 1 25:269
Disopropyl fluorophosphate, as inhibitor for Diuron
pectinesterase, 33:336 effect on sugarcane, 21:427
Di-a-L-sorbopyranose 1,2': 1,'2-dianhydride, as herbicide, 21:405
47:17 Divinyl sulfone
Displacement reactions affinity adsorbent support activation,
involving participation, 24: 167 39:432
of sulfonic esters of carbohydrates. agarose activation for affinity
24:139-197 chromatography, 39:415
Dissociation constant, 48:330-33 1 cellulose cross-linking with, 33:68
Bronsted relationship between catalytic as cross-linking agent for polysaccharides,
activity and, 24: 19 29:356
Distribution coefficient, in gel chromatography. DNA, see Deoxyribonucleic acid
25:16 Dodecanoic acid, methyl ester, trans-
Disulfide esterification of methyl OL-D-
bis(2-deoxyaltrosid-2-yl),25: I39 glucopyranoside with, 33:44
bis(methy1 5-deoxy-o-yxlofuranoside-5-yl) Dodecanucleotide, synthesis, 36: 173
5 5 ' - , 23~208 Dodecyl sodium sulfate, as inhibitor for
Disulfones, from dithioacetal oxidation, pectinesterase, 33:336
32~82-88 Doisy, E.A., 46: 12
Disulfoxides, from dithioacetal oxidation, Dolichol, 26:382
32:82 biosynthesis, 40:288-299,323, 44:350
Diterpenes, of Isodon species, bitterness. composition, 40:288
45:3 12 cytological and topological aspects,
1,3-Dithiane 40:314-321
2-lithio-, in synthetic carbohydrate 2,3-dehydro-, phosphates, 40:289
chemistry, 32:37 metabolism, 44:350-352
2-lithio-2-methyl-, in carbohydrate synthesis, plant sources, 44:348
32:38 structure, 44:346
2-lithio-2-(trimethylsilyl)-, in preparation of subcellular localization, 40:3 15-3 18
propsnr- 1,3-diyl dithioacetals, 32:39 Dolichol phosphate
Dithioacetal, 2,3:4,5-di-O-isopropylidene-n- biosynthesis. 40:289-299
gulose diethyl-, crystal structure, 43:247 inhibitors of formation, 40:322-326
Dithioacetals, see also Acetals; Thioacetals Dolichos biflorus lectin
acetylated, 22: 19 carbohydrate-binding specificity, 35:
gas-liquid chromatography of, 28: 12 I 229
of 2-amino-2-deoxyaldoses, deamination of, circular dichroic spectrum, 35:230
25: 192 hemagglutinating activity. 35:226
diethyl, of aldoses, conformation of, 26:72 isolation, 35: 138
126 SUBJECT INDEX

Dolichos hiforus lectin (continued) E

purification and properties of, 35:227-229
uses, 35:23 1 E. COSY, 51~22-23
Dolichyl phosphate Earthworms, a-o-mannosidase in, 28:405
biosynthesis, 44:350 Ebenaceae, polysaccharides from, 31 :253-254
in biosynthesis of cell-wall polysaccharides, Echinocystis lobatu lectin, isolation, 35: 138
42:325-330 Echinoderms, glycolipids, see Glycolipids
metabolism, 44:350-352 ECNSS-M, in gas-liquid chromatography,
Dopamine P-hydrolase, sialic acid effect, 28:60
40:219 EDTA, effect on a-o-mannosidase activity,
Dosaccharides 28:42543 1
derived, 21:30 Eel
furanoid, 21: 126 electric, electrolectin from, 35:3 15
mass spectra of, 21:69 serum lectin
by reversion of monosaccharides, agglutinating activity, 35:277
21:443-444 carbohydrate-binding specificity,
synthetic, 21:31 35~277-279
Dotriacontanoic acid, 17-hydroxy- purification, 35:28 1-282
2,4,6,8,10,12,14,16-octamethyl-, ester of Egg-box model, 47:33
trehalose 2-sulfate, in Mycobacterium of cell-wall for calcium inclusion, 42:305
tuberculosis. 30:236 Ehrlich cells, lectin-reactive, 35:329-330
Double bonds Eicosanucleotide, synthesis, 36: 172
radiation and radical addition reactions, Einstein-Smoluchovsky relation, modified, in
37:23 polarography, 29: 137
unsaturated monosacchrides, 52:92-95 Elastin, as urinary protein-carbohydrate
cumulative, 52:95-96 compound source, 24:450
Double-sigmoid growth-curve of fruits, 42:34 I , (+)-Eldanolide, 50: 185-1 86
344 Electrical conductivity, mutarotation
Douglas fir, cell-wall studies on, 42:271 measurement by, 23:51
Drierite, in cardiac glycoside synthesis, 21:277 Electrical phenomena, starch modification,
Drilling, well, plant galactomannans in, 35:342 51:307-3 1 0
Drug action, 45:224 Electrochemistry, of carbohydrates and
theory of, 45:227-228 derivatives, 29: 107-1 7 1
Drug design, nonmathematical approach, Electrofocusing, 53:206
45~230-23I Electrolectin, isolation and properties, 35:3 15
Drug dose-response relationships, 45:211 Electrolyte effects, 53:272
free-energy relationship, 45:224 Electron availability, of solvent, effect on sugar
parameters, 45:224 solubility, 2R87
DS-GAG chain, 49:242-243 Electron density, carbohydrate structure and,
Duanosamine, synthesis of, 2 4 2 I0 2555
Duckweed, cell-wall studies on, 42:281 Electron distribution, lone-pair orbitals and,
Dulcin, sweetness, 45:205 47: 101- 103
Dulcitol, see Galactitol Electronic absorption spectra
Dutch-elm disease, 41:89 of or$-unsaturated acids, 27:260
Dyeing, of polysaccharides, 29:350-353 of or$-unsaturated carbonyl sugars, 27:248
Dyes of anhydro-C-(p-methoxypheny1)aldoses
anionic, 53:381, 383 and anhydro- 1,3-dideoxyketoses,
cellulose sorption, 53:384 27:286
coloration scales, 53:376, 378 of C-arylated unsaturated hexitols, 27:239
neutral, 53:378, 381 of dienic carbonyl sugars, 27:25 1
 SUBJECT INDEX
of furan derivatives from sugars, 27:289
of thioenol sugars, 27:275
Electronic density, and mutarotation, 24:37
Electronic effects, on hydrolysis of glycosides.
2259
Electron impact mass spectrometry, 45:23,43,
63,71
Electron magnetic resonance, of free radicals
from irradiated sugars, 26: 15
Electron microscopy, of microfibrils. 26:307,
312,315,335
Electron-nuclear relaxation methods, carbon
atoms, 47:136-137
Electron resonance spectroscopy, 53:287-
288
Electrons, high-energy, irradiation, starch,
51:263,265-267
Electron-spin relaxation, 47: 133-1 35
epi-inositol, 47: 138-140
Electro-oxidation, of carbohydrates and
derivatives, 29: I 17-1 24
Electrophiles, with reactive halogen
substituents, glucosidase inhibition,
48:375-377
Electrophoresis, 53:206
affinity, for lectin detection, 35: 135
agarose for, 29:329
in carbohydrate-alkaline-earth hydroxide
reactions, 21:252
of carbohydrates
in alcoholic alkali metal hydroxide
solutions, 21:262
paper, 18:61-97
zone, 1223-1 15
2-diethylaminoethyl ethers of
polysaccharides as media for, 29:323
enzyme purification by, 23:284
in enzyme purity test, 30:264
of galacturonanases, 33:361
gel, in pectinesterase purification,
33~339-342
of glycoenzymes, 27:3 1 1
metal cationxarbohydrate complexes
applications, 47:35-36
paper
in carbohydrate chemistry, 36:3, 5-6
in honey analysis, 25:297
of pectic enzymes, 33:324
polysaccharide dyeing in, 29:353
of polysaccharides, 24:335
127
gels and networks, 24:268
in solutions of metal salts, 21:23 1-232,
234-235
and structural integrity of synthetic
polynucleotides, 36:20&206
sulfonylated phenylboronic acid in, 3 5 6 2
of urine protein-carbohydrate compounds,
24:441
Ekctvophortrs electricus, electrolectin,
properties, 35:3 I 5
Electroplating brighteners, dextrins as,
47:326
Electroreduction
of carbohydrates and derivatives,
29: 108-1 17
of lactones of polyhydroxycarboxylic acids,
29: 125
Electrostatic interaction. anomeric effect,
47:107-109
Electrosynthesis, of carbohydrates and
derivatives, 29: 108-126
P-Elimination, 31:2 12, 37:3
aldono- 1,4-lactones, 50: 166- 170
aldono-l,5-lactones, 503162-166
carbohydrate chains of glycoproteins,
38:411412
of carbon monoxide by radiation, 37: 14
in degradation of capsular polysaccharides,
31:239
of oligosaccharides and polysaccharides,
3 1:2 I 2-229
degradation of heparin by, 43:85-86
by depolymerases, 33:325
with ~-glucofuranurono-6,3-lactones and D-
glucofuranosidurono-6,3-lactones,
33:219--226
in dithioacetal reactions with bases, 32:57
in enzymic degradation, 33:358,367
in glucosiduronic acid preparation, 36:69
of HOR and NR,, by radiation, 37:ll-12
of HX (X = Hal. OAc, or OPO,H,) by
radiation. 37: 12-13
in proteoglycan and glycoprotein splitting,
33:8
and splitting of pectic substances, 33:323
of water, from carbohydrate radicals by
radiation, 37:9-11
Elimination reactions, radical-mediated
brominations, 49:85-9 1
Ellagic acid, 21:26
 128 SUBJECT INDEX
Ellipticine 5-iodocytidylyl-(3'+5')-guanosine,
methonolate, eicosahydrate, crystal
structure, 43:304-305
Elongation, peptide chain
following selective deprotection, 50:294-298
N-glycopeptides, 50:283-287
Elsinan
fimgal, 41:71
structure, enzymic analysis, 44:265
Elsinoe leucospila. polysaccharide, 41:7 1
Emulsifiers, anhydrohexitol esters as, 25:270
Emulsin, 50:8, 12
effect on glucosides, 50:13-14
lack of effect on methyl xylosides, 50:13
of sweet almonds, Helferich's work on,
45:4-5
Enantiomeric 2-amino-2-deoxycarbahexoses,
synthesis, 48:66-67
Enantiomeric 6a-carba-P-fructopyranoses,
synthesis, 48:51-52
Enantiomeric carba-glycosylamines, synthesis,
48:6445
Enantiomeric carba-sugars, synthesis
a-L-altro and P-o-glum modifications,
48:4647
amino carba-sugars, synthesis, 48:64-67
from o-arabinose, 48:4244
from L-arabinose, 48:4142
Diels-Alder adduct, resolution, 48:36, 38-
39
from o-glucose, 48:4549
from optically active natural products,
48:4041
from D-ribose, 48:44
from true sugars, 48:4149
from D-XylOSe, 48:44
Enantiomers, cyclic monosaccharides, 52:72
Encephalitogen, 25:468
End-group assay, 22:23,490491
Endo-P-o-mannanase, in galactomannan
degradation during germination of seeds,
35:361
Endodextranases, and dextran degradation,
30:391
Endo-o-galacturonanases
action pattern of, 33:345-354
crystalline, from Acrocylindrium. 33:363
in fruit maturation, 33:381
molecular weight of, 33:346, 362-364
occurrence and formation of, 33:359-362
purification of, 33:362-364
Endo-o-mannanases, oligosaccharide
degradation products from galacto and
gluco-mannans and, 32:3 14-3 16
Endo-D-xylanases
arabinose-liberating, 32:335-340
non-arabinose-liberating, 32:340-344
occurrence of, 32:335
Endo-galacturonanase, from Corticium rolfsii,
32:285
Endo-glucanases, mode of action, analysis of,
46:54
Endo-glycosidases, degradation in structural
analysis, 38:4 1 5 416
Endo-L-arabinanases, production of, 32:290
Endoplasmic reticulum
in cell-wall formation, 26:335, 338, 348
of yeast cells, 32:141
Endosperm, galactomannans in, 35:345,355,
356361
1,2-Enediol, sugar transformation in alkaline
medium, 47:253
etythro-elythro configuration, 41: 14
Enediol theory, 26:6
Energy of activation
of a-amylases, 23:3 12
of anomerization, 24:5 1
1,2:4,5-di-O-isopropylidene-P-~-
hydrolysis of, 26:203
rearrangement of, 26:220
thin-layer chromatography of, 26:234
effect of flameproofing on, of cellulosic
materials, 23:468
for interconversion of conformation, 26:91
of mutarotation of D-glucose, 24:53
of sugars, 2 4 5 5
of phosphorylases, 23:350
of rearrangement of acyloxonium ions,
26:136, 139
of thermal degradation of cellulosic
materials, 23:442443,446
Enitols, 1,5-anhydro-
ald- 1-,see Glycosenes
6-deoxy-6-fluoro-~-arabino-hex- 1-
3,4-di-0-acetyI-1,2-didexoy-, 'H- and I9F-
NMR data for, 46: 1 13
3,4-di-O-benzyl-, 'H- and 19F-NMRdata
for, 46: 1 13
4-O-benzyl-3-deoxy-, 'H- and 19F- n.m.r
data for, 46: 113
 SUBJECT INDEX
3,4,6-tri-O-benzoyl-2-deoxy-~-arubino-hex- Enthalpy
I , crystal structure, 43:262
Enkephalins, effect on glycosylation, 40:347,
350
Enofuranose
6-chloro-5,6-dideoxy-5,6-difluoro- I ,2-0-
isopropylidene-3-O-methyl-a-~-.qdo-
hex-5-
(E) isomer, I3C-NMR data for, 46: 176
(Z) isomer, I3C-NMR data for, 46: 1 76
5,6-dideoxy-
6,6-difluoro- 1,2-O-isopropylidene-a-~-
xylo-hex-5-
3-O-benzyl-,C-NMR data for. 46: 175
3-O-methyl-,I3C-NMR data for, 46: 176
1,2-O-isopropylidenehex-5-
6-chloro-5,6-difluoro-3-O-rnethyI-a-~- low molecular weight, research, Japan,
xylo-, IH and I9F-NMR data for,
46: 154
6,6-difluoro-3-0-methyl-a-o-ribo-, H
and I9F-NMR data for, 46: 154
6,6-difluoro-3-0-methyl-a-~-.~ido-, H Enzyme Q, in starch synthesis, 34:6
and I9F-NMR data for, 46: 154
6,6-difluoro-3-0-rnethyl-~-~-*ylo-.IH
and I9F-NMR data for, 46: I54
Enol formation, mechanism of, 26:6
Enolide, 1p,5,1 la,l9-tetrahydroxy-3b-O-a-~-
rhamnopymosyl-5P. 14b card-20(22)-,
crystal structure, 43:26&265
Enones, formation of, 46:326
Enonolactones
2-acylamido-hex-2-. 50:169-1 70
p-elimination, 50:162-165
catalytic hydrogenation, 50:170-1 73
Enopyranose, 1,4,6-hi-O-acetyl-2-(N-
acetylacetamido)-2,3-dideoxy-cr-o-
erythro-hex-2-, crystal structure,
43:243-244
Enopyranosides
ethyl 4,6-di-O-acety1-2,3-dideoxy-a-~-
erythro-hex-2-, crystal structure, 43:229
in synthesis of branched-chain sugars,
4297-98
Enopyranos-2-ulose, 1,6-anhydro-3,4-dideoxy-
P-o-g&cero-hex-3-, 47:338
Enterobacterial common antigen
f.a.b.-mass spectrometry, 4 5 3 4
perdeuteriomethylated, f.a.b.-mass
spectrometry, 45:69
structure, on f.a.b.-mass spectrometry. 45:69
I29
of activation
of hindered rotation, 23: 198-199
of mutarotation of o-glucose, 24:53
of hydrogen bonding, 25:98
Entropy
of activation
for acid-catalyzed hydrolysis of
furanosides, 2 2 4 0
in hydrolysis of pyranosides, 2 2 3 3
for mutarotation of o-glucose, 24:37,53
of hydrogen bonding. 2 5 9 8
Envelope conformation, of furanoid sugars,
26: 109
Enzyme inhibitors
active-site-directed irreversible, 29:2-3
48: 13-14
polysaccharide sulfates as, 29:336
Enzyme-metal-ion complexes, catalytic
activity of, 28:423
Enzymes, see also specific enzymes
acting on pectic substances, -579-102
active site probing, 50:13-14
active sites of, 23:296, 298
affinity chromatography purification,
39:441443
in alginic acid synthesis, 26:407
analytical methods utilizing, 30:279-284
Basidiomycetes, glucan degradation by,
30:361,363-364,367
in biodegradative hydrolysis of
galactomannans, 31:256
biosynthesis
of adenosine cyclic 3,5-phosphate in.
30:224
guanosine 5-tetraphosphate in, 30:225
of dexhans, 30:418433
of tylosin, 3 5 8 4
bound in plant cell-walls, 42:300-302
bovine spleen, dextran degradation by,
30:397
in catabolism of starch and glycogen,
30:285-302
in cellulose synthesis, 26:323-324, 327, 386
classification of metal-dependent, 28:423
coffee-bean, in galactomannan structure
study, 31:271-274
D-, 2 5 9
130 SUBJECT INDEX
Enzymes (continued)
deficiency, in certain diseases, 25:478
degradation
of dextrans by, 30:390-399
of starch and glycogen, 3:251-3 10,
17:407430
3-deoxy-o-manno-2-octu~osonicacid
metabolism, 38:378-387
depolymerization, isolation of products of
partial, 30:272
of o-galactose pathway in yeasts, 32: 176
publications on, 32:178-179
difficulties associated with use of,
30:27&279
DNA ligase, for poly(deoxyribonuc1eotide)
synthesis, 36:178-180
for poly(ribonucleotide)synthesis,
36: 189-193
endo- and exo-, 30:265
exo-, in determination of linear or branched
polysaccharides, 30:274
for galactomannan degradation. 35:36 1-375
as glycoproteins, 25:408
of glycoprotein slmcture, 27:30 1-341
halogenated carbohydrates and carrier
specificity, 22:209
for hepatic o-fructose metabolism control,
34:296
in honey, 25:302
in hydrolysis
of P-o-glucosidic linkages, 30:347-353
of starch, 36~31-35
immobilized, in starch hydrolysis, 36:34
induction of, 30:262-264
sequential, 30:273
inhibition of
anhydroalditols for, 25:269
halogenated sugars as, 22:2 10,2 12
insolubilization of, 29:361-375
by cellulose bromoacetate, 29:337
by cellulose triazine derivatives, 29:349,
372
by cellulose xanthate, 29:346
by imidocarbonates of polysaccharides,
29:373
polysaccharide derivatives in, 29:32&327
by triazine-dyed polysaccharides, 29:352
for interconversion of sugars, nucleotides,
32: 10
introduction of term, 50:8
for isomerization of o-glucose, 36:4&50
isotope-effects in reactions, 27: 171-1 76
kinetics of, 23:288
liver, dextran degradation by, 30:396
lysosomal, 25:474
mechanism of action pattern, 30:27&272
mechanistic studies, hydrogen isotope
labeled sugars in, 27:155-162
in metabolism of D-fructose, 34:330-343
nomenclature, 23:306,33:324-327
nonprotein constituents of, 23:298
pectic, classification of, 33:324-327
mode of action, properties, and function
of, 33:323-385
in plant physiology and pathology,
33~381-385
in peptidoglycan biosynthesis, 26:427
poisons, effect on sugarcane, 21:427
in polysaccharide bio-synthesis, 26:323-324,
327
polysaccharide-degrading, 26:347
properties of, 30:267
purification of, 23:282
purity criteria, 30:264
purity tests for, 23:285
Q-, 23:363,25:8,30:309
purification by chromatography, 23:283
R-, 23~363,25:9
preparation and properties of, 30:293-296
starch degrading and synthesizing,
2 3 ~ 2 1-366
8
in regulation of saccharide biosynthesis,
26:363,377
sialylated, 40:2 19
in solvent-exchange labeling of sugars with
hydrogen isotopes, 27: 134
sources, 30:261
specificity of, 30:268-270,SO: 13-15
of debranching, 30:293-299
in the domain of carbohydrates, 5:49-78
starch-metabolizing, 25:8
in starch synthesis, 26:382
stereochemistry determination at a chiral
methylene group by, 27:141
in structural analysis
of polysaccharides, 21:502
of starch and glycogen, 30:302-332
of sucrose and other disaccharides, 5:2948
in synthese and degradations, 34:8
synthesis of, 24:6
 SUBJECT INDEX
glycogen and starch, 17:371407
in UDP-apiose biosynthesis, 31: 169- I72
in vitro syntheses of natural glycosides, 30:6
water-insoluble, as polysaccharide
derivatives, 29:361-375
in yeast catabolism of sugars, 32:127
from yeasts for sugar metabolism, 32: I28
Z-, 23:331,336,25:9
as contaminant in P-amylase, 30:287,
306
nature of, 30:307
Enzyme-substrate complexes, crystals
structures of, 2593-98
Enzymic analysis, of carbohydrates, 35: 1 1
Enzymic deacylation, see Deacylation
Enzymic hydrolysis
of glycosidic linkages, 46:27&271
protein activators, 40:28 1-285
Enzymic methods, 49: 175-237
C-C bond-forming reactions, 49: 189--207
aldol reaction, 49:189-190
miscellaneous reactions, 49:205
synthesis
with glycolysis aldolase, 49: 190-1 94
with sialyl aldolase, 49: 194-204
transketolase, 49:204-207
definitions and abbreviations, 49: 177
glycosylations with transferases, see
Glycosylation
immobilization, 49: 180-1 89
agarose, 49:181-186
dialysis bags, 49: 188
poly(acry1amide) gels, 49: 186-1 88
silica gel-glutaraldehyde, 49: 188-1 89
interest in, 49: 176-177
in organic solvents, 49:235-236
phosphorylations, 49:207-2 18
nucleotides, 49:2 10-2 13
nucleotide-sugars, 49:213-2 18
sugar phosphates, 49:207-210,212
synthesis in aqueous solution, 49:234-235
transfer reactions, catalyzed by glycosidases,
49:23 1-233
Enzymic reactions, of glycosyl esters of
nucleoside pyrophosphates, 28:362-396
Enzymic synthesis, of glycosyl esters of
nucleoside 5 -pyrophosphates,
26:354-366
Enzymology, and structural analysis of
polysaccharides, 30:257-370
131
Enzymolysis
configuration of glycoside linkage by, 28:32
of o-glucose and gas-liquid chromatography,
28:40
of polysaccharides and proton magnetic
resonance spectroscopy, 27:4 1
~-6-Epicastanospermine,SO: 198-199
Epichlorohydrin, as cross-linking agent for
polysaccharides, 29:355
Epididymis
a-o-mannosidase activity in, 28:403
as a-o-mannosidase source, 28:41 I
3-Epidigiroxigenin, 21:274
3-Epi-3-fluoro-3-de(methox)sporaricinA,
48:223
Epiglucosamine, 21 :I8
Epi-isosaccharic acid, preparation of, 31: 18
Epimelibiose, isolation and structure, 37:309
Epimerases, 26:358
gas-liquid chromatography of, 28:47
and hydrogen-isotope action on sugars,
27: 156
inversion in glycosly group by, 28:369-379
Epimerization, 21: 178
and acetolysis, 31:200
of aldonic acids, 21: 1 1
of lactones, 21:17S
mechanism of, of glycosyl esters of
nucleotides, 26:358
of nitro sugars, 24: 120
in sugar moiety of nucleotides, 22:375
Epimine, cleavage by fluoride ion, 48: 155,
163-169
Epiminonucleosides, preparation of, 42:245,
257
Epimino sugars, 25:352-356
Epimycarose, acetyl-, 21: 185
Epinephrine, effect on glycogen synthetase
activity, 26:378
P-Epinoroxetanocin, 50: 196
3-Epiparomamine, preparation of, 30: 179
o-Epipurpurosamine, ethyl glycoside, synthesis
of, 30: 127
rac-4-Epishikimic acid, methyl ester triacetate,
isomenzation in hydrogen fluoride, 26: 172
Episulfides, of sugars, 22: 156, 192
1,2-Episulfonium ion, in mercaptalation, 32:32,
56
Epithelial cells, o-fructose effect on energy
metabolism of intestinal, 34:324
132 SUBJECT INDEX

Epithio sugars, 22: 156 diacetate, isomerization of, 25:258

cleavage of, 22: 192
Epivalidamine, from dihydrovalidamycin A,
30: 139
Epoxidation
of double bonds, 1,6-anhydrohexopyranoses
prepared by, 34: 112
in sugar synthesis, 40:42-44, 56-59
Epoxide ring
conformation of, 26: 124
opening reactions, in sugar synthesis,
40:44--17,56-59
Epoxides
3,4-tulo-, 51:2 15-2 16
carbohydrates, 24:168,25: 110
cleavage by fluoride ion, 48: 155, 163-169
hydroformylation and
hydro(methoxycarbony1)ation of,23 :63
sugar, 23:234
deoxy sugar from, 21:152, 159
0x0 reaction with anhydro, 23: 102
Epoxyketonucleosides, synthesis of, 42:241
Epoxypropyl-2-pyrone, 5-acetoxy-5,6-dihydro-
6-1,2-, 51:107-108
Equatorial bonds, 2 6 5 2
Equilenin, C-conjugate with P-D-~~UCO-
pyranosiduronic acid, preparation, 36: 1 33
Equilibrium constants, in polarography,
29: 137-143
Ergosterol, conjugate with methyl 2,3,4-tri-0-
acetyl-a-o-galactopyranosiduronate,36:93
Erlose, in honey, 25:295,301-302,308
Erwinia tahiticu, polysaccharide, preparation,
properties, and uses, 36:297
o-Erythorbic acid
preparation, 37:98, 106, 123
sodium salt monohydrate, crystal structure
bibliography, 38:42042 1
structure, 37:83
Erythran, as solvent for sugars, 27:88
Erythraric acid
2-methoxy-o-, 22:7
2-0-(carboxymethyl)-, 25:261
Erythritol
2-amino-2-deox y-
D-, synthesis, 40: 1 14
DL-, synthesis, 40:29-30
1,4-anhydro-, 25:230
acetalation of, 25:265
catalytic oxidation of, 25:262
infrared spectrum of, 25:252
reaction with hydrogen fluoride, 25:258
as solvent for sugars, 27:88
2,3-anhydro-, synthesis, 40:29
1,3-0-benzylidene-2,4-di-O-p-tolylsulfonyl-
L-, 23:275
1,I-bis(acetamid0)-1 -deoxy-, D-, preparation
of, 31:83
I , 1-bis(acetamido)- 1-deoxy-, L-, preparation
of, 31:82, 84, 112
1,l-bis(benzamido)-1 -deoxy-L-, preparation
of, 31:lOO
I ,4-bis[2-(methylsulfonyl)oxyethylamino]-,
cytostatic activity, 28:7
cis-2,3,-0-benzylidene-,isomerization,
39:27
2-C-methyl-n-, natural occurrence of, 42:76
conformation of, 26:68
crystallography of, 25:58,31:363, 34:371
crystal structure, 43:205
2-deoxy-2-fluoro-, 22: 199,201,207
DL-
structure, 38: 197
synthesis, 38:237,40:104
as inhibitor for Brucella abortus, 22:212
4-deoxy-~-,phenylboronate, structure, 35:43
1-deoxy-2,4-0-ethylidene- 1-iodo-D-,
reaction
with 2-lithio-l,3-dithiane, 32:37
with sodium cyanide, 28:282
2,3-di-O-acetyl- 1-arnino-.l-bromo- 1,4-
dideoxy-, hydrobromide deamination of,
31:63
di-0-acetyl- 1,4-anhydro-, rearrangement in
hydrogen fluoride, 26: 174
1,2:3,4-di-O-benzyIidene-, selective
hydrolysis, 39: 19
1,4-di-O-(methylsulfonyl)-,23:239
enzymic determination of, 30:282-283
gas-liquid chromatography of, 28:92
2,4-0-ethylidene- I ,3-di-O-(p-nitrobenzoyl)-,
aroyl migration and deacetalation,
33: 107
production by alkane-grown Candidu
zeylanoides, 32 :234
radiation chemistry, 37:34
radiolysis and free-radical chemistry,
37:27-29, 32
selective phosphorylation of, 3 3 5 0
 SUBJECT INDEX
sweetness-structure relationship, 45:248,293
synthesis, 40:29
1,2,3,4-tetra-0-p-tolylsulfonyl-, infrared
spectrum, 23:255
2,3,4-tri-O-acetyl- I -amino- 1-deoxy-r,-, p -
toluenesulfonate (salt), deamination of,
31:63
water elimination reaction by radiation,
37:lO
Erythrocyte glycoprotein, permethylated, f.a.b.-
mass spectrometry, 45:34-35
Erythrocytes
desialylated, 40:222-226
ganglisides of, 24:432
human, carbohydrate linkages of, 25:433
lectin-reactive glycoproteins, 35:3 18-325
lentil lectin in hemagglutination, 35: 193
P. vulgaris lectin receptor-site, 44:232
Erythrofuranose
4-acetamido-4-deoxy-~-,23: 196
3-C-(hydroxymethyl)-
D-, see Apiose
1,2-O-isopropyIidene-cy-o-, preparation of,
31:183
2,3-O-isopropylidene-P-~-, preparation of,
31:183
1,2:3,3'-di-O-isopropylidene-[3-C-
(hydroxymethy1)-a-o-, preparation of,
31:183
2,3,31-tri-0-methyl-3-C-(hydroxymethyl)-o-,Erythropoietin
identity with tri-0-methyl-D-apiose.
31:142
Erythrofuranoside
methyl 4-acetamido-4-deoxy-~-,23: 179
synthesis, 41:9
methyl 3-C-(hydroxymethyl)-2,3-0-
isopropylidene-P-DL-, synthesis,
40~81-82
methyl 2,3-O-ethyhdene-P-~-,formation by
acetal migration, 34:205
methyl 2,3-O-isopropylidene-
[3-C-(hydroxymethyl)]-4-thio-P-~-,
preparation of, 31: 183-1 84
[N-acetyl-4-amino-4-deoxy-3-C-
(hydroxymethyl)]-P-D-, preparation
of, 31:184
Erythrofuranosylamine, 2-deoxy-2-fluoro- p-D-,
48:242-243
Erythromycin, sugar component desosamine,
28:299
133
Erythromycin A
crystal structure of, and hydriodide
dihydrate, 25:82
formation, 35:85
pyrolysis of, 24:250
Erythromycin B, pyrolysis of, 24:250
Erythromycin C, biosynthesis, 35:84
Erythronic acid
4-bromo-4-deoxy-~~-, synthesis, 40:5
4-chloro-4-deoxy-o~-,synthesis, 40:5
2-C-methyl-o-, isolation and characterization
of, 28: I95
D-3
from 1-deoxy-o-euythro-2,3-hexodiulose,
28:196
formation from o-fructoses, 28: 194
4-deoxy-o~-,synthesis, 40:5
2-deoxy-2-fluoro-o~-,methyl ester,
synthesis, 40: 105
Erythronolactam, 4-amino-4-deoxy-o-,
23: 164
Erythrono- 1,4-lactone
2-C-methyL~-
natural occurrence of, 42:72,76
structure of, 4 2 7 0
synthesis of, 42: 110, 121
D-, 50:131
DL-, synthesis, 40:6
sulfonylation of, 23:244
desialylated, 40:22 1
neuraminidase effect, 37: 162
Erythropyrone, formation from erythrose.
28:176
Erythrose
4-acetamido-4-dcoxy-~-,23: 179
4-acetamido-4-deoxy-~-,preparation from
dithioacetal, 3 2 8 5
2-C-methyl-~-
natural occurrence of, 42:72,76
structure of, 4 2 7 0
D-, 46:32 1
in aqueous solution, 42:31, 36-37
temperature effects on, 42:33
crystallography of, 25:58
cyclic acetals, table, 34:210
from o-fructose by oxidation, 33:98
formation of aromatics from, 46:277-278
formation of-pyranone from, 46:277-278
gel chromatography of, 25:3 1
134 SUBJECT INDEX
Erythrose (continued)
high-temperature transformation of, in
alkali solution, 46:283
polarography of, 29:129
preparation from o-fructose diethyl
dithioacetal, 32:84
synthesis, 40:121-122
dehydration in acidic solution, 28: 176
DL-, synthesis, 40:6-7,90
enzymic isomerization, 36:46
1,2-Ethanedithiol
in dithioacetal preparation, 32: 19
reaction with aldosuloses, 32:24
2,3-O-isopropylidene-r-, from 3,4-0-
isopropylidene-L-arabinoseby
oxidation, 33:98
L-
crystallography of, 25:58
cyclic acetals, Table, 34:210
from r-arabinose oxidation, 33:98
synthesis, 50: 130- 131
2,3-O-benzylidene-o-, formation by acetal
migration, 34:205
2,4-O-henzylidene-o-
isomerization, 39:26
migration of acetal group in, 34:205
2,4-0-ethylidene-o-, 23:24
isomerization, 39:26
migration of acetal group in, 34:205
2,3,-O-isopropylidene-P-o-, 23:33
2,3,4-tri-O-acetyl-aldehydo-~-, ammonolysis
of, 31534
Erythrose 4-phosphate, D-, composition in
aqueous solution, 42:46
Escasany, Irene, 46: 12
Escherichia coli
078, 0-antigen polysaccharide, 47: 186
capsular polysaccharide, immune response,
41:195,206
K92, capsular polysaccharide, immune
response, 41:I94
lipid A chemical structure, 50:2 1&2 15
LP1092, polysaccharides, circular dichroism,
45: 107
M4 1
capsular polysaccharide, 52:396-398
structure, 52:434437
crystal structure bibliography, 36:33 1
polysaccharide mutant M41, crystal structure
bibliography, 40:395
serotype 08, 0-antigen polysaccharides,
f.a.b.-mass spectrometry, 45:66
synthesis of five-carbon chain of thiazole,
52:275-277
Esculin
levoglucosan from, 34:27
structure, 39:358
Esterases, mammalian, glycoenzyme, 27:308
Esterification
of I ,6-anhydrohexopyranoses, 34:74-85,
78-85
of carbohydrates
boronates, 3 5 5 3
relative reactivities of hydroxyl groups in,
33:ll-109
of ~-g~ucofuranurono-6,3-~actone,
33~203-205
effect on proton chemical shifts, 29: 14,26
selective
of anhydroalditols, 25262
of carbohydrates, 33: 12-5 1
Esters
a,P-unsaturated carbohydrate, conjugate-
addition reactions of Grignard reagents
with, 27:202-204
a-0x0, of carbohydrates, Grignard reaction
with, 27:199
of carbohydrates, reduction reactions of,
27:201
carbohydrate, reaction with ammonia,
31:81-134
of cellulose, with organic acids, 1:309-327
fluoro alcohol, mass spectrometry of, 30:38
formation
aldonolactones reaction with alcohols,
50: 148- 149
by peroxide-induced rearrangements of
acetals, 39: 150
glycopyranosyl, of nucleotides, 18:309-356
beta-ketonic (and related substances),
reactions with monosaccharides,
11:97-143
nitrate, of starch, 13:331-345
photochemical reactions with carbohydrates,
38: 129- 134
protection as, 46:189-191
as solvents for sugars, 27:106
of starch, preparation and properties of,
1~279-307
sulfonic, of carbohydrates, 8: 107-2 15
 SUBJECT INDEX
Estrogenic compounds, in biosynthesis of
saccharides, 26:439
Estrone, 3-O-(methyl2,3,4-tri-O-acetyl-P-~-
glucopyranosy1uronate)-, synthesis of,
34:253
Ethane
1 -chloro-2-(diethylamino)-,selective
etherification with, 33:54
1-(2-furyl)-l,2-dihydroxy-,substrate for
carbohydrate synthesis, 40:70
1,1,2,2-tetrabromo-, complex with amylose,
crystal structure bibliography, 33:391
1,1,2,2-tetrachloro-, complex with amylose,
crystal structure bibliography, 33:39 I
1,2-Ethanediol
oxidation with mercuric acetate, 3 3 9 9
1-phenyl-, reaction with 2-acetoxy-2-
methylbutanoyl chloride, 33:84
reaction with trimethylborane, 3 9 3 9
Ethanesulfenyl chloride
mercaptalation with, 32:25,43
reaction with 5,6-dihydro-2-methoxy-2H-
pyran, 28:274
Ethanethiol
in dithioacetal preparation, 32: 17, I9
2-(ethy1amino)-, reaction with aldoses. 32:20
Ethanethiolysis, of 3,5,6-tri-O-benzoyl-~-
glucofuranose, 32:32
1,1,2-Ethanetricarboxylicacid, 1 -(2,3,5-tri-O-
benzoyl-P-D-ribofuranosyl)-, triethyl ester.
preparation of, 33: 151, 161
Ethanol, 53:360-361
2-acetoxy-, solubility of sucrose in, 27:89
2-amino-, as solvent for sucrose, 27:99
2-butoxy-, solubility of sucrose in, 27:89
complexes
with carbohydrates and alkali metal
hydroxides, 21:256
with sodiocellulose, crystal structure
bibliography, 33:395
cyclodextrin inclusion complexes with,
46:222-224
effect on glycosylation, 40:345
2,2,2,2-(ethylenedinitrilo)tetra-,from
aminolysis of sucrose, 27:99
fermentation sources, 46:326
2,2-iminodi-, from aminolysis of sucrose,
27:99
metabolism of effect of o-fructose on,
34:317-322
I35
2-methoxy-, solubility of sucrose in, 27:87,
89
as solvent for sugars, 27:96
2-(2-methoxyethoxy)-, solubility of sucrose
in, 27:89
nitro-, reaction with aldoses, 24:72
I-phenyl-, R and S isomers, preparation of,
27: 197
2,2,2,2-(propylenedinitrilo)tetra-,from
aminolysis of sucrose, 27:99
@I-(+)- 1-cyclohexyl- 1 -phenyl-, preparation
of, 27:194
reactions with acyl halides, 33: I8
(S)-(-)- 1-cyclohexyl-~-phenyl-,preparation
of, 27:194
solubility of sucrose in, 27:87, 89
as solvent
in ammonolysis of benzoyl groups,
31:102
for sugars, 2796-97
syntheses with, 6:291-3 18
Ethanol-2-d
configuration of, 27: 144, 146
in determination of hydrogen configuration
in sugars, 27: 143
Ethanol-L-D. (+)-, absolute configuration of,
27:220
1.2-Ethenediyl carbonate, see I ,3-DioxoI-Z-one
Etherification
aldonolactones, 50: 132-134
of 1,6-anhydrohexopyranoses,34:74-85
of carbohydrate boronates, 35:55
of o-glucofi1ranurono-6,3-lactone,
33:201-203
selective, 33:51-70
Ethers, 53:365
benzyl, of sugars, 12:137-156
carboxymethyl, of cellulose, 9:285-302
of cellulose, 2:279-294
copolymerization with levoglucosan, 34:72
methyl,
of the aldopentoses, 7: 1-36, 10:257-272
of 2-amino-2-deoxy sugars, 13: 189-214
of fucose, 7:l-36,10:257-272
of o-galactose, 6:11-25, 10:273-282
Of D-glUCOSe, 5: 145-190
of hexuronic acids, 9: 13 1-148
of o-mannose, 8:217-230
of rhamnose, 7: 1-36, 10:257-272
protection as, 46:181-182
136 SUBJECT INDEX
Ethers (continued)
sugar substrates, 40: 109
trityl, of carbohydrates, 3:79-1 II
Ethoxides, 1,4:3,6-dianhydrohexitoIs,49: 171
Ethoxycarbonyl chloride, in selective acylation
in steroid field, 33:20
(p-Ethoxyphenyl)thiourea,taste properties,
45:3 1 1
(p-Ethoxyphenyl) urea, see Dulcin
Ethylamylose, 2,3,4-tn-O-, structure, 52:412
Ethyl-3,7-anhydro-6,8-O-bensylidene-4-deoxy- Ethyl methyl ether, up orientation, 47:95
2-(ethylenedithio)-o-~u~o-2-octulosonate, Ethyl orthoformate, reaction with
crystal structure, 43:348-349
Ethylation, of lipopolysaccharide, 30: 15
5-Ethylbarbituric acid, cyclodextrin inclusion
complexes with, 46:223-224
Ethyl diazoacetate, aid-catalyzed
decomposition in deuterium oxide and in
water, 24:29
Ethylene
1,2-bis(penta-O-acetyl-~-g~uconoyl)-, 24:264
effect on fruit ripening, 21:430
as plant hormone, 21:378
role in fruit development, 42:343-344,359,
363-365,371
tetracyano-, complex with anthracene and
dichloromethane, structure of, 2 5 5 5
Ethylenediamine
complex with amylose, crystal structure
bibliography, 33:392
for enhancing detectability of carbohydrates,
46:67
N,N'-diphenyl-, for selective derivatization
of aldehydes, 33: 122, 135
as solvent for reaction of carbohydrates and
alkali metal hydroxides, 21:264
Ethylenediaminetetraacetic acid, effect on CY-D-
mannosidase activity, 2k425-43 1
Ethylenedinihilotetraacetic acid, effect on
sugarcane, 21:426
1,l-Ethylenedioxacyclohexane,reaction with
organolithium reagents, 39: 138
I , I -Ethylenedioxacyclopentane,reaction with
organolithium reagents, 39: 138
Ethylene dithioacetals, 46: 196
circular dichroism, 45: 123
Ethylene glycol
radiation chemistry, 37:34
radiolysis and free-radical reactions,
37:27-28, 32
as solvent for sugars, 27:98
sweetness, 45:214,233
structure relationship, 45:293
water elimination reaction, by radiation,
37:lO
Ethylene oxide, 0x0 reaction with, 23:63
3-Ethyl-2-hydroxycyclopent-2-en-1 -one,
formation, 46:294
Ethylisohexides, 2,5-di-0-, 49: 141
Ethyl lactate, as solvent for sugars, 27: 106
ribonucleosides, 22:340
Ethyl p-aminobenzoate, effect on f.a.b.
sensitivity, 45:32
3-Ethylphenyl acetate, cyclodextrin inclusion
complexes with, 46:223-224
Ethyl phosphite, reactions with deoxyhalogeno
sugars, 28:285
Ethylpylpyrrole, 2-acetyl- 1-,formation of,
46:313-314
Ethyltetrahydropyran, (-)-(S)-2-, circular
dichroism, 45533
S-Ethyl thiophosphate, as phosphorylating
agent for nucleosides, 22:335
Ethyl (trichloromethyl) phosphonate, selective
phosphorylation of nucleosides with,
33:49
Ethyluracil, 1-(2-deoxy-2-fluoro-P-o-
arabinofuranosyl)-5-, biological activity,
48:250
Ethyne
1-cY-o-ribofuranosyi-, preparation of,
33:130
1-(2,3:5,6-di-O-isopropylidene-P-~-
mannofuranosy1)-, preparation of,
33: 130-1 3 1
1-(2,3-0-isopropylidene-P-~-lyxofurano-
syl)-, preparation of, 33:13C-13 1
1-(2,3-O-isopropylidene-5-O-trityl-a-o-
ribofuranosy1)-, preparation of, 33: 130
1-phenyl 1-2-(2,3,4,6-tetra-@acetyI-p-~-
glucopyranosy1)-, preparation of,
33: 143
tetra-O-acetyl-P-~-glucopyranosyl-2-
phenyl-, 25:242
2,3,5-tri-O-benzyl-o-ribofuranosyl-,
preparation of anomers, 33: 129, 144
Ethynyl compounds, reaction with sugar
lactones, 50: 139-140
 SlJBJECT INDEX 137

Eu3+,interaction with N-acetyl-a-o-neuraminic Evomonoside, 21:279, 288

acid, 47: 160 preparation of, 27:4
Eubacterium saburreum, polysaccharides, Evonoside, 21:28X
47: 179 Exo-anomeric effect, 4758, 69-71
Eucellulose, 26:308, 314 C-0 bond, 47:70
Euglena gracilis, aptrehalose phosphorylase definition, 47:48
from, 30:254 MO calculations. 47:94-96
Eukaryotes, cellulose biosynthesis, 41: I OX potential-function calculations, 47: 103-106
Euler angles, 51:76-77 Exodextranases, and dextran degradation,
Eumycetes, a,a-trehalose in, 30:230, 234 30:391
Eumycophyta, polysaccharides of, 23:367 Exo-glycanases, activity of, 28:402
Euonymus europeus lectin Exoglycosidases
carbohydrate-binding specificity, 35: I45 degradation in structural analysis,
purification and properties, 35:3 13 38:4 1 2 4 1 5
Europium, polysaccharide, 41 :72 enzymic specificity, monitored by jC-NMR
Europium (111) spectroscopy, 43: 10
in conformational analysis of acetals, 34: 197 glycosphingolipid catabolism, 40:268
tris (dipiva1omethanato)-, 29: 17,23 nomenclature, 40:285
tris (1 ,I, 1,2,2,3,3-heptafluoro-7,7-diniethyl- Exo-L-arabinanases, hydrolytic action on L-
4,6-octanedionato)-, 29:21 arabinanases, hydrolytic action on L-
Europium salts, for enchancing detectability of arabinan, 32:296292
carbohydrates, 46:67 Exopolysacchrides, 3-deoxy-D-manno-
Evalose octulosonic acid in acidic, 38:324,
natural occurrence of, 4 2 7 2 356-357,361-365
structure of, 4 2 7 0 Exo-( 1+4)-P-~-galactanase, production by
synthesis of, 42:97, 120 Sclerotium robii, 32:292
Evaporators, multiple-effect, in corn syrup Exotoxin, from Bacillus thuringiensis,
technology, 36:26-27 preparation of, 34: 170
Evatromonoside, 21:299. 301, 308 Explosives
Evermicose galactomannans in, 31:309, 3 11
composition in aqueous solution, 4 2 5 6 plant galactomannans in, 35:342
D-, synthesis, 40: 1 14 Extensin, 43:45,44:382
DL-,synthesis, 40:20 in plant cell-wall, 42:270, 308-309
natural occurrence of, 4 2 7 2 biosynthesis, 42:323,336-337
structure of, 42:70 interconnections, 42:3 10
synthesis of, 42:114, 119-120 External symmetry coordinates, 44:33
Evernian, lichen, 41:76 Extraction apparatus, countercurrent, 34:9
Evernia prunastri Eyring equation, 24:54
galactomannan, 41:95 for acyloxonium ion rearrangements, 26: 136,
polysaccharide, 41:76 139
Eveminose, mass spectrometry of trimethylsilyl Ezoaminouroic acid methyl glycoside,
derivative, 30:38 synthesis, 40:46
Evernitrose, 24:70, 114
composition in chloroform, 42:6(M1
3-epi-, synthesis of, 42123 F
natural occurrence of, 42:73
stiucture of, 42:70,78 Fabrys disease. 40:279-280
synthesis of, 42: 122 Factor IIa, 43: 1 17
Evertriose, mass spectrometry of Factor V, 43: I 18
permethylated, 29:88 Factor VII, 43: I 18
138 SUBJECT INDEX
Factor IX, 43: 1 17
Factor IXa, 43: 117, 122
Factor X, 43: 117
Factor Xa, 43:117, 119, 122
group proteinases, 43: 122
inhibition, 43: 129-132
Factor XI, 43: 117
Factor XIa, 43:117, 122
Factor XII, 43: 1 17
Factor XIIa, 43: 117, 122
Fagara COCO, 46: 13
y-Fagarine, 46: 13
Farina starch, dextrinization, 47:3 18
Fast atom bombardment-mass spectrometry,
45:19-72,46:70
acyl-group location by, 4 5 5 3
analysis of mixtures, 4530-3 1
applications, 45:54-7 1
background ions, 45:29
of bacterial polysaccharides, 4565-69
choice of derivatives, 4530-32
cluster ions, 4529, 70
of cyclic polysaccharides, 45:6849
experimental protocol, 4533-34
fragmentation pathways, 4543-45
p-cleavage, 45:44,46,59,67
double cleavages, 4946-47
pathway A, 4543.46, 54,69
pathway B, 45:44,46,55, 69, 70
pathway C, 45:44.46,55,69, 70
pathway D, 45:4445,69
pathway E, 4 5 4 5
A,-type cleavage, 45:43,57,59,66
fragment ions, 4529, 39,46
future developments, 4971-72
of glycolipids, 4554-58
of glycoproteins, 4 5 5 8 4 5
of glycosidic compounds, 4 5 6 3 4 5
hardware, 45:24
high-mass
definition, 4535-36
instrumentation, 4536-37
practical aspects, 4537738
of high-molecular-weight samples, 45:34-4 I
history, 45:20-23
linkage assignment by, 4 5 5 2
mapping of permethylated, high-mass
samples, 4538-41
protocol, 4 9 3 9
mass assignment, 4 5 3 7
mass range selected for observation,
4533-34
matrix, 45:24-25
acidified, 45:27,42
choice of, 4525-27
effect of addition
of ammonium thiocyanate, 45228
of dilute aq. HCI, 45:27-28
of sodium acetate, 4527-28
ionic strength, 45:27
loading sample into, 4 5 3 3
pH, 4 9 2 7
matrix additives, 4527-28
molecular-ion, 4 5 5 3
clusters, 45:29-3 1
of peracetylated and permethylated
samples, 4547-48
molecular-weight assignment with, 45:23,
4142,45
and minimum sample-loadings, 4533-34
monitoring chemical and enzymic reactions
by, 45~48-52
negative ion mode, 45:25,42
of N-glycosylic compounds, 4 5 5 8 4 3
peracetylated samples, 45:30, 32-35,46
permethylated samples, 4530-32, 34, 38,46
HexNAc cleavage, 45:47,52
of plant cell-wall polysaccharides, 4 5 6 6 4 8
principles, 45:2425
pseudomolecular ions, 45:25,28-29,41-42
produced by analysis of mixtures, 4 5 3 0
types produced, 4 5 2 5
quantitation with, 4570-71
role in carbohydrate-structure analysis, 45:23
sample purity, 4 5 3 0
sensitivity, 4533-35
in sequence assignment, 4 9 2 3
sequence ions, 45:23
sequencing by, 4 5 2 3
signal averaging, 4537-38
source, 4 5 2 5
spectra
characteristics, 4928-30
interpretation, 4 5 4 1-45
recording, 4 5 2 9
structure assignment by, 4545-53
analysis of derivatized samples, 4546-48
analysis of underivatized samples,
45:45-46
types of problems solved by, 4 9 2 3
 SUBJECT INDEX
of underivatized samples, 45:53
Fast-Fourier-transform algorithm, 44:7
Fat, metabolism of, 2 1 19-160
Fatty acids, 50:228-247,53:371-372, 386-387
amide-bound, 50:238-239
of o-galactosylglycerides, 37:326
ester-bound, 50:236-238
hexaacyl lipid A, 50:241-242
(R)-3-hydroxylated, 50:229-230
(S)-2-hydroxylated, 50:230-232
linkage to lipid A backbone, 50:235-239
location at lipid A backbone, 50:239-240
nonhydroxylated, iso-, and anti-iso, 50:234
other hydroxylated, 50:232
3-0X0,50:232-234
primary and secondary, in lipid A, 50:246
unsaturated, 50:235
of o-galactosylglycerides, 37:326-327
Fava bean lectin
agglutinating activity, 35201-202
carbohydrate-binding specificity,
35:203-205
isolation, 35: 138
purification and properties, 35202
Favism, fava bean, 35:202
Fenugreek, see Trigi)nella,foenum-grcrecum
Fermentation, 46:323
in exopolysaccharide production,
36:289-291
glycosides, 50: 1 6 11
preferential, of o-glucose and o-fructose,
32: 152
sugars, 50:8-10
of yeast, 33:4
Fermi contact shifts, 47:131
Fem, cellulose biosynthesis in, 42332
Femandez-Bolafios, J., 45: 14
Ferric chloride, in degradation of
polysaccharides, 31:239
Femc L-gulonate, preparation, 38:299
Ferricyanide number, starch, 47:294, 296
Fertility, male, o-fructose significance in,
34:303-305
Ferulic acid
attachment to primary-wall polysaccharides,
42382
esters, in ryegrass cell-walls, 36:260
in xylans, 36:242-243
in plant cell-wall polysaccharide cross-
linking, 42:315
139
Fetuin
anomeric carbon region, structural analysis,
43:20-21
carbohydrate linkage in, 25:420,444, 465,
26:461
deamination of, 31:236
glycopeptide, 44:240
hydrolysis, with trifluoroacetic acid, 46:268
methanolysis, 46:258
separation, 35:277
sialylated oligosaccharides, fractionation,
46:46
Smith degradation and methylation analysis,
38:408
structural analysis. 43: 17-20
Feulgen reaction, 52: 13
Fibers, synthetic, thermoanalytical techniques
in pyrolysis of. 22:488
Fibrillar structures, development of,
26:32&335
Fibrinogen
carbohydrate linkage in, 25:420
effect of glycoprotein structure on, 25:472
Fibrocystic disease, pancreas, glycoprotein
structure in, 25:437
Fibronectin
human amniotic fluid, lactosaminoglycan,
f.a.b.-mass spectrometry, 4 9 5 9
oligosaccharides, liquid chromatography
separation, 46:42-43
role in glycoproteins, 39:305
sialylated oligosaccharides, fractionation,
46:46
in transformed cells, 40:375-376
Ficaprenol, structure, 44:346
Ficoll
in chromatography, 33:274
conductivity and viscosity of solutions of,
21:214
gel chromatography of, 25:42
Field desorption, 4520-21
Fig, development physiology of, 42341,345,
363
Films, elastic. from O-(2-~yanoethyl)cellulose
acetate, 29:330
Filtration, of gels, 24:311
Finkelsteins reagent, 23:234
Fire, see Combustion
Fire retardation
flame-proofing agents
140 SUBJECT INDEX
Fire retardation (continued)
anhydrohexitols, 25:267
for cellulosic materials, 23:465
effect on thermal degradation of,
23:467,470
history of, 23:420
theories, of cellulosic materials, 23:465
levoglucosan formation and, 34:38
plant galactomannans in, 31:31 I , 35342
Fischer, Emil, 45: 1
asymmetric induction concept, 50:2-7
biography, 21:2
carbohydrate chemistry and, 21: 1-38
contributions to nomenclature, 52:48
probing of enzyme active site, 50: 13-14
yeast fermentations, 50:7-9
Fischer, Hermann Otto Laurenz, 4 5 9
obituaryof, 17:l-14
Fischer-Helferich method, 50:23
Fischer-Kiliani synthesis, 50:6
3-deoxy-o-munno-2-octu~osonic acid, 38:37 1
Fischer method
of glycoside synthesis, 34:243,278
of glycosiduronic acid synthesis, 36:74
Fischer projection, monosaccharides
acyclic form, 52:5&57
cyclic forms, 52:59-60
modified, 52:60-61
Fischer-Sowden reaction, 24:69
synthesis of 2-deoxy sugars, 21:149
Flambamycin, 42: 127
Flame ionization gas-liquid chromatography of
plant cell-wall components, 42:276
Flummulinu velutipes
a-L-arabinofuranosidase of, 42:387
fucomannogalactan, 41: 101
Flavanone glycosides
conversion into corresponding chalcone and
dihydrochalcone analogs, 45278-279
taste properties, 45277-278
Flavanones, as plant-growth substances, 21:410
Flavazoles, 25:398
1-(3-nitrophenyl)-, oligosaccharide
derivatives, 37:233-234
1-phenyl-, in mass spectrometry of
disaccharides, 30:40
1-phenyl-, oligosaccharides derivatives, mass
spectrometry of, 29:lOO
Flavines, preparation of, from Amadori
compounds, 22:278
Flavones
3-methoxy-, see Chrysoeriol
as plant-growth substances, 21:408,410
3,4,5,7-tetrahydroxy-, see Luteolin
4,5,7-trihydroxy-, see Apigenin
Flavonoid from Digitulispurpureu. 31: 145
Flavonoid glycosides
hydrolysis of, 28:15
trifluoroacetate, gas-liquid chromatography
of, 30:33
Flavonoid oligosaccharides, mass spectrometry
of, 29:88
Flavor enhancers, apiose-containing
nucleosides as, 31:183
Flax, cell-wall studies on, 42:269
Fletcher, Jr., Hewitt Grenville, obituary, 31:
1-7
Flies, trehalose as energy source in, 30:235
Flip-flop hydrogen bond, 46:228
Floridean starch, 2 5 9
Floridoside
in algae, 37:314-316
photosynthesis, 37:361-3 62
structure, 37:3 14
Flour, hemicellulosic composition and quality,
36:228,250
Flower drop, 21:429
Fluorene, 2-(N-hydroxyacetamido)-,o-
glucuronic acid conjugate, preparation and
isolation, 36:131-132
Fluorinated carbohydrates, 48:9 1-93, 121,
124-155
addition to glycals, 48: 169-181
from DAST treatment
with migration or configuration retention,
48: 156-158
with normal displacement, 48: 159-163
epoxide and epimine cleavage by fluoride
ion, 48:155, 163-169
glycals with MeCO,F, 48: 179-1 80
purity of compounds synthesized, 48: 178
Fluorinating agents
diethylaminosulfur [*F]trifluoride, 38:239
F,, 38:239
silver [*F]fluoride, 38:239
tetraethylammonium [I8F]fluoride, 38:239
Fluorination
of carbohydrates, 22: 182
by epoxide cleavage, 38:2 12-2 18
of nucleosides and nucleotides, 22:379
 SUBJECT INDEX
by secondary sulfonyloxy group
displacement, 38:2 18-225
by sulfonyloxy group displacement,
38:20&212
Fluorine, 4 8 9 - 9 2
chemistry, 52: 18-19
compounds, organic, 38: 195-199
introduction by DAST reagent, 48: 142-155
COSF,Net,, group, 48: 143
retention of configuration, 48: 147-148
1,2-shift, 48:145-146
sulfonyloxy group displacement, acid-
catalyzed epimerization, 48: 130-
131
as leaving group, 50:21-22
Fluorine- 18,48: 189
production, 48: 196-197
Fluorine-19 nuclear magnetic resonance
spectroscopy
Carbohydrates, 38: 197
IYF-l3Ccoupling constants, 38:270-274
'9F-chemical shifts, 46:78-80
I9F-l9Fcoupling, 46:SO
constants, 38:268-270
I9F-'H coupling constants, 38:260-268
fluorinated carbohydrates, 38:256-28 I , 285
applications, 38:274280
sugar binding to lysozymes, 38:283
(Fluoroacetyl)ation, amino sugars, 38:25 I
Fluoroadenosine
2'-deoxy-2-, synthesis, 48:268-269
5'-deoxy-5'-, synthesis, 48:277
Fluoroaldohexoses, 6-deoxy-6-, synthesis,
48: 149
Fluoro carbohydrates, 4 5 4
Fluorocarbons, 38: 195
Fluorocyclopentane, (lS,2R,3R,4S)-I -azido-4-
benzyloxy-3-(benzyloxymethyl)-2-.
48: 139
Fluorocytidine, 2'-deoxy-2'-
biological activity, 48:245-246,254
synthesis, 48:235-236
3-Fluoro-3-de(methoxy)sporaricin A. 48:223
Fluorodibekacin, 5-deoxy-5-, 48:229
Fluoroformates, carbohydrate, decomposition
of, 22: 198,38:242
2-FluorofUranoses, synthesis, 48: 132-1 33
Fluoroglycosides, 2-deoxy-2-, glucosidase
inhibition, 48:359-362
Fluorohexopyranosyl fluorides
141
2-deoxy-2-, 'H-and "F-n.m.r data for,
46: 146-147
2,6-dideoxy-2-, 'H and I9F-NMR data for,
46:153
3(or 4, or 6)-deoxy-3(or 4, or 6)-, 'H-and
I'F-n.m.r data for, 46:148-149
Fluorohydrin, synthesis, 48: 148
Fluorokanamycin A
3'-deoxy-3'-, 48:226
4-deoxy-4-, 48:226
5-deoxy-5-
4-diepi-5-, 48:225
epi-5,48:225
6-deoxy-6-. 48:224-226
2',3'-dideoxy-2'-, 48:228
Fluorokanamycin B, 3'-deoxy-3'-, 48:226-228
Fluoro-6.3-lactones. 5-deoxy-5-, 48: 153
Fluorolividomycin B, 5-deoxy-5-, 48:229-230
Fluoromaltose. 2'-deoxy-2'-, 48:212-213
Fluoromethylphosphonate, synthesis,
48:185-186
Fluoroneuraminic acid, 5-N-acetyl-
3-, 48:210
9-deoxy-9-, 48:210
2-Fluorooxane
a form preference in solvents, 47:92
conformational equilibria, 47%
Fluoropentofuranose, 1-O-acetyl-2,3,5-tri-O-
benzoyl-4-deoxy-4-
OI-L-LVXO-. 'H- and IyF-NMR data for, 46:
143
P-D-ribo-, 'H- and I9F-NMR data for, 46: 143
C'-Fluoropurine nucleosides, synthesis and
biological activity, 48:267-277
2 '-Fluoropyrimidine nucleosides
biological activities, 48:244-256
conformational analysis, 48:240-244
synthesis, 48:234240
Fluorosisomicin, 5-deoxy-5-, 48:228-229
Fluorosucrose, 6-deoxy-6-, 51: 150
Fluoro sugars
2-deoxy-2-
labeled, synthesis, 48: 193-194
synthesis, 48:170, 172-173, 181-182
3-deoxy-3-, synthesis, 48: 133-134
Fluoro sugars, antimicrobial and anticancer,
48:222-234
Fluorothymidine
3'-deoxy-3-, synthesis and biological
activity, 48:257-259
142 SUBJECT INDEX
Fluorothymidine (continued)
5 '-deoxy-5-, synthesis and biological
activity, 48:262-264
Fluorotobramycin, 5-deoxy-5-, 48:229
Fluorouracil, 1-(2-deoxy-2-fluoro-P-~-
arabinofinanosyl)-5-, biological activity,
48:250
Fluorouridine
2 '-deoxy-2'-
biological activity, 48:254
conformation, 48:240-243
synthesis, 48:234-235
5'-deoxy-5'-, synthesis and biological
activity, 48:261-262, 26&265
Fluoroxylopyranose, 3-deoxy-3-
'H-and I9F-n.m..r data for, 46:105
1,2,4-tri-O-acetyl-~-,'H- and I9F-n.m.r data
for, 46: 105
Fly sprays, anhydrohexitols in, 25:269
Foams
levoglucosan esters, 34:76
polyurethane
anhydrohexitols for, 25:267
sucrose copolymers in, 33:274
Folic acid, analogs, history, 29:2
Folin-Denis reagent, for D-fructose estimation,
22:238
Fohn-Lowry reagent for plant cell-wall
proteins, 42:275
Fomes annosus
glucuronoglucan, 41:lOl
mass spectrometry of glucuronoglucan from,
2954
Fongose, 23:384
Food
carbohydrates
analysis of, 44:22-24, 46:5&52
identification , noncomputer spectroscopic
methods, 44:22-24
soluble, liquid chromatography methods
for, 4 6 5 I
dextrins in, 47:329-332
1,4:3,6-dianhydrohexitoIsapplications,
49: 167-168
discoloration of, 46:324-325
gas-liquid chromatography of, 28:43
industry, galactomannans in, 31:3 10,312
plant galactomannans in, 35:341
processing, color-stopping reaction in,
46:32&325
Force constants, in normal coordinate analysis,
transfer from simple molecules to
carbohydrates, 44:34
Force field, models, in vibrational spectra band
assignments, 44:38-39
Formaldehyde, 46:32 1
copolymers with sugars, 21:450
as cross-linking agent for polysaccharides,
29:356
determination of, from oxidized
polysaccharides, 29:340
formation, 51:282
formose from, 29: 173-1 79
gas-liquid chromatographic determination
of, 30:35
manufacture of, 29: 178-1 80
reactions of carbonyl compounds and
ammonia in presence of, 25:324
Formamide, N,N-dimethyl-
effect on trimethylsilylation, 28:25
with inorganic acid chlorides, selective
chlorination with, 33:8&83
mutarotation of sugars in, 24:61
with phosphorus-based reagents, selective
halogenations with, 33:77-80
as solvent
for methylation of carbohydrates, 30: 11
for nucleophilic displacements, 24: 140
for sugars, 27:89, 109, 113-1 16
sucrate production in, 27:93
for trimethylsilylation, 28:29
Formates, carbohydrate, formation of, 28:25 1,
259
Formazans, 25:393
reaction, in carbohydrate research,
13: 105- 167
Formic acid, 46:296
cyclodextrin inclusion complexes with,
46:221
determination of, from oxidized
polysaccharides, 29:340
enzymic determination of, 30:282-283
formation, 51:282
as function of y-ray irradiation, 51:270
in hydrolysis of polysaccharides, 28:17,20,
22
liquid chromatography, 46:53-54
as solvent for sugars. 27: 102
Formolysis, for cleavage of glycosidic linkages,
46:269-270
 SUBJECT INDEX
Fonnose
biological efficacy, 29:21&225
definition, 29: 173
gas chromatograms of derivatives and
reduced, 29:207-208
history of research on, 29: 173-1 79
infrared spectrum of, 29: 18 1
metabolism by micro-organisms, 29: 177
nutritional tests in rats, 29:217
production of, tank-reactor for, 29: 185
sugar composition of, 29: 187,205-2 I6
sugars, synthesis and utilization of,
29: 173-227
synthesis procedure for batch, 29: I82
synthetic pathway of, 29: 187-190
toxicity of, 29:177,212
utilization by ants and other insects, 29322 I ,
224-225
by boar spermatozoa, 29: 177, 2 I8
by micro-organisms, 29:219-223
Formose reaction, 29: 178-205
addition, 29: 183
Cannizzaro reaction in, 29:192, 199-205
carbohydrates, 49: 189-1 90
carbocyclic rings from, 28: 174
catalysts for, 29: I8 I , 183
crossed-aldol reaction, 29: 184
kinetics of, 29:189-199
Formulas, see also Nomenclature
D-GhCOSe, structural, 25:4
proton spin-lattice relaxation rate,
45: 128-130
stereo-, writing of, in a plane, 3: 1-22
Formycin, 25243
analogs, synthesis of, 33: 180
2- and 3-deoxy-, preparation of. 33: I8 I
antiviral and antitumor activity of, 33: 1 I2
crystal structure of, and hydrobromide
monohydrate, 2 5 8 3
2,3-dideoxy-,preparation of, 33: I81
hydrobromide monohydrate, crystal structure
bibliography, 31:366
7-(methy1thio)-, preparation of, 33: 180
monohydrate, crystal structure bibliography,
31:357
N7-benzyl-, preparation of, 33: 18 1
N-isopentenyl-, preparation of, 33: I8 I
reaction with 2-acetoxy-2-methylpropanoyl
bromide, 33:85
structure of, 33:l 12-1 13
143
synthesis of. 33: 134, 174
Formycin B, 25:243
analogs, preparation of, 33: 180
antiviral and antitumor activity, 33: 1 12
hydrochloride, crystal structure bibliography.
38:488
0x0-, crystal structure bibliography, 37:
414
structure of, 33: I 12-1 13
crystal structure of, 25:83,37:413
synthesis of, 33: 172
Formycin hydrobromide, monohydrate, crystal
structure bibliography, 32:376
Formylaminomethylenation, aldonolactones,
50:14&148
Formyl group, selective removal, 39:35, 37
N-Formylkynurenine
interaction with receptor sites. 45288
sweetness. 45:290
2H,5H-6-Formyl-3-0xopyrrolo[ 1,2-a]pyrazin-
4-acetic acid, formation of, 46:3 12-3 14
Formylpseudaminic acid, 5-N-acetyl-7-N-,
47: 178
Forosamine, 23:155,24:161
D-, synthesis, 40: 1 14
Forosaminide, methyl, synthesis, 40: 106
Fortamine, crystal structure, 43:222
Fosfonomycin, 42: 188
structure of, 42: 150
Fourier component analysis, torsional
potentials, 47:82-85
Fourier modulus. of cellulose combustion,
23:452
Fourier transform, 38: 14,3 1, 198,41:28,34
in conformational analysis, 26:56
infrared spectroscopy, 44:7-9, 56-57
absorbance subtraction, 44:60-6 I
advantages of, 44:58,66
application to biological systems, 44:58
data-processing techniques, 44:58-6 1
factor analysis, 44:60
Fellgett advantage, 44:57-58
frequency-accuracy advantage, 44:58
Jacquinots advantage, 44:58
method, 4456-58
multiplex advantage, 44:57-58
quantitative analysis of mixtures.
44:58-60
spectral results, 44:61-67
time-resolved techniques, 44:61
144 SUBJECT INDEX
Fourier transform (continued)
pulse, in characterization of polysaccharide
degradation products, 31:239
spectra, see Proton nuclear magnetic
resonance spectroscopy
Fowl, see also specijk Wpes
metabolism of domestic, 30:6
Foxglove, see Digitalis purpurea
Fractionation
of hemicelluloses, 36:226-227
in high-D-fructose corn-syrup technology,
36:54
of polysaccharides, 24:334-337
ranges, in gel chromatography, 25: 18
of starch, 1:247-277, 16:299-333
Fragilin, gel chromatography of, 2 5 5 0
Fragmentation
of alditol acetals, 29:75-77
of alditol acetates, 29:51-55
of alditol methyl ethers, 29:56
of alditol trifluoroacetates, 29:55
of aldononitrile acetates, 29:73
of aldose dithioacetals, 29:71-73
and alkaline-degradation reactions of sugars,
28: 196,200
of alkoxyalkyl radicals by radiation,
37:14-15
analysis, of polysaccharides, 26: 16
of 1,6-anhydrohexopyranoses,34:62
of anhydro sugars, 29:74
of C-glycosyl derivatives, 29531
of dithioacetals, and mass spectrometry,
32~93-97
of formose reduction products, 29:207
of heparin heteropolysaccharide, 29:245
of inositol trimethylsilyl ethers and acetates,
29~78-79
mechanisms, of reaction of sugars with
ammonia, 25:340
of partially methylated alditol acetates,
29~58-71
of partially methylated methyl glycosides,
29~50-51
patterns
of isopropylidene acetals of pentoses and
hexoses, 34: 192-194
for sucrose derivatives, 33:279-280
of peracetylated glycosides and mass
spectrometry, 29:46
of permethylated glycosides, 29:43
of permethylated oligosaccharides, and
alditols, 29234-89
of pyranose and furanose rings, 21:47
radiation and, in neutral sugars, 37:26
of sugar carboxylic acids, 29:79-81
of trimethylsilylated glycosides, 29:47-50
of trimethylsilylated oligosaccharides,
29:92-96
Frangulin B, from Rhamnus frangula, 31:147
Free energy
of activation, glycoside hydrolases,
48:324-325
conformational. 26:99-103, 105
Free radicals
electron paramagnetic resonance studies on
sugar, 26: 15
propagation, dextrins, 47:327
reactions
in biological systems, 37:3
of carbohydrates, by radiation, 37:7-77
Freezing, starch modification, 51:29&298
French, Dexter, obituary of, 42:l-13
Freudenberg rearrangement, thiocarbamates,
38:158
Friedel-Crafts reaction
in the carbohydrate series, 6:25 1-289
C-glycosylations by, 33: 158-1 62
Friend murine leukemia virus, glycoprotein,
f.a.b.-mass spectrometry, 45:63
Frog-egg lectin, isolation and properties,
35:315
Frost resistance
of insects, a,a-trehalose function in,
30:235
oligosaccharides effect, 37:296, 304,3 19
in plants, 44:383-384
Fructans, 2:253-277, 22:230
D-
hydrolysis, 46:269
metabolism of, 34:3 15
synthesis and degradation of, 34:3 14,
316
fungal, 23:400
hydrolysis of, 28: 19
of methylated, 28:23
interaction with concanavalin A, 35: 175
methylation analysis of, 30:5
renal clearances of, 30:5
structure, 35:7
synthesis
 SUBJECT INDEX I45

and breakdown of, 22:253 2.3-0-isopropylidene-6-thio- I -0-p-

by Leuconostoc, 30:374 tolysUlfOnyl-D-, 24: 146
Fructazine 5-thio p-D-, sweetness-structure relationship,
D-, 22:303 45:256
deoxy-o-, 22:303 p-o-Fructofuranosidase
Fructofuranans, D-, carbon- 13 nuclear magnetic in catabolism of fructofuranosides.
resonance spectra, 38:7 1 32: 183-191
Fructofuranose genetic analysis, 39:372
2,6-anhydro-P-o-. 22:259 hydrolysis rates for sugars, 39:365
2,3-anhydro-o-, 22:259 kinetics, 39:366
1 '.2-anhydro-( 1 -O-a-o-fructofuranosyl)-P- location in yeast cell, 39:366-37 I
D-, conformation of, 26: 112 substrate specificity, 39:356-361
2,6-anhydro- I -0-methyl-o-, synthesis, Fructofuranosides
39: 172 3-acetamido-3-deoxy-a-~-allopyranosyl p-D-
2,3-anhydro-l,4,6-tri-O-nitro-~-, synthesis, , synthesis of, 33:269
39: I72 3,6-anhydro-a-~-glucopyranosyl
P-D- 1,4:3,6-dianhydro-P-n-
in biochemistry, 22:230 crystal structure bibliography, 30:453
I3C nuclear magnetic resonance spectra of, taste properties, 45:270, 273
33:277 3,6-dIanhydro-P-o-, taste properties,
sweetness-structure relationship, 45256 45:270, 273
D- p-0-
catabolism of, 32: 173 catabolism of, 32:183-191
1-
6-deoxy-6-fluoro-2,3,-O-isopropylidene- regulation, 39:371-374
0-p-tolylsulfonyl-P- utilization by yeasts, 39:355-374
IT-NMR data for, 46: 174 utilization by yeasts and associations of
'H- and 19F-NMRdata for, 46: I45 abilities, 32:223
1,6-dideoxy-l,6-difluoro-2,3-0- benzyl a-D-, 21: 125-126,22:247,249
isopropylidene-P-, I3C-NMR data D-
for, 46: 174 degradation, 52:445
esters of, 22:292 methyl I -deoxy-1-fluoro-
6-0-benzoyl- 1-deoxy-1 -fluoro-2,3-O- a anomer, 'IC-NMR data for, 46: 174
isopropylidene-P-, 'H- and I9F-NMR p anomer, 13C-NMRdata for, 46: 174
data for, 46: I44 3,4,6-tri-O-hen~oyI-P-,'~C-NMR data
orthoesters of, 22:292 for, 46: 174
1,4-di-O-benzoyl-o-,2,3,4-orthobenzoate, methyl 1,6-dideoxy- I ,6-difluoro-
22:248 (Y anomer. IIC-NMR data for, 46: I74

1,2:3,4-di-O-isopropylidene-o-, preparation p anomer, "C-NMR data for, 46: 174

of anomers, 26:239 methyl 3,4-di-O-acetyl- I ,6-dideoxy- I ,6-
6-O-a-D-glUcopyranoSyl-~-D-, see difluoro-
Isomaltulose a anomer, 'H- and I9F-NMR data for,
2,3-O-(benzyloxybenzylidene)-,22:248 46: 145
6-deoxy-6-iodo-di-O-(methylsulfonyl)-o-, p anomer, IH- and "F-NMR data for,
22:248 46: 145
tri-0-benzoyl-o-, 22:248 methyl 3.4,6-tri-O-benzoyl-I -deoxy-I-
26:243
2,3-O-isopropylidene-p-~-, fluoro-
penta-0-acetyl-o-, 22:252 a anomer, 'H- and "F-NMR data for,
6-S-benzyl- 46:145
1-deoxy-2,3-O-isopropylidene-6-thio-P- p anomer, 'H- and "F-NMR data for,
D-, 23:274 46: 145
146 SUBJECT INDEX
Fructofuranosides (continued)
a-o-glucopyranosyl-
3,6-anhydro-P-o-, taste properties, 45:270,
273
P-D-, 4:l-35
1,4:3,6-dianhydro-P-~-,taste properties,
45:270,273
4,6-dichloro-4,6-dideoxy-a-~-
galactopyranosyl 1.6-dichloro-1,6-
dideoxy-p-o-, sweetness, 45:265,268
ethyl a-D-,22:247
ethyl p-D-, 21:126,22:247
ethyl 3,4-di-O-acetyl- 1,6-di-O-trityI-a-o-,
22:247
p-hydroxyphenyl p-O-, 22:248
methyl a-D-,21:102-103, 126
methyl p-D-,21:103, 126, 22:247
methyl D-
conformation of, 2 I :1 O 1
formation from dithioacetal, 32:68
methyl per (trimethylsily1)-D-,mass spectra
of, 29:49
0-a-D-galactopyranosyl-
(l+3), a-D-glucopyranosyl P-D-,
occurrence, and structure, 37:294
(1+6)-a-~-g~ucopyranosy~ 0-p-D-
fructofuranosyl-(2+ 1)- p-D-,
isolation, 37:3 I 1
( 1 +4)-O-a-~-galactopyranosyl-( 1+3)-a-
o-glucopyranosyl p-D-, isolation,
37:3 1 1
( 1+6)-U-a-~-glucopyranosyl P-D-,
pentahydrate, crystal structure
bibliography, 30:455
O-n-o-vibo-hexopyranosyl-3-ulose-( 1+2) p-
D-, polarography of, 29: 145
2,3,6-tri-O-acetyl-4-azido-4-deoxy-a-~-
galactopyranosyl3,4-di-O-acetyl-1.6-
diazido-l,6-dideoxy-p-~-, 24: 147
Fructofuranosyl a-o-ghcopyranoside, 6,6-
dideoxy-6,6 dithiocyanato-p-o-
2,3,4,1,3,4-hexa-O-acetyI-, 44: 143
2,3,4,1,3,4-hexa-O-benzoyl-, 44: 143
I ,2,3,4,3,4-hexa-O-(methylsiilfonyl)-,
44: 143
Fructofuranosyl cation, 52:2 17
Fructofuranosyl fluoride, 52:2 17
a-D-,synthesis, 38:203
p-o-, synthesis, 38:203
1,3,4,6-tetra-O-acetyI-i)-
a anomer
T - N M R data for, 46: 174
H- and I9F-NMR data for, 46:144
p anomer
?C-NMR data for, 46:174
H- and I9F-NMR data for, 46:144
Fructofuranose, I ,2-anhydro-I-O-(a-~
fructofuranosy1)-p-o-, 21: 100
Fructoglucans, gas-liquid chromatography of,
28:68
Fructokinase
control enzyme in o-fructose metabolism in
liver, 34:293,296
enzymic activity in liver metabolism, 34:326
in metabolism of o-fructose, 34:330-331
occurrence of. 34:33 1
Fructolysis, by spermatozoa, 34:30&302
Fructo-oligosaccharides, liquid
chromatography, 46:39
Fructopyranose
6a-carba-p-o~-,synthesis, 48:50-5 1
6-acetamido-6-deoxy-~-,23: 178
a-D-, sweetness-structure relationship, 45:248
2,6-anhydro-p-o-, crystal structure
bibliography, 31:348
2,s-anhydro- 1 -O-methyl-p-o-, 25:203
p-D-
AH,B system, 45:221,252
2,3:4,5-bis(phenylboronate),preparation,
35:45
calcium bromide dihydrate, crystal
structure bibliography, 37:379
calcium chloride salts, hydrates, crystal
structure bibliography, 32:359
conformation of, 25:103
crystallography of, 25:60, 31:365,
38:43043 1
infrared spectrum, 45:25 1
molecular structure, vibrational
spectroscopic study, 44537
purification of, 22:234
sweetness
comparison to a-L-sorbopyranose,
45250
effect of temperature, 45:250
structure relationship, 45241, 249
taste properties, 45:242
D-
1-C derivatives of, 22:293
4-deoxy-4-fluoro-P-
 SUBJECT INDEX
I3C-NMR data for, 46: 173
'H- and "F-NMR data for, 46: 144
l-deoxy-l-fluoro-2,3:4,5-di-O-
isopropylidene-
13C-NMR data for, 46: 173
'H- and I9F-NMR data for, 46: 144
esters of, 22:292
taste properties, 45:254
1-deoxy-1-fluoro-p-o-, synthesis,
38:209-210
I ,2:4,5-di-O-isopropylidene-o-, mass
spectrum of, 21:76
2,3:4,5-di-O-Isopropylidene-o-, mass
spectrum of, 21:76
4,5-di-O-acetyl- 1,2-O-isopropylidene-3-0-
methyl-p-o-, conformation of, 26:224
2,3:4,5-di-O-benzyIidene-p-~-, 26:244
I ,2:4,5-di-O-cyclohexylidene-o-,
26:244245
1,2:4,5-di-O-isopropylidene-
3-O-methyl-p-~-,reaction with
butyllithium, 39:145
3-O-p-tO-lylSUlfOnyl-p-D-, fluorination,
38:222
2,3:4,5-di-O-isopropylidene-
1-O-methyl-P-o-, reaction with
butyllithium, 39:144
1 -O-(methykulfonyl)-p-D-, fluorination,
38:210
1-O-(tetrahydropyran-2-yl)-P-o-, reaction
with lithium diisopropylamide,
39: 146
2,3:4,6-di-O-isopropylidene-, 1-O-methyl-P-
D-, 26:244
1,2:4,5-di-O-isopropylidene-~-~-
conformation of, 26: 1 19,2 18,225
effect of catalyst on preparation of'.
26:200,202
hydrolysis of, 26:203
mass spectrum of, 26:23 1
oxidation of, 26:250
thin-layer chromatography of, 26:234
rearrangement of, 26:220
structure of, 26:2 16-2 1 7
crystal structure bibliography, 31:35 I , 367
selective hydrolysis, 39: 17
2,3:4,5-di-O-isopropylidene-P-~-, 26:220,
242-243
conformation of, 26: 1 19, 2 19, 226
crystal structure bibliography, 31:367
147
effect of catalyst on preparation of, 26:200
hydrolysis of, 26:204
preparative column chromatography of
hydrolysis products, 26:233
2,3:4,5-di-O-rnethylene-P-o-, 26:245
1 -0-acetyl-2,3:4,5-di-O-isopropylidene-~-o-,
conformation of, 26:226
3-0-acetyl- 1,2:4,5-di-O-isopropyli-dene-P-
D-, conformation of, 26:225
3-O-m-~-glucopyranosyl-p-~-, crystal
structure bibliography, 38:445446
3-O-m-o-glucopyranosyl-o-, see Turanose
5-O-~-glucopyranosyl-o-,22:230
1,2-O-isopropyIidene-p-D-, 26:203
2,3-O-isopropyIidene-p-~-, 26:204, 242
conformation of, 26:225
2,3-oxazolidine-2-thinone-o-, 22:280
I-S-ethyl-] -thio-, 22:28 1
1,3,4,5-tetra-U-acetyl-p-o-. 22:250
1,3,4,5-tetra-O-benzoyl-p-~-, ammonolysis
of. 31:91
1,3,4,5-tetra-O-methyl-p-~-, 22:275
h-thio-p-~-.taste properties, 45252
~,4,5-tri-~-acety~-2,3-O-isopropylidene-~-~-
, crystal structure bibliography, 37:398
3,4,5-tri-O-acetyl- 1,2-O-isopropyhdene-p-~-
, conformation of, 26:224
P-D-Fructopyranose calcium chloride
dihydrate, crystal structure bibliography,
32:359
o-Fructopyranose o-fructofuranose 2', I :2,I '-
dianhydride, from o-fructose in anhydrous
hydrogen fluoride, 27:94
Fructopyranoside, 53:98
a-maltosyl p-D-, 22:23 1
ethyl p-D-,l-[N,N-bis-(2-chloroethyl)
phosphoramidate]. 22:246
methyl 5-amino- 1.3-O-benzylidene-5-deoxy-
p-D-, 23: 146
methyl p-D-,sweetness-structure relation
ship, 45249-250
methyl 1,3-O-benzyhdene-4,5-di-O-
(methylsulfonyl)-P-o-, displacement
reactions of, 24: 16 1
trimethylsilyl tetra-O-(trimethylsilyl)-o-,
mass spectrum of, 29:48
Fructopyranosyl bromide, 1.3,4,5-tetra-O-
benzoyl-P-o-, 22:262
Fructopyranosyl fluoride
a-o-and p-D-,22:262
148 SUBJECT INDEX
Fructopyranosyl fluoride (coniinued)
1-0-methyl-Pa-, reaction with sodium
hydroxide, 25:203
3,4,5-tri-O-acetyl- 1-0-methyl-a-D-,
synthesis, 38:203
3,4,5-tri-O-acetyl- 1-O-methyl-P-D-,
synthesis, 38:203
Fructosans
poly-, see Fructans
review, 35:s
Fructosazine, 22:280
D-, and deca-0-acetyl derivative, 22:303
deoxy-, 22:280
preparation of, 31: 125
Fructose
acceptor products, 51:152-1 53
6-acetamid0-6-deoxy-o-, 22:280,303
composition in aqueous solution, 42:50
OL-D-, mutarotation of, isotope effect on,
24:32
1-amino- 1-deoxy-, 21 :1 8
D-, derivatives, 22:267,272, 299-302
3,4-and 4,5-di-O-methyI-~-,synthesis, 35: 1 1
anhydrides, 22:258,295
di-, 2:253-277
1-anilino- I-deoxy-D-, 22:266
p-D-
solubility in methanol, 27:97
sweetness, effect of infrared hydraxyl
absorption bands and hydrogen-
bonding strength, 45:2 17
1-chloro-1-deoxy-
D-, preparation of, 28:247
keto-D-, tetraacetate, 22:257
D-, 5 1 ~ 9 6
from 0~-2,3,dihydroxypropanal,
49:193-194
absorption of, mechanism of, 34:289-29 1
assimilation from intestine, 34:287-29 1
biosynthesis in seminal vesicles,
pathways, of, 34:298-300
camer-mediated transport system for,
34:314
degradation to triose, in liver, intestine,
and kidney, 34:292-294
D-glucose regeneration from, by D-
glucose 6-phosphate, 34:295
by triose condensation, 343294
effect on energy metabolism of
intestinal epithelial cells, 34:324
on lipid metabolism, 34:325-330
on metabolism of ethanol, 34:3 17-322
on nucleotide pool in liver, 34:322-324
hereditary intolerance of, 34:306-310
history, 34:286
in male fertility, significance of,
34~303-305
metabolism of, 34:285-343
in adipose tissue, 34:297
in blood and muscle cells, 34:298
control in liver, 34:29&297
inborn errors of, 34:30&310
key enzymes in, 34:330-343
in liver, intestine, and kidney,
34:291-297
in micro-organisms, 34:3 10-314
by spermatozoa, 34:30&302
in testes and spermatozoa, 34:298-305
phosphorylation of, by liver,
34~325-330
pyrolysis of, 34:45
respiration-coupled transport system
for, 34:312-313
sodium 1,6-bisphosphate heptahydrate,
crystal structure bibliography, 34:372
acetalation of, mechanism of, 26:218-220
acetals, 22:245
esters and ethers, 22:289-290
6-(a-hydrogen malate), 22:253
alkaline degradation of, 28:200, 46:292
degradation mechanism of, 28: 164
dehydration in acid solution, 28:176,
179
dehydration reactions of, 28: 176
determination in presence of aldoses by
gas-liquid chromatography, 28:43
ester of guanosine 5-pyrophosphate,
28:320
ester of uridine 5-pyrophosphate,
isolation of, 28:326
mutarotation and gas-liquid
chromatography of, 28:40
saccharinic acids from, 28: 1 9 4 1 9 5
trimethylsilylation and mutarotation of,
28:38
trimethylsilylation of, 28:24, 27
anomeric equilibria in aqueous solution
and Fourier-transform spectra, 27:60
solubility in alkoxy alcohols, 27:99
in anhydrous hydrogen fluoride, 27:94
 SUBJECT INDEX
in liquid ammonia, 27:91
in methanol, effect of calcium chloride
on, 27:95
in aqueous solution
composition, 42:21, 38, 62, 65
equilibrium composition, 45:248 249
furanose form stability, 42:32
inorganic compound effects on, 42:33
laser-Raman spectroscopy, 42:23,
44:73-74,76-78
NMR spectroscopy,42:18.62
solute-solvent interactions, vibrational
spectroscopic studies, 44:86
base-degraded solution, products. 46:294
1,6-bisphosphate, radiolysis, 37:42
conversion to D-erythrobic acid, 37: 106
1-phosphate, radiolysis, 37:42, 44
6-phosphate, radiolysis, 37:42,44
radiation chemistry, 37:33
radiation-induced, chain reactions in
crystalline, 37:69, 7 1, 73
radiation-induced, non-chain reactions,
37:74
blinding to taste papillae, 45:329-330
branched-chain derivatives of, 22:284,304
catabolism of, 32:173
chelates of, 22:286
complex formation with phenylboronic
acid, 35:48
polymers, 35:7
complex with germanic acid, 22:288
with telluric acid, 22:288
composition in nonaqueous solvents,
42:60,68
conformational equilibria, 23:32
effect of alkali tetraborates on rotation
of, 23:36
crystalline, technology, 36:55-56
by isomerization of D-glucose, by
enzymic catalysis, 36:46-50
by isomerization of o-glucose, by
nonenzymic catalysis, 36:4345
isomerization to D-glucose, 36:47
crystallization of, 22:232-233
cyclic acetals, 26: 198
gas-liquid chromatography of, 26:235
preparation of, 26:238
properties of, 26:258-262
retention times of per(trimethylsily1)
ethers and other derivatives, 26:235
149
decomposition, 47:220-22 1
derivatives and. 22:229-305
dicarbonyl condensation products of,
22:305
diethyl dithioacetal, oxidation of, 32:84
preparation of, 32:24
dimethyl acetal, formation from
dithioacetal, 32:68
A-(disodium phosphate), irradiation,
38: 193
dithioacetal, preparation of, 26: 13
estimation of, 22:237
fermentalation by yeasts, 32: 152
in fetal blood. 30:s
in food, liquid chromatography separation,
4652
formation of 2-( 2-hydroxyacety1)furan
from, 46:286-287
o-glucose conversion, 49: 180
halogen derivatives of, 22:226
heated neutral solutions of, antimicrobial
activity formed in, 46:326
in honey, 25:289,295
hydrazones and osazones, 22:297
irradiation of, 22:243
isomerization reactions of, and derivatives,
22:239
and L-alanine, products from, 46:319
manufacture of, 22:23 I , 243
mercaptalation of, 32:24
metabolism of, 33:4
selective oxidation with silver
carbonate-on-Celite, 33:97
methyl ethers, 22:294
estimation of, 22:239
separation of, 30:s. 20
mutarotation of, 24: 15
in nectars, 25:304
nitration of, 22:259
nitrogen-containing derivatives, 22:262
optical rotation of, 22:235
in solutions of alkali metals, 21:229
oxidation of, 22:284
oxime, hexaacetate, 22:252
phenols from, 46:290
physical properties of, 22:233
polarography of, 29: 126, 143-145
polymerization by hydrogen chloride,
2 1:462
preparation of, 22:275
I50 SUBJECT INDEX
Fructose (continued)
reaction with
acetone, effect of temperature on,
26:201
aqueous ammonia, 2 3 3 12,315
dicarbonyl compounds, 22:288
with potassium thiocyanate, 22:279
reduction of, 22:283
separation, 47:3940
solution, distribution of ketopyranose
isomers in, 45:249
structure-properties relationships,
vibrational spectroscopic study,
44%
sulfur-containing derivatives, 22:28 1, 304
sweetness, 45:23 1
and temperature, 45:221-222
sweetness of, 22:23 1
sweetness-structure relationship, 45248,
256
synthesis, 40:2
taste, 45:249
thermal mutarotation, 45221-222
thermolysis of, in acid solution, products,
46:286
thiobenzhydrazide, 22:303
treatment with HF, 48:97-98
trimethylsilyl ether, mutarotation of,
42:22-23
utilization by yeasts, 32: 147
decomposition in water, products, 52:458
1-deoxy-
composition in aqueous solution, 42:65
D-, 24:259
2,3-0-isopropylidene-6-thio-~-, 22:28 1
3,4,5,6-tetra-O-methyl-o-, keto form in
aqueous solution, 42:3 I
2-deoxy-, 2,2-bis(ethyIsulfonyi)-o-,
preparation of, 3 2 8 4
4-deoxy-, 4-flUOrO-D-, 48: I83
1,4:3,6-dianhydro-o-, 22:261,25:261
1,6-dideoxy-
1,6-difluoro-o-, preparation, 38:209
2,3-0-isopropylidene-o-, 22:28 1
dihexulose dianhydrides from, 5 2 2 1 7-21 8
1,2:4,5-di-O-cyclopentyIidene-, 22:245
1,2:4,5-di-O-isopropylidene-P-o,reaction
with carbon tetrachloride-tri-
phenylphosphine, 28:247
1,2:4,5-di-O-isopropylidene-o-, 22:246
in o-apiose synthesis, 31:17&178
reaction with
2,3:4,5-di-O-isopropylidene-o-,
triphenylphosphine and carbon
tetrachloride, 28:247
3,4-di-O-methyl-o-, 22256
4,5-di-O-methyl-o-, 22:256
1,6-di-O-trityl-o-, and oxime, 22257
DL-, 21~12-13
O-gallOyl-D-, 21:27
and its derivatives, 7:53-98
keto-o-, derivatives, 22293
L-
crystalline, 26: 14
preparation of, 22:233
sweetness-structure relationship, 49258
synthesis, 40:2
large-scale preparative liquid
chromatography, 46:62
liquid Chromatography methods for analysis
of, 46:33
1-0-acetyl-o-, 22:253,275
1-0-a-o-glucopyranosyl-o-, in honey,
25:297, 300
3-0-a-~-glucopyranosyl-~-, composition in
aqueous solution, 42:39
3-0-~-o-galactopyranosyl-o-,24:9
1-0-benzoyl-keto-D-, tetraacetate, 22:257
1,2-O-cyclohe~ylidene-3,4,6-tri-0-methyl-~-
,22:246
2,3-0-isopropylidene-6-thio-o-, 22:28 1
oligosaccharides containing residues of, I3C-
NMR data for, 42:203-204
3-0-methyl-, 26:241
1-~-methyl-D-,22~256
3-0-methyl-o-, see Digitalose
3-0-methyl-o-, composition in aqueous
solution, 42:39,4344
4-O-methyl-~-,22~256
synthesis, 35: 1 1
6-0-methyl-o-, preparation of. 26:238-239
I-0-trityl-o-, 22:257
1,3,4,5,6-penta-O-acetyl-
D-diethyl dithioacetal, hydrogenolysis,
32:75
preparation of. 32:62
keto-o-
apiose synthesis, 31:176-178
ammonolysis of, 31:91
in D-apiose synthesis, 31:178
preparation of, 32:24
 SUBJECT INDEX
reaction with ethanethiol, 32:34
2,3,4,5.6-penta-O-acetyl-aldehydo-l-.
preparation of, 32:62
penta-0-acetyl-keto-o-, 22:250
penta-O-(trimethylsilyl)-o-, 22:258
phenylosazone, 21:ll
6-S-benzyl-
1 -deoxy-2.3-0-isopropylidene-6-thio-n-,
22:281
2,3-0-isopropylidene-6-thio-o-, 22:28 1
spectral analysis and identification, 44:24
1,3,5,6-tetra-O-acetyI-, 4-0-benzoyl-keto-n-,
synthesis, 39533
3,4,5,6-tetra-O-acetyl-
1 -bromo-1-deoxy-r-, reaction with triethyl
phosphite, 28:285
1 -deoxy- 1-diazo-keto-D-,
mercaptalation of, 32:25
reaction with ethanesulfenyl chloride,
32:25,43
1,3,4,6-tetra-O-methyI-~-,22:254
5-thio-~-,composition in aqueous solution,
42:53
6-thio-o-. 22:281
composition in aqueous solution, 42:53
3,4,5-tri-O-acetyI- 1,6-di-O-trityl-krto-n-.
oxime acetate, 22:257
3,4,5-tri-O-methyl-P-n-, 22:275
1,3,4-tri-O-methyl-n-, 22:255
1,4,5-tri-O-methyl-n-, 22:255
1,4,6-tr-O-methyl-n-, 22:255
3,4,6-tri-O-methyl-n-, 22:255
tri-0-methyl-o-, synthesis, 35: 1 1
uses of, 34:286,343
o-Fructose 1,6-bisphosphate
in aqueous solution, acyclic forms, 42:21
in fruit ripening, 42366
reactions with aldolase, 49: 192
Fructose 1,6-bisphosphate, laser-Raman
spectroscopy, at varying pH, 44:8 I
o-Fructose I ,6-diphosphatase
activity, deficiency of hepatic, 34:3 10
in metabolism of D-fructose, 34:335-340
n-Fructose 1,6- diphosphatase aldolase,
enzymic activity in liver metabolism,
34:326
in metabolism of o-fructose, 34:332-335
n-Fructose 1 -phosphate aldolase, enzymic
activity in liver metabolism, 34:326
D-Fructose 1-phosphate kinase. enzymic
151
activity in liver metabolism, 34:326
in metabolism of o-fructose. 34:332
Fructose phosphates in aqueous solution
composition, 42:46
NMR spectroscopy, 42:20
[>-Fructose-I (R)-t
mechanism of osazone formation, 27: 15 1
6-phosphate, preparation of, 27: 134, 158
o-Fructose-] (.S-t,
mechanism of osazone formation, 27: I5 I
6-phosphatc, prcparation of, 27: 134
Fructose-3,4,S-t3,u-, preparation of, 27: 135
Fructose-5-t-, [I-, preparation of, 27: 132, 135
Fructoside
1)-
esters and ethers of, 22:291
ring structure of. 23:5
methyl P-DL-,synthesis, 40:71
methyl 1 .6-di-O-trityl-n-, 22:247
Fructosylamines, u-, 22:267, 272,298
Fructosyl halides, 22:261
I>-, esters and ethers and, 22:296
Fructosyl phosphate, a-n-and p-0-, 22:253
Fructo tetranose, 1,2:5,6-di-O-isopropylidene-
D-, 26:240
Fructuronamide, 1 -deoxy-,ti-, derivatives.
22303
Fructuronic acid, 1 -amino-1-deoxy-o-.
derivatives, 22:303
Fruit
climacteric of, chemical changes with,
42:365
enlargement during maturation, 42:340-345
maturation of, pectinesterase and endo-n-
galacturonanase in, 33:381
physiology of development of, 42340-382
polarographic determination of 2-
furaldehyde in. 29: I67
respiratory climacteric in, 42:361-368
ripening
cell-wall role in, 42:315, 339-382
galacturonase and, 42:38 I
Fruit drop, 21:429
Fruit juices
gas-liquid chromatography of, 28:48. 57
uronic acids, gas-liquid chromatography of,
28:76
F-substance, structure of, 33:321
Fucans, immunological aspects of complex,
39:311-316
152 SUBJECT INDEX
Fucitol, from fucoidan, determination by
gas-liquid chromatography, 2 8 5 7
Fucofuranoside
methyl a-L-, preparation, crystalline, 39:293Fucopyranosyl chloride, tri-0-acetyl-a-L-,
methyl p-L-,preparation, syrupy, 39:293
Fucohexitol, L-a-, structure of, 32:79
Fucoidan
r-fucitol determination in, by gas-liquid
Chromatography, 28:57
L-fucose, 39:301
Fucolipids
biological functions, 39:309-3 1 1
isolation, 39:315
Fucomannan, 39:303
Fuco(manno)galactans, 41 :100-10 1
Fuconic acid, L-, preparation of, 29: 120
Fucopyranose
a-DL-,crystal structure bibliography, 38:426
a-L-
calcium bromide salt, trihydrate, crystal
structure bibliography, 34:35 1
crystal structure bibliography, 34:350
p-L-,ester of guanosine 5-pyrophosphate,
enzymic preparation of, 28:343
isolation of, 28:321
tetra-0-acetyl-a-o-, preparation, 39:295
tetra-0-acetyl-a-r-, preparation, 39:295
tetra-0-acetyl-Pa-, preparation, 39:295
tetra-0-acetyl-p-L-, preparation, 39:295
2,3,4-tri-O-benzyl-l-O-(N-
methylacetimidy1)-P-i-, preparation,
39:296
Fucopyranoside
methyl a-D-,preparation of, 33:87,39:293
methyl a-L-, preparation, 39:293
methyl p-D-, preparation of, 33537
methyl p-L-,preparation, 39:293
methyl 2,3-di-O-methyl-P-o-, 23:27 1
methyl 3,4-0-benzylidene-6-deoxy-p-~-,
reaction with N-bromosuccinimide,
39: I02
methyl 3,4-0-isopropylidene-2-0-p-
tolylSulfonyl-a-D-, 23:27 1
methyl 3-0-methyl+- D-, 23:271
methyl tri-O-methyI-p-D-, mass spectrum of,
21:64
phenyl2-0-benzy1-3,4-O-benzylidene-p-o-,
endv and e m - , hydrogenolysis
regioselectivity, 39: 131
L-Fucopyranosides, 48:132-133
synthesis of complex, 39:297-299
Fucopyranosyl chloride, 3-0-acetyl-2,4-di-O-
methyl-a-r-, 51:2 16-2 17
preparation, 39:295-297
0-Fucopyranosyl trichloroacetimidates, inverse
procedure for glycosylation, 50:98,
104-107
Fucopyranose, 1,2:3,4-~i-~-isopropylidene-o-,
mass spectrum of, 21:76
Fucos antibodies, 53:223-224
Fucose
aldehydo-L-,tetraacetate aldehydrol
formation, 42:31
in corn roots, 36:245
D-, 21:172, 177
biological significance, 39:282
biosynthesis and degradation, 39:336
metabolism, 39:328-329
properties of, and derivatives (tables),
39:337-339
synthesis, 39:285-288
toxicity, 39:329
chemistry and biochemistry, 39:279-345
cyclic acetals, Table, 34:239
detection and determination, 39:289-290
ester of thymidine 5-pyrophosphate,
occurrence of, 28:323
preparation of, 28:356
gas-liquid chromatography of, 28:48
glycoside formation, by acid equilibration,
39~293-294
glycoside formation, by ion-exchange
resins, 39:293
isolation, 39:282
occurrence, 39:280-281,301-311
4-0-methyl-, see Curacose, D-
relative reactivities of hydroxyl groups
conformational effects, 39:290-29 1
enhanced reactivity of OH-4,
39:291-292
tritylation, 39:292
steric and electronic effects, of 5-
subtituent, 39:283-285
substituents and protecting groups, 39:290
2-deoxy-2-fluoro-~-
labeled, synthesis, 48:203-204
preparation, 38:23 1
2,4-di-O-methyl-~-,21: 172
1,2:3,4-di-U-isopropylidene- D-, 23:269
 SUBJECT INDEX
2,3-di-O-methyl-o-, see also Labilose
steroid glycosides, 39:302
groups, glycoproteins containing 'H-NMR
spectroscopy, 41 :305-332
L-, 21:172,48:283, 51:94
biological significance, 39:282
biosynthesis, 39:3 1 6 318
biosynthesis and degradation, 39:336
degradation, 39:326
degradation, by bacterial metabolism,
39:327
degradation, by mammalian
metabolism, 39:327-328
enzymic transfer to glycoproteins,
39:3 18-322
immune-defense system, 39:334-335
properties of, and derivatives (tables),
39:340-345
synthesis, 39:288-289
toxicity, 39:329
cyclic acetals, Table, 34:239
enzymic isomerization, 36:46
glycoenzyme constituent, 27:302, 307,
321
in glycoproteins, 25:413
in keratan sulfate, 25:441
from linseed mucilage, 24:369
from tragacanthic acid, 24:362
liquid chromatography methods for analysis
of, 46:33
4-0-rnethyl-o-, 21:172
methyl ethers of, 7: 1-36, 10:257-272
2-0-a-~-fucopyranosyI-~-, synthesis, 39:298
4-0-( P-D-glucopyranosyluronicacid)-L-,
24:363
3,4-O-isopropyhdene-o-, preparation of,
34: 186
4,5-0-isopropyIidene-o-,dibenzyl
dithioacetal, oxidation of, 32530
4-O-methyI-o-, see Curacose
2-0-methyL~-
in cell-wall polymers, 42:280-28 I , 287
occurrence, 39:281
trichloroacetimidates
reaction with N-nucleophiles, 50: 105-
I07
synthesis, 50:98, 104
L-Fucose-binding lectins. 35:277-291
Fucosidase
a-D-,39:326
153
a-L-,39~324-325,44:154,209,233
p-D-,39:325-326
p-L-, 39:326
in carbohydrate degradations, 38:413
Fucoside
I_-, urinary, 39:330
methyl CX-D-, 22:207
methyl p-n-. 21:182
Fucosidosis, 39:332-333
glycoprotein (compound 2), 'H-NMR
spectroscopy, 41:219-224
glycoprotein (compound 4), 'H-NMR
spectroscopy, 41:219.22&228
glycoprotein (compound 54), 'H-NMR
spectroscopy, 41:306,330-332
glycoprotein (compound 46 and 47). 'H-
NMR spectroscopy, 41:306,313-318
oligosaccharides from urine, structure,
37:194-195,205
Fucosphingolipids, occurrence, 39:308-309
I - Fucosyl-agarose, affinity chromatography
adsorbent, 39:444-445
Fucosylceramide. isolation, 40:238
Fucosyltransferase
a-L-,40:252
i.-fucose transfer, 39:3 18-322
glycolipid substrates, 39:322-324
in malignancy, 39:331
a-t.-Fucosyl units, attachment, in situ
anomerization, 50:280-28 1
Fucoxylomannan, 41:98
isolation, 35:282
FUClIS
cellulosic cell-wall, 41: 108
guanosine 5 '-( D-mannopyranosyluronic acid
pyrophosphate)in, 32:9
Fuels, dextrins in, 47:32&327
Fukumi, H., 46:6
Functional groups, determination by mass
spectrometry, 21:44
Functional tests, for enzyme purity, 23:286
Fungal heterogalactan, degradation of sul fone
derivative, 31:227
Fungal hyphae, cell-wall extension in, 42:35 1
Fungal polysaccharides, see Polysaccharides
Fungi
a,a-trehalose in, 30:230, 234
o-fructose transport in, 34:3 14
galactomannans from, 31:243
1.-arabinanases from, 32:282-283
154 SUBJECT INDEX
Fungi (continued)
mass spectrometry of polysaccharides from,
29:66
polysaccharides of, 23:367417,41:67-103
trehalase from, 30:247
Furaldehyde
4-(hydroxymethyl)-2-, formation,
52:457458
5-(hydroxymethyl)-2-, 46:296, 3 18
effect on color formation, under sulfate-
pulping conditions, 46:325
formation of, 46:28&285,287,47:249
from Amadori compounds, 46:3 19-320
manufacture, 47:230
reaction with reversion products, 47:252
liquid chromatography, 46:53-54
tetrahydro-, diacetate, mass spectrum of,
21:62
2-Furaldehyde
5-(benzoyloxymethyl)-, from 2,3,5-tri-O-
benzoyl-P-D-ribofiuanosyl cyanide by
reductive hydrolysis, and N , N -
diphenylimidazolidine derivative,
33:135
from dehydration of 2-amino-2-deoxy-o-
glucose, 28: 182
diethyl dithioacetal, 32:23
formation, 46:3 18,47:247-248
from 2,5-anhydroaldoses, 2 5 2 1 1
from pentoses, 28:176,46:275-276
in sugar dehydrations, 28: 1 7 6 1 7 7
from hexuronic acids by decarboxylation,
28:18&193
5-(hydroxymethy1)-, 25:215,46:323
from cellulose on pyrolysis, 23:432
from dehydration of 2-amino-2-deoxy-o-
glucose, 28: 182
in o-fructose degradation, 22:239
formation from o-fructose and other
sugars, 28:16&165
gas-liquid chromatographic determination
of, 30:36
polarography of, 29: 166
preparation of, and derivatives, 27: 101,
I04
liquid chromatography, 46:53-54
5-methyl-
formation in dehydrations of hexoses,
28: 177
substrate for carbohydrate synthesis, 40:74
polarography of, 29: 166
substrate for carbohydrate synthesis,
40~72-73
technical importance, 46:323
tetrahydro-, preparation of enantiomorphic,
25:217
Furan
3-acetamido-5-( 1,2-dihydroxyethyl)-,
fomiation of, 28:202
2-(acetoxymethyl)-4-~hloro-,formation from
1,3,5-tri-0-acetyl-2-chloro-2-deoxy-~-
arabinose, 28:305
2-acetyl-3-hydroxy; preparation of, 28: 170,
176, 179-180
2,5-bis(hydroxymethyI)tetrahydro-,half-
ethers, as solvents for sugars, 27:88
from carbohydrates, 46:323
C-glycosylated, synthesis by Wittig reaction,
27:288
compounds, formation from hexoses,
6: 83-1 06
derivatives
Garcia Gonzalez work on, 45: 12-1 3
from pyrolysis of o-glucose, 22:504
2-(~-glycero-1,2-diacetoxyethyl)-, 24:2 14
2-(o-glycero- 1,2-dihydroxyethyI)-, 24:218
formation from D-glucal dehydration,
28: I83
2,5-dialkoxy-2,5-dihydro-, sugar substrates,
40:61
Diels-Alder cycloaddition, racemic carba-
sugars, synthesis, 48:29-36
2-( 1,2-diethoxyethy)-, 24:218
2,3-dihydro-, carbohydrate substrate,
40:80-84
2,5-dihydro-
2,5-dimethoxy-
Carbohydrate substrate, 40:64-72
cis- and trans-, hydroxylation, 40:61-
62
(R)-formyl, diisobutyl dithioacetal, 24:229
transformations, sugar syntheses,
40:6 1-74
3-( 1,l-dimethoxyethyl)-2,5-dihydro-2,5-
dimethoxy-, synthesis, 40:63
2-( 1-ethoxy-2-hydroxyethyl)-,24:2 18
2-ethyl-4,5-dihydro-5-0~0-, hexitol
precursor, 40: 11 1
2-(ethylthio)-3-(ethylthiomethyl)-,
preparation of, 32:23
 SUBJECT INDEX
3-(ethylthio)-2-[(ethylthio)methyl]-, from D-
xylose, 27: 101
formation of, 46:326
Garcia Gonzalez' work on, 45: 10- I2
2-(2-hydroxyacetyl)-
acetate, formation of, 28: 184
from dehydration of o-fructose. 28: 176,
I79
isolation and identification, 28: 162. I70
2-(hydroxymethyl)-5-( p-methoxypheny1)-,
synthesis by Wittig reaction, 27:288
2-(methoxyoxalyl), formation of, 28: 185
2(3)-one, dihydro-, as solvent for sugars,
27: 106
2-(p-bromophenyl)-, synthesis by Wittig
reaction, 27:288
2-(p-methoxyphenyl)-, synthesis by Wittig
reaction, 27:288
2(R)-azidomethyl-2,5-dihydro-, 24:229
2(R)-bensoyloxymethyI-2,5-dihydi-o-,
24:229
tetrahydro-
3,4-dihydroxy-3-( 1-hydroxytheyl)-2,5-
dimethoxy-, synthesis, 40:63
2-methyl-, 24:195
solubility of sucrose in, 27:107
as solvent in lithium aluminum hydride
reductions, 23:269
2,5-Furandimethanol, tetrahydro-, alkoxyalkyl
monoethers, as solvents for sugars, 27:
107
Furanoid compounds
conformation of, 25: 104
stability of enolacetal, 29:291-298
sweetness-structure relationship, 45:25&258
Furanoid rings
conformations, 34:201,45:256
fragmentation of, 21:47
mass spectrum of, 21:61
monosaccharides with phosphorus in,
42:176-188
nomenclature for, 30:466
stability of, 21:135
Furanoid sugars, see Sugars
Furanone
3-acetoxy-5-methylen-2(5H)-, 50: I68
3-benzoyloxy-5-ethylidene-2( 5H)-, 50: 168
2-(2-hrylidene)-4-hydroxy-5-methyl-3(2H)-,
46:322
4-Hydroxy-
155
2,5-dimethyl-3(2H)-, formation, 46:294,
318
5-methyl-3(2H)-, 46:3 18
formation, 46:290-291,321
from Amadori compound and its 2,3-
enolization, 46:320
3(2H)-Furanone
5-(~-g(vcero-I ,2-dimethoxyethyl)-, 24:23 1
formation in dehydration reaction, 28: 172,
175
from methylated sugars, 28: 172. 181
2(5H)-Furanones, p-elimination, 50: 166-1 70
Furanose, 53:99-100, 167-170
a-,51:9&97
p-, 51:9&97
carba-, 48:22
conformation and tautomers, vibrational
spectra used to analyze, 44:25
D-. 3-deoxy-3-C-(difluoromethylene)-l,2-0-
isopropylidene-a-
'
eryfhro-pentodialdo- 1,4-furanose, H- and
"F-NMR data for, 46: 141
ribo-hexo-, 'H- and "F-NMR data for,
46:141
3-deoxy-3-C-(mono or di) fluoromethylene
D-hexo(or pento), 'H-and "F-NMR data
for. 46:140-141
formation from reducing sugars in solution,
42: 16-68
temperature effects on, 42:32-33
stability in solution, 42:27-29
sweetness-structure relationship, 45:25&258
Furanose amines. deamination of, 31:54-57
Furanose derivatives
proton spin-lattice relaxation rates, 45: 153
radical-mediated brominations, 49:49-5 I
Furanose polymers, 21: 138
Furanose residues, natural occurrence of,
21:139
Furanosides
dithioacetals in synthesis of, 32:16
hydrolysis of, 22:39
from pyranosides, 22:4
Furanosonic acid, 5-hexulo-5,2-, a-o-qdo-,
calcium salt, crystal structure. 37:128-129
Furanuronates. with enolacetal linkage,
preparation of, 29:285-29 I
Furcatin
hydrolysis of, 31: 175
from ViburnumJurcatum, 31: 148
156 SUBJECT INDEX
Furcatinase, furcatin hydrolysis by, 31: 175
K-Furcellaran, 24:28 1
Furcellaran, gel formation, 31:285-291
Furfuryl alcohol
degradation in acidified methanol, 28:215
levulinic acid from, 28:2 12-2 18
as solvent for sugars, 27:88
substrate for carbohydrate synthesis, 40:72
tetrahydro-, solubility of sucrose in, 27:89
as solvent for sugars, 27:88,96, 107
Furfurylidene- P-pyranone
chromophoric, 46:322
formation of, in presence of methanol,
46:322-323
Furoic acid, methyl ester, Fourier proton
magnetic resonance spectroscopy of,
21:62
2-Furoic acid
cellulose esters, and derivatives, 29:338
conversion of, into methyl 5-nitro-2-furoate,
46:289
5-formyl-, from hexuronic acids, 28:186,
189, 191
3-Furoic acid
2,3-dihydro-, carbohydrate substrate,
40:80-81
tetrahydro-3-hydroxy-5-(hydroxymethyl)-,
isolation of, 28:205
Furst-Plattner rule, 25: 123
Furylalanines, 45: 12
2- Fury1 hydroxymethyl ketone, from cellulose
on heating, 23:432
Furylpyruvic acid, 45: 13
Furylthiopyruvic acid, 45: 13
Furze seed, see Ulex europeus
Fusarium oxysporum, pectinesterase from,
33:332
Fused-ring sugars
composition in aqueous solution, 4258-60
in solution, 49:3 1
Fusicoccin, crystal structure of, andp-
iodobenzenesulfonate, 25:90
Fusicoccin A, p-iodobenzenesulfonate, crystal
structure bibliography , 3 1 :3 69
Fusicoccum amygdali, amylose, 41:68
Fucopyranosyl bromide
2-0-benzyl-3,4-di-0-( p-nitrobenzoy1)-a-L-,
preparation, 39:296
tri-0-acetyl-a+-, preparation, 39:295-296
tri-0-acetyl-cY-L-, preparation, 39:295-296
G
P-o-Gal, 47:157
Galactal
D-, 48:349-350
dehydration of, 28: 184
rnercaptalation of, 32:28
3,4,6-tri 0-acetyl-o-, 0x0 reaction with,
23:73
tri-0-acetyl-o-
addition and rearrangement reactions of,
24:214
bromination, 38:235
halogenation of, 24:203
reaction with alcohols and phenols, 24:215
Galactan, 44: 182
of beef lung, structure of, 26: 16
biosynthesis of, 26:404
LY-D-, (146)-
acetate, circular dichroism, 45: 121
benzyl derivative, circular dichroism,
45:122
D-erabino-D-, structure, enzymic analysis,
44:247
I-, from larch, 35: 10
L-erebino-D-, structure, enzymic analysis,
44:247
from plant cell-walls, 44:359
(1-+4)-~-,biosynthesis, 44:366
sulfated, from marine algae, 3 2 5
Galactanases
p-D-,44:247
(1-+3)-, 44~247
D-
assay of, 32:293
concentration of culture solutions, 32:294
definition and nomenclature of, 32:278,
292
F 111, mode of action of, 32:296-299
occurrence of, 32:292-293
separation and purification of, 32:294
unit of activity, 32:293
endo-P-(1+4)-, in plant cell-wall
fractionation, 42977,282
on plant cell-walls, 42:351
(1+3)+-~-, mode of action of, 32:296
physicochemical properties of, 32:295
(1+4)-P-o-, mode of action of, 32:296
physicochemical properties of,
32:294-295
 SUBJECT INDEX
Galactan galactanohydrolase, (143)-p-o-,
name for o-galactanase, 32:292
Galactans, 41:87-88
D-, occurrence, 37:332-334
fungal, 23:392,398
gas-liquid chromatography of, 30:Y 1-92
gel chromatography of, 25:38
hetero-, 23:410
methylation of, 30: 12
molecular-weight determination by gel
chromatography, 25:30
in plant cell-wall polymers
biosynthesis, 42:322
interconnections, 42:305
structure, 42:282-283
polysaccharides, see Polysaccharides
from red lagae, hydrolysis of, 31: I87
snail, Barry degradation of, 31:203
degradation by Weermann reaction,
31:211
Smith degradation of, 31:209
structure of snail, 30:5
Galactaric acid, dimethyl ester
methanesulfonate, p-eliminative
degradation of, 29:235
Galactinol
biosynthesis, 26:375,37:348, 35&357
in vitro, 37:348
homologs, 37:3 18
occurrence, 37:3 16
physiological role, 37:317-3 18
structure, 37:3 17
Galactitol
acetates, separation of methylated. 30:23
acetylation of, effect ofborate on, 28:35
1,5-anhydro-
D-, sweetness-structure relationship,
45:240
DL-, 43:333
3,6-anhydro-
D-, mass spectrometry of permethylated,
29:74
L-, tetraacetate, mass spectrometry of,
29:74
4-O-~-o-galactopyranosyl-o; mass
spectrum of, 29:89
2-O-methyl-~-,acetate, mass spectrometry
of, 29:74
2,6-anhydro-l, 1-bis(ethylsulfonyl)-1-deoxy-
D-, triacetate, nuclear magnetic
157
resonance spectrum of, 25:252
I ,4-anhydro-o~-,catalytic oxidation of,
25:261
I , 1-bis(benzamido)- 1-deoxy-D-, preparation
of.31:117
1,6-bis(diethylborinate)2,3:4,5-
bis(ethylboronate)
preparation, 35:40
selective cleavage, 39:55
2,3:4,5-bis(ethylboronate), preparation,
35:41
conformation of, 26:69
crystallography of, 25:64
crystal structure bibliography, 31:365
1-deoxy-
I , 1-his(ethylsulfonyl)-n-,recrystallization
of. 32:86
D-, preparation of, 32:77
1-(ethylsulfiny1)-o-, photolysis, 38: 156
1-fluoro-L-, preparation, 38:245
1-(2-methyIhydrozino)-o-,preparation of,
29: 154-155
2,3:4,5-dianhydro- 1,6-di-O-mesyl-,
synthesis, 40:26
I ,6-dibromo- 1,6-dideoxy-, crystal structure
bibliography, 30:449
1,6-dichloro- 1,6-dideoxy-, crystal structure
bibliography, 30:449
I ,6-dideoxy- 1,6-difluoro-, preparation,
38:210
2,5-di-O-benzoyl- 1,3:4,6-di-O-henzylidene-,
acetolysis of, 22: 14
1.3 :4,6-di-O-benzylidene-2,5-di-O-p-
tolylsulfonyl-, acetolysis of, 23:261
1,3:4,6-di-O-( 1-chloroethylidene)-2,5-di-O-
p-tolylsulfonyl-, hydrolysis and
acetolysis of, 23:261
esterification with acetic acid, 33:45
ethyl 2-acetamido-2-deoxy- 1-thio-
OL-D-,formation from dithioacetal,
32:66-67
p-D-,formation from dithioacetal, 3 2 6 7
ethyl P-D-, preparation from dithioacetal,
32:68
ethyl I-thio-a-o-, preparation of, and
peracetate, 32:6&67
gas-liquid chromatography as tl-imethylsilyl
ether, 28:57
halogenation with concentrated halogen
acids, 33:85
158 SUBJECT INDEX
Galactitol (continued)
hexanitrate, selective denitration, 39:58
hexa-0-acetyl-, rearrangement in hydrogen
fluoride, 26: 176
hexa-0-(trimethylsily1)-, as standard in
gas-liquid chromatography, 28:59
liquid chromatography methods for analysis
of, 46:33
in marine algae extract, 32:5
6-0-benzoyl-l,2:4,5-di-O-
isopropylidene,DL-,oxidation of,
26:254
4-0-benzoyl- 1,2:5,6-di-O-isopropylidene-3-
0-methyl-o-, 24: 158
6-O-methyl-o-, pentaacetate, gas-liquid
chromatography of, 30:32
2,3,4,5,6-penta-O-acetyI-
1-acetyl-I-O-methyI-D-, preparation of,
32:72
1 -bromo- 1&ethyl- 1-thio-o-, preparation
of, 32:43,7 I
1-chloro-1-S-ethyl-I-thio-D-, preparation
from dithioacetal, 32:71
preparation of, 32:78
selective oxidation with sodium
metaperiodate, 33:95
1-S-ethyl-I -thio-0-, preparation, 32:77-78,
3 8 ~ 1 1-152
5 1,2:3,5-di-O-isopropylidene-, 6-
sweetness-structure relationship, 45:295
tetra-0-acetyl- 1,5-anhydro-o, rearrangement
in hydrogen fluoride, 26: 173
1,3,4,6-tetra-O-acetyyl-2,5-di-U-
benzoyl-, 22: 14
p-tolylsulfonyl-, 23:26 1
1,6:2,3:4,5-tris(ethylboronate)
preparation, 35:40,43
selective cleavage, 39:55
tris(phenylboronate), preparation, 35:4 1
utilization by yeasts, 32: 147, 218
Galactitol diarsenite, 43:333
Galactocarolose, 23:392, 399
biosynthesis of, 28:325
Galactocerebroside, 24:395,44:437
dihydro-o-, 24:4 12
from marine bivalve, 44:415
natural, 24:399
in sea anemone, 44:4 11
Galactofucomannan, methylation of, 30: 12
Galactofuranan, D-, carbon- 13 nuclear magnetic
resonance spectra, 38:68-70
Galactofuranose
a-D-, ester of uridine 5'-pyprophosphate,
isolation, 28:325
1,6-anhydro-
a-D-
preparation and history of, 34: 152
selective oxidation of, 33:90
synthesis, 39: 163
p-D-,synthesis, 39:169
2,3,5-tri-O-benzyl-o-~-, polymerization
of, 34: 157
2,3,5-tri-0-benzyl-p-o-, polymerization,
39: 182
p-D-, pentaacetate, 22: 18
D-
3-deoxy-3-fluoro-l,2:5,6-di-O-
isopropylidene-a-, 'H- and I9F-NMR
data for, 46:99
l-O-acetyl-2,3,5,6-tetra-O-benzoyl-4-
fl~oro-p-,~~C-NMR data for, 46: 172
3-deoxy-3,4-C-(dichloromethylene)-1,2:5,6-
di-0-isopropylidene-a-D-
conformation of, 34:201
crystal structure bibliography, 31:368
crystal structure of, 25:74
3-deoxy-l,2:5,6-di-O-isopropylidene-3-C-
methyl-D- galacto-, synthesis of, 27:282
(@rnethyhlfonyl)-a-D-, fluorination,
38:2 10
0-p-tolylsulfonyl-a-o-fluorination,
38:210
1,2:5,6-di-O-isopropyIidene-,a-D-
formation of, 34: 185
selective hydrolysis, 39: 15
3-O-benzoyl-l,2:5,6-di-O-isopropylidene-a-
D-, selective hydrolysis, 39: 15
5,6-O-isopropylidene-o-, preparation of,
34:185
Galactofuranoside
ethyl 2-acetamido-2-deoxy- 1-thio-a(and p)-
D-, 21:116
ethyl p-D-,21:117, 121,22:113
entropy of activation for hydrolysis of,
22:39
hydrolysis of, 21: 131
preparation of, 34:278
tetraacetate, acetolysis of, 22: 18
ethyl 2,3,5,6-tetra-O-acetyl-p-u-, preparation
of, 34:279
 SUBJECT INDEX
ethyl I-thio-a-o-, 21: 116
methyl OI-D-, entropy of activation for
hydrolysis of, 22:40
methyl P-D-, 21:103
conformation, 21 :100
methyl D-,selective periodate oxidation of,
33:94
methyl 2-0-p-tolylsulfonyl-6-0-trityl-P- w,
23:244
methyl 3-0-p-tolylsulfonyl-6-0-trityl p- D-,
23:244
methyl 5-O-p-tolylsulfonyl-6-O-tr1tyl-~- I)-,
23:244
methyl 6-O-trityl-P-o, selective p -
toluenesulfonylation of, 33:35
Galactohranosylamine, N-acetyl-P-o-
configuration of. 31:108-109
preparation of, 31: 122
proton magnetic resonance spectroscopy of,
27:23
Galactofuranosyl fluoride
D-
2,3,5,6-tetra-O-acetyl-, IH- and "F-NMR
data for, 46:97
2,3,5,6-tetra-O-benzoyl-a-, 'H- and "F-
NMR data for, 46:97
L-, 3,6-dideoxy-P-
3-azido-5-O-benzoyl-2-O-benzyl-, ' H-and
"F-NMR data for, 46: 127
3-azido-5-O-benzoyl-2-O-methyl-. 'H-
and "F-NMR data for, 46: 127
5-O-benzoyl-2-O-benzyl-3-
(trifluoroacetamid0)-, 'H- and "F-
NMR data for, 46: 128
5-O-benzoyl-2-O-methyl-3-
(trifluor0acetamido)-, 'H- and "F-
NMR data for, 46: 128
per-0-benzoyl-Pa-, synthesis, 38:20 1
Galactofuranuronate, methyl 1,2,3,5-tetra-0-
acetyl-P-o-, conformation of, 26: 1 10
Galactofurnosyl bromide, 2,3-di-O-benzyl-S,6-
di-0-( p-nitrobenzoyl)-P-o-, methanolysis
of, 34:281
Galactogen, structure of snail, 3 0 5
Galactoglucan, 52:362-364,417418
Galactoglucomannans, 44: 164,46:305
Cercis siliquustrum, 44: 180
D-, composition, 37:338
occurrence, 37:337
structure, 37:339
159
hemicellulosic, analogy to galactomannans,
31:267
Nicotiuna tubacum, 44: 18 1
in plant cell-walls, 42:269
structure, enzymic analysis, 44: 180-1 86
galucro-Hept- 1-entitol, 2,h-anhydro- 1 -deoxy-
D-, 48:354-355
Galactokinase, specificity, fluorinated
carbohydrate effect, 38:282
D-Galactolipids
biochemistry, 37:322-33 1
photosynthesis, 37:362-366
Galactomannans, 24:339, 41:92-95,
52:395-396
A. niger, 44:366
biochemistry of plant, 35:341-376
biodegradative hydrolysis of, 31 :256
biosynthesis, 31:255-256,35352-356
botanical sources, 31:243,247-253
Cuesalpina pulcherimu
enzymic analysis, 44: 170-1 7 1
hydrolysis, effect of fine structure on,
44: 174
Cuesulpina spinosa
enzymic analysis, 44: 170
hydrolysis, effect of fine structure on,
44: 174
Cuesulpina vesicaria
enzymic analysis. 44: 170
hydrolysis, effect of fine structure on,
44: 174
carbon-13 nuclear magnetic resonance
spectra, 38:62, 61-68
carob, 44: 176-1 77
enzymic analysis, 44: 167-1 68, 170
hydrolysis, effect of fine structure on,
44: I74
Cussiafistulu. hydrolysis, effect of fine
structure on, 44: 174
chemistry and interactions of seed,
31:24 1-3 12
circular dichroism, 4 5 9 0
commercial exploitation of, 31:307-3 12
composition of, 31:245
conformational analysis and molecular shape
of, 31:279,281
crystallography of, 22:466, 40:391-392
Cyumopsis tetrugonolobus, enzymic
analysis, 44: I70
D-, hiosynthesis, 37:366-.369
160 SUBJECT INDEX
Galactomannans (continued)
metabolism pathway, 32369
occurrence, 37:334
properties, 37:336
structure, 37:335
depolymerase, in seed germination, 35:361
o-galactose distribution, 44: 166
o-mannose to o-galactose ratio in, 31:261
enzymic hydrolysis, effect of fine structure
on, 44: 174
extraction and purification of, 31:259-260
fine structure of, 31:269-277
function, 39375-376
fungal, 23:398,406
gas-liquid chromatography of, 28:47,56
Gleditsia, 44: 173, 175
enzymic analysis, 44: 167, 170
hydrolysis, effect of fine structure on,
44: 174
guar
a-o-galactosidase modified, hydrolysis,
effect of fine structure on, 44: 174
hydrolysis, effect of fine structure on,
44: 174
history, 31:243-246
homogeneity of, 31:261-263
I, 23:404405
II,23:404
industrial applications of, 31:246, 308-3 12
interaction with bacterial polysaccharides,
31~301-305
with carrageenan, agar, and other
polysaccharides, 31:284-307
isolation, 35345
Leucaena leucocephala, 44: 173-175
enzymic analysis, 44: 168
hydrolysis, effect of fine structure on,
44: 174
location in vivo, 35:345
metabolism during seed germination,
35:3 56-36 1
methylation analysis of, 30:25
microbial, 31:243-244,35354
molecular weights of, 31:26&261, 277-279
of non-leguminous plants, 31:254
occurrence, 35343-345
peptido-0-phosphono-, biosynthesis, 35:3 54
from plant cell-walls, 44:359
Pusa mosami, enzymic analysis, 44: 170-
171
role in seeds of Leguminoseae species,
31:255
solution properties of, 31:282-284
Sophora japonica, enzymic analysis,
44: I65
soybean, enzymic analysis, 44: 168
structure, 31:263-267,35347-351
enzymic analysis, 44:165-178
model, 44: 176
synergistic action of, 31:242
uses, 35:341-342
viscosities of, 31:283
X-ray crystallography of, 31:280
of yeast cell-wall, 32:229
Galactomanno-oligosaccharides, from enzymic
hydrolyzates of galactomannans,
32:314-315
Galactonate, methyl 3,6-anhydro-~-,mass
spectrum of, 29:75
Galactonic acid
2-amino-2-deoxy-o-, deamination of, 31:25
analytical high-performance liquid
chromatography, 46:34
2,5-anhydro-o-, preparation of, 33: 1 18
3,6-anhydro-o~-,25261
D-, preparation of, 29: 1 19
Galactono- 1,rl-lactone
2,3,6,-tri-O-rnethyl-o-, crystal structure
bibliography, 31:350
D-
crystallography of, 25:65,31:364
selective periodate oxidation of, 33:94
L-, irradiation, 37: 123
oxidation, enzymic, 37: 123
preparation, 37237
Galactono-l,5-lactone
4-C-acetyl-6-deoxy-2,3-O-methylene-o-,
synthesis of, 42: 126
6-deoxy-4-C[ 1(A-hydroxyethyl] -2,3-O-
methylene-o-
natural occurrence of, 42:73
structure of, 42:71
synthesis of, 42: 126
Galactononitrile
2,3,4,5,6-penta-O-
acetyl-D- ammonolysis of, 31:82
effect of solvent on, 31:99
propionyl-o-, ammonolysis of, 31238
penta-0-benzoyl-o-, ammonolysis of, effect
of solvent on, 31 :99
 SUBJECT INDEX 161

Galactopyranan, 2-amino-2-deoxy-~-, 1.4-anhydro-

41:88-89 2,3,6-tri-O-methyl-p-~-
Galactopyranose polymerization, 39:204
2-acetamido- 1,6-anhydro-2-deoxy- synthesis, 39: 165
p-D-,benzoylation of, 23:252,33:23, 2,3,6-tri-O-methyl-o-, synthesis and
34532 polymerization of. 21:488
3-O-bezoyl-4-(methylsulfonyl)-~-i~-,azide 1,6-anhydro-
replacement of methylsulfonyloxy p-D-
group in, 34:85, 125 acetylation of, 33:23,34:84
4-0-(methylsulfonyl)-~-D-, 23:252 from agar pyrolysis. 34:45
2-acetamido-2-deoxy- AH,B systems for. 45:27 1
CX-D- alkylation of, 34234
crystal structure bibliography, 34:354 cleavage by hypophosphorous acid,
ester of thymidine 5-pyrophosphate, 34:6849
enzymic preparation of, 28:324 copolymers with tribenzyl ethers of
ester with uridine 5-pyrophosphate, levoglucosan, 34:73
enzymic preparation and biosynthesis crystal structure of, 34:51
Of, 28~342-343 from lactose pyrolysis, 34:45
isolation of, 28:327 per-0-substituted, 34: 77
circular dischroism, 45:97 3,4-phenylboronate, 34:93
3-0-(4-deoxy-cy-i.-threo-hex-4- polymerization of, 34:71
enopyranosyluronic acid)-a-ii-. preparation of, 34:27,32
proton magnetic resonance properties of, 34:50
spectroscopy of, 27:42 sweetness-structure relationship, 45:
6-acetamido-6-deoxy-~-,23: 178 269
(Y-D-, 45:74 synthesis, 39: 163
calcium bromide trihydrate, crystal p-toluenesulfonylation of, 34:8 1
structure bibliography, 30:465 P-DL-. preparation of, 34:49
crystal structure bibliography, 3 4 3 7 1, D-
37:377 acetolysis of, 34:65
ester of adenosine 5-pyrophosphate, complexes, 34:54
enzymic preparation of, 28:340 3-deoxy-3-iodo-2-0-
isolation of, 28:3 15 (methy1thio)carhonyl-P-D-, crystal
sweetness, 45:219 structure, 43:213-214
structure relationship, 45:239-24 I 2,4-di-0-p-tolylsulfonyl-~-~-, preparation
taste properties, 45:242 Of, 34~81-82
2-amino- 1,6-anhydro-2-deoxy- 2-0-benzyl-3,4-0-isopropylidene-~-~-,
p-D-, preparation of, 34: 122 polymerization, 39: 195
4-O-methyl-p-~-,preparation of, 34: 3,4-O-isopropylidene-@~-
122 formation of, 34:46
3-amino- 1,6-anhydro-3-deoxy-p-o-, oxidation of, 34:97
preparation of, 34: 126 3,4-0-isopropylidene-2-0-
2-amino-2-deoxy- (methylsulfony1)-P-o-
CX-D-, ester of uridine 5-pyrophosphate. hydrolysis of, 23:262
preparation of, 28:355 reaction with potassium fluoride.
p-D-, hydrochloride, crystal structure 38:220
bibliography, 30:450 reactivity of, 24: I55
3 - 0 4 ~-D-g~ucopyranosyluronic acid)-ol-u- solvolysis of. 24: 197
, monohydrate, crystal structure 3,4-O-isopropylidene-2-0-p-tolysulfonyl-
bibliography, 34:358 p-D-,reactivity of, 24: I54
162 SUBJECT INDEX
Galactopyranose (continued)
2-O-(methylsulfonyI)-3,4-0-(0-
nitrobenzylidene)-P-o-, photo-
rearrangement, 39:90
2-O-p-tolylsulfonyl-p-o-, preparation of,
34:86
1(6)-thio-P-o-, preparation of, 34: 146
2,3,4-tri-O-benzyl-P-o-, polymerization,
34:73,39:182, 187
6-azido-6-deoxy- 1,2:3,4-di-O-
isopropylidene-a-o-, preparation of,
28:286
p-0-
crystal structure bibliography, 34:35 1,
372,37:378
1-mesitoic ester, 1,6-anhydride from,
34:32
pentaacetate
gas-liquid chromatography of, 30:32
proton magnetic resonance spectroscopy
of, 27:70
sweetness-structure relationship, 45:
239
taste properties, 49242
benzyl 3,4,6-tri-O-benzy1-2-0-(2,3,4,6-tetra-
0-benzyl-a-D-, glucopyranosy1)-a-D-,
preparation of, 34:268
bis (benzyloxy)isopropyl2,3,4,6-tetra-O-
benzyl-a-D-, preparation of, 34:258
P-L-, ester with guanosine 5'-pyrophosphate,
isolation of, 28:319
carba-a-DL-, 48:23, 33
synthesis, 48:27-28
carba-a-o-, 48:24, 86-87
synthesis, 48:36,40
6-chloro-6-deoxy-l,2:3,4-di-O-
isopropylidene-a-o-, 22: 183, 198
6-chloro-6-deoxy- 1,2:3,4-di-O-
isopropyhdene-a-o-, preparation
of,246,251,252,257,259 reaction with
sodium azide, 28:286
CX-D-, 43:371
D-
2-acetamido-2-deoxy, circular dischroism,
45~95-96
2-acetamido- 1,3,4-tri-O-acety1-2,6-
dideoxy-6-fluoro-, 'H- and I9F-NMR
data for, 46: 120
conformations of, 26:87
2-deoxy-2-fluoro-
a anomer, 'H- and "F-NMR data for,
46535
p anomer, IH- and 19F-NMR data for,
46:85
1,3,4,6-tetra-O-acetyl-, 'H- and I9F-
NMR data for, 46:85-86
4-deoxy-4-fluoro-
a anomer, 13C-NMR data for, 46: 163
p anomer, IT-NMR data for, 46:163
1,2,3,6-tetra-O-acetyl-P-, 'H- and 19F-
NMR data for, 46:92
1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-
a-,I3C-NMR data for, 46:161
6-deoxy-6-fluoro-
a anomer, IH- and 19F-NMRdata for,
46:95
p anomer, IH- and I9F-NMR data for,
46:95
1,2:3,4-di-O-isopropylidene-a-, IH- and
I9F-NMR data for, 46:95
3-deoxy-3-fluoro-,l,2,4,6-tetra-O-acetyI-,
'H- and I9F-NMR data for, 46:90
1,2:3,4-di-O-isopropylidene-6-0-
[(methylthio)thiocarbonyl]-a-,
photochemical cleavage of, 46: 190
1,2:3,4-di-O-isopropylidene-6-O-nitro-a-,
photolysis of, 46:191
1,2:3,4-di-O-isopropylidene-6-O-p-
tolysulfonyl-a-, photolysis of, 46: 191
orientation of hydroxyl groups for, in
4 C , ( ~conformation,
) 45:75
peracetate, ammonolysis of, 31537
sweetness, 45:264
I ,2,4,6-tetra-O-acetyI-3-deoxy-3-fluoro-
a anomer, I3C-NMR data for, 46: 162
p anomer, I3C-NMR data for, 46:162
3-deoxy-, 3-fluoro-P-o-, synthesis,
48: 134-135
6-deoxy-
a-DL-,crystal structure bibliography,
38:426
6,6-difluoro- 1,2:3,4-di-O-isopropyIidene-
a-D-,preparation, 38:226
1,2:3,4-di-O-isopropylidene-6-
phthalimido-a-o-, proton free-
induction decay signal, 27:4849,5 1,
57-58
6-[ 18F]fluoro-a-~-, synthesis, 38:239
6-fluoro- 1,2:3,4-di-O-isopropylidene-a-o-,
preparation, 38:244
 SUBJECT INDEX
6-iodo- 1,2:3,4-di-O-isopropylidene-a-~-
deiodination by irradiation, 28:304
irradiation, 38: 187
1,2:3,4-O-isopropyhdene-a-o-,
preparation by irradiation, 28:304
1,6:3,4-dianhydro-
p-D-. preparation of, and derivatives,
34:108, 111, 113
2-O-benzyl-P-u-, as synthetic
intermediate, 34:120
2-O-p-tolylsulfonyl-p-D-
de-p-toluenesulfonylationof, 34:75
hydrolysis of, 23:262
preparation of, 34:80, 110
4,6-dideoxy-4-(dimethyIamino)-u-, 23: I 55
2,3-di-O-acetyl- 1,6-anhydro-P-~,crystal
structure bibliography, 37:383
1,2:3,4-di-O-benzylidene-(~-u-, configuration
of, 34: 196
1,2:3,4-di-O-isopropylidene-
Ct-D-
carbon-I3 nuclear magnetic resonance
spectroscopy, 4 1 5 3
chlorination by carbon tetrachloride and
triphenylphosphine, 28:246
conformation of, 26: 1 19, 226
low-pressure distillation of, 34:46
6-nitrate, denitration, 3 9 5 7
reaction with (chloromethy1ene)di-
methyliminium chloride, 28:25 1
with cyanuric chloride, 28:259
with N-(2-chloro-l, 1,2-trifluoroethyl)-
diethylamine, 28:257-258
reaction with (2-chloro-l ,l,2-
trifluoroethyl) diethylamine,
38:227-228
6-O-(methylsulfonyl)-a-~-, fluorination.
38:207
6-O-p-tolylsulfonyl-a-~-
fluorination, 38:2 19
infrared spectrum, 23:256
6-O-pyruvoyl-~t-u-,photolysis,
mechanism, 38:128
6-0-[3,4-6-tri-O-acetyl-2-0-(4-
oxopentanoy1)-p-u-
galactopyranosyl]-a-D-,preparation
and hydrazinolysis, 39:42
6-[ 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-
dinitro-anilino)-a-o-,
glucopyranosyl]-a-o-, and-P-ii-,
163
anomer, preparation of, 34:269
2,4-di-O-methyl-a-~-,monohydrate, crystal
structure, 43:340-341
I ,2:3,4-di-O-methylene-6-O-p-tolysul-
fonyl-u-, displacement reactions of,
24: 144
ester of guanosine 5-pyrophosphate,
isolation of, 28:3 19
ester of thymidine 5-pyrophosphate,
enzymic preparation of, 28:340
isolation of, 28:322
ester of uridine 5 -pyrophosphate, enzymic
synthesis and fermentation production
of, 28:34&341
isolation of, 28:325
oxidation with u-galactose oxidase,
28:344
synthesis by mixed anhydride method,
28:35 1
I-
2,6-dideoxy-2-fluoro-
(Y anomer, H- and I9F-NMR data for,
46: I32
p anomer, H- and 19F-NMR data for,
46: 132
1,3,4-tri-O-acetyl-P-, H-and I9F-NMR
data for, 46:132
2,3,6-trideoxy-2-fluoro-
3-amino-, H- and I9F-NMR data for,
46: 124
1 -O-acetyl-4-O-benzoy1-2-fluoro-3-
(trifluoroacetamido)-P-, H-and IF-
NMR data for, 46: 124
methyl 6-O-benzyl-cu-o-,preparation by
methanolysis, 34:206
methyl 4,6-O-benzylidene-o-
conformation of, 34: 199
hydrolysis of, 34:202
2,3-di-O-methyI-a-o-, preparation of,
34: 189, 195
2,3-di-O-methyl-P-~-,diastereoisomers,
34: 196
methyl 3-O-benzyl-4,6-O-benzylidene-2-O-
methyl-a-u-, hydrolysis of, 34:204
methyl 3,4-O-ethylidene-(~-~-,
diastereoisomers, 34: 197
methyl 4,6-O-ethylidene-2,3-di-O- methyl-p-
D-, hydrolysis of, 34:204
methyl 4,6-O-isopropylidene-a-u-, and-P-D-,
preparation of, 34: 186
164 SUBJECT INDEX
Galactopyranose (continued)
methyl 3,4,6-tri-O-acetyI-2-amino-2- deoxy-
p-D-, synthesis of, 34:254
6-0-(2-acetamido-3,4,6-tri-O-acetyl-2-
deoxy-P-o-glucopyranosy1)- 1,2:3,4-di-
0-isopropylidene-a-D-, nitrosation of,
31:68
0-a-D-galactopyranosyl-( 1+4)-o-, in plant
tissues, 37:310
~ - ~ - ~ - D - X ~ ~ O ~ ~24~370
~ ~ O S ~ ~ - D -
, resonance spectroscopy of, 27:68
6-0-(4,6-dichloro-1,3,5-triazin-2-yl)-1,2:3,4-
di-0-isopropylidene-a+-, preparation
of, 28:259
6-0-(dimethylthiocarbonyl)-1,2:3,4-di-0-
isopropylidene-a-o-, photochemical
cleavage of, 46: 190
6-O-(fluoroformyl)-l,2:3,4-di-0-
isopropylidene-a-o-, preparation and
reactions, 38~242-243
6-0-formyl- 1,2:3,4-di-O-isopropylidene-c~-
,D, preparation of, 28:251,259
3,4-0-isopropylidene-~-, preparation of,
34:185
4,6-O-isopropylidene-o-,preparation of,
34: 185
3-0-(2-0-benzyl-a-o-, glucopyranosy1)-4,6-
0-ethylidene- 1,2-O-isopropylidene-a-
D-, preparation of, 34:263
6-0-a-iodobiphenylyl- 1,2:3,4-di-0-
isopropylidene-a-o-, irradiation,
38:187, 191
0-[3,4,6-tri-0-acetyl-2-0-(4-oxopentanoyl)-
P-o-galactopyranosyl]-( 1+2)-0-(3,4,6-
tri-0-acetyl-P-o-galactopyranosy1)-
(1+6)-( 1,2:3,4-di-O-isopropylidene-a-
D-, preparation and hydrazinolysis,
39:42
penta-0-acetyl-P-o-
acetoxonium salt, 26: 160
ammonolysis of, 31:122
penta-0-henzoyh-, ammonolysis of,
31:117, 120
effect of solvent on, 31:99-100
per-0-trimethylsilyl-o-, mass spectrometry
of, 29:48
phenyl a-D-,1,6-anhydride formation from,
34~29-30
phenyl-p-D-, alkaline cleavage of, 34:29
1,2,4,6-tetra-O-acetyI-
p-D-, synthesis, 39:35
2-deoxy-2-N-nitrosoacetamido-o-,
reaction with potassium hydroxide,
31:70
2-(N-acetylacetamido)-2-deoxy-P-~-,
crystal structure, 43:249-250
3-0-(2,3,4,6-tetra-O-acetyl-p-~-
galactopyranosy1)-a-o-, crystal
structure, 43:262
1-thio-P-D-, pentaacetate, proton magnetic
3,4,6-tri-O-acetyl- 1,2-O-(R)-(ferf-
butoxyethy1idene)-a-o, crystal
structure, 43:252
2,3,4-tri-O-benzyl-~-,preparation, 39:50
a-D-Galactopyranose calcium bromide
trihydrate, crystal structure bibliography,
31:349
Galactopyranose pentaacetate
carba-a-DL-, 48:29
synthesis, 48:27-28
carba-P-DL-, synthesis, 48:28-29
D-, nonselective spin-lattice relaxation rates,
45: 148
P-D-GalaCtOpyranOSe penta(acetate-d,),
nonselective spin-lattice relaxation rates,
45: 148
Galactopyranose tetraacetate, 2-bromo-2-
deoxy-carba-a-m-, 48:30
Galactopyranoside, 2-fluoro-p-~-,48: 131
Galactopyranosides
2,4,6,-tri-O-methyl-o-, preparation of, 30:4
3,4,-di-O-acetyl-6-
azido-6-deoxy- 1-0-(methylsulfony1)-o-
fructofuranosyl2,3,6-tri-O-acetyl-4-
azido-4-deoxy-a-o-, preparation of,
33:267,269
chloro-6-deoxy-l-O-formyl-~-o-
fiuctofuranosyl 2,3,6-tri-O-acety1-4-
chloro-4-deoxy-a-o-, preparation of,
33~262
a-D-
galactopyranosyl D-, in plant tissues,
37:310
utilization by yeasts, 32:205-208,
39:374378
p-D-, utilization by yeasts, 32:208-209
ally1 6-0-allyl-2,3,4-tri-O-benzyl-a-o-,
deallylation, 39:50
ally1 2,3,4-tri-O-benzyl-, 6-0-2-butenyl-a-
D-, isomerization and cleavage, 39:52
 SUBJECT INDEX
ally1 2,4,6-tri-O-benzyl-, 3-0-2-butenyl-a-
D-, selective and cleavage, 39:5 1
2-amino-2-deoxy-o-,mass spectrometry of
trimethylsilyl fragmentation derivatives,
30:38
methylation and gas-liquid
chromatography of, 30:22
3,6-anhydro-4-chloro-4-deoxy-a-u-
galactopyranosyl 3,6-anhydro-4-chloro-
4-deoxy-a-o-, taste properties, 45:270
anti-a-D-, as myeloma immunoglobulins,
31:346
6-azido-6-deoxy- 1,3,4-tri-0-
(methylsulfony1)- P-D-hctofuranosyl
4,6-diazido-4,6-dideoxy-2,3-di-O-
(methylsulfony1)- a-D-, preparation of,
33:267
p-0-
mtctofuranosyl a-D-
derivatives, physical properties of,
33:291-293
synthesis of, 33:270
utilization by yeasts, 39:394-397
benzyl2-acetamid0-6-0-(2-acetamido-2,4-
dideoxy-4-fluoro-~-~-glucopyranosyl)-
2-deoxy-a-~-,48:2 18
benzyl 6-deoxy-a-o-. catalytic oxidation of,
33539
benzyl 2,3-di-O-benzyl-
4,6-O-benzyhdene-p-o-, hydrogenolysis
regioselectivity, 39: 129
4,6-O-benzyl-4,6-O-benzylidene LY-D-,
hydrogenolysis regioselectivity.
39: 129
benzyl2,6-di-O-benzyl-3,4-O-benzylidene-
p-D-, endo- and exo-, hydrogenolysis
regioselectivity, 39: 131
benzyl2,3-di-O-methyl-4,6-O-benzylidene-
p-D-, hydrogenolysis regioselectivity,
39:129
benzyl 6-O-allyl-2-0-benzyl-3,4-0-
benzylidene-a-o-, endo-and e.xo-,
hydrogenolysis regioselectivity, 39: I32
benzyl3-O-benzoyl-4,6-0-benzylidene-p-~-,
acyl migration in, 33: 101
benzyl6-0-benzoyl-2-0-(tri-O-acetyl-a-~-
fucopyranosy1)-p-o-, synthesis of,
34:252
benzyl4,6-0-benzyIidene-p-o-p-u-
benzoylation of, 33:21-22
165
with benzoyl cyanide, 33:45
with N-benzoylimidazole. 33:43
selective methylation with diazomethane,
33:69
benzyl 3-0-benzyl-4,6-O-benzylidene-2-O-
(2,3,4,6-tetra-O-benzyl-P-~-,
galactopyranosyl) p-D-. hydrogenolysis
regioselectivity, 39: 130
6-bromo-6-deoxy- 1,3,4-tri-O-
(methylsulfony1)- p-D-fructofuranosyl
4,6-dibronio-4,6-dideoxy-2,,3-di-O-
(methykulfonyl)-a-D-, preparation of,
33:259
6-chloro-6-deoxy-~-~-hctofuranosyl4,6-
dichloro-4,6-dideoxy-a-~-.preparation
of, 33:262
D-
benzyl 3,4,6-hi-O-benzyl-2-deoxy-2-
fluoro-p-, I3C-NMR data for, 46: 161
2-deoxy-2-fluoro-
methyl-, 'H- and "F-NMR data for,
46:86
methyl 3,4-0-isopropylidene-6-O-trityl-
p-, 'H- and "F-NMR data for, 46536
trifluoromethyl3,4,6-tri-O-acetyl-a-,
'H- and I9F-NMR data for, 46:86
3-deoxy-3-fluoro-, methyl 2,4-di-O-
benzoyl-6-O-(bromoacetyl), IH- and
I9F-NMR data for, 46:90
4,6-dideoxy-4,6-difluoro-
methyl, IH- and IyF-NMR data for,
46:150
phenyl-, 'H- and I9F-NMR data for,
46: 150
methyl 2-acetamido-2,4,6-trideoxy-4,6-
difluoro-a-
'H- and "F-NMR data for, 46: 157
3-O-acetyl-, IH- and I9F-NMR data for,
46:157
methyl 2-benzamido-2,4,6-trideoxy-4,6-
difluoro-a-
3-O-acetyl-, 'H- and "F-NMR data for,
46:157
3-O-benzyl-, 'H- and "F-NMR data for,
46:157
methyl 2-deoxy-2-fluoro-
p anomer, I3C-NMR data for, 46:161
3,4,6-tri-O-a~etyI-p-,'~C-NMR data for,
46:161
methyl 3-deoxy-3-fluoro-
166 SUBJECT INDEX
Galactopyranosides (continued)
p anomer, I3C-NMR data for, 46:162
2,4-di-0-benzoyl-6-0-(brornoacetyl)-,
I3C-NMR data for, 46:162-163
2,4,6-tri-O-a~etyl+-,~~C-NMR data for,
46: 162
methyl 4-deoxy-4-fluoro-
a anomer, I3C-NMR data for, 46: 163
p anomer, %NMR data for, 46: 163
2,3-di-O-ber~yl-P-,~~C-NMR data for,
46: 164
2,3-di-O-benzyl-6-0-trityl-P-, I3C-
NMR data for, 46: 164
2,3-di-O-trityl-p-, 'H- and I9F-NMR
data for, 46:93
6-0-benzoyl-2,3-di-O-benzyl-P-, 'H-
and I9F-NMR data for, 46:93
2,3,6-tri-0-acetyl-au-,'H- and I9F-NMR
data for, 46:93
2,3,6-tri-0-acetyl-,I3C-NMR data for,
46: 164
2,3,6-tri-O-benzoyl-P-, 'H- and I9F-
NMR data for, 46:93
methyl 6-deoxy-6-fluoro-
a anomer, IH- and I9F-NMR data for,
46:95
p anomer, I3C-NMR data for, 46: 164
1,2,3,4-tetra-O-acetyl-a-,IH- and I9F-
NMR data for, 46:95
2,3,4-tri-O-acetyl-o-, 'H- and "F-NMR
data for, 46:95
2,3,4-tri-O-a~etyl-p-,'~C-NMRdata for,
46: 164
methyl 4,6-dideoxy-4,6-difluoro-
a anomer I3C-NMR data for, 46:175
p anomer 13C-NMR data for, 46: 175
methyl 2,6-dideoxy-6-fluoro-a-
2-acetamido-, IH- and I9F-NMR data
for, 46: 120
2-acetamido-3,4-di-O-acetyl-, 'H- and
I9F-NMR data for, 46: 120
2-benzamido-, IH- and I9F-NMR data
for, 46: 120
2-benzamido-4-0-benzoyl-3 -0-benzyl-,
IH- and I9F-NMR data for, 46: 121
2-benzamido-3-0-benzyl-, IH-and
j9F.NMR data for, 46:121
3,4-di-O-acetyl-2-benzamido-, IH- and
I9F-NMR data for, 46: 120
4-deoxy-4-fluoro-a-u-, 48: 149
2-deoxy-2-(methylamino)-o-, trimethylsilyl
ethers of methylated, gas-liquid
chromatography of, 30:29
1,4:3,6-dianhydro-~-u-fructofuranosyl3,6-
anhydro-a+, preparation of, 33:255
1,6-diazido- I ,6-dideoxy-
~-o-fi'uctofuranosyl4-azido-4-deoxy-a-o-,
preparation of, 33:267
3,4-di-0-(methylsulfonyl)-p-D-
fructohanosyl4,6-diazido-4,6-
dideoxy-2,3-di-O-(methylsulfony1)-
a-u-, preparation of, 33:267
4,6-dichloro-4,6-dideoxy-a-u-
galactopyranosyl4,6-dichloro-4,6-
dideoxy-a-o-, preparation from
trehalose, 33:77
3,4-di-O-acetyl-
6-chloro-6-deoxy-~-fructofuranosyl 2,3,6-
tri-O-acetyl-4-chloro-4-deoxy-a-u-,
preparation of, 33:262
1,6-diazido-, 1,6-dideoxy-p-o-
fructofuranosy12,3,6-tri-O-acetyl-
4azIdo-4-deoxy-a-o-, preparation of,
33:267,269
1,6-dichloro- 1,6-dideoxy-p-~-
fructofuranosyl2,3,6-tri-O-acetyl-4-
chIoro-4-deoxy-a-o-, preparation of,
33:262
2,3-di-O-rnethyl-o-, preparation of, 3 0 5
2,6-di-O-methyl-u-, preparation of, 30:4-5
3,4-di-O-methyl-o-, preparation of, 30:4
ethyl 2-acetamido-2-deoxy- 1-thio-P-o-,
formation from dithioacetal, 32:67
ethyl p-D-, entropy of activation for
hydrolysis of, 22:40
L-
benzyl2,3,6-trideoxy-2-fluoro-P-
3-amino-, IH- and I9F-NMR data for,
46: 124
3-benzamido-
I3C-NMR data for, 46:171
IH- and I9F-NMR data for, 46:124
4-0-benzoyl-3-(trifluoroacetamido)-
I3C-NMR data for, 46:171
IH- and I9F-NMR data for, 46: 124
3-(trifluoroacetarnido)-, 'H- and I9F-
NMR data for, 46: 124
methyl 6-deoxy-2,3-di-O-p-~-
galactopyranosyl-a-, synthesis of,
utilization of 2-nitrobenzylidene
 SUBJECT INDEX
protecting group in, 46: 188- I 89
methyl 2,3,6-trideoxy-2-fluoro-
3-amino-P-, IH- and I9F-NMR data for,
46: 124
P-
3-amino-,13C-NMR data for, 46: I71
3-benzamid0-4-O-benzoyl-,~~C-NMR
data for, 46:171
3-(trifluoroa~etarnido)-,~~C-NMR data
for, 46: 17 1
3-benzamido-P-, 'H- and I9F-NMR data
for, 46: 125
3-benzamido-4-0-benzoyl-P-, ' H- and
I9F-NMR data for, 46:125
3-(trifluoroacetamido)-, 'H- and "F-
NMR data for, 46: 125
trifluoromethyl 3,4-di-O-acetyl-2,6-
dideoxy-a-, IH- and I9F-NMR data
for, 46: 132
methyl 2,3,-di-0-acetyl-4,6-dichloro-4,6-
dideoxy-a-o-, reaction with sodium
azide, 28:286
with tributyltin hydride, 28:303
methyl 3, 6-anhydro-a-~-,crystal structure
bibliography, 30:45 1
methyl 2-acetamido-
3,4-di-0-acetyI-2,-6-dideoxy-6-fluoro-a-
D-, preparation, 38:208
6-0-acetyl-2- deoxy-a-o-, selective
sulfation of, 3 3 5 1
methyl 2-(acetoxymercuri)-3,4,6-tri-O-
acety1-2-deoxy-P-o-, irradiation,
38: 190-1 9 1
methyl a-D-
benzoylation of, 23:250
catalytic oxidation of, 33237
4,6-dideoxy-4,6-di(thiocyanato)-,
synthesis, 44: 125
2,3,4-di-O-acety-6-deoxy-6-thiocyanato-,
44: I43
2,3-di-O-acetyl-6-deoxy-6-thio~yanato-4-
0-p-tolylsulfonyl-, 44: 143
2,3-di-O-acetyl-4,6-di( thiocyanat0)-.
44: I43
synthesis, 44: 126
2,3-di-0-benzoyl-4-deoxy-4-thiocyanato-,
44:143
2,3-di-0-benzoyl-4,6-dideoxy-4,6-
di(thiocyanat0)-, 44: 143
formation from dithioacetal, 3 2 6 8
167
hydrolysis of, trifluoroacetic acid in,
28: 17
monohydrate, crystal structure
bibliography, 30:45 1
4,6-phosphate, hydrolysis, 39:6 1
reaction with sulfuryl chloride, 33:74.251,
259
selective benzylation of, 33:57
selective chlorination with
methanesulfonyl chloride, 33:s 1
selective esterification of, 33:27-28
sulfonylation of, 23:247
methyl 4-amino-4-deoxy-a-o-, deamination
of, 31:42
methyl 3,h-anhydro-
a-D-,crystal structure bibliography,
31:359
2,4-di-O-methyl-P-~-.23:270, 24: 146
2-0-benzyl-P-o-, 24: 196
methyl 3.4-anhydro-a-o-, 25127, 145
methyl 6-azido-6-deoxy-2-0-p-tolylsulfonyl-
a+-, 24: 145
methyl P-11-
catalytic oxidation of, 33:87
crystal structure bibliography, 3k433-434
sulfonylation of, 23:248
methyl 2-benzamido-3-O-benzyi-2,4,-6-
trideoxy-4,6-difluoro-~-,preparation,
38:222
methyl 4,6-bis(acetamido)-4,6-dideoxy-a-~-,
23:155
methyl 6-bromo-h-deoxy-. a-D-, crystal
structure of, 2 5 7 3
methyl 2-chloro-2-deoxy-
a,p-o-, crystal structure bibliography,
31:366
P-D-, reaction with sulfuryl chloride,
28:235
methyl 4-chloro-4-deoxy-2,3,4-tri-O-p-
tolylsulfonyl-a-o-, 22: 183
methyl 6-chIoro-6-deoxy-2,3,4-tri-O-p-
tolylsulfonyl-a-D-, 22: 184
methyl D-
halogen derivatives of, 22:221
reaction with sulfuryl chloride, 33:74
methyl 4-deoxy-
4-iodo-2,3-di O-methyI-2,6-di-O-p-
tolylsulfonyl-a-o-, 23:268
4-iodo-2,3-di-O-methyI-6-O-p-
tOlylSUlfOtlyl-D-, 23~268
168 SUBJECT INDEX
Galactopyranosides (continued)
4-iodo-2,3-di-O-methyl6-O-p-
tolysulfonyl-a-o-, preparation of,
28:241
4-iodo-3-O-methyl-2,6-di-O-p-
tolylSulfonyl-D-,22: 185
methyl 6-deoxy-
(Y-D-,catalytic oxidation of, 33239
CY-DL-, synthesis, 40:70
2,3-di-O-methyl-4-0-(methylsulfonyl)-~-
D-, 23:270
displacement reactions of, 24: 159, 190
6-fluoro-a-o-, hydrolysis rate of, 22:208
6-iod0-3,4-O-isopropylidene-p-o,
preparation of, 28:241
CY-L-
dibenzoylation of, 33:28
3,4-phenylboronate, preparation, 3 5 4 8
selective benzylation of, 33:57
4-O-methyI-p-o-, 23:270
methyl 4,6-diazido-2,3-di-O-benzoyl-4,6-
dideoxy-o-, 24: 160, 191
methyl 4,6-dichloro-4,6-dideoxy-
CY-D-
2,3-bis(chlorosulfate), preparation of,
33:13,259
crystal structure bibliography, 31:366
2,3-cyclic sulfate, preparation of,
28~230-231
2,3-cyclic sulfate, preparation of, 73
preparation of, 33:81
2,3-di(chlorosultate), preparation of,
2 n : z 1-232
hydrogenation over Raney nickel,
28:301
preparation of, 28:238
p-D-
2,3-di(chlorosulfate). displacement
reaction, 28:234
preparation of, 33:74, 81
~-o,2,3-bis(chlorosuIfate), displacement
reactions of, 24:162
2,3-di-O-rnethyl-a-o-, preparation of,
2n:247
2,3-di-O-(methylsulfonyl)-~~-~-,
preparation of, 28:255
2,3-di-O-p-tolyh~fony~-o-, preparation
of, 33:83
2,3-di-O-p-tolysuifony1-(~-~-, 22: 183
preparation of, 28:255
3-O-methyl-o-, hydrogenation over Raney
nickel, 28:300
methyl 4,6-dideoxy-4,6-diiodo-3-O-methyl-
~-O-~-~OI~ISUI~O~~I-CY-D-, 23:268
methyl 2,4-di-O-acetyl-3,6-anhydro-o-,
rearrangement in zinc chloride-acetic
anhydnde, 26: 193
methyl 2,3-di-O-benzoyl-
(Y-D-, preparation, 3 5 5 3
4,6-di-O-p-to~ylsulfonyl-a-o-,
displacement reactions of, 24: 159
4,6-di-(thiocyano)-4,6-dideoxy-o-, 24: 160
4,6-O-benzyhdene-a-o-, irradiation, 39:92
4-O-p-tolylsulfonyl-(~-~-, inversion of,
29:5
methyl 2,3-di-O-benzyl-
CY-D-, selective benzylation of, 33:58
6-deoxy-p-o-, 23:270
6-deoxy-4-O-(methylsulfonyl)-ol-o-,
displacement reactions of, 24: 164
4,6-dideoxy-4-iodo-a-~-
displacement reactions of, 24: 160
reaction with radioactive iodine, 28:
229
6-O-(methylsulfonyl)-a-o-, displacement
reaction of, 24: 174
6-O-(methylsulfonyl)-p-~-, solvolysis of,
24: 196
methyl 2,3-di-O-methyl-
p-D-, 23:270
p-D-,
4,6-di-O-(methylsulfonyl)
displacement reactions of, 24: 159,
190
4-O-(methylsulfonyl)-6-O-trityl-a-o-,
fluorination, 38:220
6-O-p-to~ylsu~fonyk~-o-, 23:240
reaction with methyl-
triphenoxyphosphonium iodide,
28:241
6-O-p-tolylsulfonyl-P-~-,23:240
methyl 2,6-di-O-(rnethylsulfonyl)-~~-o-,
23:247
methyl 3,6-di-O-(methylsulfonyl)-~-~-,
23:248
methyl 2,6-di-O-p-tolylsulfonyl-a-~-,
displacement reaction of, 24: 145
methyl 2,5-di-O-p-tolylsulfonyl-6-O-trityl-~-
D-, 23:244
methyl exo-3,4-O-ethylidene-P-~-, crystal
structure bibliography, 37:38 1
 SUBJECT INDEX
methyl 6-O-acetyI-p-o-, crystal structure
bibliography, 32:381,37:382
methyl 6-O-benzoyl-a-o-, synthesis, 39:29
methyl 4,6-0-benzylidene-
(Y-D-
hydrogenolysis regioselectivity, 39:
125
reaction with N-bromosuccinimide,
39:99
selective acylation of, 33:21
synthesis, 39:78
p-0-
reaction with N-bromosuccinimide,
39: 100
selective acylation of, 33:21
selective oxidation with chromium
trioxide, 33:98
2-C-(dicarbethoxymethyl)-2,3-dideoxy-3-
nitro-o-, 24: 137
3-deoxy-3-nitro-P-o-, reaction with basic
aluminum oxide, 24: 113
2,3-di-O-p-to~yhlfonyI-o-,23:25 1
2,3-O-rnethylene-o-, proton magnetic
resonance spectroscopy of, 27:66
2p-tol)lSUlfOllyl-D-,2 3 ~ 2 15
3p-tolylsulfonyl- D-, 23:25 I
methyl 3,4-O-isopropylidene-p-~-
reaction with
methyltriphenoxyphosphonium
iodide, 28:241
selective iodination with methyltri-
phenoxyphosphonium iodide, 33:77
methyl 2,3,4,6-tetrakis(acetamido)-2.3,4,6-
tetradeoxy-a-D-, 23: 187
methyl tetra-0-benzoyl-a+-, selective
deacylation, 39:29
methyl 2,3,4,6-tetra-O-benzoyl-o-, 24: 160
methyl tetra-0-methyl-cu-D-, mass spectrum
of, 21:61
methyl 3,4,6-trideoxy-3,4-epimino-a-i--,
23:278
methyl 2,3,6-tri(rnethylsulfonyl)-~~-~-~
23:24712
methyl 2,3,4-tr-O-acetyl-6-deoxy-6-iodo-
thio-a-o-, reaction with sodium nitrite,
28:282
methyl 2,4,6-tri-O-acetyl-3-deoxy-3-nitro-~.
D-, dehydroacetylation of, 24: 129
methyl 2,3,4-tri-O-benzoyl-6-bromo-6-
deoxy-pa-, synthesis, 39: 100
169
methyl 2,3.6-tri-O-benzoyl-4-0-
(methylsulfony1)-u-D(and P-D)-%
displacement reactions of, 24: 159
methyl tri-0-methyl-o-, gas-liquid
chromatography of acetates of, 30:26
methyl 2,3 4-tri-O-methyl-6-O-p-
tolylsulfonyl-a-o-, displacement
reactions of, 24: 144
2-0-methyl-o-, preparation of, 30:4
3-O-rnethyl-o-, in leaves, gas-liquid
chromatography of as nitrile, 30:33
trimethylsilyl ether and gas-liquid
chromatography of, 30:28
0-nitrophenyl p-D-
6-phosphate, preparation, 39:63
reaction with phospboryl chloride-
trimethyl phosphate, 33:46
phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-
(Y-D-, hydrogenolysis regioselectivity,
39: 129
p-D-,hydrogenolysis regioselectivity,
39:129
pheny14,6-O-benzylidene-P-o-,
benzoylation of, 33:21
p-nitrophenyl, (Y-D-and p-o-, 42:390
t ,3,4,6-tetra-0-acetyl-p-~-fructofuranosy1
2,3 -di-O-acetyl-4,6-dichloro-4,6-dideoxy-
(Y-D-, preparation of, 33:263
2,3,4,6-tetra-O-acetyl-a-o-, nuclear
magnetic resonance spectra and
structure of, 33:275
2,3,4,6-tetra-O-methyl-o-, acetate, gas-liquid
chromatography of, 30:29
trimethylsilyl ether and gas-liquid
chromatography of, 30:29
Galactopyranosid]uronate, methyl [methyl 2,3-
di-O-benzyl-4-O-(methylsulfonyl)-a-~-,
conformation of, 29:262
Galactopyranosiduronic acid
cholesterol 2,3,4-tri-0-acetyl-a-~-,methyl
ester, preparation, 36:93
ergosterol 2,3,4-tri-O-acetyl (Y-D-. methyl
ester, preparation, 36:93
methyl CY-D-, methyl ester, benzoylation of,
33:30
methyl p-D-, acid-catalyzed hydrolysis,
36:84
methyl D-, methyl ester, preparation, 36:74
methyl methyl, reaction with sodium
methoxide in methanol, 28:206
170 SUBJECT INDEX
Galactopyranosiduronic acid (continued)
p-nitrophenyl a-and p-D-,preparation,
36:7 1
sitosterol2,3,4-tri-O-acetyI-a-~-,methyl
ester, preparation, 36:93
Galactopyranosyl
amine, N-acetyl-D-, oxidation and
configuration of, 31:103, 105
O-2-acetamido-2-deoxy-a-~-, linkage with
amino acids, 2 5 4 2 5 4 3 4
2,4,6-tri-0-acetyl-2-deoxy-2-fluoro-a-o-,
48: 175
Galactopyranosyl benzothiazole, 2-(tetra-O-
acetyl-l -bromo-p-D-, synthesis, 49:60
Galactopyranosyl bromide
L-, 4-0-benzoyl-2,3,6-trideoxy-2-fluoro-3-
trifluoroacetamido)-a-, 'H- and I9F-
NMR data for, 46: 125
2,3,4,6-tetra-@acetyl-a-o-, reaction with
trimethylamine and anhydridization,
34:32
tri-O-acetyl-6-bromo-6-deoxy-a-~-,
22:181
Galactopyranosyl bromide uronic acid, 2,3,4-
tri-0-acetyl-a-o-, methyl ester,
preparation, 36:65
Galactopyranosyl chloride
D-, methyl 2,4-di-0-benzoyl-6-0-
(bromoacetyl)-3-deoxy-3-fluoro-0~-,
I'C-NMR data for, 46: 172
4,6-dichloro-4,6-dideoxy-~-,2,3-
di(chlorosulfate), preparation of,
28:235
tetra-0-acetyl-
OL-D-,acetoxonium salt, 26: 160
p-D-,acetoxonium salt, 26:160-161
Galactopyranosyl chloride uronic acid, 2,3,4-
tri-0-acetyl-a-o-, methyl ester,
preparation, 36:65
Galactopyranosyl cyanide, 2,3,4,6-tetra-O-
acetyl-P-o-, crystal structure bibliography,
31:396
Galactopyranosyh-arabinitol, 3-0-p-o-, taste
properties, 45275
Galactopyranosyi-o-erythritol, ~-O-OL-D-, taste
properties, 45275
Galactopyranosyl dipotassium phosphate, 6-
deoxy-6-fluoro-a-o-, preparation, 38:245
Galactopyranosyl fluoride
2-bromo-2-deoxy-a-o-, preparation, 38:235
2-deoxy-2-fluoro-o-
01 anomer, 'H- and I9F-NMR data for,
46: I46
3,4,6-tri-O-acetyI-, IH- and I'F-NMR data
for, 46: I46
2,6-dideoxy-2-fluoro-
a - ~ -48:176
,
L-
anomer, ')I-and I9F-NMR data for,
(Y
46: 153
3,4-di-O-acetyl-, 'H- and I9F-NMR data
for, 46: 153
peracetyl-4-deoxy-4-fluoro-
OL-D-,synthesis, 38:204
p-D-, synthesis, 38:204
2,3,4,6-tetra-O-acetyi-~-
OL anomer, I3C-NMR data for, 46: 160
p anomer, I3C-NMR data for, 46:160
IH- and "F-NMR data for, 46:82
3,4,6-trideoxy-3,4,6-trifluoro-a-o-
I3C-NMR data for, 46:177
IH- and I9F-NMR data for, 46: 158
3,4,6-tn-0-acetyl-2-deoxy-o-
2-bromo-, IH- and I9F-NMR data for,
46: I29
2-1odo-, 'H- and I9F-NMR data for,
46: 129
2,3,6-tn-0-acety~-4-deoxy-4-fluoro-o-
a anomer, 'H- and 19F-NMR data for,
46: I48
p anomer, 'H- and I9F-NMR data for,
46: 148
Galactopyranosyl glycerol, 2 - 0 - a - ~ -taste
,
properties, 45:275
Galactopyranosyl isothiocyanate, 2,3,4,6-tetra-
0-acetyl-p-o-, 44: 141
Galactopyranosyl-L-serine, 3-0-2-Acetamido-
2-deoxy-a-o-, 43:5
Galactopyranosyl-L-threonine,3-0-2-
acetamido-2-deoxy-a-~-,43:5
Galactopyranosyl- 1,4-oxidiazole, 5-methyl-2-
tetra-0-acetyl- 1-bromo-p-o-, synthesis,
49:59
Galactopyranosyluronic acid, WD-
ester with uridine 5 '-pyrophosphate, enzymic
preparation of, 28:343
isolation of, 28:326
methyl ester, ester with uridine 5'-
pyrophosphate, preparation of, 28:355
D-Galactopyranuronate, diaxial and
 SUBJECT INDEX
axial-equatorial processes in p-
elimination, 29:25&265
Galactopyranuronic acid
a-D-
calcium sodium salt hexahydrate, crystal
structure bibliography, 34:347
sodium strontium salt hexahydrate, crystal
structure bibliography, 34:348
circular dichroism. 45: 109-1 10
u-, methyl ester, and pectinesterase activity,
33:329
1,2,3,4-tetra-O-acetyl-p-~-, methyl ester,
crystal structure bibliography, 34:360
L-Galactosaccharinic acid, a-and p-, formation
from L-, 28: 195
D-Galactosamine, see Galactose, 2-amino-2-
deoxy-o-
Galactosamine trichloroacetimidates
glycosylation, 50:98-102
as glycosyl donors, 50534, 92-1 02
Galactosaminidase, endo-N-acetyl-a-u-. 44:240
Galactosan, D-, polymerization of, 21:483
Galactose
4,5,6-tri-O-benzoyl-o-, diethyl dithioacetal.
2,3-di-O-methyI-o- galactose from,
32:65
preparation of, 32:45
3,6-anhydro-2,4.5-tri-O-methyl-~-, diinethyl
acetal and dithioacetal, mass spectra of,
29:74-75
2-acetamido-2-deoxy-
a-D-,crystal structure bibliography.
32:361
U-, 24:134,47:186-187
diethyl dithioacetal, partial
demercaptalation of, 32:66
ester of thymidine 5-pyprophosphate,
and epimer, 28:323
in glycopeptides, 25:433
protein linkage with, 25:418
lectins, 35:22&254
nitrosation of, 31:67
3-O-~-~-galactopyranosyl-u-, 24:425
5-thio-u-, composition in aqueous
solution, 42:52-53
1 -O-acetyl-2,3,5,6-tetra-O-benzoyl-4-bromo-
p-D-,synthesis, 49:49
acyl migration in esters, 30:4
a-D-
crystallography of, 25:6 1
171
mutarotation of, 23:20-2 I , 23
sweetness, effect of infrared hydroxyl
absorption bands and hydrogen-
bonding strength, 45:2 16-2 17
aldehydo-n-
acetate, 26:8
pentaacetatc, aldehydrol, and hemiacetal,
23:25
aldehydo-ui.-.aldehydrol heptaacetate,
26: 192
2-amino-2-deoxy-u-. 24: 1 12.208
composition in aqueous solution, 42:47,
67
deamination of, 25: 186,31:25
determination of, 25:2 16
in glycoproteins. 25:413
decarboxylation of, 28: I87
dehydration in acid solution, 28: I82
derivatives, 24: 161
gas-liquid chromatography of, 28:78-79
in glycoprotein of urine, 24:441442
microdetermination of, 31:26
polysaccharides containing, 23:402
3-amino-3-deoxy-o-, 22: 132
4-amino-4-deoxy-o-, composition in aqueous
solution. 42:49
6-amino-6-deoxy-~-,24: 147
6-amino-6-dcoxy-l,2:3,4-di-O-
isopropyhdene-D-, 23:235
deamination of, 31:51
4-amino-4,6-dideoxy-o-, 23: 155, 24: 160
4,5-anhydro-u-, formation of, 31:3 1
I .6-anhydro-
2-O-benzoyl-3,4-O-isopropylidene-~-11-,
photobromination, 49:53-54
D-, formation of, 34:36
3,4-0-isopropylidene-i,-,22:4
3,6-anhydro-
D-, 24:321,25:140
in agar-agar, 22:4
composition in aqueous solution, 42:58
dithioacetals, hydrolysis of, 32:64
mass spectra of derivatives of, 29:74
hydrazones, 23:266
L-
in agar, 25:6
mass spectra of derivatives of, 29:74
polarography of, 29: 142
(4-O-~-o-galactopyranosyl)-,dimethyl
acetal, 24:280
172 SUBJECT INDEX
Galactose (continued)
24:277
4-O-(p-~-galactopyranosyl)-~,-,
p-0-
crystallography of, 2 5 6 1
mutarotation of, 23:20, 23
4,7-O-benzylidene-P-o~-carba-,
synthesis,
48~60-61
configuration of, 21: 15
D-, 48:282
absorptive rate by human jejunum, 34:289
acetonation of, 34: 185
derivatives, cyclic acetals, Table,
34:224-227
pyrolysis of, 34:185
acyloxonium rearrangement of, 26: 159
anomers, correlation between CH
orientation and vibrational
frequencies observed, 44:2 1
in aqueous solution, 42:16
composition, 42:26,28, 31, 63
polarimetry, 42: 17
ascorbic acid synthesis, 37: 146
occurrence in plant kingdom,
37:284-289
radiation chemistry, 37:33
toxicity, 37:342-345
cx and p pyranose anomers, circular
dichroism, 4579-80
catabolism by yeasts, 32:232
catalytic oxidation of, 33237
diethyl dithioacetal, selective
benzoylation of, 33:41
dithioacetals, selective esterification of,
33:40
selective methylation of, 3 3 6 6
reaction with (methoxycarbonyl-
methylene)triphenylphosphorane,
33: 154
with sulfuryl chloride, 33:76
selective oxidation with silver
carbonate-on-Celite, 33:97
C-C and C-0 bond-lengths in, 44: 15
complex with germanic acid, 22:288
composition in nonaqueous solvents,
42:68
dialkyl dithioacetals, reaction with
sulfonyl chlorides, 32:49
dibenzyl dithioacetal
reaction with mercury(I1) chloride in
methanol, 32:68
sulfonylation of, 24: 175
effect of mutarotase on mutarotation of,
24:3 1
in glycoprotein of urine, 24:441,443
mutarotation of, 24: 15
3-sulate, 24:404
diethyl dithioacetal
hydrogenolysis of, 32:77
methylation of, 32:47
oxidation of, 32:8&82
partial demercaptalation of, 32:66
preparation of, 32:2 1
reaction with tert-butyl vinyl ether,
32:54
irradiation, 39:94
utilization by yeasts, oxygen
requirement, 39:397401
photolysis, 38: 151-152
dimethyl acetal
hydrolysis of, 22: 1 13
preparation of, 32:65
o-tagatose from, 31:71
o-talose from, by acyloxonium
rearrangement, 26: 161
in endosperm during germination, 35357
enzymes of pathway in yeasts, 32: 176
publications, 32: 178-1 79
enzymic phosphorylation of, 32:9
gas-liquid chromatography of,in blood,
28:46
methanolysis of, 28: 19
mutarotation and gas-liquid
chromatography of, 28:40-41
gel chromatography of, 2 5 3 1
in glycoenzymes, 27:302,307, 321
in glycoproteins, 25:413
halogen derivatives of, 22:220
in honey, 25:290
intramolecular hydrogen bonding in,
4 5 2 16-2 17
lectins, 35:254-277
liquid chromatography analysis, 46:55
mercaptalation of, 32:21
mutarotation of, 23:12, 16
nonselective spin-lattice relaxation rates,
45: 148, 150
pernicotinate, ammonolysis of, 31539
polarography and reactions with
hydrazine, semicarbazide, and
hydroxylamine, 29: 152
 SUBJECT INDEX I73

protein linkage with, 25:418 4-O-methyl-o-, 23:270

proton spin-lattice relaxation rates.
45: 150-1 5 I
pyrophosphate ester in red alga, 32:9
solubility in liquid ammonia, 27:91
in methanol, 27:97
in methanol, effect of calcium chloride
on, 27:95
in tnchloroacetonitrile, 27: 1 I3
sweetness, 45220
transport into Saccharomyces cerevisiae,
32: I53
trimethylsilyl ethers, mutarotation of,
42:22
uridine 5'-pyrophosphate ester, in mung
bean, 32:9
utilization by yeasts, 32:17&177,
224225
2-deoxy-, 2-flUOrO-D-, 48: I3 1
labeled, 48: 192-1 94, 198
metabolism, 48:207
preparation, 38:23 1
3-deoxy-
3,4-C-(dichloromethylene)-1,2:5.6-di-0-
isopropylidene-a-o-, 24:247
1,2:5,6-di-O-isopropylidene-3,4-C-
methylene-a-D-, 24:247
3-fluoro-o-, preparation, 38:222
4-deoxy-, 6-fluoro-o-, preparation. 38:220
6-deoxy-
a-L-
1,2:3,4-bis(phenylboronate),preparation
of, 35:45
mutarotation of, 23:23
composition
in aqueous solution, 42:63
in methanol, 42:68
D-, 21~176
6,6-difluoro-o-, 48: 152
2,4-dimethyl-o-, 23:270
6-flUOrO-D-, 22: 179
enzyme activity and, 22:211
preparation, 38:207
6-hydrazino- 1,2:3,4-di-O-isopropylidene-
D-, 23:235
6-iod0-2,3:4,5-di-0-isopropylidene-u-,
diethyl and dibenzyl dithioacetsls,
preparation of, 28:242
L-, see Fucose, L-
diethyl dithioacetal, oxidation of. 32:85
4,5-O-isopropylidene-o-, dibenzyl
dithioacetal, digitalose from, 3 2 6 5
in protein-carbohydrate compounds of
urine, 24:442443,450
determination of enantiomeric form, 4 6 6 6
2,3-diamino-2,3-dideoxy-o-, 24:135
2,6-diamino-2,6-dideoxy-o-, 22: 136
4,6-diamino-4,6-dideoxy-~-, composition in
aqueous solution, 42:52
4,6-dideoxy-
4-dimethylamino-o-, 24: 160
4-[(R)-3-hydroxybutanamido]-~-.
47: 175-1 76
4-methylamino-o-, 24: 160
3,6-dideoxy-3-( r-glyceroylamino)-D-,
47:175-176
I ,2:3,4-di-O-isopropylidene-
D-, 23:269
oxidation of, 22:4
preparation of, 34: 185
6-O-p-tolylsulfonyl-cu-o-,hydrolysis of,
34:204
6-O-p-tolylsulonyl-o-, displacement
reaction of, 24: 143
1,2:5,6-di-O-isopropylidene-, D-, selective
hydrolysis, 39:15
2,3:4,5-di-O-isopropylidene,-u-, diethyl and
dibenzyl dithioacetals, reactions with
methyltriphenoxyphosphonium iodide,
28:242
2,3-di-O-methyl-o-
composition
in aqueous solution, 42:4344
in nonaqueous solution, 4 2 6 1
preparation of, 32:65
2,4-di-O-methyl-3-0-(2,3,4-tri-O-rnethyl-~-
glucopyranosyluronic acid)-o-, from
mesquite gum, 24:349
DL-,synthesis, 40:93
0-galactosyl, 21:3 1
y-D-. gas-liquid chromatography of, 28:40
0-glucosyl-, 21:31
I , 1,2,3,4,5,h-hepta-O-acteyl-aldehydo-~1.-,
22:205
4,7-~-isopropylIdene-a-o~-carba-, synthesis,
48:60-61
L-
ascorbic acid synthesis, 37: 146
residue in plant polysaccharides, 24:369
174 SUBJECT INDEX
Galactose (continued)
6-sulfate, 25: 10
liquid chromatography, 42:23-24,46:33,
52-5 3
methylation analyses of, 30: 19
methyl ethers, 30:6
Of D-, 6: I 1-25,10:273-282
periodate oxidation and gas-liquid
chromatography of, 30:34
methyl glycosides of oligosaccharides
containing, ' T - N M R data for,
42:2 12-2 13
3-0-(2-acetamido-2-deoxy-a-u-
galactopyranosyl)-2-0-a-~-
fucopyranosyl-u-, synthesis, 40: 127
~-O-(Y-D-, glucopyranosyl-o-, preparation of,
34:263
6-0-a-o-, glucopyranosyl-o-, preparation of,
34:263
4-O-(a-o-galactopyranosyluronic acid)+,
24:366
2-O-a-~-fucopyranosyl-o-,synthesis, 39:
296
0-a-L-rhamnopyranosyl-(1+2)-[0-P-D-glU-
copyranosyl-( 1+3)-~-, see Solatriose
4-0-p-o-, galactopyranosyl-o-, synthesis,
41:9
3-O-P-o-galactopyranosyl-o-, 24:355
synthesis, 41:9
6-0-P-o-galactopyranosyl-o-, 24:355
0-P-o-galactopyranosyl-(1+6)-0-P-u-
galactopyranosyl-( 1+4)-u-, 24:376
3-04P-o-galactopyranosy~uronic acid)+,
24:353
3,0-P-~-galacto~yl-~-, 25:34
6-~-(~-o-g~ucopyranosy~uronic acid)+,
24~350,354,359-360
from Acacia gums, 24:345-346
3-0-( P-o-glucosyluronic acid)+-, 2 5 3 4
0-P-o-xylopyranosyl-( 1+3)-[O-P-o-
glucopyranosyl-( 1+2)-[0-P-o-
glucopyranosyl-( 1+4)-o-, see
Lycotetraose
6-0-benzoyl-u-, dimethyl dithioacetal,
reaction with benzaldehyde, 32:54
6-0-benzyl- 1,2:3,4-di-O-isopropylidene-a-
D-, methanolysis of, 34:206
O-o-galactopyranosyl-
(1-+4)-3,6-anhydro-~-,polarography of,
29: 142
( 1+2)-0-a-o-galactopyranosyluronic
acid- (1+4)-o-, 24:367
5,6-0-ethylidene-o-, diethyl dithioacetal,
mass spectrometry of, 32:96
preparation of, 32:5&55
1,2-~-isopropylidene-a-~-, preparation of,
34: 188
4,5-0-isopropylidene-u-
diethyl dithioacetal, dimethyl acetal from,
32:65
dithioacetals, demercaptalation of, 32:64
preparation of, 3 2 5 4
3,4-0-isopropylidene-6-0-methyl-~-,
preparation of, 34: 186
0-L-rhamnopyranosyl-( 1+4)-O-o-
glucopyranosyl-( 1+6)-D-, 24:35 1
6-O-methyl-o-, isolation of, 35:7
6-0-( methylsulfonyl)-o-, hydrozones,
23:265
O-(N-acetylneuraminic acid)-(2+3)-a-o,
24:425
4-0-(4-0-methyl-a-u-glucopyranosyluronic
acid)-o-, 24:364
from mesquite gum, 24:349-350
6-O-(4-0-methyl-~-o-glucopyranosyluronic
acid)+-, 24:359-360
from mesquite gum, 24:349
6-O-p-tolylsulfonyl-, D-
hydrozones, 23:265
mercaptalation of, 32:28,49
6-0-p-tolylsulfonyl-
a-D-,23:261
P-D-, 23:261
in pectic polysaccharides, 42:277-278
2,3,4,5,6-penta-O-acetyl-o-
diethyl dithioacetal, dimethyl acetal from,
32:65
reactions with halogen compounds,
32:7 1
ethyl methyl and benzothiazolyl ethyl
dithioacetals, ethyl
pseudothiouronium salt, and ethyl
dithiohemiacetal, preparation of,
32:43
penta-0-acetyl-o-, structure of cyclic
isomers, 32:4
1,2,3,4,6-penta-O-benzoyl-o, ammonolysis,
39:31
2,3,4,5,6-penta-O-methyl-aldehydo-o-,
preparation of, 32:62
 SUBJECT INDEX
polarography of, 29:127
pseudo-a-o-, occurrence of, 42:116
relation to rhamnose, 21: 16
6-sulfonates, displacement reactions of,
24: 143
2,3,4,6-tetraamino-2,3,4,6-tetradeoxy-n-,
24:147, 160
2,3,4,6-tetra-O-
acetyl-
6-deoxy-6-iodo-aldehydo-o-,
rearrangement in zinc chloride-acetic
anhydride, 26: 192
6-deoxy-6-iodo-o-, diethyl dithioacetal, a-o-Galactosidase B, 40:279-280
hydrogenolysis by Raney nickel,
32:76
6-deoxy-h-thio-o-, diethyl dithioacetal,
hydrogenolysis of, 32:63
6-O-p-tolylsulfonyl-aldehydo-o-,
rearrangement in zinc chloride-acetic
anhydride, 26: 192
6-S-acetyl-6-thio-o-, diethyl
dithioacetal, hydrogenolysis by
Raney nickel, 32:76
benzyl-o- synthesis, 39:50
tetra-O-benzoyl-6-bromo-6-deoxy-n-. diethyl
dithioacetal, 22: 181
6-thio-o-, derivatives, 24: 147
thio linkage to cysteine, 43:4647
trimethylsilyl ethers of methylated.
gas-liquid chromatography of, 30:28
2,4,5-tri-O-acetyl-3-6-anhydro-~-,dimethyl
acetal and dithioacetal, mass spectra of,
29:75
UDP-D-, in polysaccharide biosynthesis,
42:322, 33 1
Galactose antibodies, 53:2 18-2 19
D-Galactose dehydrogenase, 44:232
D-GalaCtoSe diethyl dithioacetal, photochemical
decomposition of, 46: 197
D-(;akiCtoSe oxidase, 44: 186, 234
Galactose pentaacetate, p-D-,proton
spin-lattice relaxation, 45: 157
Galactoseptanose
5-0-acetyl- 1,2:3,4-di-O-isopropylidene-a-o-. 4,6-dideoxy-4,6-difluoro-o-, 48: 137
crystal structure, 43:237-238
pentaacetyl-6-thio-aY-o-,23:230
penta-O-acetlyI-6-thio-u-, 23:230
2,3,4,5-tetra-O-
acetyl-o-, preparation of, 32:63
methlyl-6-thio-o-, 23:230
I75
Galactoseptanoside
methyl 2,3.4,5-tetra-O-acetyl-a-~-,
preparation of, 34:283
methyl 6-thio-a-o-, and-P-D-, derivatives,
preparation of, 34:283
Galactoseptanosyl chloride, 2,3,4,5-tetra-O-
acetlyI-6-thio-a-o-, 23:230
Galactose-4-1, 24:247
D-, preparation of, 27: 136
Galactosioase, 2-acetamido-2-deoxy-a-~-,in
glycoprotein structure determination, 33:7
a-o-Galactosidase A, 40:279-280
Galactosidases, 16:239-298
p-D-,39:394-397,42:383-384.44: 154, 186,
202,208-209,247
acidic and neutral, 40:274-276
from Corticium rolfiii, 32:285
in plant cell-walls, 42:30 I-302,373-377
purification by affinity chromatography,
39:442
in yeasts, purification and molecular
weight of, 32:208-209
in carbohydrate degradations, 38:4 13
a-D-, 39:375-378,44: 165- 167
Aspergillus n iger, 44: 22 9-2 30
for biodegradative hydrolysis of
galactomannans, 31 :256
in galactoniannan degradation during
germination of seeds, 35:362-366
molecular weight of, 32:205
multimolecular forms, 35:365
in plant cell-walls, 42:301, 376
in Saccharomyces. 32:205--208
specificity, 35:364
endo-p-n-, 44: 148,216, 240-242,408
a-D-Galactaside galactohydrolase, in
galactomannan degradation, 35:362
Galactosides
D-, of glycerol, 37:36&362
of polyols, 37:3 12-322
of sucrose, 37:289-3 1 1
4-deoxy-4-fluoro-o-, 48: 137
ethyl a-D-
isolation and properties, 37:320
in soybean extracts, 2 8 5 4
mass spectrometry of, 30:38
methyl 3-acetamido-2-(methylsulfonyl)-~-,
22: I29
176 SUBJECT INDEX
Galactosides (continued)
methyl a-D-,selective periodate oxidation of,
33:95
methyl 4-amin0-4,6-dideoxy-o-, 23: 154
methyl 3,6-anhydro-~-,synthesis of, 2 2 4
methyl-p-D-, C-C and C-0 bond-lengths in,
44: 15
methyl 6-bromo-6-deoxy-u-o-, crystal
structure bibliography, 31:366
rnetnyl3,4-anhydro-6-deoxy-P-o-, 22: 179
2-0-acetyI-l,6-anhydro-P-o~-, synthesis,
40:55
p-aminophenyl p-D-, synthesis, 39:42 1 4 2 2
refractive index and specific rotation of, 30:4
a-o-Galactosidic linkages, biochemistry of, in
plant kingdom, 37:283-372
Galactosiduronic acid
a-D-,methyl, methyl ester hydrate, crystal
structure bibliography, 34:372
methyl D-, preparation, 39:3,5
Galactosyl, 2-acetamido-2,6-dideoxy-~-,
glycosidic linkages, 47: 188
Galactosylamine, N-@romoacetyl)-P-D-,
48:315-376
Galactosylation, with transferases, 49:2 19-
224
Galactosylceramide
biosynthesis, 40:247-248
catabolism, 40:274
glycosphingolipids, 40:238
isolation, 40:238
Galactosylceramide sulfate sulfatase, activator
for enzymic hydrolysis, 40:281,283
Galactosyl chloride, 3,4,6-tri-O-acetyI-2-deoxy-
2-nitroso-a-o-, 24:207
D-GalaCtOSyl di- and tri-saccharides,
48:2 18-220
P-o-Galactosylmethyl carbenium ion,
formation, 48:373-374
~-~-Galactosylmethyl-4-(nitrophenyl)tnazene,
48~373-374
Galactosyl phosphate, 2-amino-2-deoxy-a-o-,
monohydrate, crystal structure,
4 3 ~ 17-2
2 18
Galactosyltransferase, 49:220-22 1
a-,40:249,252
4-p-, 44:202
p-D-,40:248
D-, 44:203,371
UDP-, 44~244
0-Galactosyl trichloroacetimidates
acetylated, glycosylation with, 5053, 56-57
benzylated, glycosidation, 50:53-55
as donors, 50:49, 52-59
glycosylation with sphingosine derivatives,
50:58-59
synthesis, 5052-53
Galactosyluronic residues in plant cell-wall
polysaccharides, 42:280
Galacturonic acid
Ci-D-
calcium salt, tetrahydrate, crystal structure
bibliography, 32:380
calcium sodium salt, hexahydrate, crystal
structure bibliography, 32380
D-
enzymic phosphorylation of, 32:9
mercaptalation of, 32:26
methyl ester, dimethyl dithioacetal,
reaction with benzaldehyde, 32:54
2,3:4,5-di-O-benzylidene-o-, methyl ester
dithioacetals, reduction of, 32:55
2,3,4,5-tetra-O-acetyyl-~-,methyl ester,
preparation of, 32:6243
Galacturonamide, 2-acetamido-2-deoxy-~-,
47: 177-178
Galacturonan, 44: 182
D-, metabolism by pseudomonad enzyme,
and p-eliminative degradation,
29:247-249
from plant cell-walls, 44:359
Galacturonanases
D-
action pattern and specificity of,
33:345-359
assay of, 33:365-367
definition, 33:327
molecular weight of, 33:346
occurrence and formation of, 33:359-362
purification of, 33:362-364
effect on plant cell-walls, 42346-347,
369-372,376377,381
endo-a-( 1+4), in primary plant cell-wall
fractionation, 42:270,275
endo-( I+~)-c~-D-, 44: 183-1 84
exo-o-
action pattern of, 33:354-359
assay of, 33:366
definition, 33:327
occurrence and formation of, 33:359-362
 SUBJECT INDEX
purification of, 33:364
Galacturonans
biosynthesis of, 26:399402
in cell walls, 26:298,300, 337,348
crystallography of, 22:480
D-
enzymic degradation by lyase, 33:378
pectinesterase specificity for, 33:329, 334
in plant cell-walls
in ripening, 42:372,374
role in structure, 42:305
Galacturonic acid
acid hydrolysis of, correction factors, 46:254
01-D-, calcium sodium salt hexahydrate,
crystal structure bibliography, 37:377 n-Galactosyltransferase, glycoside synthesis,
aldehvdo-D-,tetraacetate methyl ester ethyl
hemiacetal, 23:25
antibodies, 53:227,229
n-
circular dichroism, 45: 102-103
decarboxylation of, 28: 187
degradation, 39:4
diethyl dithioacetal, synthesis, 3 9 5 a-D-Galp group, 47: 157
isolation, 39:3
dehydration of, 28:188-189
electro-oxidation of, 29: 1 17
gas-liquid chromatography of, 28:64
isomerization and gas-liquid
chromatography of, 28:40
in L-ascorbic acid synthesis, 37: 146- 148
mass spectrometry of trirnethylsilyl
isomerization products, 30:38
methyl ester, preparation, 36:74
methyl-'4c ester, preparation, 36:65
in mosses, 46:324
mutarotation kinetics, 2 3 5 7
phenols from, 46:290
preparation of crystalline, 39:4
DI--, crystalline, isolation, 39:4
L.-, preparation of crystalline, 39:4
4-0-(a-o-galactopyranosyluronic acid)+,
24:361,364
3-O-(~-o-glucopyranosyluronic acid)-[)-.
24:366
3-0-( P-D-xylopyranosyl-o-, 24:362
4-0-(4-deoxy-P-~-threo-hex-4-enosyluronic
acid)+-, 26~400
oligosaccharides, plant cell-wall, f.a.b.-mass
spectrometry, 4566-67
in pectic polysaccharides, 42:277-278.28 I
177
tetra-0-acetyl-aldehydo-D-, methyl ester
ethyl hemiacetal, isolation. 3 9 3
synthesis, 39:5
treated with trifluoroacetic acid. recoveries
of, 46:261-262
UDP-, in polysaccharide biosynthesis,
42:33 I
UDP-D-, in poly(ga1acturonic acid)
biosynthesis. 42:321
in xylans, 363236-237
Galacturonorhamnan, 24:37 1
Galacturonorhamnan polysaccharides, see
Polysaccharides
P-D-Galatosidase. production of, 30:263
39:430
P-u-Galf-( I-+5)-D-GaK 50: 180-1 8 1
Gallic acid. tri-0-methyl-, esters of methyl OI-D-
glucopyranoside, 33:43
Gallotannins, 21:26
3-0-a-D-Gal-L-Ser, Gd3' and Mn2+effect,
47: 15 1-1 54
3-O-a-u-GalpNAcC-~--Ser, Gd" and MnZ'
effect, 47:151-154
Gamma-ray irradiation
cereals, 51:29&291
effects on saccharides, 52: 17
saccharides. 47:276
starch modification by, 51:245-247,
267-290
carbonyl compounds as function of,
51:268-269
degree of depolymerization. 51:272, 275
effect on
reducing power and viscosity,
51 ~286-287
shear and molecular weight,
51:286-287
ESR spectra and water content,
51:283-285
formic acid and total acidity as function
of, 51:270
gaseous product, 51:276
glycolaldehyde concentration, 51:280-
28 1
hydrogen peroxide, 51:276-277
induced acidity, 51:269,272,275
induced hydrogen peroxide as function of
water content, 51:270
178 SUBJECT INDEX
Gamma-ray irradiation (continued)
mass as function of amylose content,
51:268
nitrogen-containing components, 51:276
peak-to-peak widths, 51:284
polymer bond splitting, 51:276
properties, 51:245-246
radiodecomposition products, 51:278-279
radioproduct yield, 51:289
shear-humidity relationships, 51:288
solvent composition effect on radiative
depolymerization, 51:289-290
water-soluble dextrins as function of water
content, 51:27 1
weak versus strong irradiation, 51:272
gA myeloma protein, carbohydrate-peptide
linkage in, 25442,445
Ganglio-N-biose-I, 24:425
Ganglio-N-tetraose, 2423,423
Gangliosides, 24:383,4 13433,44:388-390
acetolysis of, 31:199
acid hydrolysis of, 31:190
asialo GMl, biosynthesis, 40:259,263
catabolism, 40:27&276
asialo GM2, biosynthesis, 40:259,263
catabolism, 40:276-279
biosynthesis, 26:442450,40:253-265
deficiency disease, 40:265-266
transient intermediate, 40:264
brain, 24%
"C-NMR data for, 4 2 2 2 6 2 2 5
definition, 40:237
degradation by sialidase, 40:27 1-274
discovery, 40:235
of erythrocytes and spleen, 24:432
f.a.b.-mass spectrometry, 4555-56
gas-liquid chromatography, 28:84, 87
and mass spectra of, 30:38
GD1, biosynthesis, 40:260,263
GD2, biosynthesis, 40:256-257,262
GD3, biosynthesis, 40:256255,262
GDla, biosynthesis, 40:258,261
GDlb, biosynthesis, 40:257-258,262
G, 24:423
GI,, 24:427
G, 24:427
GI, 24:427,429
GM1, biosynthesis, 40:257-258, 261,263
catabolism, 40:27&276
sialidase action, 40:272
GM2, biosynthesis, 40:255-257,261
catabolism, 40:276-279
sialidase action, 40:272
GM3, biosynthesis, 40:254,261
sialidase action, 40:273
GTla, biosynthesis, 40:258-259, 261
GTlb. biosynthesis, 40:258,262
sialidase action, 40:271, 273-274
isolation, 40:235, 242-243
and purification of, 24:414
methanolysis, 28: 19
trimethylsilylation and gas-liquid
chromatography, 28:52
oligosaccharides of, structure of, 24:423
from pathological tissues, 24:428
sialic acids, 24:417,40:139-140
sialylation, 40:217
structure, nomenclature, and abbreviations,
40~242-243
synthesis of carbohydrate chain of brain,
34:159
Tay-Sachs, 24:430
toxin binding, 40:230-231
Gangliosidosis
GM,, 40:274-276
glycoprotein (compound 7), 'H-NMR
spectroscopy, 41:219,232-233,
235-237
glycoprotein (compound lo), IH-NMR
spectroscopy, 41:2 19,232-233,
242-244
glycoprotein (compound 1 l), 'H-NMR
spectroscopy, 41:219,232-233,
244-246
glycoprotein (compound 12), 'H-NMR
spectroscopy, 41:219,232-233,
246-248
glycoprotein (compound 17), IH-NMR
spectroscopy, 41:219,261-264
glycoprotein (compound 18), 'H-NMR
spectroscopy, 41:2 19,262-266
GM,, variant 0, see Sandhoff s disease
oligosaccharides from urine and tissues,
structure, 37: 196
Ganglio-type gangliosides, biosynthesis,
40:255-265
Garamine, preparation from sisomicin
derivative, 30: 129
Garcia Gonzalez. Francisco, 45:7-17
coauthors, 45: 17
 SUBJECT INDEX
doctoral dissertations, 4 9 9
doctorates, 45:9
early life, 45:7
education, 45:7-8
family, 45:7
marriage, 45: 1 1
research, 45:X-15
Garcia Gonzalez reaction, 45: 13
Garosamine
DI.-, synthesis (attempted), 40:23
4-epimer of, synthesis, 42:98
in Gentamicin and Sisomicin, 29: 105
gentamicin component, structure of. 30: 126
L-, biosynthesis, 35: 1 12
natural occurrence of, 42:70
structure of, 42:73
synthesis of, 42:78-79, 104
Gasification, 46:273-274,323
Gas-liquid chromatography
of aldonic acids, 38:3 18
for methylation completeness, 38:391
of partially methylated sugars, 38:398402
applications to carbohydrates, 28: I 1-160,
30:9-110
column packing, 28:60, 30:45-52.
105-106
history, 28: 12
and infrared spectroscopy, techniques of,
30:43
and mass spectroscopy
in structural studies, 30: 103-104
techniques of, 30:43
of methylated glycosides. 30:23-24
molar response factors in, 30:50-52
and periodate degradation of methylated
sugars, 30:33
of trimethylsilyl ethers of methylated
methyl glycosides, 30:25-26
boronic acids in, 35:65
of carbohydrate derivatives, 19:95-147
of cyclic acetals, 26:235
of deuterated sugars, 27: 15 I
1,4:3,6-dianhydrohexitols,49:118
of formose, 29: 177
and mass spectrometry, 29:42
of methylated monosaccharides, 29 :3 I 1
in mutarotation studies, 24:60
of sialic acids, 40: 16k-165
sugars in solution, 49:21-22
of trimethylsilyl ethers of sugars, 42:22
179
Gastric secretions, analysis by gas-liquid
chromatography, 28:44, 81
(+)-guuche-(-)-guuche arrangement, 47: 14
Gaucher's disease, 40:282
glycoprotein (compound 3), 'H-NMR
spectroscopy, 41:219, 225-226
glycoprotein (compound 61), IH-NMR
spectroscopy, 41 :344-347
glycoprotein (compound 62); 'H-NMR
spectroscopy, 41:344, 346-348
Gaussian coil, 29:3 18
Gd3-
N-acetyl-a-u-neuraminic acid
binding to, computer modeling,
47:160-161
effect on "C-NMR, 47:159-160, 164-165
effect on u-gluconamides 13C-NMR,
47:146-147. 149
electron-nuclear relaxation methods,
47:136-137
exchange for CaZi and Mg2+in biological
systems, 47:134
epi-inositol electron-spin relaxation effect,
47:138-139
interactions
with complex glycopeptides, 47: 155-158
with glycosylated amino acids,
47: 15 1-1 54
with inositol, see Inositols
medical uses, 47:135-136
Gelatin
Junction zones in, 24:306
mutarotation of. 23: 13
Gelatinization, 53:402405
of alginic acid sulfate and cellulose sulfate,
29:336
Gelation, 53:378
of agars, mechanism of, 24:321
mechanism of, 24:314
Gel chromatography, see Chromatography
Gel electrophoresis. mucus glycoproteins,
47:359
Gel filtration of plant cell-wall polysaccharides,
42:27&275
Gel isoelectrofocusing, 53:206
Gellan, 47:192-193, 199, 52:385-391
Gel-permeation chromatography. mucus
glycoproteins, 47:358
Gels
agar, 24:277
180 SUBJECT INDEX
Gels (continued)
alginate. 24:323
alginic acid, 24:298
biological, 24:314, 326
birefiingence of, 24:305
carrageenan, 24: 28 1-2 82
carrageenan-galactomannan, 31:289-29 1
dextran, in cariogenic dental plaques, 30:438
filtration of, 24:311
hysteresis of, 24:306
pectate, 24:323
from pectic substances, 24:302
pectin-sugar, 24:324
polysaccharide, structure, conformation and
mechanism in formation of 24:267-332
properties of, 24:268
spectroscopy and optical rotation of, 24:309
syneresis, 24:303
synthetic, 24:3 13
thermodynamic properties of, 24:306
ultracentrifugation of, 24:3 1 1
from water-insoluble dextrans, 30:4 1 7 4 18
from water-soluble dextrans, 30:414416
X-ray diffraction by, 24:305
Genes, role in utilization of sugars by
Sacchavomyces, 32:180-181, 198,
206-207
Genetic mutations, in cellulose biosynthesis,
41 :143- 144
Genetics
genotype improvement of industrial
microbes, 36:286
genotype maintenance of industrial microbes,
36:273
Gentamicin acetyl transferase, origin and
purification of, 30:2 11-2 I5
Gentamicin C,
inactivated, nuclear magnetic resonance
spectrum of, 30:214
minimum inhibitory concentrations of,
30:221
Gentamicin C,
derivatives, preparation of, 30: 180
synthesis and antibacterial activity of, 30:173
Gentamicin C,a
acetyl-, properties of, 30:212
minimum inhibitory concentrations of,
30:221
tetra-N-benzyl-, preparation and antibacterial
activity of, 30: 180
Gentamicin-kanamycin adenylyl transferase, in
Escherichia coli. 30:204
Gentamicin-kanamycin nucleotidyl transferase,
in Escherichia coli, 30:204-208
Gentamicins
adenylylation of, 30:20&208
discovery of, 30: 112
isolation and structures of, 30:125-127
structure, 35: 1 1 0 - 1 15
Gentamines, from gentamicin C, 30:126
Gentamicin C, mass spectrometry of, 29:105
Gentiobiitol, per-0-trimethylsilyl derivatives,
gas-liquid chromatography of, 28:69
Gentiobiose, 21:29
P-
octaacetate, 23:264
synthesis of, 34:246,250,256
undecaacetate, synthesis of, 34:247
circular dichroism, 45:87
crystal structure, 43:23 1-232
in honey, 25:297
liquid chromatography methods for analysis
of, 46:33
nonselective spin-lattice relaxation rates,
45: 149
octaacetate, gas-liquid chromatography of,
28:70
preparation of, 34:266
proton magnetic resonance spectra, 29:39
pyrolysis of, 34:45
radiolysis and radical-induced scission,
3752
sweetness-structure relationship, 45:248
synthesis, Helferichs work on, 45:3
Gentiobioside, methyl hepta-0-benzoyl-a-,
preparation of, 34:272
Gentiodextrins, 21:457
Gentiotetraose, 21:456
Gentosaminide, methyl, synthesis of, 30: 125
Germacrolide, taste properties, 45:3 14
Germanic acid, sugar complexes with, 22:288
Germination
galactomannan degradation during, of seeds,
35:356-361
lectins during, 35:149
gG Globulin
heterogeneity in, 25:447
rabbit, carbohydrate-peptide linkages in,
25:442443
gG Immunoglobulin, 25:446
 SUBJECT INDEX
y-Globulin, synthesis of, 27:33 1
Gibberellic acid
abscission promotion by, 21:429
effect on sugarcane, 21:427428
as plant-growth substance, 21:416
Gibberellins, 21:378,416
in fruit ripening, 42:342-345
Gibbs energy, anomeric effect, 47:53-59
Gitostin, 39:302
Gitoxin, 43:333
penta-0-acetyl-. mass spectrum of, 29: 104
Glactofuranose, 1,2:5,6-di-O-isopropylidene-
D-, mass spectrum of, 21:77
Glass, porous
for affinity chromatography adsorbent,
39:407,417418
in chromatography, 25: 15
Glaucoma, 1,4:3,6-dianhydro-~-gIucitol in
treatment of, t5:269
Glebidine, see Bluensidine
Glebomycin, see Bluensomycin
Gkditsiu umorphoides, galactomannan from X-
ray crystallography of, 31:280, 282
Globoid leukodystrophy, see Krabbes disease
Globopentaosylceramide, biosynthesis. 40:250
Globoside, discovery, 40:236
Globotetraosylceramide
biosynthesis, 40:249
catabolism, 40:276-279,286
Globotriaosylceramide, biosynthesis. 403249
Glocopyranoside-6-ylsulfonicacid, methyl 6-
deoxy-a+, sodium salt, 24:258
Gloeosporium kuki, a-L-arabinofuranosidase
from, 42387
Glomerelh cingulutu, cu-L-arabinofuranosidase
of, 42388
Glossopharynageal nerves, taste units, taste
perception by, 45:339
Glow electrolysis technique, starch, 51 :308
Glucagon, effect on o-fructose conversion into
D-glUCOSe, 34~297
Glucal, 21:18
2-acetamido-
D-, 24:225
3,4,6-tri-O-acetyl-o-, 24:225
2-acetoxy-
3,4,6-tri-O-acetyh-, hydroformylation
and methoxymercuration of, 24:220
tri-0-acetyl-D-, alkaline degradation of,
28:205
181
2-acetoxytriacetyl-o-. 0x0 reaction with,
23:92
D-
acid degradation of, 24:2 18
catalytic selective oxidation of, 33:87
selective oxidation with silver
carbonate-on-Celite, 33:97
dehydration of, 28: 183
as inhibitor of a-o-mannosidase activity,
28:420
oxidation of. 24:2 18
triacetate, reaction with lead tetrafluoride,
25: I96
3,4-di-0-acetyl-6-0-p-tolylsulfonyl-~-,
24:206
fluorination, 38:206
3,4-di-O-benzoyl-6-O-p-tolylsulfony-~-.
fluorination, 38:206
3,4-di-O-benzyl-6-deoxy-6-fluoro-o-,
preparation, 38:209
2-hydroxy-, dehydration of, 28: 184
2-methoxy-3,4,6-tri-O-methyl-~-,
dehydration of, 28: 184
4-0-benzyl-3,6-dideoxy-6-fluoro-o-.
preparation, 38:209
4,6-0-benzylidene-3-deoxy-3-C-
(iodoniethyf)-~-,preparation of, 28:306
3(S)-d. 4,6-0-benzylidene-3-deoxy-~-,
synthesis of, 27: 131
3,4,6-tri-O-acetyl-
2-
(N-acety1acetamido)-D-,24:225
(NJ-dimethyldithiocarbamoy1)-o-,
24:224
th1ocyanato-D-. 24:209,224
2-bromo-~-,24:224
2-chloro-o-, preparation and chlorination
of, 28:61,262
D-, 0 x 0 reaction with, 23:70, 89-90
tri-0-acetyl-D-
acid degradation of. 24:2 18
alkaline degradation of, 28:203
bromofluorination, 38:203,205
chlorination of, 28:261-262
chlorofluorination, 38:237
conformation of, 26: 122
halogenation of, 24:203
mass spectra of, 24:219
photochemical cycloaddition with acetone,
38: 106, I 17
182 SUBJECT INDEX
Glucal (continued)
photochemical reaction with 2-propano1,
38:119-120
reaction with 2-acetamido-6-
chloropyridine, 24:218
with alcohols and phenols, 24:2 I5
with sulfur-containing reagents, 24:209
reaction with hydrogen bromide, 28:263
with iodobenzene dichloride, 28:263
with nitryl iodide, 28:273
reaction with N-bromosuccinimide and
hydrogen fluoride, 38:234
with N-iodosuccinimide and hydrogen
fluoride, 38:234
rearrangement reactions of, 24:2 13
synthesis of, 24:202
tri-@benzoyh-, reaction with hydrogen
fluoride, 24:216
3,4,6-tri-O-benzyl-2-(benzyloxy)-o-, 24:220
Glucan, 25:9
p-0-
from oat flour, Smith degradation of,
31:206
structure, 3 3 7 , 8, 10
carbon-I 3 nuclear magnetic resonance
spectra, 39:200
D-
from Acetobacter xylinum, crystal
structure bibliography, 40:388
p-, in plant cell-walls, 42:285. 293-294
hiosynthesis, 42:323
chains, in plant cell-wall cellulose, 42:296
+3)-a-D-, 52~361-362,416
crystal structure bibliography, 40:386
polymorphs, crystal structure
bibliography, 40:386
+4)-a-0-, (glycogen), biosynthesis in
liver, 32: 1 1
(1+2)-p-o-, biosynthesis in Rhizobium
japonicum, 32: 11
(1+3)-p-~-, 52~356-361
biosynthesis, 41:147
in Acetobacter xylinum, 32: 1 1
in higher plants, 41:139-142
in plant cell-walls, 41:128
crystal structure bibliography, 36:326,
40:389
(1+4)-p-~-
biosynthesis, 41 :1 I7
in Acetobacter xylinum, 32: 1 1
in vitro, 41:106, 152
cellulose biosynthesis, 41:110
polymerization mechanism, 41: 125-132
Glucanases
p-0-, of yeast cell-walls, 32:229
endo-( 1+3)-a-o-, 44~258
endo-( 1+6)-a-o-, 44:258
endo-( 1+3)-p-O-, 44:267, 272
endo-(1 +4)-@-0-, 44: 180
endo-(1+6)-P-o-, 44:225-226, 272
exo-p-o-, activity of, 28:42 1
exo-( l+4)-a-~-, 44:262
exo-( l+3)-p-~-, 44: 149,266
Eisinia bicyclis, 44: 148-149
(I+~)-CX-O-,42~379
activity of, 30:343-347
(1+6)-a-o-, on plant cell-walls, 42:351
(1+2)43-0-, preparation of, 30:352
(1+3)(4)-p-~-, 44~273
(143)-p-D-
ex-0-, occurrence of, 30:351
nonspecific and specific, 30:350
on plant cell-walls, 42:351-352, 377,
379
(1+4)-p-o-
endo, in primary plant cell-wall
fractionation, 42:275, 277
isolation and purification of. 30:348
specificities of, 30:349
( 1+6)-p-0-
on plant cell-walls, 42:351
preparation and specificity of, 30:352
a-Glucan 3-glucanohydrolases, dextran
hydrolysis by, 30:397
P - D - G I u chydrolases,
~~ in structural analysis of
p-D-glucans, 30:353-370
Glucans, 21:455,472,485
acetylated, circular dichroism, 45: 122
a-D-, 51:I04
branched (1-+4)(1+6)-, structure,
enzymic analysis, 44:252-256
carbon- I3 nuclear magnetic resonance
spectra, 38:3748
enzymic cleavage, 44: 147
(1+6)-, benzyl derivative, circular
dischroism, 45: 122
structure, enzymic analysis, 44:252-266
a-o-linked, 23:368,41:68-72
a - ~ -I+3)-linked,
( 23:374
p-0-
 SUBJECT INDEX
based on (1+6)-b chains, structure,
enzymic analysis, 44:275-276
P-D-glucan hydrolases in structural
analysis of, 30:353-370
biosynthesis, 44:366-367
carbon- I3 nuclear magnetic resonance
spectra, 38:48-52
in cereals, 36:246-248
cyclic (l+2)-, structure, enzymic analysis.
44:276
enzymic analysis of, 30:347-370
enzymic cleavage, 44: 147-149
extracellular and reserve, 30:366- 370
(1+3)-p-, from plant cell-walls, 44:359
( 1 - 4 - p - , from plant cell-walls, 44:359
(1-3) (l+4)-a-~-, structure, enzyme
analysis, 44:265-266
(1-3) (1+4)-p-~-, structure, enzyme
analysis, 44:273-275
structure, enzymic analysis, 44:266 276
P-o-linked, 23:376
linear, 41:72-73
p-o-( 1+3)-linked, 23:378, 380
P-D-( 1+6)-linked, 23:378, 380
p-( 1+2)-, f.a.b.-mass spectrometry. 45:68
branched-chain
P-D-, 41:73-75
preparation from cellulose acetate, 29:332
cyclic, 46:60
p-C l+2)-, f.a.b.-mass spectrometry, 4 5 3 4
u-
p-amylase action on, 23:337
synthesis of linear. 23:304
based on (1+3)-p backbone and (1+3)-p
chains, structure, enzymic analysis,
44:266-273
circular dichroism. 45:88-90
formation in yeast cell-wall, 32:229
from fungi, antitumor activity of,
32:245-248.270
from lichens, antitumor activity of.
32248-249
in yeast cell-walls, 32: 138-140
degree of polymerization of, deterniination
of, 30:284
deuteropermethylated, cyclic p( l+2)-,
molecular ion clusters obtained from, in
f.a.b.-mass spectrometry, 4 5 3 7 3X
gas-liquid chromatography of, 28:50. 59.
30:90-91
183
hydrolysis products from mcthylated.
23:385
lichen, 41:75-76
methylation of, 30:12
proton magnetic resonance spectroscopy of.
30:381
(1+3)u-u-, occurrence and enzymic
degradation of, 30:343-347
( I +2)-@-0-. biosynthesis of, 26:393
(l+3)-p-o-, biosynthesis of, 26:392
reactions with o-phenylenediamine,
polarography of, 29: 159
side-chain substitution, 41:74-75
structure of yeast, 30:6
synthesis, 26:325
enzymes catalyzing, 51:138-139
inhibition, 51:150-151
from sucrose by glucansucrases, 51: 134
yeast, 23:380
Glucansucrases
acceptor products, 51: 154-155
molecular weights and structures, 51: 139
purification, 51: 138-139
reactions, formulation and kinetics,
51: 163-1 64
Cilucan synthetase, 26:383
assay of solubilizcd, 41: 146
p-D-, in plant tissues, auxin effects on,
42350
1, 41:129
11, 41: 129
Glucaric acid
2,5-anhydro-o-. preparation of, 33: 119
D-
p-eliminative degradation of, 29:234
calcium salt tetrahydrate, crystal structure
bibliography, 37:375
potassium salt, crystal structure
bibliography. 38:422423
i>-Glucaro-1.4-lactone, monohydrate, crystal
structure bibliography, 37:375
Glucaro- 1,4-lactone. D-, crystal structure
bibliography, 34:371
Glucitol
2-acetanlido-
2-deoxy-o-. methyl ethers. separation of,
30:22
3,4,5,6-tetra-O-acetl- I -bromo-2-deoxy- I-
S-ethyl- 1 -thio-o-. preparation from
dithioacetal, 32:71
184 SUBJECT INDEX
Glucitol (continued)
1-acetamido-l -deoxy- 1-p-
toluenesulfonamido-o-, preparation of,
31:124
2-amino- 1,5-anhydro-2-deoxy-~-,
deamination of, 31:24
5-amino- 1,5-anhydr0-5-deoxy-~-,proton
magnetic resonance spectroscopy of,
27:27
1-amino-l,5-anhydro-r-deoxy-o-, 23: 132,
144
I-amino-l -deoxy-D-, deamination of, 31:60
2-amino-2-deoxy-o-
acetylation of, 31:63
deamination of, 25:191,31:63
and migration of carbon atom, 31:64
2,6- and 3,6-di-O-methyl-o-, trimethylsilyl
ethers, gas-liquid chromatography of,
30:30
2- and 3-O-methyl-~-,trimethylsilyl ethers,
gas-liquid chromatography of, 30:30
1,3-anhydro-
5,6-di-O-methyl-2,4-0-methylene-o-,
29243
2,4-O-benzylidene-o-, 2 5 2 4 4 2 4 5
I,/l-anhydro-, D-
oxidative cleavage of, 25:209,261
preparation of, 31:60
sweetness-structure relationship, 45257
tetraacetate, ring opening and
isomerization of, 29259
1,4:3,6-anhydro-, D-, mass spectrum of,
21534
1,5-anhydro-
2-chloro-2-deoxy-~-,25239
2-C-phenyl-o-, 25240
D-, 23:110,25:237-238
formation of, 31:24
infrared spectrum of, 25250
preparation of, 32:75
sweetness-structure relationship, 45:
240
2,4-O-benzylidene-o-, 25244
4,6-O-benzylidene-~-
acylation of, 25263
sulfonylation of, 23:253
4,6-0-benzylidene-2-O-p-tolylsulfonyl-o-,
23~253
displacement reactions of, 24: 169
2-9benzyl-2-thio-o-, 24:209,25:238
I ,6-anhydro-
D-, 25245
DL-, infrared spectrum of, 25250
2,5-anhydro-
6-chloro-6-deoxy-o-, 2521 I
D-, preparation of, 33:121
1,6-dibromo- 1,6-dideoxy-, preparation of
racemic mixture, 33:128
1,6-dibrorno-l,6-dideoxy-4-O-
(methykulfonyl)-o-, preparation of,
33: 127-128
1,6-di-O-benzoyl-o-, preparation of,
33:120-121. 131
1,6-di-O-benzoyl-3,4-di-p-tolylsulfonyl-
D-, preparation of, 33:128-129
4,6-di-0-benzoyl-3-O-p-tolylsulfonyl-I -
0-trityl-o-, preparation of,
33: 123-124
1,3-O-isopropyhdene-o-, preparation of,
and oxidation with carbodiimide-
dimethyl sulfoxide, 33:121-122
2,6-anhydro-
I , 1-bis(ethylsulfonyl)- I-deoxy-o-,
triacetate, nuclear magnetic
resonance spectrum of, 25:253
D-, 25:237,245
structure of, 25251
structure of, infrared study in, 28:8
D-L-,25237
3,6-anhydro-, D-, infrared spectrum of,
25251
5,6-anhydro-
D-, hydrolysis of, 28:5
2,4-O-benzylidene- 1 -0-p-tolylsulfonyl-
D-, displacement reaction of, 24:
174
2,4-O-benzylidene-O-p-tolysulfonyl-o-,
25244
2,4-O-benzylidene- 1,6-dichloro-1.6-di-
deoxy-o-, 49: 158-159
1, I -bis(acetamido)- 1-deoxy-o-, preparation
of, 31:86
I , 1 -bis(benzamido)- 1 -deoxy-
D-
effect of benzoyl groups on formation
of, 31:114117, 121
preparation of, 31:84-85, 88, 117,
121-122
4-O-cu-~-glucopyranosyl-o-, synthesis,
39:227,239
 SUBJECT INDEX
D-
acetylation of, effect of borate on,
28:3435
anhydridation of, 25:233
catalytic oxidation of, 33:88
selective oxidation with mercuric
acetate, 33: 100
with sodium metaperiodate, 33:95
conformation of, 25: 105, 26:69
crystallography of, 25:60
crystal structure bibliography, 30:450
methyl ethers, separation of, 30:2 1
determination in blood by gas-liquid
chromatography, 28:57
from o-fructose, 22:232,283
from o-glucose and its conversion into u-
fructose, 36:53-54
effect of alkali tetraborates on rotation of,
23:36
hexaacetate, mass spectrum of, 21:89
hexanitrate, selective denitration, 3 9 5 8
reaction with butanal, 39:26
irradiation, 38: 147-148
L-ascorbic acid synthesis, 37: 149
oxidation, chemical, 37: 1 13-1 I5
fermentative, 37: 112-1 13
to L-sorbose, in L-ascorbic acid
synthesis, 37:9 1-92
radiolysis and free-radical chcmistry,
37:27,32
in mammalian nerve, determination by
gas-liquid chromatography, 28:58
utilization by yeasts, 32:146, 218
1-deoxy-
1,1-bis(nicotinamido)-o-,preparation of,
31:88
1 -C-methyl-I.-, preparation of, 27:242
1,l -di-C-(p-methoxypheny1)-D-,
preparation of, 33: 125
I -( 2,4-dinitroaniIino)-o-, irradiation.
38: 173
1-(2-methylhydrazino)-~-,preparation of,
29:153
2,5-diamino-l,4:3,6-dianhydro-~-,
deamination of, 31:55
1,4-diamino, 1,4-dideoxy-3-0-(4-deoxy-4-
propionamido-a-o-glucopyranosyl-i>-,
hydrobromide dihydrate, crystal
structure bibliography, 38:463
1,4:3,6-dianhydro-
I85
D-, 49:96-97, I 17
benzoylation with N-benzoyliniidazole,
33:43
esterification with p-phenylazobenzoyl
chloride, 33: 15
p-toluenesulfonylation of, 33: 14
sweetness-structure relationship,
45:257, 274
taste properties, 45:270
2,5-di-O-p-tolylsulfonyl-u-, 23:252
displacement reactions of, 24: 149
L-, catalytic oxidation of, 2S:261
2-S-benzoyl-5-O-methylsulfonyl-2-thio-
I>-, 49: 153
2-0-
(p-bromopheny1sulfonyI)-u-, 5-nitrate,
crystal structure bibliography, 31:367
(p-bromophenylsulfonyl)-(exo/-o-,
crystal and niolecular structures of,
25:255
5-O-p-tolylsulfonyl-~-,23:252
2,5:3,6-dianhydro-,D-, 29246
preparation of, 33: I3 1
ring opening of, 25257
1,5:3,6-dianhydro-2,4-0-methylene-~-,
25:245
2,4:3,5-di-0-benzylidene-l,6-dichloro-l,6-
dideoxy-o-, 49: 158
1.6-dichloro- I,h-dideoxy-u-, 25:256.
49: 158- I59
preparation of, 28:280
2,5-dideoxy-2,5-diiodo-u-, 49: 149- 150
1,4-dideoxy- 1,4-imino-o-, SO: 198
I ,S-di-0-acetyl-2,3,4,6-tetra-0-mcthyl-~-,
mass spectrum of. 29:62
1,6-di-0-benzoyl-2,4:3,5-di-O-methylene-o-,
acetolysis of, 22:13,39:25
1,3:2,4-di-0-ethylidene-
selective
5,6-bis-O-(trifluoroacetyl)-i~-,
deacylation, 39:29
11-
5,6-dinitrate, selective denitration,
39:57
oxidation, 38:301
2,4:3,5-di-0-isopropylidene-o-
acetolysis, selective, 39:25
selective hydrolysis, 39:23
1,3:5,6-di-O-isopropylidene-2,4-0-
methylene-o-, selective hydrolysis,
39:23
186 SUBJECT INDEX
Glucitol (continued)
1,2:5,6-di-O-isopropylidene-3-O-methyl-4-
O-(methykulfonyl)-o-, displacement
reactions of, 24: 158
DL-, crystalline, 26: 14
hexa-0-acetyl-o-
mass spectrum of, 2 9 5 2
rearrangement in liquid hydrogen fluoride,
26: 176
L-, crystallography of, 25:60
liquid chromatography methods for analysis
of, 46:33
mono-0-methyl-, trifluoroacetates,
gas-liquid chromatography of, 30:32
5-0-acetyl- 1,6-di-O-benzoyl-2,4-0-
methylene-o-, preparation, 39:25
6-0-(2-arnino-2-deoxy-p-o-
mannopyranosy1)-o-, deamination of,
31:46
4-0-P-o-glucopyranosyl-o-, crystal structure,
43:232-233
6-0-benzoyl- 1,3:2,4-di-O-ethylidene-o-,
oxidation of, 26:247
2,3-O-benzylidene-o-, isomerization,
39:27
2,4-U-benzylidene-~-,structure of, 28:4
2,3-0-butylidene-
D-, isomerization, 39:27
1-deoxy-o-, isomerization, 39:27
1,4:3,6-0- dianhydro-o-, reaction with boron
trichloride, 28:280
2,3-0-ethylidene-o-, isomerization, 39:27
0-ethyl-0-methyl-, acetate, gas-liquid
chromatography of, 30:3 1
0-methyl-0-propyl-, acetate, gas-liquid
chromatography of, 30:3 1
2,3,4,5,6-penta-O-acetyl- 1-deoxy-o-,
preparation from dithioacetal, 32:75
(I-S)-l-(6-chloropurin-9-yl)-l-.S-ethyl-l-
thio-o-, crystal structure bibliography,
38:493494
1,2,5,6-tetra-O-acetyI-, 3.4-O-methylene-o-,
oxidation of, 26:254
1,3,5,6-tetra-O-acetyl-, 2,4-0-benzylidene-
D-, oxidation by chromium oxide, 39:83
1,4,5,6-tetra-O-acetyI-, 2-3-di-O-methyl-o-,
mass spectrometry of, 29:59
2,3,4,6-tetra-O-acetyyl-
1,5-anhydro-2-C-phenyI-o-, preparation
of, 33: 143
1,5-anhydro-2-ethynyl-o-, preparation of,
33:143
3,4,5,6-tetra-O-acetyI-
1-bromo-2-deoxy-2-(2,4-dinitroanilino)- 1-
S-(l,l-dichloroethyl)-2-(2,4-
dinitroanilin0)- 1-thio-o-, preparation
of, 32:71
1-chloro-2-deoxy- 1-S-( 1,l -dichloroethyl)-
2-(2,4-dinitroanilinio)-1-thio-D-,
preparation of, 32:71
tetra-0-acetyl-
1,4-anhydro-o-, rearrangement in
hydrogen fluoride, 26: 175
1,5-anhydro-o-, 24:221
stability in hydrogen fluoride, 26: 173
1,5-anhydro-3-deoxy-3-C-
(hydroxymethy1)-o-, 23:98
I ,2,3,5-tetra-O-benzoyl-4,6-O-ethylidene-o-,
aroyl migration and deacetalation of,
33:107
1,2,3,4-tetra-O-benzoy1-5,6-0-
isopropylidene-o-, oxidation by
triphenylmethyl fluoroborate,
39536
2,3,4,6-tetra-O-methyl-, acetate, gas-liquid
chromatography of, trifluoroacetate,
gas-liquid chromatography of, 30:32
1,5,6-tri-O-acetyI-2,3,4-0-methyl-o-, mass
spectrometry of, 29:59
3,4,6-tri-O-acetyl-2-S-acetyl- 1,5-anhydro-2-
thio-o-, 24:209
1,3:2,4:5,6-tri-O-benzylidene-o-, selective
hydrolysis, 39:22
tri-0-methyl-o-, separation of, 30:22
o-Glucitol dehydrogenase, in metabolism of D-
fructose, 34:340-341
Glucitol 5-nitrate, 1,4:3,6-dianhydro-2-0-(p-
bromophenylsu1fonyl)-o-, 49: 1 14-1 15
o-Glucitol-pyndine, crystal structure
bibliography, 30:450
Glucoamylase, 23:358,50:16, 53:211,247-
249
amino acids of, 27:315,317
carbohydrate content of, 27:306307
carbohydrate-peptide linkages in, 25:418
I 3C-NMR spectroscopy, 43: 8-1 0
a-D-(;~uCopyranOSe
crystal structure, 43:2 1 6 2 17
monohydrate, 43:371
1 and I1
 SUBJECT INDEX
'3C-NMRstructural analysis, 43:4043
glycosidic linkage formation, from
anomeric region, 43:43
degradation o f starch and glycogen to I)-
glucose, 30:280-281
in hydrolysis of starch, 36:33, 42
hydrolytic action of, 30:398
kinetics, 23:289
preparation and properties of, 30:29 1-293
structure of, 27:327
Glucobiose
')C-NMR data for, 42195-196
peracetates, I3C-NMR data on, 42: 195
Glucobrassicin, 21 :392
Glucocerebrosides, 24:395,44:437
in sponges, 44:410
Glucodextranase, 44:258
Gluco-l,4:6,3-difuranose,1,2-0-
isopropylidene-5-O-p-tolylsulfonyl-ol-i~-,
preparation of, 33:218
o-Gluco-o-mannan, biosynthesis of, 26:403
Glucofructans, 22:6
a-~-Glucofurano[2,1 -d]imidazolidine-2-thione,
1-phenyl-, crystal structure bibliography,
37:391
Glucofurano[2,1 -d]imidazolidine-2-thione
D-, I-allyl-, crystal structure bibliography.
37:384
1.-
I-(p-bromopheny1)-, crystal structure
bibliography, 37:389
1-p-chloropheny1)-, crystal structure
bibliography, 37:389
Glucofuranose
1,2,-O-isopropylidene-5-O-p-tolylsulfonyl-
a-D-,preparation of, 33:2 17-2 18
a-D-
6-deoxy- 1,2;3,5-di-O-isopropylidcne-6-
isothicyanato-, 44: 141
3-deoxy-l,2:5,6-di-O-isopropylidene-3-
thiocyanato-, 44: 143
3-deoxy-1,2-0-isopropylidene-3-
thiocyanato-, 44: 143
1,2:3,5-di(benzeneboronate),reaction with
carbon tetrachloride and
triphenylphosphine, 28:246
5,6-di-O-acetyl-3-deoxy- 1,2-0-
isopropylidene-3-thiocyanato-,
44:143
taste properties, 45:242
I87
5-amino-5-deoxy-1,2-0-isopropylidene-a-
D-, 23: I76
1,6-anhydro-
p-D-. 22:501
from cellulose on heating, 23:432,441
formation, 47:340
formation during pyrolysis o f starch and
cellulose, 34:42-43
gas-liquid chromatography of, 28:43
hydrolysis, of, 34: 153
preparation of, 34: I52
properties of, 34: I52
selective oxidation of, 33:90
2,3-di-0-methyl-4,6-dithio-p-~-,and 3.5-
dinitrobenzoate, 23:244
2,4-di-O-methyl-1(6),4-dithio-P-~-,
preparation of, 34: 150
3,5-di-O-methyl-6-thio-P-~-, 23:228
l(h)-thio-p-o-, preparation of, 34:150
3,6-anhydro-
5-deoxy-5-iodo- 1,2-O-isopropylidene-a-
D-. preparation of, 28:271
5-0-benzoyl- 1,2-O-isopropylidene-a-~-,
synthesis, 39: 103-104
1,2-0-isopropylidene-5,-0-p-
tOlylSUlfOIlyl-Ci-D-, 24: 196
displacement reactions of, 24: 152
I ,2-0-isopropylidene-a-~-,23:257
conformation of. 26: 120
1,2-O-isopropylidene-5-0-~-tolysulfonyl-
(Y-D-, 23:257
5-0-p-tolysulfonyl-~-,hydrazone and
osazone, 23:265
5,6-anhydro-
1,2-O-isopropylidene-a-r~-,22:202.
25:112, 162
0x0 reaction with, 23: 102, 104
polymerization, 39:210
synthesis of, 28:2
I ,2-0-Isopropylidene-3-O-methyl-a-~-.
polymerization, 39:209
3-azido-3-deoxy-
1,2:5,6-di-0-isopropylidene-a-o-,
photolysis of, 34:207
1,2-0-1sopropylidene-6-0-[3,4,6-tri-
acetyl-2-deoxy-2-(2,4
dinitroanilino-a- and-p-o-,
glucopyranosyl]-a-D-,preparation of,
34:269
p-D-.taste properties, 45242
188 SUBJECT INDEX
Glucofuranose (continued)
3-bromo-3-deoxy- 1,2:5,6-di-0-
isopropyhdene-a-D-, preparation of,
28:280
6-bromo-6-deoxy-l,2:3,5-di-0-
isopropylidene-a-o-
preparation of, 28:240,249
synthesis, 39:115-116
6-bromo- I ,2:3,5-di-O-isopropylidene-a-~-,
21:165
3-C-(difluoromethylene)-I,2:5,6-di-0-
isopropyhdene-a+-, preparation,
38:249
3-chloro-3 -deoxy-3-deuterio- 1,2:5,6-di-0-
isopropylidene-a-D-, preparation and
reduction of, 28:303
6-chloro-6-deoxy- 1,2:3,5-di-0-
isopropylidene-a-o-
preparation of, 28:239,247,252,254, 259
reaction with anhydrous hydrazine, 28:285
synthesis, 39: 1 16-1 17
D-
3,6-anhydro-5-deoxy-5-fluoro- 1,2-O-
isopropylidene-a-, 'H- and I9F-NMR
data for, 46: 1 15
3,6-anhydro-5-deoxy-5,6,6-trifluoro- I ,2-
O-isopropylidene-
I3C-NMR data for, 46:177
IH- and I9F-NMR data for, 46: 158
3,6-anhydro-6,6-difluoro-
a-
1,2-0-ben~ylidene,'~C-NMR data for,
46: 175
1,2-0-isopropylidene,13C-NMR data
for, 46: 175
1,2-O-benzylidene-a-, 'H- and I9F-
NMR data for, 46: 152
1,2-0-isopropylidene-P-, 'H- and I9F-
NMR data for, 46: 152
3-deoxy-3-fluoro-
3-C-(acetoxymethyl)- 1,2-0-
isopropylidene-a-, IH- and I9F-NMR
data for, 46: 138
3-C-[ 1,2-di(hydroxyethyI)]- 1,2:5,6-di-
0-isopropylidene-a-, 'H- and 19F-
NMR data for, 46: 139
3-C-(ethoxyallyl)-l,2-0-isopropylidene-
a-, 'H- and I9F-NMR data for,
46:139
3-C-[(etboxycarbonyl)(formylimino)-
methyl]- 1,2:5,6-di-O-isopropylidene-
a-, IH- and I9F-NMR data for,
46:139
3-C-[ethoxy(ethoxycarbonyl)-
(formylamino)methyl]- 1,2:5,6-di-0-
isopropylidene-a-, IH- and 19F-NMR
data for, 46:139
3-C-(hydroxymethyl)- 1,2:5,6-di-0-
isopropylidene-a-, 'H- and I9F-NMR
data for, 46: 139
I ,2:5,6-di-O-isopropylidene-a-, IH- and
I9F-NMR data for, 46:99, 138-139
I ,2:5,6-di-O-isopropylidene-3-C-
(methoxycarbony1)-a-, 'H- and "F-
NMR data for, 46: 140
1,2:5,6-di-O-isopropylidene-3-deoxy-3-
M R for, 46:166
f l ~ o r o - a - , ~ ~ C - N data
6-0-benzoyl- 1,2-0-isopropylidene-a-,
'H- and I9F-Nh4R data for, 46:139
1,2-0-isopropylidene-a-
5,6-carbonate, IH- and I9F-NMR data
for, 46:99
'H- and "F-NMR data for, 46:99, 139
1,2-O-isopropylidene-3-C-
(methoxyally1)-a-, 'H- and I9F-NMR
data for, 46:139
5,6-phenylboronate, IH- and I9F-NMR
data for, 46:99
5-deoxy-5-fluoro-
a anomer, I3C-NMR data for, 46:166
P anomer, 13C-NMRdata for, 46: I66
1,2-0-isopropylidene-a-,I3C-NMR data
for, 46: 167
6-deoxy-6-fluoro-
1,2:5,6-di-O-isopropylidene-a-, IH- and
I9F-NMR data for, 46: 100
1,2:3,5-di-O-methylidene-a-, 'H- and
I9F-NMR data for, 46: 100
3,5-0-benzylidene- 1,2-0-
isopropylidene-a-, 'H- and I9F-NMR
data for, 46: 100
1,2-0-isopropylidene-a-,'H- and I9F-
NMR data for, 46: 100
1,2-0-isopropyIidene-5-O-benzyl-a-,
'H- and I9F-NMR data for, 46:lOO
1-0-acetyl-2,3,5,6-tetra-O-benzoyl-4-
fluoro-P-,I3C-NMR data for, 46: 172
p-toluenesulfonylation of, 30:4
3-deoxy-
3-C-ethoxalyl-3-fluoro,l,2: 5,6-di-0-
 SUBJECT INDEX
isopropylidene-a-o-, preparation,
38:249-250
3-deuterio- 1,2:5,6-di-O-isopropylidene-a-
D-, preparation of, 27: 135
3-[(ethoxycarbonyl)(formylimino)methyl]-
3-flUOr0- I ,2:5,6-di-O-isopropyIidene-
a-D-,preparation, 38:249-250
3-[ '8F]fluoro-l ,2:5,6-di-0-isopropylidene-
a-D-, preparation, 38:227,239
3-fluoro-3-C-[ethoxy(ethoxy-
carhonyl)(formylimino)methyl]-
1,2:5,6-di-O-isopropylidene-a-u-.
preparation, 38:249-250
3-fluoro-3-C-(hydroxymethyl)-1,2:5,h-di-
0-isopropylidene-a-o-, preparation,
38:250-25 1
3-fluoro-o-, preparation, 38:224
3-fluoro- 1,2:5,6-di-O-isopropylidene-a-n-,
preparation, 38:219,227
3-flUOrO-1,2-0-isopropylidene-a-r~-.
22: 180
3-fluor0-1,2-O-isopropylidene-a-o-,5.6-
phenylhoronate, preparation, 3 5 4 5
3-iOdO- 1,2:5,6-di-O-isopropylidene-o-,
21:166
3-iodo- 1,2:5,6-di-O-isopropylidene-a-o-
irradiation, 38: 187
preparation of, 28:279
5,6-deoxy-, 1,2-( l-bromoethylidenej-3-0-
(methykulfonyl)-a-o-, 23:265
5-deoxy-
5-flUOrO-D-, 48~138-139
5-iodo- 1,2-O-isopropylidene-6-0-
trifluoroacetyl-a-o-, preparation of,
28:271
I ,2-0-isopropylindene-3-0-
(methylsulfonyl)-a-o-, 23:268
6-deoxy-
I,2:3,5-di-O-isopropyIidene-6-
phthalimido-a-o-, proton magnetic
resonance spectroscopy of, 27:29,79
1,2:3,5-di-O-isopropyIidene-6-
phthalimido-'5N-a-~-,proton
magnetic resonance spectroscopy of,
27:29,76,79
6-hydrazino- 1,2:3,5-di-O-isopropylidene-
a-D-,preparation of, 28:285
6-iodo- 1,2:3,5-di-O-isopropyIidene-w-o-
methylphosphonite, preparation of,
28:280
189
preparation of, 28:240
reaction with potassium phthalimide-
IsN, 28:283
synthesis, 39: 1 15-1 16
1,2-~-isopropy!idene-a-o-, 23:274
selective catalytic oxidation of, 33:9 I ,
99
1,2-O-isopropylidene-5-C-phenyl-a-~-,
preparation of, 27:214-216
5,6-dIdeoxy-a-o, 21: 193
1,2:5,6-di-O-isopropylidene-a-o-, mass
spectrum of, 21:77
1,5-di-O-acetyI-l-6-deoxy-2,3-di-O-methyl-
4-thio-~-,23:224
3,5-di-O-acetyl-6-deoxy-6-halo- I ,2-0-
isopropylidene-a-o-. 22: 187
5,6-di-O-acetyl- 1,24 1-ethoxyethylidenej-3-
O-(methylsulfonyl)-a-D-, 23:265
1,2:3,5-di-O-benzylIdene-a-~-, conformation
of, 26:121
2,3-di-0-benzyl-5-0-(methylsulfronyl)-6-0-
trityl-o-, displacement reactions of,
24:171
I ,2:5,6-di-O-cyclohexylidene-
a-D-, hydrogenolysis regioselectivity,
39: I25
3-0-(phenylglyoxylyl)-a-o, reduction of,
27:20 I
1,2:3,5-di-O-isopropylidene-, a-~-
formation of, 34: 182-1 83
mass spectrum of, 29:77
1,2:5,6-di-O-isopropylidene-
a-D-
conformation of, 34: 182-1 83
and derivatives, carbon- 13 nuclear
magnetic resonance spectroscopy,
4153
formation of, 34: 182
fragmentation pattern for, 34: 193
hydrogenolysis, over copper chromite,
39: 135
hydrogenolysis regioselectivity, 39: 125
irradiation, 39:88
levoglucosan from pyrolysis of, 34:46
migration of 5,6-acetal group,
39:115-116
paper chromatography of. 26:233
preparation of, 30:4
proton magnetic resonance spectra of,
29: 17, 20, 23
190 SUBJECT MDEX
Glucofuranose (continued)
reaction with diethylaminosulfur
trifluoride, 38:226-227,239
reaction with N-bromosuccinimide and
triphenylphosphine, 28:249
with bromotriphenoxyphosphonium
bromide, 28:240
with carbon tetrachloride-
triphenylphosphine, 28:247
with (chloromethy1ene)-
dimethyliminium chloride, 28:252
with cyanuric chloride, 28:259
with N-(2-chloro-l, 1,2-trifluoroethyl)-
diethylamine, 28:258
with phosphorus pentachloride, 28:239
with triphenylphosphine-carbon
tetrachloride, 28:254
stereoselectivity of Grignard reaction in
presence of, and its derivatives,
27:194195
sulfonylation of, 23:236
D-, 26:240
3-~-(methyh~fony~)-cu-o-, 23:268
3-0-( 1-propenyl)-a+-, acid hydrolysis,
39:49
3-0-p-tolysulfonyl-WD-
displacement reactions of, 24: 148
solvolysis of, 25:207
1,2:3,5-di-O-rnethylene-
reaction with (2-chloro-I, 1,2-
(Y-D-,
trifluoroethyl)diethylamine, 38:227
6-@~~-to~ysu~fony~-cu-o-, fluorination,
38:208
(E)-3-C-[2-(carboxamido)- 1-(ethoxy-
carbonyl)ethylene]-3-deoxy-3-fluoro-
1,2:5,6-di-O-isopropylidene-ol-o-,
preparation, 38:250,252
I -0-(2-acetoxy-2-propyl)-1,3,5,6-tetra-O-
acetyl-o-, 22: 15
3-0-acetyl-
1,2-O-benzoyl-1,2-0-isopropylidene-5,6
di-O-p-tolylsu~fony~-o-, displacement
reactions of, 24: 145
6-0-benzoyl- 1.2-O-isopropylidene-5-0-p-
tolysulfonyl-D-, 24: 145
1,2-0-isopropylidene-5,-O-p-tolylsulfonyl
6-0-, tityl-~l-o-,displacement
reaction of, 24: 174
I ,2-0-isopropylidene-5,6 di-0-p-
tolylsulfonyl a-D-,displacement
reactions of, 24: 176
6-S-acetyl-l,2-0-isopropylidene-6-thio-5-
O-p-tolylsulfonly-cu-D-, 24: 145
6-0-acetyl-
1,2:3,5-di-O-isopropylideneLY-D-,
selective hydrolysis, 39:24
1,2:3,5-di-O-methylene-a-~-
deacetalation, 39:24
oxidation by potassium permanganate,
39:82
1,2-O-isopropylidene-ol-o-,3,5-dinitrate,
selective denitration, 3 9 5 7
5-0-benzoyl-6-bromo-1,2-0-isopropylidene-
LY-D-, synthesis, 39: 103-104
6-0-benzoyl- 1,2isopropylidene-5-0-p-
tolylsulfonyl-LY-D-,23~244
3-0-(benzyl4-deoxy-~-~-gulopyranosid-4-
yl)- 1,2:5,6-di-O-isopropyIidene-a-~-,
synthesis, 40: 126
3,5-0-benzylidene-
6-deoxy-6-fluoro- 1,2-O-isopropylidene-a-
D-, preparation, 38:207
1,2-O-isopropylidene-cu-~-
bydrogenolysis regioselectivity, 39: 126
isomerization, 39:27
reaction with N-bromosuccinimide,
26:166,39:103
1,2-0-isopropylidene-6-0-
(methykulfonyl)-a-D-, fluorination,
38:207
5.6-0-benzylidene-
1,2-0-isopropylldene-~~-~-,
hydrogenolysis regioselectivity,
39: 125
1,2-U-isopropylidene-3-0-
(methykulfony~)-cr-D-
reaction with potassium fluoride,
38:220
reaction with tiphenylmethyl
fluoroborate and
tetrabutylammonium bromide,
39:108-109
3-0-benzyl- 1,2-0-cyclohexylidene-cu-o-,
complex with lithium aluminum
hydride, stereoselectivity of reductions
with, 27:196-199
3-0-benzyl- 1,2-O-isopropylidene-
(Y-D-, synthesis, 39: 126
5,6-di-O-p-tolylsuIfonyl-ol-~-
solvolysis of, 24: 196
 SUBJECT INDEX
sulfonate displacement in, 33: 126
5,6-di-O-p-tolysulfonyl-o-, solvolysis of,
25:203
5-~-p-tolysulfony~-6-~-trityh-~-,
displacement reaction of, 24: I56
6-0-henzyl- 1,2-0-isopropylidene-, 5-0-1,-
tolysulfonyl-a-o-displacement reactions
of, 24:156
3-0-crotonyl- 1,2:5,6-di-O-cyclohexylidene-
a-o-,Grignard reaction with, 27:202
1,2-0-cyclohexy~idene-a-o-, and 3-methyl
ether, complexes with lithium aluminum
hydride, reductions with, 27: 196
1,2-O-ethylene-a-~-,from 0-(2-
hydroxyethyl) starch, 29:3 18-3 I9
3-O-formyl-l,2:5,6-di-O-isopropylidene-(~-
D-, preparation of, 28:254
1,2-0-isopropylidene-3,5,6-
0-phosphino-a-o-, crystal structure.
43:223
tri-O-(methy~sulfonyI)-(Y-D-, reaction with
potassium fluoride, 38:220
1,2-0-isopropylidene-3,5-
di-O-methyl-6-O-p-tolysulfonyl-a-o-,
solvolysis of, 24:195
O-[(endo-methoxy)methyIidene]-6-0-p-
tolylsulfonyl-a-o-, proton magnetic
resonance spectra, iterative analysis
of, 27:78
0-(methoxymethylidene)-6-0-p-
tolylsulfonyl-a-o-, conformation of,
26:121
1,2-O-isopropylidene-ol-o-
acetolysis of, 22: 15
3- and 6-chloroacetates, preparation, 3 5 3 4
3,5-horate, preparation, 3 5 3 1
conformation of, 26: 120
crystal structure, 43:223-224
esterification with methyl octadecanoate,
33:44
and 3-ethers, complexes with lithium
aluminum hydride, reduction with,
27:196
hydrogenolysis, over copper chromite,
39:135
oxidation of, 33:232
3,5-phenylboronate, preparation and use,
35:32
phosphorylation of, 33:46
reaction with triphenyl phosphite and
191
methyl iodide, 28:280
selective oxidation with silver carbonate-
on-Celite, 33:98
synthesis of, 28:4
1,2-0-isopropylidene-5-0-(methylsulfonyl)-
(Y-D-, preparation of, 33:218
1,2-0-isopropylindene-5,6-di-O-p-
tolylsulfonyl-a+-, 23:244
3-0-o-iodobiphenylyl- I ,2:5,6-di-0-
isopropyhdene-a-o-, irradiation,
38:187, 191
solvolysis of. 25:206
2,3,5,6-tetra-0-benzoyl-o-, ammonolysis of,
31:116, 121
1,2,6-tri-0-acetyl-3,5-di-O-methyl-a-~-,
selective deacylation, 39:28
3,5,6-tri-O-acetyl-1,2-O-isopropy~idene-a-o-
acetolysis and bromination, 39:114
reaction with hydrogen fluoride, 39: 1 17
3,5,6-tri-O-benzoyI-
D-
ammonolysis of, 31:85, 116, 121
ethanethiolysis of, 32:32
1,2-O-isopropylidene-a-~-, oxidation by
triphenylmethyl fluoroborate, 39:85
Glucofuranose-5,6,6'-4,,1,2-O-isopropylidene-
a-D-,preparation of, 33:219
Glucofuranose-d,,, 6-deoxy-l,2:3,5-di-O-
isopropylidene-a-o-, proton magnetic
resonance spectra, iterative analysis of,
27:79
Glucofuranoses, 3-fluoro-o-, 3-C-branched, 'H
and "F-NMR data for, 46:138-140
Glucofuranoside
alkyl I-thio-a-o-, formation from
dithioacetals, 3 2 6 8
3,6-anhydro-a-o-glucofuranosyl 3,6-
anhydro-a-o-, tetrabenzoate, proton
magnetic resonance spectroscopy of,
27:33
3,6-anhydro-a-o-glucofuranosyl 3,6-
anhydro-a-o-
sweetness-structure relationship, 45:257,
274
taste properties, 45:270
benzyl 1-thio-a-o-, 21:115, 118
ethyl 2,3,5,6,-tetra-O-acetyl- 1 -thio-a-o-,
preparation of, 3 2 4 6
ethyl (Y-D-, 21:95,102
ethyl p-D-,2195, 102, 125
192 SUBJECT INDEX
Glucofuranoside (continued)
preparation of, 34:278
ethyl 2-ucetumido-2-deoxy-1 -thio-a (and p)-
D-, 21:116
ethyl I-thio-a-D-, 21:114, 118
crystal structure of, 25:71,31:366
preparation of, 3 2 6 6
rearrangement by dilute acid, 32:60
ethyl 1-thio-pa-, 21:115
isopropyl OL (and P)-D-, 21:125
methyl 2-acetamid0-2-deoxy-o-, preparation
from dithioacetal, 3 2 6 8
methyl a-D-, formation of, 31:32
methyl a-D-, 21:102, 125
entropy of activation for hydrolysis of,
2240
methyl 3,6-anhydro-a-o-
sweetness-structure relationship, 45:257,
274
taste properties, 45:270
methyl 3,6-anhydro-a-o-, mass spectrum of,
21:81
methyl p-D-, 21:117, 125
acidic methanol action on, 21 :1 10- 1 1 1
conformation of, 21: 100
3-deoxy-3-thiocyanato-2-0-p-
tolysulfonyl-5-O-trityl-, 44: 143
entropy of activation for hydrolysis of,
22:40
formation of, 31:32
sweetness-structure relationship, 45256
methyl D-, 21:21
selective periodate oxidation of, 33:94
methyl 3-deoxy-3-iodo-2,5,6-tri-O-methyl-p- elimination reactions with, 33:219-226
D-, 22: 185
preparation of, 28:241
methyl 2,5-di-O-methyl-a-~-,21: 125
methyl 2,5-di-~-p-to~ylsu~fony~-~-~-,
preparation of, 33:2 18
methyl 3-0-benzyl-5,6-di-O-p-tolylsulfonyl-
D-, 25:205
methyl 2-O-methyl-o-, reaction with acetone,
30:4
methyl I-thio-a-D-, 21: 115
methyl 2,5,6-tri-O-methyI-p-o-, reaction
with methyltriphenoxyphosphonium
iodide, 28:241
phenyl-p-o-, acetolysis of, 2220
propyl 1-thio-a-o-, 21:115
tert-butyl 1-thio-a(and P)-D-, 2 1:121
Glucofuranosiduronamide
akyl 1-thio-a+-, preparation, 36: 101
ethyl I-thio-a-o-, preparation from
dithioacetal, 32:66
methyl a-D-and p-D-, preparation of, 33:213
methyl 2,5-di-O-(ethoxycarbonyl)-a-~-,
preparation of, 33:2 14
methyl 2-0-(ethoxycarbonyl)- p-D-,
preparation of, 33:214
purin-6-yl 1-thio-o-, preparation, 36:98
Glucofuranosiduronic acid
alkyl D-, reducing ability of derivatives of,
33:22&229
alkyl 1-thio-a-o-, sodium salts, preparation,
36:lOl
ethyl 1-thio-a-o-, sodium salt, 21: 115
preparation from dithioacetal, 32:66
methyl 2,3,5-tri-O-methyI-
a-D-, and methyl ester, preparation of,
33:201
o-. methyl ester, preparation of, 33: 197
propyl I-thio-a+-, sodium salt, 21:115
Glucofuranosiduronic N-phenylhydrazide,
preparation of, and hepato-protective
activity, 33:215
Glucofuranosiduronolactone
2-naphthyl p-D-, 21: 121
phenyl p-D-, 21:121
Glucofuranosidurono-6,3 -lactone
alkyl and aryl, preparation of, 33: 195-197
ammonolysis, aminolysis, and hydrazinolysis
Of, 33:213-216
conformational analysis of, 33:205-210
ethyl 2,5-di-O-benzoyl-p-~-,preparation of,
33: 196
infrared measurements and hydrogen
bonding for, 33:209-2 10
methyl a-D-and p-D-
oxidation of, 33:230
preparation of, 33: 196
proton magnetic resonance spectroscopy
of, 33:207-209
reducing ability of, 33:227-229
selective acylation of, 33:204
methyl D-, preparation, 36:74
methyl 2,5-di-O-acetyl-P-o-, reducing ability
of, 3 3 ~ 2 2 1
methyl 2,5-di-O-methyl-a-o-, preparation of,
33:196,201
 SUBJECT INDEX
methyl 2,5-dj-O-rnethyl-P-o-, preparation of,
33:201
methyl 2,5-di-O-(methylsulfonyl)-~-~-,
preparation of, 33:203
methyl 2,5-di-O-p-tolylsulfonyl-p-~-,
preparation of, 33:203
methyl 5-O-benzoyl-P-~-,preparation of,
33:205
methyl 5-O-benzyl-P-o-, oxidation of,
33:23 1
methyl 5-O-benzyl-2-O-methyI-a-~- and+
D-, preparation of, 33:231
methyl 5-O-benzyl-2-O-methyl-p-~-,
elimination reaction with, 33:222-223
methyl 5-O-benzyl-2-O-(methylsulfonyl)-
D-, preparation of, 33:203
methyl 5-O-(benzyloxycarbonyl)-
p-D-, preparation of, 33:204
2-O-(ethoxycarbonyl)- OL-D- and+-[)-,
preparation of, 33:205
methyl 2-O-(ethoxycarbonyl)-a-~-and-p-~-, 2,5-di-O-acetyki-o-, preparation of, 33: 192
preparation of, 33:205
methyl 5-O-(ethoxycarbonyl)-p-~-,
preparation of, 33:204
oxidation of, 33:230
phenyl5-O-acetyl-p-~-,preparation of.
33:214
reduction with complex metal hydrides,
33:217,220
Glucofuranosylamine
N-acetyl-a-o-
configuration of, 31: 109
mechanism of formation of, 3 1 : l l l
oxidation and configuration of,
31: 104-1 06
preparation of, 31533, 85-86, 122
proton magnetic resonance spectroscopy
of, 21:23
N-acetyl-6-O-a-~-galactopyranosyl-p-~-, GIucofuranosylurono-6,3-lactone
preparation of, 31:94
N-acyl-, oxidation and configuration of,
3 1:104-1 05
N-nicotinoyl-o-, preparation of. 31:88
(Glucofuranosylamine)uronamides, W a r y -D-,
preparation of, 33:200
(Glucofuranosy1amine)uronic acids, D-,
biological importance of, 33:200
(Glucofuranosylamine)urono-6,3-lactone
N-aryl-D-, preparation of, 33:200
h'-cyanomethyI-o-, preparation of, 33:20 I
193
Glucofuranosyl fluoride
D-
2,3,5,6-tetra-O-acetyl-
13C-NMR data for, 46: 165
'H- and "F-NMR data for, 46:97
2,3,5,6-tetra-O-benzoyl-,'H- and I9F-
NMR data for, 46:97
2,5,6-tri-O-acetyl-3-O-methyl, I3C- NMR
data for, 46: 166
3,5,6-tri-O-a~etyl-2-O-methyl-,'~C-NMR
data for. 46: 166
per-0-benzoyl-pa-, synthesis, 38:20 1
3,5,6-tr-O-acetyl-2-O-methyl-a, p-O-,
26: 184
p- (ri-Glucofuranosyl fluoride)urono-6,3-lactone
2,5-di-O-acetyl-P-, 'H- and 19F-NMRdata
for, 46: 1 16
2,5-di-O-benzoyl-p-, IH- and I9F-NMR data
for, 46: 1 16
Glucofuranosylurono-6,3-lactonebromide
2-O-acetyl-5-O-benzoyl-p-~-, preparation of,
33: 193
Glucofuranosylurono-6,3-lactonechloride
2,5-di-O-acetykx-~-,preparation of,
33:194
2,5-di-O-acetyI-p-o-
preparation of, 33: 193
reaction with methanol, 33: 196
2,5-di-O-benzoyI-P-o-
preparation of, 33: 193
reaction with ethanol, 33: 196
2-O-acetyl-5-O-benzoyl-p-~-, preparation of,
33: 193
Glucofuranosylurono-6,3-lactonefluoride
2,5-di-O-acetyl-p-o-, preparation of, 33: 194
2,5-di-O-benzoyl-P-o, preparation of,
33:194
halides.
preparation and properties of, 33: 192-194
Glucofuranuronamide
3-O-acetyl- 1,2-O-isopropyIidene-a-~-,
preparation of, 33:2 13
3-0-benzoyl- 1.2-O-isopropylidene-a-~-,
preparation of, 33:213
5-O-(ethoxycarbonyl)- 1,2-O-isopropyIidene-
a-D-,preparation of, 33:2 14
1,2-O-isopropylidene-5-0-
(rnethykulfonyl)-a-D, preparation of,
33:214
194 SUBJECT INDEX
Glucofuranuronamide (continued)
p-tolylsulfonyl-a+-, preparation of,
33:214
Glucofuranuronic acid
D-,structure of, 33: 190
6-deoxy- 1,2-O-isopropylidene-a-~-, methyl
ester, 23:104
3,5-di-O-benzoyl- 1,2-O-isopropylidene-a-
D-, methyl ester, preparation, 36:74
1,2:3,5-di-O-benzylidene-a-~-, preparation
of, 33:200
1,2:3,5-di-O-isopropylidene-a-~-, methyl
ester, preparation of, 33: 199
1,2-O-alkylidene-a-o-, reducing ability of
derivatives of, 33:226-229
1,2-O-isopropylidene-3,5-di-O-methyl-a-~-,
methyl ester, preparation of, 33:202
3,5-O-isopropylidene-2-O-(methoxy-
isopropy1)- I-0-methyl-a-o-,
preparation of, 33: 199
2,3,5-tri-O-methyl-o-, methyl ester,
preparation and reaction with N-
acylamino acid, 36: 113-1 14
Glucofuranuronic hydrazide
1,2-O-cyclohexylidene-5-0-
(methyisulfony1)-a-D-, fragmentation
of, 33:226
1,2-O-isopropylidene-5-O-(methylsulfonyl)-
a-D-, fragmentation of, 33:226
Glucofuranurono-6,3-lactones
aldehydo-o-, N-acylhydrazones,
disproportionation of, 33:215
crystallography of, p-O-,25:65
D-
alcoholysis reactions of, 33:212
ammonolysis, aminolysis, and
hydrazinolysis of, 33:213-216
elimination reactions with, 33:219-
226
hydrolysis reactions of, 33:2 1&2 1 1
oxidation of, 33:230
reaction with hydroxylamine, 33:214
with phenylhydrazine, 33:2 14
reduction with complex metal hydrides,
33:217,220
syntheses with, 33:23 1-234
catalytic hydrogenation, 38:288
reactions, 38:305, 308, 3 10
esterification of, 33:203-205
etherification of, 33:201-203
methylation of, 33:202
reactions of, 33: 189-234
reaction with aromatic amines, 33:200
structure of, 33: 190
thermodynamic stability of, 33: 19 1-192
hydrogenation, 37: 120
synthesis, 37:118-119
5-deoxy-5-fluoro-a-o-, 1,2-0-
isopropylidene-,C-NMR data for,
46: 170
5-deoxy-5-fluoro-l,2-O-isopropylidene-a-
D-, H-and 9F-n.m.r data for, 46:116
1,2-di-O-acetyl-5-O-benzoyi-ol-o-and-~-~-,
preparation of, 33:204
1-O-acetyl-2,5-di-O-benzoyl-a-~-and-p-~-,
preparation of, 33:204
5-0-acetyl- 1,2-0-( 1-methoxyethylidene)-a-
D-, preparation of, 33:195
1,2-O-alkylidene-a-o-
preparation of, 33: 197-200
transacetalation of Ssubstituted, 33: 197
1,2-O-alkylidene-5-O-(methylsulfonyl)-a-
D-,reaction with hydrazine, 33:216
5-0-benzoyl- 1,2-O-cyclohexylidene-a-~-,
preparation of, 33:203
5-0-benzoyl- 1,2-O-isopropylidene-a-~-
acetolysis of, 33:204
elimination reaction with, 33:220
preparation of, 33:203
reactions of, 33:20&205
syntheses with, 33:231
1,2-O-cyclohexylidene-a-~-
benzylation of, 33:202
synthesis of, 33: 199
1,2-O-cyclohexylidene-5-0-
(methykulfonyl)-a-D-, preparation of.
33:203
1,2-O-isopropyiidene-a-~-
benzylation of, 33:202
methylation of, 33:202
oxidation of, 33:230
preparation of, 33: 198,36:74
proton magnetic resonance spectroscopy
of, 33:207-209
reducing ability of, 33:227-229
1,2-O-isopropylidene-5-O-methyl-a-~-
preparation of, 33:202
reducing ability of, 33:227
1,2-O-isopropylidene-5-O-(methylsulfonyl)-
a-D-,preparation of, 33:203
 SUBJECT INDEX
1,2-0-isopropylidene-5-0-p-tolylsulfonyl-a-
D-
preparation of, 33:203
reduction with lithium aluminum hydride,
33:217
1,2-0-(S)-benzylidene-a-o-, preparation of,
33:200
1,2,5-tri-o-acetyl-a-o- and-p-o-, 33:O
1,2,5-tri-0-benzoyl-p-o- preparation of,
33:203
Glucofuranurononitrile, 3,5-di-O-acetyl- I ,2-0-
isopropylidene-a-D-, elimination and
degradation reactions of, 33:226
Glucofuranuronos, 6,3-lactone-5-d, 1.2-0-
isopropylidene-a+-, preparation of.
33:219
Glucogalactans, 41: 100
Glucogenes, 45202
gluco-Hept-l -enitol, 2,6-anhydro-1-deoxy-u-.
48:356
Glucoheptose,-p-D-. crystal structure
bibliography, 38:436
Glucohydrolase, exo-( 1+6)-cx-~-,44:258
Glucoisosaccharinic acid
a- and p-, formation of, 28: 194
a-D-
calcium and strontium salts,
crystallography of, 25:68
electric charges on atoms of, 25: 100
D-, 25:343
formation of, 28: 199, 46:292
structure, 46:291
Glucokinase, enzymic activity in liver
metabolism, 34:326
Glucomannans, 24:339,41:91,44:164
acetolysis of, 22:22
antitumor activity of, 32:25 1-252,26 1-262
biosynthesis, 35:353,41:127
carbon-13 nuclear magnetic resonance
spectra, 38:66,39:200
D-ghCOnyl isothiocyanate, 2,3,4,5,6-penta-
0-acetyl, 44: 141
formation in cellulose, biosynthesis,
42318-3 19
fungal, 23:397
degradation of, 31:192
methylation analysis of wood, 30: 17
in plant cell-walls, 42:269,44:359
properties and antitumor activity of, 32:263
reaction with diamines, 44: 120
195
structure, enzymic analysis, 44: 178-1 80
synthesis, 44:366
yeast, 41:99
Glucomanno-oligosaccharides, from enzymic
hydrolyzates of glucomannans,
3 2 3 1 4 3 I6
Glucometasaccharinic acid
D-, 25:343
formation of, 28: 199
structure, 46:291
D-, formation of, 46:292, 303
Glucomylase, gas-liquid chromatography of,
2850
Gluconamides, 50: 15 1
2,5-anhydro-, D-, preparation of, 33: 1 17
2,5-anhydro-, N,N-dimethyl-D-, preparation
of,33:117
D-, 47:144-150
"-C-chemical-shift data, 47: 145-146
I3C-NMR
Gd3+effect, 47:146-147, 149
MnZ' effect, 47:146. 148-149
structures, 47: 144
N-(2-chloroethyl)-o-, crystal structure
bibliography, 34:356,38:438439
n-Gluconate ion, conformation of, 26:69
Gluconic acid
2-amino-2-deoxy-o-
deamination of, 33:116-1 17
in muscarine synthesis, 31:70
ethyl ester. deamination of, 31:58
2-amino-2-deoxy-~-
deamination of, in muscarine synthesis,
31:70
methyl ester, deamination of, 33: I 17
2-amino-4,6-0-benzylidene-2-deoxy-~-,
ethyl ester, deamination of, 3 1 5 9
2,5-anhydro-
D-, preparation of, and methyl ester,
33: 1 16-1 17
L-, and methyl ester, preparation of.
33:117-118
D-
analytical high-performance liquid
chromatography, 46:34
and calcium salt, preparation of,
29:118-119
3-deoxy-3-fluoro-, 'H- and "F-NMR data
for, 46: 1 16
in honey, 25:290
196 SUBJECT INDEX
Gluconic acid (continued)
lactones, 23: 15
0-isopropylidene derivatives, 45: 1 1
potassium salt, crystal structure
bibliography, 31: 105, 364
potassium salt monohydrate, crystal
structure bibliography, 30:448
trisodium salt, monohydrate, crystal
structure bibliography, 32:356,367
2-deoxy-2-diazo-o-, methyl ester
tetraacetate, preparation of, 3 1 5 9
2-deoxy-2-(2,4-dinitroaniho)-o-, sodium
salt, irradiation, 38: 173
3-deoxy-3-fluoro-o-, preparation, 38:245
4-O-p-o-gaIactopyranosyl-~-,calcium
bromide tetrahydrate, crystal structure
bibliography, 31:351
6-O-phosphono-~-,trisodium salt, dihydrate,
crystal structure bibliography, 32:355
2,3,4,6-tetra-O-acetyl-o-, ethyl ester, reaction
with phosphorus pentachloride, 28:239
3,4,5,6-tetra-O-acetyl-2-deoxy-2-(N-
nitrosoacetamid0)-o-, reaction with
potassium hydroxide, 31:70
Glucono- I ,5-lactam, 5-arnino-5-deoxy-o-,
23: 165-166
Glucono- 1,6-lactam, 6-arnino-6-deoxy-o-,
23:165
D-GluCOnO- 1.5-lactone
crystal structure bibliography, 30:448
electro-oxidation of, 29: 117
preparation of, 25:4
Glucono- 1,4-lactone
2-acetamido-2-deoxy-~-,effect on
hexosaminidases, 31:6
6-O-(N,N-dimenthylglycyl)-o-, synthesis,
3554
Glucononitrile
2,3,4,5,6,-penta-O-acetyI-~-, reaction with
ammonia, 31:81-82
2,3,4,5,6,-penta-O-benzoyl-o-, ammonolysis
of, effect of solvent on, 31:99
2,3,4,5,6,-penta-O-propionyI-~-,
ammonolysis of, 31:88
2-acetamido-tetra-O-acetyI-2-deoxy-o-,
ammonolysis of, 31:87
Gluconylhydrazides, 1-aroyl-2-o-, 50: 155-1 56
Gluco-oligosaccharides, a-(1+4)-linked, liquid
chromatography analysis, 46:3840
Glucophore, 45:202-205,218
Glucopyranan
CK-D-, fungal, 41:70
anti-a+-, as murine immunoglobulins,
31:337-342
p-D-,fungal, 41:73
Glucopyranose
1,3,4,-tri-O-acetyl-6-deoxy-6-thiocyanto-2-
0-p-tolysulfonyl-a+-, 44: 143
2-acetamido-
1,6-anhydr0-4-azido-3-O-benzoyl-2-
deoxy-P-D-, preparation of, 34:85,
125-126
2-deoxy-a-~-,crystal structure
bibliography, 34:354
2-deoxy-a-D-esterof adenosine 5-
pyrophosphate, 28:3 15,342
of thymidine 5 -pyrophosphate,
enzymic synthesis of, 28:324, 342
of uridine 5- pyrophosphate, enzymic
preparation of, 28:341
fermentation production and
biosynthesis, 28:327,343
2-deoxy-o-, laser-Raman spectroscopy,
44533
4-0-[2-acetamido-2-deoxy-P(ol)-o-
glucopyranosyl]-2-deoxy-o-,
monohydrate, crystal structure
bibliography, 38:46&467
4-0-(2-acetamido-2-deoxy-p-~-
g~ucopyransoyl)-2-deeoxy-p-~-,
trihydrate, crystal structure, 43:246
~-O-(D- l-carboxyethyl)-2deoxy-a-~-,
hydrate, crystal structure
bibliography, 32:364
1,3,4,6-tetra-O-acetyI-2-deoxy-a-~-,
methane chemical-ionization mass
spectrum of, 29:81
1,3,4-tri-O-acetyl-2-deoxy-6-O-(p-
nitrophenylsulfonyl)-P-D-,
fluorination, 38:206
1,3,4-tri-0-acetyl-2,6-dideoxy-6-fluoro-~-
D-, preparation, 38:206
4-acetamido-, 1,2,3,6-tetra-O-acety1-4-
deoxy-o-, 23: 187
a - D - , 45:74
2-acetamido-2-deoxy, circular dichroism,
45:9495
I3Cnuclear magnetic resonance spectra of,
33:277
crystallography of, 25:61
 SUBJECT lNDEX
ester of
adenosine 5-pyrophosphate, 28:309,
314
enzymic preparation of, 28:337
in sucrose synthesis, 28:395
8- bromoadenosine 5 -pyrophosphate,
preparation of, 28:355
cytidine 5-pyrophosphate, 28:309. 3 15,
338
2-deoxyadenosine 5-pyrophosphate,
enzymic preparation of, 28:338
2-deoxyuridine 5-pyrophosphate.
enzymic preparation of, 28:338
5,6-dihydrouridine 5 -pyrophosphate.
preparation of, 28:354
guanosine 5 -pyrophosphate, 28:309,
338
5-hydroxyuridine 5-pyrophosphatc,
enzymic preparation of, 28:338
inosine 5- pyrophosphate, enzymic
preparation of, 28:338
N6-hydroxyadenosine pyrophosphate,
preparation of, 28:355
Nh-methoxyadenosine5 I-
pyrophosphate, preparation of,
28:355
N-methyluridine 5 - pyrophosphate,
preparation of, 28:355
thymidine 5-pyrophosphate, 28:309,
338
epimerase action on, 28:375
isolation of, 28:322
mechanism of conversion of, 28:38 I
uridine 5-pyrophosphate. 28:309,
3 12-3 13
carbodiimides in synthesis of, 28:353
degradation of, 28:356
enzymic preparation of, 28:33&337
isolation of, 28:325
mechanism of epimerase reaction with,
28:372
synthesis by mixed anhydride method,
28:351
synthesis by phosphoramidate method,
28:345
hydrogen bonds in, 25:99
ionization constants and mutarotation of,
24:25
monohydrate
configuration of, 25:55
197
hydrogen bonding in, 25:56
mutarotation is deuterium oxide and in
water, 24:31
sweetness-structure relationship, 45:239
taste properties, 45242
2-amino- I ,6-anhydro-2-deoxy-p-~-
deamination of, 31:41,34:128-129
4-ethers, preparation of, 34: 124
preparation of, and N-derivatives. 34: 122
3-amino- 1,6-anhydr0-3-deoxy-p-o-
conformation of, 34: 127
crystal structure bibliography, 38:424
deamination of, 34:128
hydrochloride
conformation of, 34:59
monohydrate, crystal structure
bibliography, 38:425
preparation of, 34: 123
4-amino- 1,6-anhydro-4-deoxy-p-~-.
deamination of, 34: 128
2-amino- I ,6-anhydro-2,4-dideoxy-4-fluoro-
p-D-,preparation, 34:124, 135,38:216
4-amino- 1,6-anhydr0-2,4-dideoxy-2-fluoro-
p-D-,preparation of, 34: 124
2-amino-2-deoxy-a-o-, esters of uridine,
adenosine, cytidine and thymidine 5-
pyrophosphates, enzymic syntheses of,
2 8 ~338-339
5-amin0-5-deoxy-o-, 23:116, 132-133,
51:150
2-amino-2-deoxy-4-0-a-~-g~ucopyranosy~-
D-, isolation and synthesis, 39:240
4-amino-4,6-dideoxy-p-~-, 23: I87
1,2-anhydro-a-o-, from cellulose pyrolysis,
22502
1,4-anhydro-a-n-
from cellulose on heating, 23:441442
from 2-0-methylcellulose pyrolysis, 34:44
1,4-anhydro-P-o-, synthesis, 39: 165
1,6-anhydro-P-o-. 47:16, 304, 51:112-1 14
acetobrominolysis, 39: 1 15
acetolysis of, 34:65
conformation of, 25:101, 103. 107
crystal structure bibliography, 30:448,
34:348
determination of, in corn syrup, 28:25
effect of flame retardants on pyrolysis of,
23:47 1
formation from cellulose on heating,
23:43 1,433
198 SUBJECT INDEX

Glucopyranose (continued) 1,6-anhydro-2.4-di-O-benzyl-3-O-crotyl-P-

pyrolysis of, 23:460462 D-, polymerization, 39:181-183, 195
gas-liquid chromatography of, 28:42 1,6-anhydro-2,3-di-O-benzyi-4-0-(2,3,4,6-
history, preparation, and uses of, 34:25 tetra-O-benzyhx-D-ghcopyranosyl)-P-
hydrogenolysis, 39: 133 D-, polymerization, 39: 195
mass spectrum of, 21:81 1,6-anhydro-2,3-di-O-rnethyl-P-~-,
potassium alcoholate, structure of, preparation of, 34:79
21:266 1,6-anhydro-2,4-di-O-p-tolylsulfonyl-~-~-,
per-0-substituted, 34:77 23:25 1
2,4-phenylboronate, preparation, 3 5 4 8 preparation of, 33:24
polymerization, 39: 179 5,6-anhydro- 1,2-0-isopropylidene-3-0-
preparation and history of, 34:27 methyh-, polymerization of, 21:491
production of, 22:498499, 50 1 1,6-anhydr0-4-methyl-2-0-p-tolylsulfonyl-~-
proton spin-lattice relaxation rates, D-, 23:262
45: 160 ~,6-anhydro-4-O-a-~-g~ucopyranosyl)-~-~-,
pyrolysis of, 22:497 synthesis, and hexaacetate, 39:235
selective esterification of, 33:23 1,6-anhydro-2-0-benzoyl-4-0-p-
sweetness-structure relationship, 45269, tolylsulfonyl-P-D-, 23~251
271 1,6-anhydro-4-O-benzyl-~-~-, p-
synthesis, 39: 160, 163 toluenesulfonylation of, 34:80
1,6-anhydro-2 deoxy- 5,6-anhydro- 1,2-0-isopropylidene-cy-o-,
2-fluoro-P-o-, reaction with hydrogen synthesis, 39: 173
bromide, 28:278 5,6-anhydro- 1,2-0-isopropylidene-3-0-
2-flUOr0-P-D- methyl-a-o-, synthesis, 39: 173
hydrolysis or acetolysis of, 34: 135 1,6-anhydro-2-O-methyl-P-~-, from 2-0-
preparation of, 34:67 methylcellulose pyrolysis, 34:44
1,6-anhydr0-4-deoxy- 1,6-anhydro-2-0-p-toIylsulfonyl-~-~-,
4-fluoro-2-O-p-tolysulfonyl-P-~-, 23:25 I , 262
preparation of, 34: 134 1,6-anhydro-4-O-p-tolylsulfonyl-~-~-,
4-fluoro-P-o-, preparation of, 34: 133 23:251
3-O-methyl-2-~-p-to~y~sulfony~-~-o-, acid
1,6-anhydro-4-S-benzyl-4-thio-P-~-,
cleavage of, 34:64 preparation of, 34: 136
1,6-anhydro-2,4-diazido-2,4-dideoxy-P-~- 1,6-anhydro-4-S-henzyI-4-thio-2-O-p-
conformation of, 34: 127 tolysulfonyl-P-o-, preparation of,
crystal structure, 43:209-2 10 34:138
1,6-anhydro-2,4-dideoxy-2,4-difluoro-P-u- 1.6-anhydro- 1 (6)-thio-P-o-, crystal structure
crystal structure, 43:209 bibliography, 38:423424
hydrolysis or acetolysis of, 34: 135 1,6-anhydro- 1(6)-thio-P-~-,preparation of,
preparation of, 34: 133,38:2 16-2 18 34: 146
1,6-anhydro-2,3-di-O-benzoyl-~-u-, 1,2-anhydro-3,4,6-tri-O-benzyI-a-o-,
oxidation of, 34: 100 synthesis, 39:172
1,6-anhydro-2,4-di-O-benzyl-P-~-, p- 1,4-anhydro-2,3,6-tri-O-benzyl-a-~-
toluenesulfonylation of, 34:80 polymerization, 39:205
1,6-anhydro-3,4-di-O-benzyl-2-deoxy-~-~-, synthesis, 39: 164
debenzylation of, 34:75 1,6-anhydro-2,3,4-tri-O-benzyl-~-o-
1,6-anhydro-2,3-di-O-benzyl-4-0-(2,3,4,6- acetolysis of, 22: 16
tetra-O-benzyl-a-o-ghcopyranosyl)-P- polymerization, 39: 179, 18 1-1 82, 187,
D- 207
polymerization, 39: 195 preparation of, 34:32
synthesis, 39:223 synthesis, 39: 170-17 1
 SUBJECT INDEX
1,6-anhydr0-2,3,4-tri-O-benzyl-o-
preparation of, 34:47
reaction with ethanethiol and zinc
chloride, 34:64
1,6-anhydro-2,3,4-tri-O-ethyl-p-~-,
polymerization, 39: 181-1 83
1,6-anhydr0-2,3,4-tri-O-methyl-P-~-
copolymerization with Lewis acids, and
with styrene, 34:74
polymerization, 39: 159, 179-1 80, 182
I ,4-anhydr0-2,3,6-tri-O-methyl-~-, synthesis,
39: 164
I ,6-anhydr0-2,3,4-tri-O-(p-bromobenzyl)-P-
D-, polymerization, 39: 182-1 83
1,6-anhydro-2,3,4-tri-O-(p-rnethylbenzyl)-P-
D-, polymerization, 39: 182-1 83
1,6-anhydro-2,3,4-tri-O-p-xyIyl-P-~-,
polymerization, 39: I83
I ,6-anhydr0-2,3,4-tri-O-tolylsulfonyl-~-i~-,
23:25 1
p-0-
and p-L-, superpositioned over same
receptor site, 45:236
conformation of, 25: 106
crystallography of, 25:6 I
2,3,4,6,2',3 '-hexa-0-acetyl- 1,6-anhydro-
4-0-P-glucopyranosyl-
interproton distances, 45: 156
spin-lattice relaxation rates, 45: 155
hydrogen bonding in, 2 5 5 6
ionization constants and mutarotation of,
24:25
I-mesitoic ester,I ,6-anhydride from, 34:32
sweetness-structure relationship. 45:239
taste properties, 45:242
5,6-bis(acetamid0)-2,3,4-tri-O-acetyl- 1,6-
anhydro-5,6-dideoxy-P-~-, 23: I34
C-allyl-S-P-o-glucopyranosyl-0-
sulfo(thiocarbohydroximidate)
4-deoxy-4-fluoro-a-o-galactopyranosy l-ol-
D-, preparation, 38:222
6-deoxy-6-fluoro-ol-~-glucopyranosyl-a-
D-
biological activity, 38:283
synthesis, 38:2 11
potassium salt monohydrate, crystal
structure bibliography, 38:440
carba-a-o-, synthesis, 48:38
carba-P-DL-, 48:23, 33, 87
synthesis, 48:27
I99
carba-P-D-, synthesis, 48:36
(Y-D-, derivatives, vibrational spectra, 44:20
2,3',3 '-d3, penta-O-acetyl-3-deoxy-3-C-
(hydroxymethy1)-a-D-,23:96.98
D-
2-acetamido-2-deoxy-
circular dichroism, 45:98
ohgomers, circular dichroism, 45: 100
2-acetamido-2,6-dideoxy-6-fluoro-
u anomer, H- and "F-NMR data for,
46:121
I ,3,4-tr-O-acetyl-, 'H- and "F-NMR
data for, 46: 12 1
01 form preference in solvents, 47:92
1,6-anhydro-2-deoxy-2-fluoro-~-
3,4-di-O-acetyl-, 'H- and I9F-NMR data
for, 46: 1 14
3,4-di-O-benzyl-, 'H- and l9F-NMR
data for, 46: 114
3-0-acetyl-4-O-benzyl-, 'H- and I9F-
NMR data for, 46: 1 14
1,5-anhydro-2-deoxy-2-fluoro-l -C-
methyl-a-,3,4,6-tri-O-acetyl-. I H- and
I9F-NMR data for, 46: 1 13
anomeric equilibnum, solvent effects,
47:68
anomers, 47:54-55
2-deoxy-2-fluoro-
ol anomer, I'C-NMR data for, 46: 162
P anomer
I3C-NMR data for, 46: 162
IH- and IyF-NMR data for, 46:86
1,3,4,6-tetra-O-acetyl-, 'H- and lYF-
NMR data for, 46:86
I ,3,4,6-tetra-O-acetyI-a-, 'H- and "F-
NMR data for, 46:162
3-deoxy-3-fluoro-
(Y anomer
I3C-NMR data for, 46: 163
'H- and IyF-NMR data for, 46:90
(3 anomer
13C-NMR data for, 46: 163
'H- and IyF-NMR data for, 46:91
6-phosphate, 'H- and "F-NMR data for,
46:9 1
1,2,4,6-tetra-O-acetyI-, '1-1- and "F-
NMR data for, 46:9 I
4-deoxy-4-fluoro-
OL anomer
I3C-NMR data for, 46: 164
200 SUBJECT INDEX
Glucopyranose (continued)
'H- and I9F-NMR data for, 46:93
p anomer
I3C-NMR data for, 46: I64
'H- and I9F-NMR data for, 46:93
1,2,3,6-tetra-O-acetyl-P-, 'H- and I9F-
NMR data for, 46:93
6-deoxy-6-fluoro-
a anomer
I3C-NMR data for, 46: 164
'H- and I9F-NMR data for, 46:95
p anomer
I3C-NMR data for, 46: 164
'H- and I9F-NMR data for, 46:95
1,2,3,4-tetra-O-acetyyl-, 'H- and I9F-
NMR data for, 46:95
derivatives, equilibrium compositions,
47:4849
2,4-difluoro-P-, 'H- and I9F-NMR data
for, 46: 151
mutarotation and polarography,
29: 139-141
3-0-acetyl- 1,6-anhydro-2,4-dideoxy-P-
2-acetamido-4-fluoro-, IH- and I9F-
NMR data for, 46: 114
4-acetamido-2-fluoro-, 'H- and I9F-
NMR data for, 46: 114
orientation of hydroxyl groups for, in
4 C , ( ~conformation,
) 4975
phosphorus derivatives of, physical
properties, 42: 191
polymerization of, 21:436
proton magnetic resonance spectroscopy
of derivatives of, 27:26
2-deoxy-
2-(fluoroacetamido)-o-, preparation,
38:252
2-fluoro-3-O-methyl-o-, labeled, 48:
I98
4-0-(4-deoxy-a-~-threo-hex-4-
enopyranosyluronic acid 2-sulfate)-2-
sulfoamino-~-,6-suifate,29:243
2-(trifluoroacetamido)-o-, preparation,
38:252
3-deoxy-
3-fluoro-o-, preparation, 38:2 16
s-nitro-p-o-, tetraacetate, 24: 115
5-deoxy-, 5-phosphonyl-o-, synthesis and
structures of, 42:155-161
6-deoxy-, 6-fluoro-4-O-(methylsulfonyl)-a-
o-glucopyranosyl-a-o-, biological
activity, 38:283
2,4-diamino- 1,6-anhydro-2,4-dideoxy-p-~-
conformation of, 34: 127
preparation of, 34:124-125
5,6-diamino- 1,6-anhydr0-5,6-dideoxy-p-o-,
formation of, 34: 149
2,7-diamino-2,7-dideoxy-a-DL-carba-,
48:63
4,7-diamino-4,7-dideoxy-a-DL-carba-,
48:63
1,4:3,6-dianhydro-
a-D-
from cellulose on heating, 23:433,441
crystal structure bibliography,
38:42 1 4 2 2
p-D-, 47~306-308
D-
from amylose pyrolysis, 22:500
from o-glucose pyrolysis, 22:501
4,6-dideoxy-
4,6-difluoro-a-o-ga~actopyranosy~-a-o-,
preparation, 38:222
4-(dimethylamino)-~-,23: 154
3,4-di-O-acetyl-2-amino-l,6-anhydro-2-
deoxy-p-o-, deamination of, 34: 128
2,3-di-O-acetyl-l,6-anhydro-P-o-, in
synthesis of oligosaccharides, 34: 160
3,6-di-O-acetyl-l,2-anhydro-4-0-(2,3,4,6-
tetra-0-acetyl-a-o-glucopyranosy1)-a-
D-, synthesis, 39: 171
1,6-di-O-acetyI-2,3,4-tri-0-benzy~-o-,
22:16
1,2:4,6-di-0-benzyIidene-3-0-
(methylsulfonyl)-ol-o-, proton magnetic
resonance spectroscopy of, 27:67,78
I ,2:4,6-di-O-ethylidene-a-o-,
diastereoisomers, 34: 197
2,3 :4,6-di-O-isopropylidene-5-thio-a-o-,
crystal structure, 43:230-23 1
2,3:4,6-di-0-isopropylidene-5-thio-a-o-,
synthesis, 39:77
1-O-(indole-3-acetyI)-P-o-, 21:390
I.-, 2,6-dideoxy-2-fluoro-
a anomer, 'H- and I9F-NMR data for,
46: 132
p anomer, IH- and I9F-NMR data for,
46: 132
1,3,4-tri-O-acetyl-, 'H- and I9F-NMR data
for, 46: 133
 SUBJECT INDEX
methyl 2-acetamid0-3,4-di-O-acetyl-2,6-
dideoxy-6-fluoro-a-~-,preparation,
38:208
methyl 2-acetamido-3,4-di-O-acetyl-2,4-
dideoxy-4-fluoro-a-~-,preparation,
38:220
methyl a-D-,crystal structure bibliography,
38:434
methyl P-D-, hemihydrate, crystal Struchire
bibliography, 38:435436
methyl 2-benzamido-2-deoxy-3-0-[~- 1-
(methoxycarbonyl)ethyl]-6-0-p-
tolylsulfonyl-P-o-, fluorination,
38:205
methyl 4-deoxy-4-fluoro-a-o-, structure,
38: 197
methyl 2-deoxy-2-(trifluoroacetamido)-a-~-,
biological activity, 38:283
methyl 2,3-di-O-benzyl-4-0-(p -
bromophenylsulfonyl)-6-O-trityl-~-i~-,
fluorination, 38:222
methyl 4,6-0-benzylidene-
2,3-di-O-(methylsulfonyI)-a-o-, reaction
with potassium fluoride, 38:22 1
2,3-di-@~-tolyhlfony]-cY-o-, reaction
with potassium iodide, 38:22 I
3-0-(methyhlfonyl)-a-o-, reaction with
potassium fluoride, 38:221
methyl 6-~-p-to~yhlfonyi-a-o-,
fluorination, 38:205,207
methyl 2,3,4,6-tetra-O-acetyl-P-o-, crystal
structure bibliography, 38:46 1 4 6 2
methyl 2,3,6-tri-O-benzoyI-4-0-(p-
bromophenylsulfony1)-P-o-,
fluorination, 38:222
1-naphthyl 2,3,4,6-tetra-O-acetyl-P-r,-,
crystal structure bibliography, 38:
478
l-O-abscisoyl-P-D-, synthesis, 39:36
1-0-(2-acetamidoacyl)-2,3,4,6-tetra-O-
acetyl-P-o-, 25:420
2-O-acetyl-l,6-anhydro-3,4-di-O-benzyl-~-
D-, formation of, 34:47
6-~-a-~-galactopyranosy~-a, P-O-
monohydrate, 43:37 1
monohydrate, crystal structure
bibliography, 37:388,38:448449
4-0-a-o-glucopyranosyl-a,-~-~-, crystal
structure bibliography, 38:44&447
4-0-a-o-glucopyranosyl-~-~-, monohydrate,
201
crystal structure bibliography, 30:453,
38:449450
0-a-D-glucopyranosyl-(1+4)-0-[a-o-
glucopyranosyl-( I+~)]-D-,in honey,
25297
0-a-o-glucopyranosyl-( 1+6)-0-[a-u-
glucopyranosyl-( I+~)]-D-,in honey,
25297.302
0-a-o-glucopyranosyl-( 1-+3)-0-a-o-
glucopyranosyl-( 1+6)-0-a-o-
glucopyranosyl-( 1+6)-0-, from
dextran, 30:339-340
O-a-L-fucopyranosyl-( 1+3)-0-p-o-
galactopyranosyl-( 1-.4)-2-acetamido-
2-deoxy-o-, preparation, 3 9 5 3
1,2-0-alkylidene-a-o-, conformation of,
34:200
1,2-O-(aminoisopropylidene)-a-~-
conformation of, 25: 102
hydroiodide, crystal structure
bibliography. 25:68, 31:366
4-0-P-o-galactopyranosyl-a-~-,
monohydrate, crystal structure
bibliography, 30:453
4-0-P-~-galactopyranosyl-o-,see Lactose
0-P-o-galactopyranosyl-(1+4)-P-o-, see
Lactose, p-
3-O-P-~-glucopyranosyl-a,-~-~-,0. 19-
hydrate, crystal structure bibliography,
38:447448
2-0-P-~-glucopyranosyl-a-~-, monohydrate,
crystal structure bibliography,
38:45045 I
6-~-P-D-glUCOpyranOSyl-P-D-, crystal
structure, 43:23 1-232
O-P-o-glucopyranosyl-(1+4)-P-o-, see
Cellobiose
O-P-o-glucopyranosyl-( 1+6)-0-a-o-
glucopyranosyl-( 1+4)-o-, in honey,
25:297
0-P-o-glucopyranosyl-( 1+3)-0-P-o-
glucopyranosyl-( 1+4)-~-,from oat and
barley glucans, and lichenan, 30:355,
359
0-P-o-glucopyranosyl-( 1+3)-0-P-o-
glucopyranosyl-( 1+6)-o-, from yeast
glucan, 30:363
0-P-o-glucopyranosyl-( 1+4)-0-P-~-
glucopyranosyl-( 1+3)-o-, from p-D-
glucans, 30:352,355,357, 360
202 SUBJECT INDEX
Glucopyranose (continued)
O-p-~-ghcopyranosyl-(1+6)-0-p-D-
glucopyranosyl-( 1+3)-o-, from cell-
wall polysaccharide, 30:364
0-p-o-glucopyranosyl-( 1+3)-O-p-o-
glucopyranosyl-( 1+4)-0-P-o-
glucopyranosyl-( 1-+4)-o-, from
lichenan and P-o-glucans, 30:354355,
357
0-P-o-glucopyranosyl-( 1 +4)-0-p-o-
glucopyranosyl-( 1+3)-O-P-o-
glucopyranosyl-( 1+4)-o-, from
lichenan and p-D-glucans, 30:354-355,
357
0-P-o-glucopyranosyl-( 1+4)-O-p-o-
glucopyranosyl-( 1-+4)-0-p-o-
glucopyranosyl-(l+3)-~-, from p-D-
glucans, 30:355,360
O-p-~-xy~o-hexopyranosy~-3-ulose-( 1+4)-
D-, polarography of, 29: 145
1,2-O-benzylidene-a-o-, diastereoisomers,
34: 197
1,2-O-benzylidene-o-, preparation of, 34: 191
2-0-benzyl- 1 -O-(methylsulfonyl)-3,4,6-tri-
0-(p-nitrobenzoy1)-a+-, preparation
of, 34:262
1,2-O-cyclohexylidene-o-, preparation of,
34:191
1,2-O-cyc~openty~idene-o-, preparation of.
34:191
4-0-(2-deoxy-2-fluoro-a-o-
mannopyranosy1)-o-, 48:2 13
1,2-O-ethyIene-a-o-and-p-~-, from 0-(2-
hydroxyethyl)starch, 29:3 19
1,2-O-ethylidene-a-~-,diastereoisomers,
34: 197
4,6-0-isopropylidene-a,~-~-, preparation of
34: 188
1,2-O-isopropylidene-o-,preparation of,
34:191
O-N-acetylneuraminoyI-(2+8)-0-(N-
acetylneuraminoyl)-(2+3 )-O-p-o-
galactopyranosyl-( l+4)-a-~-, 2 5 3 5
LO-( p-acetoxybenzoyl)-2,3,4,6-tetra-O-
acetyl-a-o-
acyl migration in, 33: 103
deacetylation, 33:103,39:34
1-0-( p-acetoxybenzoyI)-2,3,4,6-tetra-O-
acetyl-pa-, deacetylation, 39:34
1,2-0-[2-(S)-2-(2-oxotetrahydro-5-
fury1idene)lethylene-a-o-,
monohydrate, crystal structure
bibliography, 31:350
0-( 3,4,6-tri-O-acetyl-2-0-p-tolylsulfonyl-~-
o-glucopyranosy1)-(I +6)-tetra-O-
acetyl-a-o-, 23:264
1,2,3,4,6-penta-O-acetyI-a-~-, reaction with
methanolic ammonia, 31:85
penta-0-acetyl-a-o-, 22: 16
reaction with piperidine, 39:30
penta-0-acetyl-p-o-, reaction with
piperidine, 39:30
selective deacylation, 39:28
1,2,3,4,6-penta-o-acetyl-o-, ammonolysis of,
mechanism of, 31:lll
penta-0-acetyl-o-, anomerization of, 24:44
penta-O-acetyl-3-deoxy-3-C-
(hydroxymethy1)-a-o-, 23:94,98,
24:242
nucleoside, 23:99
I ,2,3,4,6-penta-O-acetyI-5-thio-a-o-, 43:372
penta-O-acetyI-5-thio-a-o-, and sulfoxide
and sulfone, 23:216
1,2,3,4,6-penta-O-benzoyl-a-o-,
ammonolysis of, 31535
1,2,3,4,6-penta-O-benzoyl-p-o-,
ammonolysis of, 31:86
penta-0-benzoyl-o-, ammonolysis of, 31: I1 7
effect of solvent on, 31:99
1,2,3,4,6-penta-~-nicotinoyl-a-~-,
ammonolysis of, 31 :88
per-O-acetyl-4-acetamido-4,6-dideoxy-6-
fluoro-a-o-galactopyranosyl a-D-,
preparation, 38:2 12
per-O-trimethyisilyl-D, mass spectrometry of,
29:48
phenyl2,3-di-O-acetyl-6-0-
(methylsulfonyl)-4-0-(2,3,4,6-tetra-O-
acetyl-a-o-glucopyranosy1)-a-o-,
fluorination, 38:205
S-p-o-galactopyranosyI-4-thio-~-,synthesis,
44:135
2-S-ethyl-2-thio-o-, preparation of, 32:30,32
1,2,3,4-tetra-O-acetyl-
6-amino-6-deoxy-D-, deamination of,
31:51
p-0-
1,6-anhydride formation from, 34:46
reaction with aryl cyanate and
hydrochloric acid, 28:257
 SUBJECT INDEX
reaction with 2-0-substituted 3,5-di-0-
benzoyI-i--arahino- and-D-riho-
furanosyl bromides, 34:280
6-chloro-6 deoxy-P-o-, preparation of,
28:257
6-chloro-6-deoxy-~-,22: 182
6-deoxy-6-iodo-a-o-,3,6-anhydride from,
34:33
2-deoxy-2-thiocyanto-a-~-, 44: 143
6-~-p-to~ylsulfonyk-~-o-, 44: 144
reaction with sodium methoxide, 34:33
6-O-trityl-P-u-,1,6-anhydride formation
from, 34:46
1,2,3,6-tetra-O-acetyI-, 4-0-[2,3,6-tri-0-
acety1-4-0-(2,3,4,6-tetra-C)-acetyl-p-~-
glucopyranosyl)-P-~-glucopyranosyl]-
p-D-,crystal structure bibliography,
38:483485
1,2,4,6-tetra-O-acetyI-
3-O-(ch~oroacetyl)-P-o-,selective
deacylation, 39:35
3-0-formyl-P-o-, selective removal of
formyl group, 39:36
1,3,4,5-tetra-O-acetyI-, 2-deoxy-2-fluoro-i)-,
48:163
1,3,4,6-tetra-O-acetyl-
a - ~and++-,
- methylation and acyl
migration in, 33: 104
2-amino-2-deoxy-o-, ammonoiysis of,
mechanism of, 3 1 : l l l
2-deoxy-2-C-(4,6-di-O-acetyI-2,3-
dideoxy-a-~-eryfhro-hex-2-
enopyranosy1)-p-o-, 24:2 14
2-deoxy-2-(N-nitrosoacetamido)-a-r-,
decomposition of, effect of solvent
on, 31:68-70
2-deoxy-2-(N-nitrosoacetamido)-~-~-,
reactions of, 31:69-70
2-deoxy-2-thiocyanto-a-o-, 44: 143
2-deoxy-2-thiocyanto-P-~-, 44: 144
2-,6-dideoxy-2,6-di( isothiocyanato)-a-o-,
44:141
2-[N-(benzoyloxycarbonyl)glycylamino]-
2-deoxy-P-~-,synthesis, 43: 146
2-0-[3,6-di-0-acetyl-2-deoxy-2-iodo-4-0-
(2,3,4,6-tetra-O-acetyl-a-
glucopyranosyl)]-c~-~-, synthesis.
39:243
2-O-methyl-P-o-, 25: 195
preparation of, 28:289
203
2,3,4,6-tetra-O-acetyI-
1-0-(indol-3-ylacetyl)-p-~-, proton
magnetic response spectroscopy,
36:l 10
I -0-(2,4,6-trimethylbenzoyl)-a-~- and+
D-, deacetylation and acyl migration
in, 33: 102
1-0-(tri-0-acetylgalloy1)-a+-,
deacetylation, 33: 103,39:34
1-thio-D-
reaction with ethanethiol, 32:34
reductive cleavage to 1,5-anhydro-i)-,
glucitol, 32:75
tetra-0-acetyl-2-amino-2-deoxy-a- and-pa-,
deamination of, 31:22
I ,2,4,6-tetra-O-benzoyl-3-0-1,-
tolylusulfonyl-a-o-, (and P-D-),
displacement reactions of, 24: 16 1
2,3,4,6-tetra-O-benzyl-~-,selective
acetolysis, 39:47
tetra-0-methyl-a-D-, mutarotation of, 24: 15,
27-28,3 I , 27: 104
5-thio-a-~-,23:2 16
5-thio-~-,biochemical activity of, 23:212
3,4,6-tri-O-acetyl- 1,2-anhydro-~-,polymer-
ization of (Brigls anhydride), 21:490
trifluoromethyl 3,6-di-O-acetyl-2-deoxy-2-
fluoro-4-O-(2.3,4,6-tetra-O-acetyl- p-D-
galactopyranosy1)-a-D-, preparation,
38:232
trifluoromethyl 3,4,6-tn-O-acetyl-2-deoxy-2-
fluoro-a-o-, preparation, 38:23 1
2,3,6-tri-O-acetyl- 1,4-anhydro-a-o-,
synthesis, 39: 172
3,4,6-tri-O-acetyl- 1,2-anhydro-a-o-, 25: 164,
53:150-152
Brigls synthesis, 39: 17 1
levoglucosan synthesis from, 34:29.48
polymerization, 39:207-208
2,3,4-tri-O-acetyI- 1,6-anhydro-P-o-
crystal structure bibliography, 32364-365
polymerization, 39: 179-1 80, 183
reaction with hydrogen bromide, 28:278
tri-0-acetyl- 1,2-anhydro-o-,0x0 reaction
with, 23: 105
1,2,4-tri-O-acetyl-5,6-dIdeoxy-3-O-methyl-
5-[(S)-phenyIphosphinyl]-p-o-, crystal
structure bibliography, 38526
1.4,6-tri-O-acetyl-0-3-(methylsulfonyl)-
a-u-, 23:261
204 SUBJECT INDEX
Glucopyranose (continued)
3,4,6-tri-0-acetyl-1-0-benzoyl-2-chloro-2-
deoxy-a-o-, partial proton nuclear
magnetic resonance spectrum, 29:38
1,2,3-tri-O-acetyl-4,6-O-benzylidene-P-o-,
irradiation, 39:92
1-
3,4,6-tri-O-acetyI-1,2-0-(
cyanoethy1idene)-a-o-
crystal structure bibliography, 37:396
preparation of, 33: 132-133
3,4,6-tri-O-acetyl- 1,2-0-( 1-exo-
ethoxyethy1idene)-a-o-, crystal
structure bibliography, 31:353,32:370
3,4,6-tri-O-acetyl-I -0-(indol-3-ylacetyl)-2-
O-(trideuterioacetyl)-o-, synthesis,
36: 110
2,3,4-tri-O-benzyl-P-o-, azeotropic
dehydration with p-toluenesulfonic acid,
34:47
3,4,6-tri-O-benzyl-I ,2-0-( 1-
ethoxyethy1idene)-a-o-, anhydridization
with mercuric chloride, 34:47
2,3,4-tri-O-methyl-P-o-, azeotropic
dehydration of, 34:47
Glucopyrano~e-~~C, a-D-,ester with uridine 5-
pyrophosphate, enzymic preparation of,
28:336
Glucopyranose hydrochloride, 2-amino-2,6-
dideoxy-6-fluoro-a-o-, 48: 139
Glucopyranose pentaacetate
5a-carba-a-o-, synthesis, 48:49
carba-a-or.-, 48:27, 34
carba-P-L-, synthesis, 48:44
D-, nonselective spin-lattice relaxation rates,
45: 148
Glucopyranoses, 2-azido-2-deoxy-, 53: 167- 170
Glucopyranose 6-sulfate, 2-deoxy-4-0-(4-
deoxy-a-~-threo-hex-4-enopyranosyl-
uronic acid 2-sulfate)-2-sulfoamino-o-,
from heparin, 27:41
Glucopyranose-t, a-D-,esters with uridine 5 I-
pyrophosphates, 28:337
a-o-Glucopyranose-urea, crystal structure
bibliography, 30:450
a-D-Glucopyranoside hydrolases
molecular weights, 39:388
yeast, substrate specificities, 39:384390
Glucopyranosides
4-acetamido-4,6-dideoxy-6-fluoro-a-o-
ga!actopyranosyL-o, 48:2 11
a-D-
acetylation of, 33: 19
hydrolysis by glucoamylase, 50: 17-1 8
oxidation products of, hydrolysis of,
22:58
structures and catabolism of, 32: 191-200
uptake by yeasts, 39:381-391
utilization by yeasts, Michaelis
constants, 39:382
utilization by yeasts and associations of
abilities, 32:223
xylopyranosyl a-D-,enzymic preparation
of, 30:254
alkyl tetra-0-acetyl-P-o-, synthesis and
history of, 34:245
ally1 3-0-allyl-2,3,6-tri-O-benzyl-o-,
synthesis, 39: 170
2-amino-2-deoxy-a-o-g~ucopyranosyl a-o,
48:72
from Streptomyces, 30:236
4-amino-4,6-dideoxy-6-fluoro-a-o-
galactopyranosyl-a-o-, 48:2 1 1-21 2
3,4-anhydro-, proton magnetic resonance
spectra of, 27:8 1
3,6-anhydro-a-o-glucopyranosyl3,6-
anhydro-a+-, taste properties, 45:270
aryl, hydrolysis of, estimated thermodynamic
activation functions for, 22:84
aryl D-, rates of hydrolysis and substituent
constants for, 22:80
p-0-
acetylation of, 33: 19
alkaline degradation, 52:44&445
enzymic hydrolysis, 48:323-324
fmctofuranosyl-a-o-, see Sucrose
hydrolysis of, rate constants and kinetic
parameters for, 22:48, 72
non-enzymic hydrolysis, 48:322-323
synthesis, 49:74
utilization by yeasts, 32:201-205,
39: 39 1-394
and association of abilities, 32:222
benzyl-, 2,3,4,-tri-O-benzyI- 1-thio-P-0-,
reaction with methyl iodide, 34:32
benzyl2-acetamido-
6-0-benzyl-2,4-dideoxy-4-fluoro-a-~-,
48: 149
2-deoxy-6-O-a-~-mannopyranosy~-a-o-,
mannopyranosyl-a-o-, deacetylation
and hydrolysis of, 31:195
 SUBJECT INDEX
2-deoxy-3-~-~-~-galactopyranosy~-a-~-cholesterol-3-yl 2,3,4-tri-O-acetyl-P-o-,
mannopyranosyl-a-o-,
deacetylation and hydrolysis of, 31: 195
deamination degradation of, 31:234
3,4-di-O-acetyl-2-deoxy-p-~-,synthesis,
39:35
3,6-di-O-acetyl-2-deoxy-4-U-(tetra-O-
acetyl-a-D- galactopyranosy1)-,
synthesis of, 34:25&25 I
3-0-acetyl-2-deoxy-4.6-di-0-
(methylsu1fony)-a-o-, displacement
reactions of, 24: 160
4,6-0-benzylidene-2-deoxy-p-~-, selective
etherification with 2-chloropropionic
acid, 33:55
4,6-0-benzylidene-2-deoxy-3-0-( tetra-0-
acetyl-P-o-galactopyranosyl)-a-n-,
synthesis of, 34:252
benzyl2-amino-2-deoxy-6-0-a-~-
mannopyranosyl-a-o-, deamination
degradation of, 31:234
benzyl2,3-di-0-allyl-4-0-benzyl-p-~-.
hydrogenolysis, 39: 130
benzyl2,3-di-0-benzyl-4,6-0-benzyl idene-
p-D-,hydrogenolysis regioselectivity,
39:128
benzyl3-0-acetyl-2-[henzyl-
oxycarbonyl)amino]-2-deoxy-4.6-di-0-
(methylsulfony1)-a-o-, displacement
reactions of, 24:160
henzyl4-0-(a-~-glucopyranosyluronic
acid)++-, synthesis of, 33:88
benzyl4,6-0-benzylidene-
p-D-, selective acylation of, 33:20
2-( benzyl-oxycarbonyl)amino-2-deoxy-a-
D-, hydrogenolysis regioselectivity,
39: 127
benzyl 6 - ~ - p - t o ~ y ~ s u ~ f o n 23:240
y~-~-~-,
benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-
p-D-,selective deacylation, 39:29
benzyl 2,3.4-tri-O-benzyl-P-~-,oxidation,
36:72
benzyl 3,4,6-tri-0-benzyl-2-0-triflyl-p-~-,
48:124-125
bis(benzy1oxy) isopropyl 2,3,4,6-tetra-O-
benzyl-a-o-, preparation of,
34:258-259
butyl 2-acetamido-2-deoxy-P-o-,
transglycosylation of, 31:5
carha-glucopyranosyl a-D-,synthesis, 48: 7 1
20s
preparation, 36:82
2-d, methyl 2-deoxy-a-D- and-P-D-,
preparation of, 27: 132
D-
2-acetamido-2.6-dideoxy-6-fluoro-a-
benzyl 3,4-di-O-acetyl-, 'H- and "F-
NMR data for, 46: 121
methyl 7,4-di-O-acetyI-, 'H- and I9F-
NMR data for, 46: 121
methyl 3,4-di-O-methyI-, 'H-and I9F-
NMR data for, 46: 121
2-deoxy-2-fluoro-
methyl 4,6-di-O-acetyl-3-0-benzyl-P-,
IH- and I9F-NMR data for, 46:86
methyl 3-0-acetyl-4,6-0-benzylidene-
p-, 'H- and IyF-NMR data for, 46:87
methyl 4,6-0-benzyhdene-3-0-methyl-
p-, 'H- and IyF-NMR data for, 46:87
methyl 3-0-benzyl-4,6-0-benzylidene-
p-, 'H- and I9F-NMR data for, 46537
phenyl 3,4,6-tri-O-acetyl-P-, IH- and
I9F-NMR data for, 46:87
tnfluoromethyl 3.4,6-tn-O-acetyl-a-,
'H-and I9F-NMR data for, 46:87
3-deoxy-3-fluoro-
benzyl p, 'H- and I9F-NMR data for,
46:91
benzyl 2,4,6-tn-O-acetyl-P-, 'H- and
I9F-NMR data for, 46:91
methyl 2-0-acetyl-4,6-0-benzylidene-
p-, 'H- and "F-NMR data for, 46:91
6-deox y-h-fluoro-
methyl. 'H- and 19F-NMR data for,
46:96
methyl 2,7,4-tn-O-benzyl-a-, 'H- and
'"F-NMR data for. 46:96
phenyl, 'H- and IyF-NMR data for,
46:96
p-nitrophenyl p-, 'H- and IyF-NMR
data for, 46:96
methyl 2-acetamido-3-0-acety1-2,4,6-
trideoxy-4,6-diffluoro-a-, 'H- and
I9F-NMR data for. 46: IS7
methyl 4-azido-4,6-dideoxy-6-fluoro-a-,
"C-NMR data for, 46: 171
methyl 2-benzamido-2.6-dideowy-6-
fluoro-a-
3,4-di-O-acetyl-, 'H- and "F-NMR data
for, 46: 12 1
206 SUBJECT INDEX
Glucopyranose (continued)
3-O-benzyl-, 'H- and I9F-NMR data for,
46:122
3-O-benzyl-4-O-mesyl-, 'H- and I9F-
NMR data for, 46: 122
methyl 2-benzamido-2,4,6-trideoxy-4,6-
difluoro-a-
3-O-acetyl-, IH-and I9F-NMR data for,
46:157
3-O-benzyl-, 'H- and 19F-NMRdata for,
46:157
methyl 4-deoxy-4-fluoro-
a anomer, 'H- and I9F-NMR data for,
46:93
2,3-di-O-methyl-a-, IH- and I9F-NMR
data for, 46:94
6-O-acetyl-2,3-di-O-methyl-a-, IH- and
19F-NMRdata for, 46:94
2,3,6-tri-O-acetyl-a-, 'H- and I9F-NMR
data for, 46:93
2,3,6-tri-O-benzoyl-a-, 'H- and 19F-
NMR data for, 46:94
methyl 6-deoxy-6-fluoro-
a anomer, I3C-NMR data for, 46: 165
P anomer, I3C-NMR data for, 46165
methyl 4,6-dideoxy-6-fluoro-a-
4-amino-, 'H-and I9F-NMR data for,
46:122
4-azido-, 'H- and I9F-NMRdata for,
46: 122
methyl 3,6-di-O-acetyl-2,4-ddeoxy-4-
fluoro-a-
2-acetamido-, 'H- and I9F-NMR data
for, 46:119
2-benzamido-, 'H- and I9F-NMR data
for, 46: 119
4,6-O-benzylidene-2,3-dideoxy-3-fluoro-
a-
benzyl2-acetamid0, 'H- and 19F-NMR
data for, 46: 119
benzyl2-azido-
I3C-NMR data for, 46:171
'H- and I9F-NMR data for, 46:119
benzyl2-benzamido-, I3C-NMR data
for, 46: 171
methyl 2-benzamido-, IH- and 19F-
NMR data for, 46: 119
phenyl p-, photoinduced, electrontransfer
reaction of, with 1,4-
dicyanonaphthalene,46: 184-1 85
phenyl6-deoxy-6-fluoro-
a anomer, I3C-NMR data for, 46: 165
P anomer, I3C-NMRdata for, 46:165
p-nitrophenyl6-deoxy-6-fluoro-, I3C-
NMR data for, 46: 165
pyrolysis of, 34: 152
decyl a-D-, crystal structure bibliography,
34:372,37:401
6-deoxy-a-~-glucopyranosyl a-D-, enzymic
preparation of, 30:254
2-deoxy-p-~-,derivatives, 24:210
derivatives, mutorotation, 44:25
a-D-glucopyranosyla-D-,see Trehaloses
4,6-dideoxy-4,6-difluoro-a-~-
galactopyranosyl-o-, 4821 1
4'-5-dhydroxyflavon-7-yl2-0-[3-C-
(hydroxymethy1)-p-0-
erythrofuranosyl]-p-~-,see Apiin
4-dimethylepipodophyIlotoxin-9-yl4,6-O-
thenylidene-P-o-, 43:372
2,4-dinitrophenyl2-deoxy-2-fluoro-P-o-,
48:207
ethyl 2-amino-2-deoxy-a-~-,deamination of,
31:21
ethyl-P-D-, hydrolysis of, rate constants and
kinetic parameter of, 22:35-36
ethyl 1-thio-a-~-
hydrolysis of, 22:42
preparation of, 32:21
structure, 39:357
transport into Saccharomyces cerevisiae,
32:159
utilization by yeasts, 32:197
ethyl I-thio-Pa-, hydrolysis of, rate
constants and kinetic parameter of,
22:35-36
interaction with concanavalin A, 35: 188-
190
isopropyl2,3,4,6-tetra-O-acetyl-p-~-,
acetolysis of, 22: 18
isopropyl3,4,6-tri-O-acetyl-
2-deoxy-P-~-,acetolysis of, 22: 18
2-O-methyl-P-~-,acetolysis of, 22: 18
L-, trifluoromethyl3,4-di-O-acetyl-a-, 'H-
and I9F-NMR data for, 46: 133
methyl 2,3,-di-O-benzoyl-4-O-p-
23~238
tolylsdfonyl-6-O-trityrityl-cw-D-,
methyl 2-acetamido-
2,6-dideoxy-6-iodo-a-~-, crystallography
of, 2393
 SUBJECT INDEX
3,4-di-O-acetyl-6-bromo-2,6-dideoxy-c~-
D-, preparation by Pinner reaction,
28:257
3-O-acetyl-6-chloro-2,6-dideoxy-4-0-
(methylsulfonyl)-(Y-D-,preparation
of, 28:256,33:83
3-O-acetyl-2-deoxy-a-o-,
methanesulfonylationof, 28:256
4,6-O-benzylidene-2-deoxy-a-~-and-
p-D-, selective etherification
with 2-chloropropionic acid,
33:55
3,4,6-tri-O-acetyl-2-deoxy-p-~-,
nitrosation of, 31:67
methyl 3-acetamido-
3,6-dideoxy-a-~-,acylation and
sulfonylation of, 33:30
3,6-dideoxy-p-~-,reaction with acetyl
chloride, 33:29
2,4-di-O-acetyl-3,-6-dideoxy-a-~-,
selective deacylation, 39:29
2-O-acetyl-3,6-dideoxy-P-~-, reaction
with acetyl chloride, 33:29
4-0-acetyl-3,6-dideoxy-P-~-, reaction
with acetyl chloride, 33:29
methyl (Y-D-
acetals, taste of, 45243
2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O-
(methylsufonyl)-S~2nucleophilic
displacement, 44: 125-126
acylation with N-(tri-0-
methylgalloyl)imidazole, 33:43
4,6-benzeneboronate, acetylation and
benzoylation of, 23:267
benzoylation of, 23:249
sulfonylation of, 23:247,249
2,3-bis(diethylborinate)4,67-
ethylboronate, selective cleavage,
3955
catalytic oxidation of, 33:88
C Z and C-0 bond-lengths in, 44: 15
crystal structure bibliography, 31:366
cyclic 4,6-phosphate
cyclohexylammoniumsalt, crystal
structure bibliography, 37:392
4-deoxy-4-(thiocyanato)-, synthesis,
44: 126
4,6-dideoxy-4-thiocyanato-2-O-p-
tolylsulfonyl-, 44: 144
4,6-dideoxy-4-thiocyanato-2-O-p-
207
tolylsulfonyl-3-O-(trimethylsilyl)-,
44:144
2,3-di-O-acety1-6-deoxy-4-0-
(methylsulfonyl)-6-thiocyanato-,
44: 144
2,3-di-O-acetyl-4,6-dideoxy-4,6-
di(thiocyanat0)-, 44: 144
2,3-di-O-acetyl-4,6-dideoxy-4-
thiocyanato-, 44:144
2,3-di-O-benzoyI-4,6-didexoy-4-
thiocyanato-, 44: 144
2,3-(diphenylcyclodiboronate)-4,6-
phenylboronate, selective cleavage,
3953
electro-oxidation of, 29: 117
formation from dithioacetal,32:68
gel chromatography of, 2332
hydrolysis of, 22:3 1-32,34
trifuluoroacetic acid in, 28: 17
methyl derivatives, sweetness, 43262
methyl ethers, taste properties, 49262
mono-and dideoxy derivatives,
sweetness-structure relationship,
45259-260
2-O-acetyl-4,6-dideoxy-4-thiocyanto-,
44: 144
phenylboronate, preparation, 3538, 46,52
4,6-phenylboronate 2,3-(diphenyl-
cyclodiboronate), hydrolysis, 3552
preparation, 35:47
4,6-phosphate, hydrolysis, 39:6 1
preparation of, 27:101,31:31-32,34:256,
266
reaction with N-bromosuccinimideand
triphenylphosphine,28:249,33:78
with sulfur monochloride, 28:256
with sulfur monochloride in N,N-
dimethylformamide,33: 82
with sulfuryl chloride, 28:230-23 1
relative reactivities of hydroxyl groups in,
335657
selective acetalation of, 33:71
selective acetylation with acetic anhydride
in pyridine, 33:30
selective benzylation of, 3357
selective chlorination
with carbon tetrachloride and
tris(dimethylamino)phosphine,33:79
with methanesulfonyl chloride, 33:8 1
with sulfuryl chloride, 33:73-74
208 SUBJECT INDEX
Glucopyranose (continued)
selective esterification of, 33:27-28
selective methylation with diazomethane,
33:68
structure, 32: 192,39:356
sulfonylation and chlorination of, 33:83
sweetness, 49263
structure relationship, 45241, 244245
threshold, determination by triangular
test, 45:245
synthesis, 40: I13
tetraacetate, proton magnetic resonance
spectroscopy of, 27:32
2,3,4,6-tetra(chlorosulfate),preparation of,
methyl 6-azido-6-deoxy-a-o-, preparation of.
28:232
transesterification with methyl esters of methyl 3-azido-4,6-O-benzylidene-3-deoxy-
fatty acids, 33:44
transport into Saccharornyces cerevisiae.
32:159
2,3,4-tri-O-acetyl-6-deoxy-6-thiocyanato-, methyl p-D-
44:144
2,3,6-tri-O-benzoyl-4-deoxy-4-
thiocyanato, 44: 144
true sweetness of, 45:240
utilization by yeasts, 32:194199
vinylation and reduction of vinyl ethers,
gas-liquid chromatography of, 30:26
methyl (Y-DL-, synthesis, 40:70
methyl 2-amino-
2-deoxy-a-~-,deamination of, 25: 185,
31:21-22,47,233
2-deoxy-P-o-, deamination of, 25: 185,
312-22,47,233
2-deoxy-4,6-O-ethylidene-3-O-methyl-o-,
deamination of, 25:188,31:21
4,6-O-benzylidene-2-deoxy-p-~-,
deamination of, 25:188,31:21
4,6-O-benzylidene-2,3-dideoxy-3-nitro-P-
D-, 24: 134
methyl 3-amino-
3-deoxy-cu-o-
deamination of, 31:28
reaction with nitrous acid, 24:193
3,6-dideoxy-a-L-, sulfonylation of, 23:248
4,6-O-benzylidene-3-deoxy-(~-~-,
deamination of, 31:77
methyl 4-amino-
4-deoxy-a-o-, deamination of, 31:3 1,44
4-didexoy-a-o-, 23: 153
methyl 3,6-anhydro-
(Y-D-
formation from methyl 2,3-anhydro-c*-
D-aiiopyranoside, 24:46
reaction with boron trichloride, 28:280
sulfonylation of, 23:253
taste properties, 45:273
p-D-,preparation of, 28:287
2-benzamido-2-de0xy-P-o; 22: 135
2,4-di-O-methyl-cu-o (am++)-,
hydrolysis of, 22:46
2,4-di-O-p-tolysulfonyl-cu-~-,
displacement reactions of, 24: 153
4-O-p-tolyl~~Ifonyl-cu-~-, 23~253
28:286
p-D-, preparation of, 28:286
2-O-(methy~su~fonyl)-cu-o-, displacement
reactions of, 24: 164
acetolysis of, 22:20
2.3-di-O-acetyl-6-deoxy-6-thiocyanato-,
44:144
formation from dithioacetal, 32:68
hydrolysis of, 22:28, 32,28:305
rate constants and activation energies
for, 22:70
oxidation, 37: 119
4,6-(phenyl phosphate), hydrolysis, 39:6 1
preparation of, 33:55,37:119
relative activities of hydroxyl groups in,
33:58
selective acetylation with acetic anhydride
in pyridine, 33:30
selective methylation of, 33:56
selective oxidation with chromium
trioxide, 33:99
sulfonylation of, 23:247-248,28:255
2,3,4,6-tetranitrate, selective denitration,
39:56-57
2,3,4-tri-O-acetyl-6-deoxy-6-thiocyanato-,
44:144
3,4,6-tri-O-acetyl-2-deoxy-2-thiocyanato-,
44: I44
3,4,6-tri-O-acetyl-2-S-(N-
acetylthiocarbamoyl)-2-thio-,
synthesis, 44: 131
3,4,6-tri-O-acetyl-2-thio-2-S-
(thiocarbamoy1)-, synthesis, 44:13 1
true sweetness of, 45:240
 SUBJECT INDEX
methyl 2-benzamido-2-deoxy-a-~-~
benzoylation of, 33:30
methyl 2-(benzylamino)-4,6-0-benzylidcne-
2-deoxy-a-~-,23:278
methyl 2-(benzyloxycarbonyl)amino-2-
deoxy6-O-p-tolysulfonyl-a-~-, 23:24 I
methyl 2-chloro-2, deoxy-P-D-, hydrolysis
of, 28:305
methyl 4-chloro-4-deoxy-, a - ~ -22:200
, reaction, 28:233-234
methyl 6-chloro-6-deoxy-
a-D-,22: 183
displacement of chloro by benzoate
group, 28:285
preparation of, 28:256,280
reaction with sodium azide, 28:286
2,3,4-tri(chlorosulfate),preparation of,
28:232
2,3,4-tri(chlorosulfate), preparation of,
33:73
4-0-(4,6-dichloro-4,6-dideoxy-a-~-
galactopyranosy1)-o-, synthesis,
39:232
tetra-0-p-tolylsulfonyl-a-D-and-P-D-.
preparation of, 28:255
2,3,4-tr-0-rnethyl-a-o-and-a-~-,
preparation of, 28:257
2,3,4-hi-0-(methylsulfonyl)-a-~-and 0-D-,
preparation of, 28:255
2,3,4-hi-0-p-tolylsulfonyl-a-~- and+-[>-,
preparation of, 28:255,33:83
methyl-d, D-, nonselective spin-lattice
relaxation rates, 45: 148
methyl 4-deoxy-
4-fluoro-a-o-, crystal structure
bibliography, 34:352
4-iodo-2,3-di-O-methyl 6-0-p-
tolylsulfonyl-a+, preparation of,
28:241
4-iodo-2,3-di-O-methyI-6-0-p-
tolylsulfonyl-D-, 22: 185,23:268
methyl 6-deoxy-
a-, 2,4-phenylboronate, preparation. 35:48
WD-, dibenzoylation of, 33:28
3,4-di-O-methyl-a-o-, 23:270
6-(methylsulfinyl)-a-~-,crystal structure
bibliography, 30:451
6-nitro-a-o-, 24:99
methyl 4,6-diazido-4,6-diazido-4,6. dideoxy-
(Y-D-, preparation of, 28:286
methyl 4,6-dichloro-4,6-dideoxy-
209
a-D-
crystal structure of. 25:73
2,3-di( chlorosulfate), preparation of.74
preparation of, 33:8 1
p-0-
2,3-bis (chlorosulfate), displacement
reactions of, 24: 162
2,3-di(chlorosulfate), displacement
preparation of, 33:83
2,3-di-O-(methylsulfonyl)-~-~-,
Preparation of, 28:256
methyl 2,3-di-O-acetyl-
4-O-benzoyl-6-deoxy-a-~-,synthesis,
39: 150
4,6-O-benzylidene-
a-D-, and-@+-, preparation and
stereochemistry of, 34: 195
a-D-,proton magnetic resonance
spectroscopy of, 27:68
a-D-. reaction with di-revr-butyl
peroxide, 39: 150
methyl 2,3-di-O-allyl-4,6-O-benzylidene-a-
D-, selective deallylation, 39:5 I
methyl 2,3-di-O-benzoyl-
4,6-di-O-(methylsuIfonyl)-a-~-,
displacement reactions, 24: 160, 191,
28:230
4,6-O-benzylidene-a-~-
irradiation, 39:92
peroxide-induced rearrangement,
39: 150
reaction with di-tert-butyl peroxide,
39: I50
methyl 2,3-di-O-benzyl-
4,6,-di-0-( methysulfonyl)-a-~-,
displacement reaction of, 24: 145
4,6-dideoxy-4-iodo-a-~-
displacement reactions of, 24: 160, 191
reaction with radioactive iodine,
28:229
4,6-dideoxy-4-(methylamino)-a-r,-,
23: I54
4,6-0-benzylidene-a-o-, hydrogenolysis
regioselectivity, 39: 128
methyl 3,4 di-0-benzyl-
a-D-,23:270
6-deoxy-a-~-,23:270
methyl 2.3 :4.6-di-O-cycIohexylidene-ol-o-,
preparation by acetal exchange, 34: 187
210 SUBJECT INDEX
Glucopyranose (conrinued)
methyl 2,3 :4,6-di-O-isopropyIidene-a-~-.
synthesis, 39:77
methyl 2,3-di-O-methyl-
a-D-and-P-D-, selective methylation of
Cu(1I) derivatives of, 33:54
6-O-p-tolylsulfonyl-a-~-,reaction with
methyltriphenoxyphosphonium
iodide, 28:241
methyl 4,6-di-O-methyl-, a-D-, reaction with methyl 4,6-O-anisylidene-a-o-, synthesis,
triphenylphosphine-carbon
tetrachloride, 28:247
methyl 2,6-di-U-(methylsulfonyl)-
a-D-
displacement reaction of, 24: 145
preparation of, 33:27
P-0-, 23:248
methyl 4,6-di-O-(methylsulfonyl)-~-~-,
23:248
methyl 2,3-di-O-p-tolylsulfonyl-a-~-, 23:247
4,6-benzeneboronate, 23:267
distillation and attempted cyclization of,
34:47
methylation of, 23:266
methyl 4,6-di-S-acetyI-2,3-di-O-methyl-4,6-
dithio-P-o-, 23:224
methyl 4,6-ethylidene-P-~-,methylation with
dimethyl sulfate, 3 3 5 3
selective oxidation with chromium
trioxide, 33:98
methyl 2-0-acetyl-
6-deoxy-6-iodo-3-0-(methylsulfonyl)-4-
0-(2,3,4-tri-O-acetyI-
6-deoxy-6-iodo-a-~-glucopyranosyl)-P-
D-, synthesis, 39:229-230
6-~-p-tolysu~fony~-a-0-
glucopyranosy1)-P-o-, synthesis,
39~229-230
6-deoxy-3-0-(methylsulfonyl)-4-0-(2,3,4-
tri-O-acetyl-6-deoxy-a-~-
glucopyranosy1)-P-o-, synthesis,
39:236
4,6-0-benzylidene-3-deoxy-3 -phenylazo-
a-D-, proton magnetic resonance
spectroscopy of, 21:69,78
methyl 3-0-acetyl-
4.6-0-benzylidene-2-bromo-2-deoxy-a-~-
, preparation of, 28:268
2-0-methyl-P-o-, 4,6-dinitrate, selective
denitration, 39:56
methyl 4-O-acetyl-, 6-chloro-6-deoxy-2,3-di-
O-p-tolysulfonyl-a-D-, 22: 183
methyl 6-0-acetyl-, p-D-
crystal structure bibliography, 32:381
preparation, 39:63
methyl 6 - 0 4 1-alkoxyethyl)-a-o-, formation
of, 33:7 1
methyl 2-0-allyI-3,4,6-tri-O-benzyl-a-~-,
selective acetolysis, 39:47
39:79
methyl 3-0-P-o-galactohranosyl-a-~-,
synthesis of, 33:3 19
methyl 4-0-P-~-glucopyranosyl-~-~-,
methanolate, crystal structure
bibliography, 30:454
methyl 6-0-benzoyl-a-~-,preparation,
28:285,39:29
methyl 4-0-benzoyl-6-bromo-6-deoxy-a-~-,
preparation, 39:98
methyl 3-0-benzoyl-4,6-0-benzylidene-
a-D-, imidazole-catalyzed acyl migration
in, 33:42
2-0-(trifluoroacety1)-a-D-, selective
deacylation, 39:36
methyl 2-0-benzoyl-4,6-0-benzylidene-a-
D-, acyl migration in, 33:lOl
methyl 6-0-benzyl-a-o-, relative reactivities
of hydroxyl groups in, 3 3 5 7
methyl 4-0-benzyl-P-o-, selective
methylation of, 3 3 5 6
methyl 4,6-0-benzylidene-
a-D-
benzoylation with benzoyl chloride-
triethylamine, 33:22
with benzoyl cyanide, 33:45
with N-benzoylimidazole, 33:42
complex with lithium aluminum
hydride, reduction with, 27: 196
conformation of, 26: I 15,34: 199
2,3-dinitrate, selective denitration,
39:5&57
etherification with 1-chloro-2-
(diethylamino)ethane, 33:54
hydrogenolysis regioselectivity, 39: 125,
130
oxidation with dimethyl sulfoxide,
33:92
reactions with sulfuryl chloride, 33:
74
 SUBJECT INDEX
reaction with N-bromosucciniinide,
39:97-98
selective acylation of, 33: 19,2 I , 29
selective methylation of, 3354
selective methylation of Cu(1l)
derivatives, 3 3 5 4
with diazomethane, 33:68
selective sulfation of, 33:5&5 1
selective sulfonylation of, 33: 14
sulfonylation of, 23:238
transesterification with methyl
benzoate-sodium methoxide. 33:44
p-0-
acetylation of, 33: 19
benzoylation with benzoyl chloride-
triethylamine, 33:22
with N-benzoylimidazole, 33:42
etherification with 1-chloro-2-
(diethy1amino)ethane. 33:54
methylation with dimethyl sulfate,
3353
2-C-dicarbethoxymethyl-2,3-dideoxy-3-
nitro-D-, 24:137
D-, hydrolysis of, 34:202
2-deoxy-2-(ethyIamino)-cr-~-,23:278
3-deoxy-3-nitro-a-o-, (and-p-o)-. reaction
with basic aluminum oxide, 24: 1 13
3-deoxy-2-0-ethyl-3-nitro-p-o-, 24: 13 1
2,3-di-O-benzyI-P-~-,hydrogen01ysis
regioselectivity, 39: 125, 128
2,3-dI-O-methyl-n-~-
preparation of, 34: 189- 190
preparation of diastereoisomers. 34: 195
2,3-di-O-p-tolylsulfonyl-ol-o-,
displacement reaction of, 24: 16Y
2.3-di-O-p-tolylsulfonyl-~-o-, 23:25 1
2,3-di-O-(trifluoroacetyl)-a-o-, selective
deacylation, 39:29
2-m(andp)-carboxyphenylamino-3-deoxy-
3-nitro-o-, 24:136
2-o-carboxyphenylamino-3-deoxy-3-nitro-
D-, and methyl ester, 24:136
2,3-0-methylene-u-o-, proton magnetic
resonance spectroscopy of, 27:65
2-0-methyl-3-0-(methylsulfonyl)-~-~-,
hydrolysis of, 23:261
3 - ~ - ( m e t h y l s u ~ f o n y ~ ) 2-nitrate,
-a-~-
denitration of, 23:266
2-0-p-tolylsulfonyl-a-~-,23:238, 250
oxidation of, 23:258
211
2-0-p-tolylsulfonyl-~-~-, 23:25 1
3-O-p-tolylsulfonyl-@-o-, 23:25 1
2-O-p-tolylsulfonyl-01-~-, displacement
reactions of, 24: 169
methyl 3-0-benzy1-4,6-0-benzylidene-ol-o-,
hydrogenolysis regioselectivity, 39:
128
methyl 2-0-benzyl-4,6-0-benzylidene-3-
deoxy-3-nltro-p-o-, 24: 13 1
methyl 6-0-( I-ethoxyethy1)-a-o-,
preparation of, 33:71
methyl 4.6-0-ethylidene-
OI-D-
2,3-dinitrate, selective denitration,
39:56
preparation by acetal exchange, 34: 187
preparation of, 33:7 1
p-D-, 2,3-dinitrate, selective denitration,
3956
methyl 4,6-0-isopropylidene-a-~-,
hydrolysis of, 34:204
methyl 4,5-0-(4-methoxybenzyylidene)-2,3-
di-0-methyl-a-o-, hydrogenolysis
regiospecificity, 39: 130
methyl 6-0-( I -methoxyethyl)-a-D-,
preparation of. 33:71
methyl 3-0-methyl-
D-, reaction with sulfuryl chloride, 28:300
2,6-di-O-p-tolylsulfonyl-a-~-, 23:240
methyl 4-O-methyl-p-o-, hydrolysis of, rate
constants and activation energies for,
22:70
methyl 6-0-(methyIsulfonyl)-cu-~-, 23:240
methyl 6-O-octadecanoyl-@-~-, preparation,
39:63
methyl 4.6-0-( 1-phenylethyl)-a-n-,
hydrolysis of, 34:204
methyl 2-0-(p-nitrophenyh1~fonyl)-a-o-,
solvolysis of, 24:193), 25:208, 31:25
methyl 3-0-(1.-nitrophenylsulfonyI)-ol-~-,
solvolysis of, ring contraction by,
24: 193
methyl 4-0-Ip-nitrophenylsulfonyl)-cy-o-,
displacement reactions of, 24:19 1
methyl 4,6-0-propylidene-a-o-, 2.3-
dinitrate, selective denitration, 39:56
methyl 6-O-p-tolylsulfonyl-a-~-,23:240
methyl 3-O-p-tolysulfonyl-o-, 25:207
methyl 4,6-0-syringylidene-a-o-, synthesis,
39:79
212 SUBJECT INDEX
Glucopyranose (continued)
methyl 6-O-(tetrahydropyran-2-yl)-a-~-,
relative reactivities of hydroxyl groups
in, 33:57
methyl 4-O-(tetrahydropyran-2-yl)-p-o-.
selective methylation of, 33:56
methyl 4,6-O-(tetraisopropyIdisiloxane- I ,3-
diyl)-a-D-, preparation and
isomerization, 39:69
methyl 6-o-trity~-a-o-and-p-o-, selective
oxidation with chromium trioxide,
33:98
methyl 4,6-O-veQlidene-a-o-, synthesis,
39:19
methyl 2-S-benzyl-4,6-O-benzylidene-3-
chloro-3-deoxy-2-thio-a-o-, 22: 161
methyl S-benzyl-6-thio-a-o-, 24:258
methyl 2,3,4,6-tetrakis-O-(trimethylsiIyl)-
01-D-,selective methanolysis, 39:62-
63
methyl tetra-0-acetyl-a+, 23:264
carbon-13 nuclear magnetic resonance
spectrum, 41:38
selective deacylation, 39:28
methyl 2,3,4,6-tetra-0-acetyl-P-~-
acetolysis of, 22:18
oxidation by chromium trioxide, 39533
selective deacylation, 39:28
methyl tetra-0-benzoyl-a-o-, 24: 159
methyl tetra-0-benzyl-a-o-, preparation of,
34:266
methyl 2,3,4,6-tetra-O-(chlorosulfonyl)-a-~-,
reaction with aluminum chloride,
34:3&35
methyl tetra-0-methyl-P-D-, preparation of,
34274
methyl tetra-O-(methylsulfonyl)-ru-D-,
displacement reactions of,24: 161
methyl 2,3,4,6-tetra-O-(tnmethylsilyl)-a-o-
methanolysis os, 28:32
methyl 5-thio-
a-D-,6-phosphate, preparation, 39:63
D-, 23:216
methyl 2,3,4-tri-O-acetyI-
a - ~and-P-o-,
- methylation and acyl
migration, 33:103
2-amino-2-deoxy-p-~-,hydrobromide,
deamination of, 31:22
p-D-, methylation and acyl migration in,
33:103
6-bromo-6-deoxy-01-D-,preparation of,
28:249,251
6-bromo-6-deoxy-P-o-, reaction with
barium hydroxide, 28:287
6-chloro-6-deoxy-a-o-, preparation of
Pinner reaction, 28:257
6-deoxy-P-o-, acetolysis of, 22: 18
6-deoxy-5-C-niethoxy-a-~-, preparation
of, 29:293
6-deoxy-6-iodo-a-o-, hydrolysis of,
28:305
6-deoxy-6-nitro-a-o-, deacetylation of,
24:118
6-0-(3,4,6-tri-O-acetyl-2-deoxy-2-
oximino-a-o urubino-
hexopyranosyl)-P-D-, 24:208
methyl 2,4,6-tri-O-acetyl-
3-deoxy-3-nitro-p-~-,dehydroacetylation
of, 24: 129
3-O-p-tolylsulfonyl-cu-o-,(and p-D-),
displacement reaction of, 24: 162
methyl 3,4,6-tri-O-acetyl-
2-amino-2-deoxy-P-o-, hydrobromide,
synthesis of, 34:254
2-deoxy-2-iodo-P-o-, reaction with
bromine and silver acetate, 28:288
with sodium cobalt tetracarbonyl and
carbon monoxide, 28:292
2-(methyhlfonyl)-P-o-, 23:264
methyl tri-0-acetyl-
2-bromo-2-deoxy-P-o-, 0x0 reaction with,
23:112
6-deoxy-6-C-(methylsuIfinyl)-a-D-,
crystal structure bibliography,
37:395
2-deoxy-2-iodo-P-o-
brominolysis of, 25: 194
0x0 reaction with, 23: 110, 112
methyl 2.3.6-tri-O-acetyI-4-S-acetyl-4-thio-
01-D-,23:225
methyl 2,3,4-tn-O-benzoyl-a-o-, preparation
of, 29:5
methyl 2,3,4-tri-O-methyl
a-D-, reaction with aryl cyanate and
hydrochloric acid, 28:257
p-D-, reaction with aryl cyanate and
hydrochloric acid, 28:257
methyl 2,3,4-tri-O-(N-phenylcarbamoyl)-P-
D-, methylation and acyl migration in,
33:103
 SUBJECT INDEX
methyl 2,3,4-tri-O-(trimethylsiIyl)-w-i~-,
preparation, 39:62
methy 3,4,6-tri-O-acety1-2-bromo-2-deoxy-
p-0, reaction with sodium cobalt
tetracarbonyl and carbon monoxide,
28:293
2-naphthyl p-D-,hydrolysis of, 31: I93
6-nitroveratryl p-D-,photochemical cleavage
of, 46:18&185
O-ct-o-galactopyranosyl-
(I+ l)-P-~-fructofuranosylCX-D-.
occurrence, 37:290
(1+3)-P-~-fructofuranosyl a+,
occurrence, 37:291
( 1+6)-0-p-o-fructohranosyl a+-,
dihydrate, crystal structure
bibliography, 30:455
O-oc-o-glucopyranosyl-
(I+3)-~-~-fructofuranosyl,see Melezitose
( 1+3)-~-o-fructofuranosyl a-D-,
monohydrate, crystal structure
bibliography, 37:404
(1+6)-O-ct-~-ga~actopyranosy~-( I +6)-0-
a-o-galactopyranosyl-(1-6 )-a+
galactopyranosyl a-D-.isolation.
37:3 11
0-P-o-fructofuranosyl- (2- l)-O-p+
fructofuranosyl a-D-.see I-Kestose
0-P-o-galactopyranosyl-(( 1+3)-O-u-r)-
galactopyranosyl-( 1+3)-O-a-i)-
galactopyranosyl-( 1+ 3 ) - a - ~ -
galactopyranosyl a-D-,isolation, 37:3 1 I
0-nitrophenyl
p-D-,hydrolysis of, 22:37
I-seleno-p-o-, hydrolysis of, 22:37
tetra-0-acetyl-P-o-, selective deacylation,
39:28
I-thio-p-o-, hydrolysis of, 22:37
phenyl a-D-
1,6-anhydride formation from, 34:29
methanolysis of, 22:34
selective methylations with diazomethane,
33:68
phenyl p-D-
alkaline cleavage of, 34:29
hydrolysis of, rate constants and kinetic
parameter of, 22:35-36
methanolysis of, 22:34
selective methylations with diazomethane,
33:68
213
synthesis and history of, 34:245
phenyl2,3-di-O-benzyl-4,6-O-henzylidene-
a-D-. hydrogenolysis regioselectivity,
39:128
phenyl4,6-O-benzylidene-p-o-, selective
acylation of, 33:20
phenyl tetra-0-acetyl-a-o-. and-p-ii-,
preparation of, 34:265-266
phenyl I-thio-p-o-
1,6-anhydrohexopyranose from, 34:28
hydrolysis of, rate constants and kinetic
parameter of, 22:35-36
phenyl 2,3,4-tri-O-acetyl-p-o-, benzylation
and acyl migration in, 33: 103
p nitrophenyl
2-acetamido-
2-deoxy-P-o-, monohydrate, crystal
structure bibliography, 34:359
4,6-0-benzylidene-2-deoxy-P-r,-.
selective etherification with 2-
chloropropionic acid, 33:55
a-D-
catabolism by yeasts, 32:233
structure, 39:357
utilization by yeasts, 32: 197
p-D-,hydrolysis of, 22:37
1-seleno-p-o-, hydrolysis of, 22:37
I-thio-p-o-, hydrolysis of, 22:37
2-(R)-methylcyclohexyl a+-, 43:333
6,6-selenobis[methyI 2,3,4-tri-O-acetyl-6-
deoxy-P-D-, 22:205
tert-butyl and triethylmethyl-p-o-, rate
constants and kinetic parameters for
hydrolysis of, 22:74
tetrahydropyran-2-yl P-D-, selective
etherification with acrylonitrile, 33:
67
6,6-thiobis[methyl2,3,4-tri-O-acetyI-6-
deoxyl-p-D-,22:204
vinyl p-D-,levoglucosan from, 34:28
glucopyranosides, 2-azido-3-fluoro-a-r,-.
48: I45
Glucopyranosiduronamide
alkyl 1-thio-a-D-, preparation, 36: I0 I
ethyl I -thio-p-D-, preparation, 36:98
ethyl 2,3,4-tri-O-acetyI- 1-thio-p-o-.
preparation and deacetylation, 36:98
preparation, 36:80
Glucopyranosiduronate, (5R)-tri-O-acetyl-5-
bromo- 1-thio-p-o-, 49:40
214 SUBJECT INDEX
Glucopyranosiduronates
a-D-, methyl benzyl3-0-henzyl-2-
(benzyloxycarbonyl) amino-Z-deoxy-4-
0-(methylsulfony1)-, p-elimination
reactions of, 29:261,302
D-, proton magnetic resonance spectroscopy
of, 27:26
methyl cholest-5-en-3 p-yl 2,3,4-tri-O-
acetyl-, proton magnetic resonance
spectroscopy of, p-D-,27:26
Glucopyranosiduronic acids
2-acetamido-5-ethoxyhenyl
(Y- and P-D-, preparation, 36:70,9 1
2,3,4-tri-O-acetyl-a-~-, methyl ester,
preparation, 36:70
5-acetamido-5-ethoxyphenylp-D-,
preparation, 36:70, 91
4-acetamidop benyl
P-D-, synthesis and properties, 36:91
2,3,4-tri-O-acetyl-p-o-,methyl ester,
preparation, 36:92
aldosterone- 18-yl2,3,4-tri-O-acetyl-a-o-,
methyl ester, isolation, 36:95
alkyl p-D-,acid catalyzed hydrolysis,
36:8485
aryl, estimated thermodynamic activation
functions for hydrolysis of, 2 2 8 4
p-0-
methyl 2,3-di-O-methyl-4-0-(2,3,4,6-
tetra-O-methyl-cx-D-glucopyranosyl)-,
methyl ester, degradation,
39~247-248
synthesis, 39:222, 246
2-naphthy1, hydrolysis of, 31 :193
proton magnetic resonance spectroscopy,
36~87-88
benzothiazol-2-yl 1-thio-p-D-, in dog urine,
36: 103
benzyl2,3-di-O-benzyl-a- and p-D-, methyl
esters, preparation, 36:69
2-benzyloxy-4-formylphenyl2,3,4-tri-O-
acetyl-D-, methyl ester, preparation,
36:78
benzyl 2,3,4-tri-O-benzyl-p-o-, and methyl
ester, preparation, 36:72
benzyl2,3,4-tri-O-(ch~oroacety~)-~-~-, and
methyl ester, preparation, 36:64
bile acid-3-yl p-D-, preparation, 36:95
4-butyl-3,5-dioxo- 1,2-diphenylpyrazolidin-4-
yl2,3,4-tri-O-acetyl-o-, methyl ester,
preparation, 36: 134
cholesterol-p-o-, preparation and
characterization, 36:94
cholesterol-3-yl 2,3,4-tri-O-acetyl-P-o-,
methyl ester, conversion into glucoside,
36532
cyclohexyl2,3,4-tri-O-acetyl-P-o-, methyl
ester, deprotection, 36530
D-, conjugate with 2-(N-hydroxy-
acetamido)fluorene, isolation, 36: 132
equilenin-3-yl2,3,4-tri-O-acetyl-
a-D-,methyl ester, preparation, 36:77
p-D-,methyl ester, preparation, 36:77, 133
estrone 2,3,4-tri-O-acetyl-P-~-, methyl ester,
preparation, 36:78
menthyl 2,3,4-tri-O-acetyl-o-~-,preparation,
36:68
methyl, methyl ester, photochemistry,
38: 140-141
methyl a-D-, preparation of, 33:88
methyl 2,3,4-tri-O-benzyl-o-, and benzyl
ester, preparation, 36:62
morphin-3-yl p-D-, preparation, 36:78
2-naphthyl p-D-,hydrolysis, kinetics, 36:85
N,N-diethylthiocarbamoyl
1-thio-p-D-, from urine, 36:103
2,3,4-tri-O-acetyl- 1-thio-p-D-, methyl
ester, identification, 36: 103
2 1-O-acetylaldosterone-18-yl2,3,4-tri-O-
acetyl-a-and p-D-, methyl esters,
preparation, 36:77
p-[bis(2-chloroethyl) aminolphenyl 2,3,4-tri-
0-acetyl- 1-thio-p-D-, methyl ester,
preparation, 36:98
phenolphthalein 2,3,4-tri-O-acetyl-~-,
preparation, 36:77
phenyl a- and p-D-,formation, 36:71
pheny12,3,4-tri-O-acetyl-a-o-, methyl ester,
preparation, 36:75, 77
p-nitrophenyl 2,3,4-tri-O-acetyl-p-o-,methyl
ester, preparation, 36:75
pregnanediol-3-yl p-D-, preparation, 36:93
2-pyridyl p-D-, synthesis, and p-D-
glucosiduronase action, 36: 125-126
1-thio-, biosynthesis, 36: I03
1-thio-p-D-, preparation and properties,
36~96-98
2,3,4-tri-0-acetyl-o-, methyl ester, conjugate
with 2-(N-hydroxyacetamido)fluorene,
36: 132
 SUBJECT INDEX 215

p-o-Ghcopyranoshahdamine, 48:75 acetyl-p-o-, methyl ester, preparation,

Glucopyranos-4-ulose, 1,6-anhydro-2,3-di-0- 36: 122
benzoyl-P-o-, preparation and reactions Glucopyranosyl bromide
of, 34:lOO-101 6-0-acetyl-2.3,4-tri-O-acyl-a-o-, preparation
Glucopyranosylamine from levoglucosan triesters, 34:66
2-acetamido-l -N- 2-amIno-2-deoxy-a-o-, 48:72-73
p-~-aspartyl-2-deoxy-P-o-,protein-linking 6-deoxy-6-thIocyanato-a-o-, synthesis,
with, 2 5 4 2 0 4 2 5 44: I23
(~-aspart-4-oy1)-2-deoxy-P-o-, 3,4-di-O-acetyl-
40:287-288 6-bromo-2,6-dideoxy-2-fluoror-a-~-
hydrate, crystal structure, 43:23 I preparation of, 28:278
2-acetamido-3,4,6-tri-O-acetyl-N-[N- 2,6-dibromo-2-6-dibromo-2,6-dideoxy-~-
(benzylocycarbonyl)-~-aspart-4-oyl]-2- D-, preparation of, 34: 135-1 36
deoxy-P-o-, synthesis, 43: 146 2,3-di-O-benzyI-4,6-di-O-( p-nitrobenzoy1)-
D- p-D-
mutarotation of, 24:48 methanolysis of, 34:274
selective esterification with methyl preparation of, 34:258
octadecanoate, 33:44 4-O-benzoyl-2-bromo-2,6-dideoxy-3-0-
N-acetyl-D-, structure of, 31:102-103 formyl-a-r-, synthesis, 39: 120
N-benzoyl-P-u-, preparation of, 31:86 2-0-benzyl-3,4.6-tri-O-( p-nitrobenzoy1)-
N-(~-Aspart-4-oyl)-p-o-,synthesis. a-D-,34:274
43: 136-137 P-D-, 34:258, 274
N-p-tolylsulfonyl-P-o-, preparation of, 2,3,4,6-tetra-O-acetyl-a-~-
31:124 preparation to, 28:279
2,3,4,6-tetra-O-acetyI-N- reaction with
[N-(benzyloxycarbonyl)-~-aspart-4-oyl]-2- diethyl 2-fomamidomalonate, 33: 146
deoxy-b-D-, synthesis, 43: 146 with ethynylmagnesium bromide,
p-tolylsulfonyl-P-o-, ammonolysis of, 33: I43
31:124 with phenylmagnesium bromide,
2,3,4,6-tetra-o-benzoyl-o-, ammonolysis of, 33: 142
31:88, 121 with silver cyanide, 33: I32
2,3,6-tri-O-acetyl-4-0-(2,3,4,6-tetra-O- trimethylamine and anhydridization.
acetyl-a-o-glucopyranosyl)-P-t~-, 34:32
synthesis, 39:239 tetra-0-acetyl-a-o-
(Glucopyranosylamine)uronamides,D-. anomerization of, 24:45
preparation of, 33:200-201 crystal structure bibliography, 37:393
(Glucopyranosylamine)uronic acid, 2,3,4-tri-0- 0x0 reaction with, 23: 109
acetyl-N-(6-ethylthio-5-nitro-pyrimidin-4- tetra-0-acetyl-P-o-, acetoxonium ion in
yl)-P-~-,methyl ester, preparation, 36: 122 reaction with alcohols, 26:135
Glucopyranosylaminobenzoate, 2- 2,3,4,6-tetra-o-benzyl-a-~-,methanolysis of.
diethylaminoethyl 4-P-o-, monohydrate, 34:274
crystal structure, 43:252 2,3,4-tri-O-acetyI-
Glucopyranosyl azide a-D-,preparation of. 34:67
p-D-, 1,6-anhydride from, 34:32 6-bromo-6-deoxy-a-~-~ preparation of,
2,3,6-tn-O-acetyl-4-0-(2,3,4,6-tetra-O- 34:61
acetyl-a-o-glucopyranosyl)-p-i>-, 3-O-(rnethylsulfonyl)-a-o-, 23:265
synthesis, 39:239 2,3,4-tri-O-acetyl-6-
(Glucopyranosyl azide)uronamide, 2.3,4-tri- 0- deoxy-6-thIocyanato-a-o-, 44: 144
acetyl-P-o-, preparation, 36: 122 0-propionyl-a-o-, preparation of, 34:66,
(Glucopyranosyl azide)uronic acid, 2,3,4-tri-0- 68
216 SUBJECT INDEX
Glucopyranosyl bromide (continued)
tn-O-acetyl-6-bromo-6-deoxy-~-,22: 18I
2,4,6-tn-0-acetyl-3-deoxy-3-nitro-a-o-,
24:115
3,4,6-tri-O-acetyl-2-deoxy-2-
(trifluoroacetamid0)-a+-, preparation,
38:253
2,3,4-tri-O-benzyl-6-
O-(p-nitrobenzoyl)-a-D-, methanolysis of,
34:274
O-(p-nitrobenzoyi)-p-D-, preparation of,
34:258
(Glucopyranosyl bromide)uronamide, 2,3,4-tri-
0-acetyl-a-o-, preparation, 36:62
(Glucopyranosyl bromide)uronic acid
2,3,4-tri-U-acetyl-
a-D-, methyl ester, intermediate in p-D-
glucosiduronic acid synthesis, 36:59,
62
p-D-. methyl ester, preparation, 36:59,62
2,3,4-tri-O-benzyl-a-~-
benzyl ester, preparation, 36:62-63
reaction with N-acylamino acid silver
salts, 36:113
Glucopyranosyl chloride
3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-a- (Glucopyranosyl ch1oride)uronic acid
D-, acetoxonium rearrangement of,
26:161
6-acetamido-2,3,4-trii-O-acetyl-6-deoxy-a- 2,3,4-tn-0-acetyl-ar- and++-, methyl ester,
D-, acetoxonium salts, 26:163
2,3,4,6-tetra-O-
acetyl-a+-, reaction with phenyllithium,
33:143
acetyl-p-o-, preparation of, 34:258
(chlorosulfonyl)-6-O-methyl-a-~-,
formation of, 34:34-35
methyl-a+-, methanolysis of, 34:274
tetra-0-acetyl-a-o-, crystal structure
bibliography, 31:368
tetra-0-benzoyl-a-o-, benzoxonium
rearrangements of, 26: 15 1
2,3,4-tri-O-acetoxonium rearrangement of,
26: I62
2,3,4-tri-O-acetyl-
6-O-(dichloromethyl)-a-o-,preparation of,
34:68
6-O-formyl-a-o-, preparation of, 34:68
3,4,6-tri-O-acetyl-
p-D-,preparation of, 34:257
2-chloro-2-deoxy-a-D- and-P-o-,
Koenigs-Knorr reaction with, 34:259
2-chloro-2-dexoy-~-~-preparationof,
28:262
2-chloror-2-deoxy-a-o-, preparation of,
28:26 1-262
2-deoxy-2-nitroso-a-~-,24:207
2-deoxy-2-thiocyanato-a-~-,44: 144
2-0-benzyl-a-D- and-@-, Koenigs-Knorr
reaction with, 34:259-260
2-O-nitro-P-o-, preparation of, 34:257
2-@(trichloroacety~)-p-o-
methyl-a-o-glucopyranosidefrom,
34:256
selective deacylation, 39:35
tri-0-acetyl-
6-deoxy-
D-, acetoxonium salts, 26:157-158
6-iodo-o-, acetoxonium salts,
26~157-158
6-O-p-tolylsulfonyl-o-, acetoxonium salts,
26: 157-1 58
2,3 ,4-tri-O-acety~-6-O-p-to~ylsu~fony~-p-o-,
23:265
Glucopyranosyl chloride or bromide, 2,4-di-O-
acetyl-3,6-di-O-methyI-a-~-, 51 :207-208
3,4-di-O-acetyl-2-deoxy-2-nitroso-rw-o-,
methyl ester, preparation, 36:61
preparation, 36:60
2,3,4-tri-O-benzyl-a-~-,benzyl ester,
preparation, 36:62-63
reactivity, 36: 109
2,3,4-tri-O-benzyl-p-o-, benzyl ester,
preparation, 36:6243
reactivity, 36:109
Glucopyranosyl cyanide, 2,3,4,6-tetra-O-acetyI-
a-D,preparation of, 33:132-133
Glucopyranosyl2-2-deoxy-2-methylamino-a-
L-, a-L-streptohranosylstreptidine, oxime,
selenate, tetrahydrate, crystal structure,
43: 349-35 0
Glucopyranosyl-D-erythritol
2-O-a-o-, taste properties, 45:275
2-0-P-D-, taste properties, 45:275
a-o-Glucopyranosyl dibenzyl phosphate, 3,4,6-
tri-0-acetyl-, phosphono migration in,
during acetylation, 33: 109
c t - ~ - ~ ~ u c o p y r a n(dipotassium
osy~ phosphate)
dihydrate, crystallography of, 25:66
 SUBJECT INDEX
Glucopyranosyl fluorides
2-acetamido-2-deoxy-
a-D-,synthesis, 38:203
p-D-, synthesis, 38:203
a-D-
cyclization of, 34:3 1
as glycosyl donor for glucansucrases,
51:140- 14 1
as substrate for dextransucrases, 30:423
p-D-, cyclization of, 34:3 1
4-0-benzoyl-6-deoxy-3-0-methyl-2-0-
triflyl-L-, 48:127
2-chloro-2-deoxy-P-~-,preparation, 38:237
D-
2-acetamido-2-deoxy-P-
IH- and I9F-NMR data for, 46: I I7
3,4,6-tri-O-acetyI-. 'H- and 19F-NMR
data for, 46: 146
a anomer
I3C-NMR data for, 46: 160
'H- and I9F-NMR data for, 46:82
p anomer
I3C-NMR data for, 46: 160
'H- and I9F-NMR data for, 46:X2
2-deoxy-2-fluoro-
Q anomer, 'H- and '"F-NMR data for,
46: 146
3,4,6-tri-O-acetyl-, 'H- and I9F-NMR
data for, 46: 146
3-deoxy-3-fluoro-,2,3,6-tri-O-acetyl-, I H-
and lYF-NMRdata for, 46:148
4-deoxy-4-fluoro-,2,3,6-tri-O-acetyl-, 'H-
and I9F-NMR data for, 46: 14X
6-deoxy-6-fluoro-,2,3,4-tri-O-acetyl-, 'H-
and IyF-NMR data for, 46: 148-
149
2,3-di-O-acetyl-4,6-O-benzylidene-, I H-
and I9F-NMR data for, 46532
2,3-di-O-benzoyl-4,6-di-O-methyl-, 'H-
and I9F-NMR data for, 46:83 84
2,3,4,6-tetra-O-acetyyl-
I3C-NMR data for, 46: 160
'H- and I9F-NMR data for, 46:82
2,3,4,6-tetra-O-benzoyl-, IH- and "F-
NMR data for, 46:83
2,3,4,6-tetra-O-benzyl-a-, 'H- and "F-
NMR data for, 46534
2,3,4,6-tetra-O-methyl-, 'H- and l"F-NMR
data for, 46:84
3,4,6-tri-O-acetyl-2-deoxy-
217
2-bromo-, 'H- and I9F-NMR data for,
46: 129
2-chloro-, 'H- and "F-NMR data for,
46: 129
2-iodo-. 'H- and IyF-NMR data for,
46: 129- 130
3,4,6-tri-O-acetyl-2-O-methyl-
I3C-NMR data for, 46: 160
'H- and I9F-NMR data for, 46:83
2,4,6-tri-O-acetyl-3-0-methyl-,"C-NMR
data for, 46: 160
2,4,6-tri-O-benzoyl-3-O-methyl-, 'H- and
"F-NMR data for, 46:83
3,4,6-tri-O-benzoyl-2-O-methyl-, ' H- and
I9F-NMR data for, 46233
2-deoxy-
2-fluoro-o-, labeled, 48:203
2-( p-tolylsulfonamido)-a-D-, synthesis,
38:203
2-( p-toly~sulfonamido)-~-~-, synthesis,
38:203
3-deoxy-, 3-fluoro-~-,preparation, 38:2 15
6-deoxy-
6-fluoro-cu-o-, synthesis, 38:204
6-fluoro-P-D-, synthesis, 38:204
3,6-di-O-acetyl-2-deoxy-2-fluor0-4-0-
(2,3,4,6-tetra-O-acetyl-p-~-
galactopyranosy1)-a-o-. preparation,
38:232
L-
3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-a-,
'H- and I9F-NMR data for, 46: 153
2,3,4-tri-O-a~etyl-6-deoxy-a-,'~C-NMR
data for, 46: 172
per-0-acetyl-
a-D-,synthesis, 38:202
P-D-, synthesis, 38:201-202
6-brom0-6-deoxy-a-o-, synthesis, 38:203
2-bromo-2-deoxy-P-o-, synthesis, 38:201
6-bromo-6-deoxy-P-~-,synthesis, 38:203
2-chloro-2-deoxy-o-, synthesis, 38:202
2-deoxy-2-fluoro-a-o-, synthesis, 38:204
3-deoxy-3-fluoro-a-o-, synthesis, 38:204
2-deoxy-2-fluoro-P-~-,synthesis, 38:204
3-deoxy-3-fluoro-P-~-,synthesis, 38:204
2-deoxy-2-fluoro-4-0-p-~-
galactopyranosyl-a-D-, synthesis,
38:204
tetra-0-acetyl-
a-D-.preparation of, 34:67
218 SUBJECT INDEX

Glucopyranosyl fluorides (continued) 2,3,6-tri-O-acetyl-4-0-(2,3,4,6-tetra-O-

CX-D-, synthesis, 38: 199 acetyl-a-D-glucopyranosyl)-p-D-,
p-D-,24:45 44: 142
3,4,6-tri-O-acetyI-, 2-deoxy-2-fluoro-a-o-, 13C.NMR,44:141
preparation, 38:23 1 infrared spectrum, 44: 141
tri-0-acetyl- 2,3,6-tri-O-acetyI-4-0-(2,3,4,6-tetra-0-
2-brom0-2-deoxy-a-o-, preparation, acetyl-P-o-glucopyranosyl j-p-o-,
38:234-235 44:142
2-bromo-2-deoxy-P-o-, preparation, I3C NMR, 44:141
.38:234-235 infrared spectrum, 44:141
2-chloro-2-deoxy-~~-o-, preparation, 3,4,6-tri-0-acetyI-4-0-(2,3,4,6-tetra-O-
38:237 acetyl-P-o-glucop yranosy1)-pa-,
2-deoxy-2-Iodo-a-~-,preparation, 38:234 44: 142
2-deoxy-2-iodo-P-o-, preparation, 38:234 I3C NMR, 44:141
3,4,6-tri-O-benzoyl-2-0-1nethyl-a-o-, infrared spectrum, 44: 141
26: 183 (Glucopyranosyl isothiocyanate)uronic acid,
Glucopyranosyl gallate, 2,0-cinnamoyl-p-~-, 2,3,4-tri-O-acetyl-p-~-,methyl ester,
hydrolysis, 39:35 preparation, 36: 123
Glucopyranosylglycerol Glucopyranosylmalonate, diethyl2,3,4,6-tetra-
2-0-a-o-, taste properties, 45:275 0-acetyl-, proton magnetic resonance
2-0-p-o-, taste properties, 45:275 spectroscopy of, p-D-, 27:27
N-P-o-Glucopyranosylhydroxylaniine,crystal Glucopyranosyl mesitoate, P-D-,
structure, 43:338 polymerization of, 21:460
s-(~-~-Glucopyranosyl)-3-indolylthioace- trang-O-P-D-Glucopyranosyl methyl
tylhydroximyl 0-sulfate, as growth acetoacetate, crystal structure
regulator, 21:392 bibliography, 32:363-364
(Glucopyranosyl iodide)uronic acid, 2,3,4-tri- Glucopyranosyl nitrate, OI-D-, 1.6-anhydride
0-acetyl-a+-, methyl ester, preparation, from, 34:32
36:60 s-(~-o-Glucopyranosyl)-N-methyl-3-
Glucopyranosyl isothiocyanate indolylthioacetylhydroximyl 0-sulfate, as
2-acetamido-4-0-(2-acetamido-3,4,6-tri-0- growth regulator, 21:392
acety~-2-deoxy-~-~-g~ucopyranosyl)- Glucopyranosyl perchlorate, 3,4,6-tri-O-acetyl-
3,6-di-O-acetyl-P-~-,44: 142 2-0-benzyl-a-D- and-p-o-,
2-acetamido-3,4-6-tri-0-acetyl-2-deoxy-p- Koenigs-Knorr reaction with, 34:259-260
D-, 44: 142 Glucopyranosyl phosphate
synthesis, 44:94 2-acetamido-2-deoxy-ax-o-,carbon-I3
2,3,4,6-tetra-0-acetyI-p-~-, 44: 142, 144 nuclear magnetic resonance spectra,
I3C NMR, 44:141 38532, 85
formation of amino acid diastereoisomers a-o-,synthesis of, 26: 15
using, 44: 117 o-Ghcopyranosyl polymer, catalyzed by p-D-
infrared spectrum, 44: 141 galactosyltransferase, incorporation of D-
synthesis, 44:94 galactose into, 46: 187
3,4.6-tri-0-acetyl-2-benzamido-2-deoxy-, ~-~-o-GIucopyranosy~procaine, monohydrate,
44:142 crystal structure, 43:252
2,3,4-tri-O-acetyl-6-bromo-6-deoxy- Glucopyranosylpropanonitrile,3-tetra-O-
p-D-,44: 144 acetyl-a-o-, synthesis, 49:73-74
CX-D-, 44:141 O - C X - D - G ~ U C O ~ ~ ~ ~ I I O145)-p-D-
S~~-(
synthesis, 44:94 fmctopyranose, monohydrate, 43:37 1
3,4,6-tri-0-acetyl-2-deoxy-2-thiocyanato-~~-Glucopyranosyl sulfone, 2,3,4,6-tetra-O-acetyyl-
D,44:141, 144 p-D-,photolysis, 38:155-157
 SUBJECT INDEX
(Glucopyranosylthioureide)uronamide,
preparation, 36: 122-123
(G1ucopyranosylthioureide)uronicacid, 2,3,4-
tri-O-acetyl-N'-p-o-, methyl ester,
preparation, 36: 122
r)-Glucopyranosyltoluene, surface activity of,
25:256
Glucopyranosyl 2,4,6-trimethylbenzoate.
2,3,4,6-tetra-0-acetyI-
a-D-,deacetylation, 39:34
P-D-, deacetylation, 39:34
9-(P-o-Glucopyranosyluronamide)adenine,
preparation, 36: 129
1 -(~-~-Glucopyranosyluronamide)cytosine,
preparation, 36: 129
(Glucopyranosyluronamide)thiocarbamate,
preparation, 36:123
(Glucopyranosyluronamide)thiosemicarbazide,
derivatives, preparation, 36: 123
(Glucopyranosyluronamide)thiourea,
derivatives, preparation, 36: 123
Glucopyranosyluronic acid
2-acetamido-2-deoxy-ol-o-
ester of uridine 5'-pyrophosphate,
isolation of, 28:327
methyl ester, ester of uridine 5'-
pyrophosphate, preparation and
reduction of, 28:355
o~-D-, ester of uridine 5'-pyrophosphate,
decarboxylation of, 28:385
enzymic preparation of, 28:343
isolation of, 28:326
4-0-( ~-D-Glucopyranosy~uronic acid)-D-
glucaric acid, hydrolysis of, rate of, 22:78
(Glucopyranosyluronic acid)-2-4-
dioxothiazolidine, preparation,
36:123-124
Glucopyranosyluronic acid epitope, 4-
acetamido-4-deoxy-2-0-methyl-~-1.-
fucopyranosyl-( 1+4)-p-o-, 51:2 18
Glucopyransoylamine,2-acetamido-N-( I -
aspart-4-oyl)-2-deoxy-p-o-
analogs, synthesis, 43: 140-141
elongation of
cabohydrate chain, 43: 155-156
peptide chain, 43: 152-154
synthesis, 43:137-138, 140
Glucopyransoyl isothiocyanate, 3,4,6-tri-0-
acetyl-2-deoxy-2-thicoyanato-a-o.24:
209
219
Glucopyranuronamide
a-D-, crystal structure bibliography, 32:3S6
D-, preparation of, 33:201
D-Glucopyranuronate, diaxial and
axialequatorial processes in p-elimination,
29:258-265
Glucopyranuronic acid
a- and p-D-. 1-esters, preparation, 36: 106
(Y-D-, calcium bromide salt trihydrate, crystal
structure bibliography, 34:347
D-
methyl ester. preparation, 36:59, 64
structure of, and lactone, 33:190
3,4-di-O-acetyl-l,2-0-[ I -(4-methyl ester,
preparation, 36: 102
1-0-acyl-a- and-p-o-, kinetics of p-D-
glucosiduronase action, 36: 1 12
1-0-anisoyl-a- and-p-o-, preparation,
36: I08
1 -0-benzoyl-a- and-@+-, preparation,
36: 108
I -0-(1 8p-glycynhet-30-yl)-o-, preparation,
36:109-110
1 -0-(3-carboxypropanoyl- 18P-glycynhet-
30-yl)-p-o-, preparation, 36:109-110
I -0-(5-hydroxyindol-3-ylacetyl)-p-~-,
chromatography, 36: 108
l-O-(indol-3-ylacetyI)-P-~-,
chromatography, 36: 108
I-0-indomethacin-pa-, synthesis, 36: 104,
Ill
I -0-(N-acylaminoacyl)-tri-~-benzyl-p-o-,
benzyl esters, preparation, 36: 1 13
I -0-[N-(rerr-buty1oxycarbonyI)-~-alanyl]- p-
D-, preparation, 36: I 14
1-0-veratroyl-a- and-p-o-, preparation.
36:lOS
tetra-0-acetyl-u-, methyl ester, preparation,
3659
1,2,3,4-tetra-O-benzyl-a- and-@+, benzyl
ester, preparation, 36:78
1,1 '-thiobis(methy1 2,3,4-tri-0-acetyl-P-~-,
dimethyl ester, preparation, 36:99
2,3,4-tri 0-acetyl-D-, methyl ester,
preparation, 36:60,62
2,3,4-tri-0-acetyI-l-O-
acetyl- 1-0-4-methoxybenozyl-p-~-,
methyl ester, preparation, 36: 106
acyl-o-, methyl esters, proton magnetic
resonance spectroscopy, 36: 1 I &I I 1
220 SUBJECT INDEX
Glucopyranuronic acid (continued)
benzoyl-P-u-
methyl ester, preparation, 36: I06
preparation, 36: 105
cinnamoyl-a-and p-D-,methyl ester,
preparation, 36: 106
phenylacetyl-P-o-, methyl ester,
preparation, 36: 106
propanoyl-P-D-, methyl ester, preparation,
and anomerization, 36: 106
salicyloyl-Pa-, methyl ester, preparation,
36: 105
2,3,4-tri-O-benzyl-
D-
benzyl ester, I-acyl ester,
debenzylation, 36: 108
preparation, 36:62-63
reaction with N-acylamino acids,
36:113
1-0- [N-(tert-butyl-oxycarbony1)-L-
alanylI-P-o-, benzyl ester,
preparation, 36: I 14
1-0-(p-methoxybenzoy1)-a-D-, benzyl
ester, preparation, 36: 109
2,3,4-tri-0-(2,2,2-trichloroethoxycarbonyl)-
~-,2,2,2-trichloroethylester,
preparation, 36:64
Glucopyranurono-6,1 -lactone
derivatives, 33:190
2,3,4-tri-O-acetyl-P-~-,and 2,3,4-tris-(2,2,2-
trichloroethoxycarbonyi) ester, 34: 150
Glucopyranurono-6,3-lactonederivatives,
33: 190
thermodynamic stability of, 33: 191
Glucopymoside
ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-
deoxy-I-thio-a(and P)-D-, 21:116
methyl 3,6-anhydro-a-o-, mass spectra of,
21:81
methyl tetra-0-methyl-a-o-, mass spectrum
of, 21:61,73
phenyl tetra-0-methyl-a(and b)-D-, mass
spectra of, 21:56
Glucosacchannic acid
a-D-, formation, 46:292-293
D-, 25343
formation of, 28: 199
structure, 46:291
Glucosamine
D-, 47:19
trichloroacetimidates, synthesis, 50:68-71
as donors, 50:61, 68-77
trichloroacetimidates, as glucosyl donors,
50:60-61,68-77
chitobiose donors, 50531, 89
glucosamine donors, 50:61, 68-77
lactosamine donors, 50:73,78-88
muramic acid donors, 50:81, 84, 9&91
Glucosamine sulfatase, N-acetyl-a-o-, 44:2 14
Glucosaminidase
amino acids of, 27:315-316
carbohydrate content of, 27:306-307
endo-N-acetyI-P-D-, 44:232
glycoprotein structure examined with,
44:238-239
groups, 44:237-238
N-acetyl-a-o-, 44:214
in plant cell walls, 42:301
N-acetyl-P-o-, 44: 196,208-209
from jack bean, 44:229-230
in plant cell-walls, 42:301-302
Glucosaminide, methyl N-acetyl-tri-0-methyl-
D-, mass spectrum of, 21:67
Glucosaminide-( 1+4)-P-~-galacto-
syltransferase, N-acetyl-P-o-, 44:245-246
Glucosaminyldeacetylase, N-acetyl-o-, 44:215
Glucosan
p-. see Levoglucosan
from cellulose in anhydrous hydrogen
fluoride, 27:93
Glucose, see also Dextrose
2-,3-,4-, and 6-fluoro-o-, composition in
aqueous solution, 42:45
2-acetamido-2-deoxy-
a-D-
biological activity of, 42: 135
structure of, 42: 136
crystal structure bibliography, 31:366
D-
crystallography of, 2 5 9 3
gel chromatography of, 2 9 3 2
crystal structure of, 2 9 7 0
diethyl dithioacetal, hydrogenolysis of,
32:78
oxidation of, 32:85
reactions of, 32:55
thioglucoside from, 32:66
glycoenzyme constituent, 27:302, 307,
321,329
lectins, 35206-226
 SUBJECT INDEX
nitrosation of, 31:67
reaction with
(methoxycarbonylmethylene)tri-
phenylphosphorane, 33: 154
unsaturated derivatives, 31:5
uridine 5-pyrophosphateester, in mung
bean, 32:9
6-O-a-~-fucopyranosy~-~-, preparation of,
34:263
4-O-a-~-fucopyranosyl-3-O-@-~-
galactopyranosyl-D-, preparation of,
34:268
6-O-P-o-mannopyranosyb, derivative,
preparation of, 34:259
3,4-O-isopropyhdene-o-, diethyl
dithioacetal, oxidation of, 32:XI
5-thio-~-,composition in aqueous
solution, 42:52-53
3-acetamido-3-deoxy-, D-, synthesis, 41 :9
2-acetamido-2,6-dideoxy-6-fluoro-u-,
preparation, 38:208
4-acetamido-2,4-dideoxy-2-fluro-~-i~-,
preparation, 38:2 16
2-acetarnido-4-0-(2-acetam~do-2-deoxy-~-~-
glucopyranosyl)-2-deoxy-~-,diethyl
dithioacetal, oxidation of, 32:8 I
2-acetamido-4,6-O-benzylidene-2- deoxy-o-
methylation of, 33:55
reaction with (methoxycarbonyl-
methylene)triphenylphosphorane,
33: 154
2-acetamido-3,4,5,6-tetra-O-acetyl-
2-deoxy-~-
demercaptalation of, 32:63
diethyl dithioacetal, oxidation of, 3 2 8 3
1,2-dideoxy-l,1-bis(ethylsulfonyl)-o-,
preparation of, 32:83, 85
2-acetamido-tetra-O-acetyl-2-deoxy-~~-.
ammonolysis of, 31:87
2-acetamido-2,4,6-trideoxy-4-[(S)-3 - alanine, 27:206
hydroxybutanamido]-D-, 47: 175-176
2-acetamodi-2-deoxy-o-
ally1 radical formation by radiation, 37: 14
radiation-induced, free-radical reactions,
37:74
radiolysis, 37:48, 50-5 1
acetobromo-a-D-, 21:20
acetodibromo-, 21: 17
4-(N-acetylglycyl)amido-4,6-dideoxy-n-,
47: 175-176
22 1
3-(N-acetyl-~-seryl)amIdo-3,6-dideoxy-~-,
47: 175-1 76
1-O-acetyl-2.3.4,6-tetra-O-methyl-@-~-,
mass spectrum of, 21:56
Ci-D-
effect of isotope of mutarotation of, 24:32
energies, heats, and entropies of activation
of mutarotations of, 24:53
hydrate, 24:60
infrared spectroscopy of, 27: 149
monohydrate, crystal structure
bibliography, 30:465
mutarotation, 23:22,24:14
in cresol and pyridine or pyridinone,
27: 104
history of, 23: 12
and proton magnetic resonance
spectroscopy, 27:59
nuclear magnetic resonance spectrum of,
23:45
proton magnetic resonance spectroscopy
of, 27:28
sweetness, 45:207
effect of infrared hydroxyl absorption
bands and hydrogen-bonding
strength, 4 5 2 I &2 17
ADP-D-, biosynthesis of, 42:3 16
aldehydo-D-,ammonolysis of, effect of
solvent on, 31:100
2-amino-2-deoxy-
Ci-D-
hydorbromide and hydrochloride,
crystal structures of, 25:69-70
hydrobromide and hydrochloride,
crystal structure bibliography, 31:365
D-, 21:18.24:112,208
composition in aqueous solution, 4247,
67
configurational relationship to L-
deamination, by radiation, 37: 12
deamination of, 25:185, 195,31:18, 24,
33:115
dehydration of, 28: 182
diethyl dithioacetal, deamination of,
25: 192,32:32
diazotization of, 32:56
methylation of, 32:55
diethyl dithioacetal, deamination of, and
effect ofpH on, 31:65
222 SUBJECT INDEX
Glucose (continued)
diethyl dithioacetal hydrochloride,
deamination of, 31: 16
ethylene dithioacetal, deamination of,
32:57
ethylene dithioacetal, dearnination of,
effect of pH on, 31:65
gas-liquid chromatography of, 28:78-
79
in glycoprotein of urine, 24:441,443
glycosarnin, 25: 181
inhibition of lipid-linked
oligosaccharide formation, 40:326,
334-336
isolation from heparin, 36: 10
nitrous acid deamination, 43:86-87
6-phosphatq preparation of, 33:47
phosphorylation with metaphosphoric
acid, 33:47
polymerization by hydrogen chloride,
resistance to, 21 :464
protein linkage with, 25419
radiolysis and deamination, 37:48-50
L-, conversion into L-(+)-muscarine,
27:207
6-U-p-tolylsulfonyl-o-, anhydride
formation from, 34:33
6-thio-o-, derivatives, 24: 146
6-amino-6-deoxy-, 21: 18
D-
derivatives, 22:205
from kanamycin A, 30: 12I
preparation of, 33:233
3-amino-3-deoxy-o-
diethyl dithioacetal, preparation of, 32:22
from kanamycin A, 30: 12I
structure of, 31:29
4-amino-4-deoxy-o-, 23: I52
composition in aqueous solution, 42:49
5-amino-5-deoxy-o-, 23: 116
as antibiotic, 42: 136-137
composition in aqueous solution, 42:49
4-amino-4,6-dideoxy-o-, 23: 153,24:159
hydrochloride, composition in aqueous
solution, 42:49
6-amino-2,6-dideoxy-2-fluoro-o-,
preparation, 38:246
3-amino-6-0-(2-arnino-2-deoxy-~-~-
glucopyranosy~)-3-deoxy-~-, synthesis
of, 34:255
3-amino-2-O-[o(and ~)-l-carboxyethyl1-3-
deoxy-o-, 24~132
3,4- and 4,6-di-U-methyl-o-, trimethylsilyl
ethers and gas-liquid chromatography
of, 30:28-29
1,6-anhydro-
p-D-,47:306
~-,2,4-phenylboronate,reaction with
methacrylic anhydride, 35:55
6-thio-p-o-, 23:226
2,3,4-tri-O-benzyl-P-o-, acetolysis, 39:45
2,5-anhydro-
aldehydo-o-,I ,6-hemiacetal, 25:213
D-, 25: 187
diethyl dithioacetal, 25: 192
preparation of, 33: 1 16
3,4,6-tri-U-benzoyl-o-, reaction with
(ethoxycarbonyl-rnethylene)
phosphorane, 33: 136
3,6-anhydro-
D-, composition in aqueous solution, 42:58
2,4-di-U-methyl-o, composition in
aqueous solution, 42:58
2-(anisylideneamino)-2-deoxy-o-,selective
phosphorylation with diphenyl
phosphorochloridate, 33:47
p-D-, 45322
crystal structure bibliography, 31:365
infrared spectroscopy of, 27: 149
mutarotation of, 23:23,24: 14
(p-bromophenyl) hydrazone, crystal
structure of, 2 5 9 2
sweetness, 45207
effect of infrared hydroxyl absorption
bands and hydrogen-bonding
strength, 45216-217
minus P-o-xylose, difference-circular
dichroism spectra, 4 5 8 1
2-benzamido-tetra-O-benzoyl-2-deoxy-~-,
ammonolysis of, 31237
4,6-O-benzylidene-~-,acetolysis of, 22: 14
2-(benzyloxycarbonyl)amino-2-deoxy-~-,
selective phosphorylation with 2-
cyanoethyl phosphate, 33:47
biosynthesis of aromatic compounds from D-,
19235-270
5,6-bis(acetamido)-5,6-dideoxy-~-, 23: 175
3-bromo-3-deoxy-o-, preparation of, 28:229
6-brom0-6-deoxy-o-, 22: 185,23: 133
preparation of, 28:246
 SUBJECT INDEX
from boronate, 3 5 5 6
0-(2-acetamid0-2-deoxy-ol(andP)-D-
glucopyranosy1)-(1+6)-2-amino-2-
deoxy-D-, 21 :464
2-acetamido-2-deoxy-~-,polymerization by
hydrogen chloride, 21:464
2-chloro-2-deoxy-~-,enzyme activity and,
22:211
3-chloro-3-deoxy-~-,preparation of, 28:229
6-chloro-6-deoxy-~-,22: 184
preparation of, 28:246, 35:56
3-chloro-3-deoxy- I ,2:5,6-di-0-
isopropyiidene-a-o-, preparation of,
28:247
component of cardenolides, 21:311
configuration of, 21: 13
conversion into o-(-)-muscarine, 27:208
CY-D-,pyrolysis, 47:304-305
5,6,6-d3,(Y-D-, nuclear magnetic resonance
spectrum of, 23:45
D-, 48~281-285
absorption from intestine, 34:287-288
caramelization of, 34:46
derivatives, cyclic acetals, Table,
34:228-233
pyrolysis of, 34:45, 152
reaction with acetone, 34: 182-1 83
regeneration from o-fructose, by 11-
glucose 6-phosphagq 34:295
by triose condensation, 34:294
transport in mammalian intestine,
34:289
2-acetamido-2-deoxy-
circular dichroism, 45:97-98
nonselective spin-lattice relaxation
rates, 45:148
acetoxonium rearrangements of 6-C
derivatives, 26: 157
acetylation of, 33:37
with acetic acid, 33:44
acid and base catalysts in mutarotation of,
24:23
acid-catalyzed reversion, 47:252
acyloxonium rearrangement into D-idose,
26: 146
aerobic catabolism of, 32: 163-166
aerobic respiration by yeasts on, 32: 144
alkaline degradation of, 46:292
Amadori compounds from, 46:307-308
2-amino-2-deoxy-, reaction product with
223
ethyl acetoacetate, pyrrole structure,
4510-1 I
from 2-amin0-2-deoxy-o-mannose, 25: I87
anaerobic catabolism of, 32: 162-163
anaerobic fermentation of. 32: 145
anomerization and gas-liquid
chromatography of, 28:4 1
anomers
aqueous solutions versus crystalline,
laser-Raman spectroscopy, 44:80
p, 44:19-20
correction between CH orientation and
vibrational frequencies observed,
44:21
spectral differences, 4452-53
vibrational spectra, calculation of
frequencies, 44:3946
antiketogenic action, Garcia Gonzalez
work on, 45: 10
aqueous
laser-Rainan spectroscopy, 44:73-74,
76-78
versus solid, laser-Raman spectroscopy.
44:75
solute-solvent interactions, vibrational
spectroscopic studies, 44:86
in aqueous solution, 42: 16
composition, 42:21,26.31,3&35,63
inorganic compound effects, 42:34
polarimetry, 42: 17
polarography, 42:2 1
p-D-,vibrational spectra
atomic displacements for calculated
frequencies, 44:4146
calculated frequencies, with potential
energy distributions, 44:41,4445
observed and calculated frequencies,
44:4043
binding to taste papillae, 45:329-330
2,3-bis( acetamido)-2,3-dideoxy-~-
dideoxy-, circular dichroism, 45:99
1,2:3,5-bis(phenylboronate),preparation,
35:45
01 and p pyranose anomers, circular
dichroism, 45:79-80
catabolism of, 32: 159-162
non-oxidative pathway, 52:289-290
oxidative pathway, 52:289
catalytic constants for mutarotation by
weak acids and anions, 24: 19
224 SUBJECT INDEX
Glucose (continued)
catalytic oxidation of, 335.37
C-C and C-0-bond-lengths in, 44: 15
I4C-labeled, alkaline degradation of,
28:200
complex formation
with germanic acid, 22:288
with phenylboronic acid, 3 5 4 9
with potassium bromide, 21:215
with potassium iodide, 21:215
with sodium ethoxide, 21:258
with sodium methoxide, 21:258
composition of evolved gases, 47:272,274
conversion into o-fructose, 49: 180
course of total gas evolution, 47:272-273
cryoprotective effect, 44:89
decomposition, 47:220-221,272
degradation of, 28: 164,46:296
determination of hydration numbers, 44:87
D-fructose from, 22:232
dibenzyl dithioacetal, reaction with lead
tetraacetate in acetic acid, 32:70
diethyl dithioacetal
ethyl I-thio-D- glucoside from, 32:66
mass spectrometry of, 32:96
preparation of, 32:20
reaction with mercury(I1)chloride in
methanol, 32:68
reaction with silver benzoate, 32:60
hydrolysis of, 22: 1 13
irradiation, 39:94
selective benzoylation of, 33:41
selective methylation of, 33:66
dimethyl acetal
crystalline, 26: 14
hydrolysis of, 22: 113
diphenyl dithioacetal, preparation of,
32:21
6-(disodium phosphate), irradiation,
38:192-193
irradiation, 38: 147-149
dithioacetals
reaction with sulfonyl chloride, 32:48
selective esterification of, 33:40
dithioacetal with 1,2-dithiolycerol, 32:99
effect of alkali tetraborates on rotation of,
23:36
effect of histidine and histidylhistidine on
mutarotation of, 24:32
mutarotase on mutarotation of, 24:3 1
mutarotation of, 24:24
electro-oxidation of, 29: 1 I7
electroreduction of, 26: 15,29: 109-1 17
enantiomeric carba-sugars, synthesis,
48:4549
enzymic degradation of starch and
glycogen to, 30:281
fermentation by yeasts, 32: 152
in food, liquid chromatography separation,
46:52
gas-liquid chromatography of, 28:4C41
gas-liquid chromatography of, in blood,
28:46-47
gel chromatography of, 25:3 1-32
glycoenzyme constituent, 27:302,307,
32 1
glycolysis control and Pasteur effects,
32~168-173
in glycoproteins, 25413
halogen derivatives of, 22:222-223
heated neutral solutions of, antimicrobial
activity formed in, 46:326
in honey, 25:289,295
in hydrolyzates of non-endospermic
hemicelluloses, 36:246
isomerization to o-fructose, by enzymic
catalysis, 36:46-50
by nonenzymic catalysis, 36:4345
production from starch, 36:20-22
technology of crystalline, 36:30, 3 9 4 3
enzyme catalysis, 36:3943
5-(hydroxymethyl)-2-firraldehyde from,
46~284-285
infrared spectrum of, 23:39
inhibitory effect on pectinesterase, 33:337
in L-ascorbic acid synthesis, 37:89-105
oxidation, fermentative, 37: 137-140
oxidation to L-ascorbic acid,
37: 126-129
6-phosphate, radiolysis, 37:42,44
radiation chemistry, 37:33-35
radiation-induced, non-chain reactions,
37:73
radiation-induced, radical reactions,
37:3642
radiolysis, 37:35
with L-asparagine, pyrazines formed from,
4 6 ~ 16-3
3 17
with L-phenylalanine, products obtained
from, 46:3 17
 SUBJECT INDEX
Maillard reaction between glycine and,
46:309
mass spectrometry of ethylene oxide
reaction products of, 30:38
methanolysis of, 28: 19
methyl ethers, 49:29
periodate degradation and gas-liquid
chromatography of, 30:34
separation of, 30:20
monohydrate, C-C and C-0 bond-lengths
in, 44: 15
mutarotation of, 28:404 1
catalytic coefficients of, 24: 16
kinetics of, 23: 16
reaction constants for, 23:40
mechanism of, 24:41
molten and unmelted, 22497
in nectars, 25:304
in nonqueous solvents, 4262, 68
nonselective spin-lattice relaxatilon rate,
45:148, 150
nucleotide esters of, 42:338
(p-bromophenyl)hydrazone, crystal
structure bibliography, 31:367
a-D-, crystal structure bibliography.
31:36S
monohydrate, crystal structure
bibliography, 31:349
pentaacetate, 22: 14
methane chemical-ionization mass
spectrum of, 29:81
penta-0-acetyl-, 45:s
phenols from, 46:290,295
6-phosphate, synthesis of, 33:4647
phosphorylation of, 33:48
in plant cell-wall hydrolyzates, liquid
chromatography analysis, 46: 55
in plant glycoproteins, 42:329-330
polarography of, 29: 126
and reactions with hydrazine,
semicarbazide, and hydroxy lamine,
29: 152
preparation from potatoes, 25:7
proton spin-lattice relaxation rate,
45: 150-1s 1
pyrolysis of, 22497, 501,47:272
course of, 47:273, 276
liquid products, 47:272, 275
volatile products, 47:274, 276
volatile products from, 22:504-505, 508
22s
reaction of
with glycine, pyrarines formed.
46:3 15-3 16
with methylamine in dilute acetic acid,
46:314
reaction with
aqueous ammonia, 25:3 12.3 15
boric acid, 35:31
ethyl acetoacetate, 45: 10-12
sulfuryl chloride, 28:235,33:76
reducing properties, 47:2 18,220
reduction in alcohols, 27:99-100
regional consumption evaluation,
48: 186-1 89
saccharinic acids from, 28: 194-195
selective methylation of, 3 3 5 6
separation, 47:3940
solubility in alkoxy alcohols, 27:99
in anhydrous hydrogen fluoride, 27:94
in ethanol, 27:97
in isobutyl alcohol, 27:98
in liquid ammonia, 27:9 I
in methanol, 27:97
in methanol, effect of calcium chloride
on, 27:95
in thiocyanates. 27:95
solution, Fourier-transform infrared
spectroscopy, 44:6 1
structural formula of, 25:4
structure-properties relationships,
vibrational spectroscopic study,
44:88
sucrose phosphorylase reaction with, 3 2 8
sweetness, 49220
structure relationship, 45:259
syrups, taste, effect of aglycons on,
45245
1,2,3,4-tetra-O-acetyI-, 45:4
6-0-trityl-. 45:3
2,3,4.6-tetra-0-acetyl-, 4 5 5
trehalose as intermediate in resorption or
motility of, 30:2S6
trichloroacetimidates, 50:27-29
trifluoroacetylation and mutarotation of,
28:38
trimethylsilyl ethers of, mutarotation,
42:22
uridine 5-pyrophosphate ester, in mung
bean, 32:9
utilization by yeasts, 32: 146
226 SUBJECT INDEX

Glucose (continued) metabolism, 48:209

vibrational spectra, isotopic substitution preparation, 38:222
studies, 44:54 3-nitro-~-,24: 118
water loss, 47:218-219 4-deoxy-, 4-fluOrO-D-
Wittig five-membered anhydro products preparation, 38:216,2 18,220
from, and its derivatives, 27:284 synthesis, 48:135-136
yeasts unable to utilize anaerobically, 5-deoxy-, 5-fluoro-o-, synthesis, 48: 137-
32: 166-168 138
in de novo polysaccharide synthesis, 6-deoxy-
51:1 4 6 1 4 9 composition in aqueous solution, 42:45,
I-deoxy-, I , 1-bis-p-toluidino-aldehydo-D-, 63
tetrabenzoate, 22:276 D-, 21:173, 175, 177
2-deoxy- ester of thymidine 5'-pyrophosphate,
D-, 21~19 28:323
catabolism of, 32:177, 181-183 2,3-di-O-methyl-o-, 21: 173
dithioacetals, hydrolysis of, 32:67 6-fluoro-o-, enzyme activity and, 22:210
effect on biosynthesis of cell-wall a-L-,21:177
polysaccharides and glycoprotein, 6-nitro-o-, 24:98, 100, 118
32:229 dextro-, structure, 50:5
utilization by yeasts, 32:23 1 2,3-diamino-2,3-dideoxy-~-, 24: 135
2-flUOr0-D-, 24:206,48:171, 175 2,6-diamino-2,6-dideoxy-o-, synthesis of,
[I4C]-, preparation, 38:240 30:116
['HI-, preparation, 38:239 5,6-diamin0-5,6-dideoxy-o-, composition in
inhibition of lipid-linked aqueous solution, 42:5 1-52
oligosaccharides, 40:326, 332-333 4,6-dideoxy-4-
labeled, PET technique, 48: 199-202 dimethylamino-o-, 24: 159
labeled, synthesis, 48: 121, 124, methylamino-o-, 24: 159
143-144, 192-1 94, 197-1 98 2,4-dideoxy-2,4-difluoro-~-, preparation,
metabolic fate, 48: 188-189 38:216
metabolism, 48:207 2,6-dideoxy-2,6-difluoro-o-, preparation,
preparation, 38:216,231 38:216
2-fluoro-3,4:5,6-di-O-isopropylidene- 2,4-di-O-cu-~-rhamnopyranosyl-~-, see
aldehydo-o-, 48: 155, 163 Chacotriose
2- (methylamino)-D-, trimethylsilyl ethers 2,3:4,5-di-O-isopropylidene-
of methylated, gas-liquid D-
chromatography of, 30:29 dithioacetals, preparation of, 32:54
2- (methylamino)+-, synthesis of, 30: 114,K diethyl dithioacetal, partial
35: 107-109 demercaptalation of, 32:69
2-(trifluoroacetamido)-cu-~-,biological4-O-( 4.6-O-isopropylidene-cu-o-
activity, 38:283 glucopyranosy1)-ddehydo-D-,
2-(trifluoroacetamido)-p-~-,biological dimethyl acetal, synthesis, 39:238
activity, 38:283 1,2:5,6-di-O-isopropylidene-cu-o-, from
3,4,6-tri-0-methyl-2-(methylamino)-~-, levoglucosan, chloral, and acid, 34:65,
composition in aqueous solution, 93
42:47 3,4:5,6-di-O-isopropylidene-o-,
3-deoxy- dithioacetals, preparation of, 32:54
3-[18F]fluoro-~-,synthesis, 38:239 trimethylene dithioacetal, preparation of,
3-flUOrO-D-, 48: 183 32:38
biological activity, 38:28 1 1,2:3,4-di-O-isopropyIidene-5-thio-o-,
labeled, 48: 199 synthesis, 39:77
 SUBJECT INDEX
2,3-di-O-methyI-o-, composition in aqueous
solution, 42:44
2,4-di-O-methyl-~-,preparation of, 3 0 5
2,6-di-O-methyI-o-, preparation of, 30:4
3,4-di-O-methyI-o-
preparation of, 3 0 5
synthesis of, 33:27
3,5-di-O-methyI-o-, 24: 195
3,6-di-O-methyl-o-, preparation of, 30:4
4,6-di-O-methyl-~-,preparation of, 30:4
5,6-di-O-methyl-o-, composition in aqueous
solution, 42:4546
DL-
crystalline, 26: 14
synthesis, 40:93
effect of calcium chloride on specific
rotation of, 21:230
electrophoretic migration of, 21:234
0-galactosyl-, 21:3 I
3-O-galloyl-~-,2 1 ~ 2 7
GDP-D-, in cellulose biosynthesis,
42:3 17-320
in polysaccharide biosynthesis,
42:329-330
1,1,2,3,4,5,6-hepta-O-acetyl-~-,preparation
from dithioacetal, 32:70
hydrogen bonding, Raman and infrared
spectral study of, 4498-29
1-O-(indole-3-propionyl)-P-~-, 21:39 1
inositol-o-glucuronic acid-2-amino-2-deoxy-
D-, 24:4 10
3-keto-o-, polarography of, 29:145
L-
derivatives of cyclic acetals, Table,
34: 22 8-2 33
sweetness-structure relationship. 45259
liquid chromatography
methods for analysis of, 46:33
separation, 46:52-53
4-O-methyI-o-, 22:7
methyl ethers of D-, 5:145-190
methyl glycosides of, oligosaccharides
containing, IT-NMR data for,
42212-2 13
mutorotation, 44:25
6-N-amino-6-deoxy-~-,synthesis of,
28:283
O-a-o-glucopyranosyl-
(l-+2)-O-a-~-glucopyranosyl- (I+~)-D-.
from dextran, 30:386,389
227
(1+3)-0-a-~-glucopyranosyl- ( I + ~ ) - D - ,
from dextran, 30:393
(1+6)-~-a-~-g~ucopyranosyl- ( ~+Z)-D-,
from dextran, 30:389
(1+6)-0-a-o-g~ucopyranosy~-( 1 +3)-D-,
from dextran, 30:388
(1-6)-0- [a-o-glucopyranosyl- (1+2)]-
D-, from dextran, 30:386,389
(1+6)-O- [a-o-glucopyranosyl- (l+3)]-
D-, from dextran, 30:388
(1+6)-~-a-~-glucopyranosy~- (1+6)-O-
a-D-glucopyranosyl- ( l+2)-o-, from
dextran, 30:389
(1-+2)-0-a-~-glucopyranosyl- ( 1+6)-O-
a-u-glucopyranosyl- ( 1 +6)-0-a-~-
glucopyranosyl- (1+6)-0-. from
dextran, 30:394
( l+6)-O-a-~-g~ucopyranosy~- (1+2)-0-
a-o-glucopyranosyl- ( 1 +6)-0-a-o-
glucopyranosyl- ( I + ~ ) - D - , from
dextran, 30:394
4-O-a-~-glucopyranosyl-2,3 :5,6-di-O-
isopropylidene-aldeh,ydo-D-, dimethyl
acetal, synthesis, 39:238
4-O-(c~-~-glucopyranosyluronic acid)-$-,
synthesis, 39:246
4-O-a-o-ma~opyranosyl-u-,24:357
4-~-(a-~-riho-hexosy~-3-u~ose)-~-, by
maltose microbial oxidation, 39:246
6-0-a-D xylopyranosyl-o-, 24:373
76-0-(2-arnino-2-deoxy-P-~-
mannopyranosy1)-0-, deamination of,
31:46, 78, 234
3-O-P-o-galactopyranosyI-o-, 24:9
0-P-D-galactopyranosyl-( I+3)-0-2-
acetamido-2-deoxy-P-~-
glucopyranosyl-
(1+3)-O-P-o-galactopyransoyl-( 1+4)-a-
D-, 24:l
( 1-+4)-O-P-~-galactopyransoyl-( I+~)-D-,
24:8
6-O-benzoyl-n-
ammonolysis, 39:3 I
diethyl dithioacetal. preparation of, 32:45
2-O-benzyI-o-. synthesis, 39:30
2-O-carbanihno-o-, synthesis, 39:30
1,2-O-isopropyIidene-a-~-
5,6-diphenylcyclodiboronate,preparation,
35:45
3,5-phenylboronate, preparation, 35:45
228 SUBJECT INDEX

Glucose (continued) aldehydo-o-

2,3,4,5,6-penta-O-benzoyl-,
5,6-O-isopropylidene-~-,
composition in ammonolysis of, 31:84
aqueous solution, 42:45 diethyl dithioacetal, preparation of, 32:29
oligomers of, "C-NMR data for, 42:196- mercaptalation of, 32:29
199 preparation of, 32:62
4-O-~-rhamnopyranosyl-o-,24:35 1 2,3,4,5,6-penta-O-methyl-
2-O-methyl-o- aldehydo-o-, preparation of, 32:62
composition in solution, 42:34,45 D-, in aqueous solution, 42:33
diethyl dithioacetal, hydrogenolysis of, penta-0-( tnmethyl-d,,-silyl)-o-, gas-liquid
32:78 chromatography and mass spectrometry
preparation of, 32:46-47 of, 28:32
synthesis, 39:30 periodate oxidation of methyl derivatives,
3-O-methyl-o- 21500
composition in aqueous solution, 42:45 phenylosazone, 21:ll-12
selective oxidation with silver carbonate- polymerization of, 21:437,441,468,475
on-Celite, 33:97 by hydrogen chloride, 21:462
5-0-methyl-D- in hydrogen fluoride, 21:445
composition in solution, 42:4546 by ion-exchange resins, 21:464
synthesis of, 28:4 in solid state by boric acid, 21:466
6-O-methyl-o- in sulfuric acid, 21:446
preparation, 3 5 5 5 2-s-ethyl-2-thio-o-, 25: 193
synthesis of, 30:4 preparation of, 31:65,32:56
6-O-(N,N-dirnethylglycyl)-o-, synthesis, 6-S-methyl-6-thio-o-, preparation of, 34: 147
35:54 spectral analysis and identification, 44:24
2-0-,3-0-,4-0-, and 6-O-methyl-, synthesis of, 21:12
trimethylsilyl ethers and gas-liquid system with sodium chloride, 21:211
chromatography of, 30:27-28 2,3,4,6-tetra-O-methyl-o-, reaction with
2,3,4,5,6-penta-U-acetyl- methyl sulfoxide, 21:45 1
aldehydo-o- 1,2,3,4-tetra-O-acetyl-
ammonolysis of, 31:85 6-deoxy-6-thiocyanato-a-~-, synthesis,
diethyl dithioacetal, hydrogenolysis of, 44: 123
32:75 6-deoxy-6-thio-cyano-P-~-,23:235
oxidation of, 32:83 2-O-methyl-o-, 22: 115
preparation of, 32:29 2,3,4,5-tetra-O-acetyl-, 6-0-p-tolylsulfonyl-
reaction with mercury@) chloride, aldehydo-o-, rearrangement in zinc
32:62 chloride-acetic anhydride, 26: 193
mercaptalation of, 32:29 3,4,5,6-tetra-O-acetyl-
preparation of, 32:62,70 2-acetamido-2-deoxy-aldehydo-o-,
Wittig reaction with, 27:23 1 preparation of, 32:63
D- D-, diethyl dithioacetal, preparation of,
dibenzyl dithioacetal, oxidation of, 32:45
32:81 tetra-O-acetyl-2-benamido-, 2-deoxy-~-,
diethyl dithioacetal, demercaptalation ammonolysis of, 31:87
of, 32:62 2,3,4,5-tetra-O-benzoyl-
ultraviolet photolysis of, 32:78 D-, reaction with ethanethiol, 32:34
ethylene dithioacetal, reaction with 6-deoxy-6-iodo-~-,diethyl dithioacetal,
bromine, 32:70 hydrolysis of, 32:63
penta-0-acetyl-o-, ammonolysis of, 31236 2,3,4,6-tetra-O-benoyl-
1,2,3,4,6-penta-O-benzoyl-, D-, D-, synthesis, 39:50
ammonolysis, 39:3 1 5-hydroxy-P-~-,synthesis, 49:79
 SUBJECT INDEX
3,4,5,6-tetra O-benzoyl-
uldehydo-o-
ammonolysis of, 31:114
preparation of, 32:62
reaction with ethanethiol and
hydrochloric acid, 32:30
D-, diethyl dithioacetal, preparation of,
32:30,45
2-S-ethyl-2-thio-o-, diethyl dithioacetal,
preparation of, 32:30
tetra-0-methyl-, D-, mutarotation of, i n
pyridine, 28:39
2,3,4,5-tetra-O-methyl-o-
alkaline degradation of, 28:202
in aqueous solution, 4 2 3 4
septanose form of, 42:29
2,3,4,6-tetra-o-methyl-o-
acetate, gas-liquid chromatography of,29
trimethylsilyl ether and gas-liquid
chromatography of, 30:29
enediol theory and, 26:6
2,3,5,6-tetra-O-methyl-o-, dehydration of,
28:181
I-thio-o-, composition in aqueous solution,
4254
4-thio-o-, composition in aqueous solution,
4253
5-thio-o-, antitumor activity of, 42: 136-
137
composition in aqueous solution, 4 2 5 2
6-thio-o-, 23:226
derivatives, 24: 146
thio linkage to cysteine, 43:4&47
(6S)-2,3,4,tri-O-acetyl- 1,6-anhydro-6-bromo-
p-o-. synthesis, 49:5 1
tri-0-acetyl-o-, 1,6-dinitrate, preparation of, Glucose 6-phosphate, 2-de0xy-2-['~F]fluoro-~-,
34:67
4,5,6-tri-O-acetyl-2,3-di-O-methyl-uldrhydo-Glucose 6-phosphate dehydrogenase in fruit
D-, ammonolysis of, 31: 114
3,4,4-tri-O-methyl-u-, synthesis of, 33:27
3,4,6-tri-O-rnethyl-~-
composition in solution, 42:45
trimethylsilyl ethers and gas-liquid
chromatography of, 30:29
UDP-D-, biosynthesis of, 4 2 3 16
in cellulose biosynthesis, 42:319
in polysaccharide biosynthesis, 42:322,
325-326,331
Glucose aldehydrol. 1(R)-1,3,4,5,6-penta-O-
acetyl- 1,2-0-isopropylidene-u~~~h~~d~~-o-, crystal structure bibliography, 30:465
229
reaction with hydrogen bromide in acetic
acid, 39: 1 14
Glucose antibodies, 53:21&215,217
Glucose-5,6.6-dj,
(Y-D- and (Y, p-D-, proton magnetic resonance
spectroscopy of, 27:28
D-, nuclear magnetic resonance spectroscopy
of, 27:148
Glucose-5-d
01. p-D-.proton magnetic resonance
spectroscopy of, 27:28
D-
nuclear magnetic resonance spectroscopy
of. 27: 149
preparation of, 27: 129
Glucose-d,, p-D-,mass-spectrometric analysis
of, 27: 15 1
Glucoseen, tetramethyl-, dehydration of,
28: 184
Glucose-I-d, D-, effect of mutarotase on
mutarotation of, 24:32
o-Glucose isomerase
isomerization kinetics and mechanism.
36:4849, 5 1
production, 36:50-52
sources and activity, 36:46-50
D-Glucose oligosaccharides, a-(1+4)-linked,
liquid chromatography analysis, 46:3740
D-Glucose oxidase
amino acid content of, 27:3 15-3 16
carbohydrate components of, 27:326
electrophoresis and sedimentation of,
27:3 12-3 13
glycoenzyme, 27:309
Glucose-I-P, 53:25 1-252
synthesis, 38:245
climacteric, 42:364
o-Glucose-procollagen glucosyltransferase,
UDP-, 44:244
Glucoseptanose
D-, 1,2:3,4-diacetal, selective hydrolysis,
39: 16
1,2:3,4-di-O-iso-propyIidene-c~-~-. formation
of, 34: 183
2.3:4,S-dI-O-isopropylidene-n-~-, formation
of, 34: 183
3-0-acetyl- 1.2:4,5-di-O-isopropylidene-(~-~-,
230 SUBJECT INDEX
Glucoseptanose (continued)
5-O-(chloroacetyl)- 1,2:3,4-di-O-
isopropylidene-a-o-
conformation of, 26: 113
crystal structure bibliography, 30:465,
31:353
Glucoseptanoside
ethyl 2,3:4,5-di-O-isopropylidene- I-thio-p-
D-
conformation of, 26: 114
crystal structure bibliography, 30:454,465
preparation from dithioacetal, 32:69
methyl 2,3 :4,5-di-O-isopropyIidene-a-~-
and-p-D-, preparation of, 34:279
methyl 3,4-O-isopropylidene-2-O-(p-
nitrophenylsulfonyl)-a-D-,fluorination,
38:224
methyl 2,3,4,5-tetra-O-acetyl-P-~-
conformation of, 26: 1 14
crystal structure bibliography, 30:465
methyl 2,3,4,5-tetra-O-methyl-p-~-,
preparation of, 34:279
Glucose-6-sulfonic acid,+-, sodium salt,
preparation of, 34:69
Glucose-t, 6-deoxy-~-,detection and
localization in tissue by autoradiography,
27:181
Glucose-1-r, D-
osazone formation, mechanism of, 27: 152
preparation of, 27: 129
Glucose-2-t, D-
6-phosphate, preparation of, 27: 158
preparation of, 27:134
Glucose-3-r, D-, preparation of, 27: 129, 135
Glucose-4-t, D-, preparation of, 27: 135
Glucose-5-r, D-
6-phosphate, preparation of, 27: 135
preparation of, 27: 129
Glucose-6-t, D-, preparation of, 27: 129
Glucosidases
2-acetamido-2-deoxy-p-~-,25:446
OL-D-, 44:230,234,236
activity in utilization of a - ~ -
glucopyranosides by yeasts,
32:191-199
buckwheat, 44: 149
of honey, 25:303
molecular weight of, 32: 194-195
in plant cell walls, 42:301-302
preparation and activity of, 30:301
regulation, 39:388-390
snythesis by yeasts, 32:233
specificities of, 32: 196
substrate specificity, 39:387
p-, Helferichs work on, 45:5
p-D-.23:2 12,44: I49
almond emulsin, 44: 149
inhibition, 48:207-333-334
by castanospermine, 48:342-344
pH-dependence, 48:338-339
in plant cell-walls, 42:301-302, 379
purification and carbohydrates of, 27:305
specificity of, 30:270,353-370
substrate specificities, 39:392-393
in yeasts, 32:201-205
molecular weights of, 32:202
specificities of, 32:204
1-deoxy-~-g/uco-hept-l-enitol, reaction with
a-D-, 48:356-357
halogenated sugars and a-and p-, 22:209
Glucosidase-transferase
and P-amylase, in characterization of
amylaceous polysaccharides, 30:329,
33 1
preparation and properties of, 30:297-299
Glucoside
1,4-benzoxazin-3-one,2,4-dihydroxy-7-
methoxy-,2-~-,21 :407
3-deoxy-3-fluoro-o-, 48: 166
Glucosides
a-D-
mannosyl 2-amino-2-deoxy-oc-o-,
discovery of, 30: 112
production and properties of, 30: 137
sweetness-structure relationship, 45:239
synthesis, 36: 108
2-amino-2-deoxy-o-, deamination of,
31:233
p-D-, sweetness-structure relationship,
45:239
benzyl2-acetamido-2-deoxy-4-O-p-~-
galactopyranosyl-p-D-, degradation of
peracetylated with ferric chloride,
31:239
D-
containing 2-deoxy-2-fluoro-~-~-glucosyl
group, 48:208
phenolic, gel chromatography of,
25:49-50
emulsin effect, 50:13-14
 SUBJECT INDEX
ethyl CX-D-, in sake, gas-liquid
chromatography and, 28:54-55
ethyl 1 -thio-o-, preparation from
dithioacetal, 32:66
ethyl 2,3,4-tri-O-benzyl-I -thio-a-m.
preparation of, 34:64
mass spectrometry of, 30:38
melthyl4,6-O-benzylidene-a-o-, 0x0
reaction with, 23: 107
methyl 2-acetamido-2-deoxy-3,4,6-tri-O-
methyl-a-o-, mass spectrum of, 21:67
methyl a-D-,21:21
periodate oxidation of, 33:95
methyl (3-D-. 21:21
ring structure of, 25:4
methyl 4,6-0-benzylidene-3-deoxy-3-iodo-
a-D-, 21:162
methyl 3-bromo-3-deoxy-a-o-, hydrolysis
rate of, 22:208
methyl 6-bromo-6-deoxy-a-~-,21: 182
methyl 3-chloro-3-deoxy-a-o-, hydrolysis
rate of, 22:208
methyl 6-chloro-6-deoxy-~~-o-, 21: 182
methyl D-, halogen derivatives of, 22:224
methyl 2-deoxy-, mass spectrum of, 21:64
methyl 3-deoxy-, mass spectrum of, 21:64
methyl 4-deoxy-, mass spectrum of, 2164
methyl 2,6-diamino-2,3,4,6-tet~a-deoxy-~-,
preparation of, 30: 167
methyl 2,3-di-U-acetyl-4,6-O-ethyIidene-p-
D-, acetolysis of, 22: 14
methyl 4-0-( 1-acetoxyethyl)-2,3,6-tri-O-
acetyl-pa-, 22: 14
methyl 4,6-O-benzylidene-a-o-
preparation by acetal exchange, 34: 1 X7
reaction with carbon tetrachloride-
triphenylphosphine, 28:247
methyl 4,6-O-benzylidene-p-~-,preparation
by acetal exchange, 34: 187
methyl 4,6-0-benzylidene-3-deoxy-3-iodo-
(Y-D-,22: 189
methyl 4,6-0-benzyhdene-P-o-, 0x0 reaction
with, 23:107
methyl 3-0-methyl-2,4,6-tri-O-propyl-~-,
gas-liquid chromatography of, 30: I5
methyl 6-0-methyl-2,3,4-tri-O-propyl-~-,
gas-liquid chromatography of, 30: 15
methyl 3-S-acetyl-4-6-U-benylidene-2-
deoxy-2-(methylsulfonamido)-o-,
22: 153
23 1
methyl 2,3,4,6-tetra-O-methyl-
a(and P)-D-, mass spectra of, 21:56
D-, effect of volatility on methylation
analysis of, 30: I7
methyl 2,4,6-tri-O-methyl-P-~-, reaction
with methyl sulfoxide, 21:450
methyl 2,3,6-tn-O-benzoyI-a-~-, synthesis
of, 30:4
4-methylumbelliferyl p-D-, hydrolysis,
48:359-360
phenyl I-thio-, 21:22
p-nitrophenyl (Y-D-, aryl migration in, 33:109
pyrolysis of, 34:46, 152
synthesis, S0:21-117
anomeric 0-alkylation, 50:23-25
p-D-Glucosidic linkages, enzymes in hydrolysis
of, 30:347-353
Glucosiduronase
p-, isolation of carbohydrates from, on
analytical-scale columns, 46:60
p-D-,44: 199-200,204,214
action on glycosiduronic acid conjugates
of N-hydroxy compounds,
36: I3 1-132
activity with 1 -0-acyl-o-glucuronic acids,
36:112, 124
oligosaccharides, liquid chromatography
separation, 46:4243
specificity, 36: 125
carbohydrate content of. 27:306-307
P-o-Glucosiduronates, synthesis, 50: I I I , I 13
Glucosiduronic acids
p-D-, cardenolides. preparation, 36:7 1
phenacetin-related, 36:9 1-92
properties. 36:s 1
D-, deprotection and purification, 36:79-82
digitoxigenin-3P-yl 2,3,4-tri-O-acetyl-P-~-,
methyl ester, 21:291
gas-liquid chromatography of phenolic and
terpenoid, 28:77
retinyl p-D-, biosynthesis of, 26:440
Glucosinolates
allyl, carbon- I3 nuclear magnetic resonance
spectroscopy, 41 :65
gas-liquid chromatography of, 28:25, 54
Glucosone, D-, from o-fructose, 22:245
Glucosylamine
p-0-
2-acetamido- 1-N-acetyl-2-deoxy-, NMR,
45:98
232 SUBJECT INDEX
Glucosylamine (continued)
2-acetamido- 1-N-(~-aspart-4-oyl)-2-
deoxy-
circular dichroism, 45:98-99
NMR, 45:98
D, tetra-0-acetyl-, 45:s
N-benzyl-, 45:5
N-aCetyl-6-0-a-D-galaCtOpyranOSyl-p-o-,
configuration of, 31:lOS
Glucosyl arsenate, fast Fourier-transform
proton magnetic resonance spectroscopy
in preparation of, 27:59
Glucosylation, of cellulose acetate, 29:332
Glucosyl bromide
2,3,4-tri-0-acetyl-6-bromo-6-deoxy-~-,
21:17
3,4,6-tri-0-acety~-2(methylsulfonyl)-a-~-, Clucosyluronorhamnomannan, carbon- 13
23:264
Glucosylceramides
biosynthesis, 40:247-248
glycosphingolipids, 40:239-240
isolation, 40:238
in starfish, 44:429
Glucosyl chloride
3-acetamido-tri-O-benzyl-3-deoxy-o-,
preparation of, 30: 143
3,4,6-tri-0-acety~-2-0-p-to~y~su~fonyl-P-~-, Glucuronic acid, 53:224-226
23:264
Glucosyl cobalt tricarbonyl triphenyl-
phosphine, 2,3,4,6-tetra-0-acetyl-P-~-,
23:109
Glucosyl dipotassium phosphate, a+-,
irradiation, 38: 190-191
Glucosyl fluoride, D-, 2,3,4-tri-O-benzoyI-6-0-
trityl-, 45:3
(Glucosyl fluoride)urono-(6,3)-lactone, per-0-
acetyl-p-D-, synthesis, 38:203
Glucosylimidazole, 1+D-, inhibition by,
48:334-335
P-D-GIUCOSYI isothiocyanate, 48:377-378
D-GIUCOSYI oxocarbonium ions, 47:304
Glucosyl phosphate
WD-, preparation of, 32:6
D-
conversion into amylopectin, 34:6
radiolysis, 37:42
o-Glucosylselenophosphates, 53: 152-1 54
~-Ghcosyl-3-tphosphate, synthesis of, 27: 130
Glucosyltransferase, 44:262
D-, 44:179
in cellulose biosynthesis, 42:3 18
glycoside synthesis, 39:429
membrane-bound, 44:284
0-Glucosyl trichloroacetimidates
acetylated, glycosides and saccharides from,
50:41,4344
benzyl-protected, 50:35-39
as donors, 50:34-49
acid catalyst, 50:35
glycosylation, 50:3940
azidosphingosine derivatives, 50:4 1,
4548
ceramides, 50:49-5 1
solvent effects, 50:35, 39
synthesis, 50:34-35
Glucosyluronate-rhamnose, 53:236,238-240
nuclear magnetic resonance spectra, 38:64
Gluco tetranose, 1,2:4,5-di-O-isopropylidene-
D-, 26:240
Glucupyranosyl bromide, 2,3,4-tri-O-acetyl-c-
D-, polymerization of, 21:441
Glucuralone, trimethyl-, structure of, 29:235
Glucuronamide, D-, diethyl dithioacetal
preparation, 36: 101
thioglucoside from, 32:66
2-acetamido-2-deoxy-o-, polymer, 41:88
uldehydo-o-, structure of, and lactone,
33: 190
2-amino-2-deoxy-o-. decarboxylation of,
28:187
p-0-
per (trimethylsilyl)ated, mass spectrometry
of, 29:47
potassium salt dihydrate, crystal structure
bibliography, 31:364
rubidium salt dihydrate, crystal structure
bibliography, 31:364
D-
alkaline degradation of, 28:206
in apiose biosynthesis, 31: 160-162
bilirubin conjugates, 36: 105, 117-1 19
derivatives, 36:59-65
diethyl dithioacetal sodium salt,
preparation, 36: 101
I-esters, occurrence in urine, 36: 104
preparation, 36:74
steroid conjugates, synthesis, 36:92-96
in xylans, 36:236-238,240
 SUBJECT INDEX
catalytic hydrogenation, 38:289
chemical synthesis of, 8:23 1-249
circular dichroism, 45: 102, 1 0 4 105
conjugates of, of animal origin, 9: 185-246
degradation, 39:4
enzymic phosphorylation of, 32:9
epimenzation of, 28:40
in fungal polysaccharides, 23:412
gas-liquid chromatography of, 2 8 6 4
isomers, structures of, 33: 190
synthesis of, 33: 190
r-ascorbic acid synthesis, 37: 1 15-1 19
mercaptalation of, 32:26
in metabolism, tk251-275
methyl ethers, synthesis, 35: I 1
phenols from, 46:290
phenylhydrazide dialkyl dithioacctals,
preparation of, 32:55
uridine 5-pyrophosphateester, in mung
bean, 32:9
L-, crystalline, 39:4
4-O-methyl-u-, 46:306
I -O-acyl-o-, P-D-ghcosiduronase action,
36:112
I -0-(I8P-glycyrrhet-3O-yl)-o-, preparation,
36: 109
4-O-methyl-~-,22:7
gas-liquid chromatography of, 28:64- 65
in mesquite gum, 24:349
I -O-retinoyl-P-o-, biosynthesis of, 26:440
residues in Acacia gums, 24:345
tetra-0-acetyl-a-, methyl ester, acetoxonium
salts, 26:157-158
trichloroacetimidates, SO: 1 1 I , I 13
Glucuronic hydrazide, aldehydo-D-, N-acyl-, N-
acylhydrazones, preparation of, 33:215
Glucuronic phenylhydrazide, aldehydo-,
phenylhdrazone, preparation of, 33:2 14
P-Glucuronidase, preparation and properties of,
14:381428
Glucuronoarabinoxylan
in plant cell-walls, 42:285
interconnections, 42:307,3 14
purification, 42:276
structure, 42:289,291-292
wheat-straw, enzymic analysis, 44: 163
Glucuronoglucans, 41: 101
fungal, mass spectrometry of, 29:66
mass spectrometry of, from fungus Fonies
unnosus, 29:54
233
Glucurono-6,3-lactone
aldehydo-
acylhydrazones, preparation of, 33:2 15
N-isonicotinoylhydrazone,preparation of,
33:215
oxime. preparation of, 33:214
P-D-. crystal structure bibliography, 31 :364
color reaction with alkali, 33:224
u-
diethyl dithioacetal. thioglycoside from,
3256
dithioacetals, reduction of, 32:55
mercaptalation of, 32:26
polarography of, 29: 163
2,4-O-benzyhdene-o-, dialkyl dithioacetals,
reaction with p-toluenesulfonyl
chloride, 32:51
2,4-O-ethylidene-o-, dithioacetals, hydrolysis
of, 32364
Glucuronomannan polysaccharides, see
Polysaccharides
Glucuronomannans, 24:357
Glucuronoxylans
carbon- 13 nuclear magnetic resonance
spectra, 38:95
4-0-methyl-
birch, structure of, 31:277
structure of, 32:350-352
Gluopyranoside
methyl 3-acetamido-2,4-di-O-acetyl-3,6-
dideoxy-a-o-, selective deacylation,
39:30
methyl 6-O-benzoyl-3-bromo-3-deoxy-~-~-,
synthesis. 39: 100
methyl 4-O-benzoyl-3-bromo-3,6-di-deoxy-
D-, synthesis, 39: 102
P-u-Glucose-2-yl dibenzyl phosphate, 1,3,4,6-
tetra-O-acetyl-2-deoxy-, preparation by
phoshono migration and acetylation,
33: 109
Glutaconic acid, 3-methoxy-, crystal structure
bibliography, 38:422
L-Glutamate 1-decarboxylase, in fruit
climacteric, 42:365
Glutamic acids
1:1 cytidine-A-benzyloxycarbonyl-L-,
dihydrate, crystal structure
bibliography, 34:362-363
L-
carbohydrate substrate, 40: 118
234 SUBJECT INDEX
Glutamic acids (continued)
o-ribose synthesis from, 28:294
in glycoprotein, 25:419
from sheep and ox, 33:7
N-benzyloxycarbonyl-L-, cytidine-,
dihydrate, crystal structure
bibliography, 34:362-363
L-Glutamine, o-fructose 6-phosphate
aminotransferase, in metabolism of u-
fructose, 34:341-343
Glutaraldehyde, in neoglycoprotein preparation,
37:250
Glutaraldehydic-2,4-d, acid, 2-0xo-,
preparation of, 27: 165
Glutarimide, 3-[2-(3,5-dimethyl-2-
oxocyclohexyl)-2-hydroxyethyl]-,
inhibitor of galactomannan degradation,
35:361
Glutathione, ketonucleside reaction with,
42:263-264
Gluten, 53:398
Glutose, 3:113-128
Glycals, 7:209-245,53:154-158
acid degradation of, 24:218
addition to, fluorinated carbohydrates,
48: 169-1 81
alkaline degradation of, 28:203
allylic rearrangements of, 24:2 13
D-, 48:349-357
hydration stereochemistry, 48:354
inhibition patterns, 48:35 1
interaction with glycosidases, 48:350-352
intermediates formed in slow inhibition,
48: 352-3 53
kinetics of hydration, 48:355
proton transfer to C-2,48:353
dehydration in acid solution, 28: 182.-186
deoxyhalogeno sugars by addition reactions
with, 28:261
dinitrogen tetraoxide addition to, 24:206
effect on glycosidases, 31:6
electrophilic additions, 38:234-237
furanose-related, preparation of, 31:4
halogen and hydrogen halide addition to,
24:202
hydroformylation of, 24:210
2-hydroxy-, 24:2 19-223
addition reactions, 24:220
0x0 reaction with, 23:92
rearrangement reactions of, 24:22 1
synthesis of, 24:219
lead tetrafluoride action on pyranoid, 25: I95
methoxymercuration of, 24:210
nitrosyl chloride addition to, 24:206
nucleosides from, 24:217
0x0 reaction with, 23:66,86
preparation from ketoses, 24:254
reaction with
alcohols and phenols, 24:215
hydrogen fluoride, 38:229-237
synthesis of, 24:200,39:147
in synthesis of 2-deoxy sugars, 21: 148
Glycanase, 44: 148
endo, plant cell-wall and, 42:337, 346
ex0 action pattern, 44: 149
Glycans
a-and p-, carbanilyl derivatives, circular
dichroism, 45:119-120
antitumor activity of, 32:259
p-D-,crystal structure bibliography,
35:379-381,36:320-327
biological role, 37:158-164
biosynthesis, 39:3 18
complex, gl ycoprotein-derived, reversed-
phase chromatography, 46:4344
(Y-D-, crystal structure bibliography, 35:378,
36:3 19-320
f.a.b.-mass spectrometry, 45:58
fucose occurrence, 39:301-311
glycosaminoglycan, 25:436,477
configuration determination of, 25: 185
gel chromatography of, 25:47
of degradation products of, 25:34,44
in mucopolysaccharidoses, 25475
protein complexes, 25:416
structure of carbohydrate chains in,
25:459462
maturation, 37: 188
N-glycosylically-linked,behavior during
reaction sequence of hydrazinolysis,
4 5 ~ 1-52
5
periodate degradation and gas-liquid
chromatography of, 30:34
primary structure, and catabolism,
37:189-199,222-223
development and improvement of
procedures, 37:200-205
of glycosidically linked, 37:217-218
of N-glycosylically linked, 37:214-217
of N-linked
 SUBJECT INDEX
and biosynthesis, 37: 182-1 89, 2 18-22 1
and glycosylation, 37: 184-187
and metabolism, 37: 182, 218-22 I
role, 37:2 13-2 14
spatial conformation, 37:206-2 12
structure of glycoprotein, 37: 157-223
antenna and variable fraction, 37: 170,
172-173, 177
core and invariant fraction, 37: 170
glycan-protein linkages, 37: 164- I70
N-acetyllactosaminic type, 37: 171, 173,
178-179
n-glycans and isoglycans, 37: 170
oligomannosidic type, 37:171-176, 178
Glycenoses, 23:234
Glyc-3-enuloses, l-bromo-l,3,4-trideoxy-,
synthesis of, 27:295
Glyceraldehyde, 46:32 1
carbon monoxide elimination by radiation,
37:14
composition in solution, 42:20, 3 I , 37
D-
(+)-,synthesis of, 21:17
configurational correlation with L-serrne,
27:207
configuration of, 26: 13
from u-fructose in liver, 34:292--293
diethyl dithioacetal, physical constants of,
32: 102
gel chromatography of, 2 5 3 I
3-phosphate hydrate, carbon- 13 nuclear
magnetic resonance spectroscopy,
41:53
reaction with 1,3 dicarbonyl compounds,
45: 13
dehydration to pyruvaldehyde, 28: 174
acidic conditions, 46:278-279
2-deoxy-2-fluoro-o~-,22: 199
synthesis, 40: 105
DL-
dimer, crystal structure bibliography,
31:359
reaction with ammonia, 25:325
gas-liquid chromatography of, 28:96
high-temperature transformation, in alkali
conditions, 46:284
kinetic currents in polarography of, 29: I36
2,3-0-isopropylidene-~-, carbohydrate
substrate, 40: 120-122
3-phosphate, radiolysis, 37:42
235
polarography of, 29:133, 150-151
radiation chemistry, 37:32-33
separation from glycolaldehyde as
trimethylsilyl oxrmes, 28:3 I
Wittig reaction with, 27:245, 288-289
Glyceric acid
2-deoxy-2-fluoro-, 22:206
3-0-phosphono-
u-, calcium salt trihydrate, crystal structure
bibliography, 30:447
in photosynthesis, 32:7-8
trimethylsilylated, mass spectrometry of.
29:80
Glyceride, 0-a-u-galactosyl-, occurrence,
37:322-328
Glycerol
I - and 2-phosphates. phosphono migration
in. 33: 108
1.2-anhydro-3-deoxy-or -,sulfonylation of,
23:239
2-C-(hydroxymethyl)-,synthetic and
formose component, 29:209
cluster ions, 45:29
3-deoxy-
I-O-p-tolylsulfonyl-o~-, 23:239
2-O-p-tolylsulfonyl-o~-, 23:239
1 -deoxy- 1 -fluoro-
D-, preparation, 38:210
L-, selective phosphorylation with
dibenzyl phosphorochloridate, 33:50
2-deoxy-2-fluoro-, synthesis, 38:237
6-deoxy-6-sulfo-a-o-glucopyranosy1-( 1 4 I )-
D-, rubidium salt, crystal structure
bibliography, 31:366
o-galactosides, 37:3 12-3 16. 360-362
1,2-dithio-. in dithioacetal preparation, 32: 19
enzymic determination of, 30:282-283
ester of cytidine 5'-pyrophosphate, isolation
of, 28:334
esters, acyl migration in. 33: 107
ethylboronate, structure, 35:43
gas-liquid chromatography of, 28:57,91
inhibitory effect in pectinesterase, 33:337
manufacture from yeast and sugar,
32:127-128
as matrix for f.a.b.-mass spectrometry,
45:25-26
2,2'-0-methylenebis-
1 -deoxy- I -fluoro-L-, 'H-and I9F-NMR
data for, 46: 158
236 SUBJECT INDEX
Glycerol (continued)
3-0-benzoyl- I-deoxy- I-fluoro-L-, IH-and Glycerol glycosides, sweetness-structure
19F-NMR data for, 46:158
1-0-a-o-glucopyranosyl-, from dextran,
30:389
1-0-a-D-isomaltosyl-, from dextran, 30:389
2-0-(2-amino-2-deoxy-~-galactopyranosyl)-,
deamination and structure of, 31:76
1-0-(6-deoxy-6-sulfo-a-~-glucopyranosyI)-, Glycine
crystal structure of, 25:72
3-0-glycopyranosyl-, mass spectrometry of
phenylboronates, 3 5 6 8
1,2-0-isopropyiidene-~~-, isomerization, Glycine rnax lectin, see Soybean, lectin
39:27
1,3-0-methylidene-, as solvent for sugars,
27:88-89
2,3-0-methylidene-, as solvent for sugars,
27~88-89
1-0-[O-a-D-galactopyranosyl-( 1+6)-P-o-
galactopyranosyl]-D-, occurrence,
37:326
1-0-palmitoyl-m-, preparation of, 33:42
1,3-O-@henyIboranediyl)-, nomenclature,
35:36
1,3-0-@henylborylene)-, nomenclature,
35:36
1-0-p-tolylsulfonyl-, infrared spectrum,
23:255
1,2 (or 2,3)-O-isopropyhdene-o~-,
hydrogenolysis, stereoselectivity,
39: 124
oxidation with mercuric acetate, 33:99
phenylboronate, nomenclature, 35:36
properties and structure, 35:42
3-phosphate disodium salt hexahydrate,
crystal structure bibliography, 30:465
radiation chemistry, 37:34
radiolysis and free-radical chemistry,
37~27-28,32
reaction with benzaldehyde, 34: 181
selective acylation of, 33:42
as solvent for sucrose, 27:98
sweetness-structure relationship, 45:293
triesters, rearrangement of acyloxonium ions
in, 26:135
utilization by yeasts, 32: 146
Glycerol 1-(diethylborinate) 2,3-ethylboronate,
selective cleavage, 3 9 5 4
~-Glycero-~-gfuco-heptofurano[2,1-
d]iniidazolidine-2-thione,1-phenyl-,
crystal structure bibliography, 38:458
relationship, 45:248
Glycerolipids, biosynthesis of, 26:450453
Glycerol kinase, S.cerevisiue, 49:208
Glycerone phosphate, from o-fructose in liver,
34:292-293
Glycerose, 21:12
2-~-glucopyranosyl-,synthesis of, 33: 146
in glycoprotein from sheep and ox, 33:7
sweetness, 45:233
Glycoasparagines, structure of, from
asparaginylglucosaminuria urine, 37: 198
Glycoaspartamidase, activity of, 28:438
Glycobiose peracetates, I3C-NMRdata for,
42:216-217
Glycobiosyluronic acid, 51:216-217
Glycocalicin, sialylated oligosaccharides,
fractionation, 46:46
GIycoconjugates
acid hydrolysis of, 46:265-269
biological significance, 50:2 1
classification, 37:157
degradation of, by deamination, 31:232-237
by Weermann and Lossen rearrangements,
31:237
f.a.b.-mass spectrometry, fragmentation
pathways, 45:43
hydrolysis (partial) of, 31:196
methanolysis, 46:258-259
mixtures, f.a.b. mapping, 45:39
neutral and amino monosaccharides of,
measurement of, 46:268
nondialyzable, by hydrochloric acid, 46:267
primary structure, conclusions, 37:2 12-2 13
sialic acids occurrence, 40:138, 140
structure of, 31: 185
enzymic analysis, 44:231, -246
Glycoconjugates isolation, 53:211-212
GIycodiuloses
3-deoxy-, alkaline degradation of, 28: 196
4-deoxy-, alkaline degradation of, 28:196
Glycoenzymes
amino acid sequences in glycopeptides of,
27:319-323,333
amino acids of, 27:3 15-3 18
biological and structural significance of,
27~337-341
 SUBJECT INDEX
biosynthesis of, 27:303, 308
mechanism of, 27:328-337
carbohydrate components, 27:306, 32 1-327
cellular locale, reactions and mechanisms,
27~328-332
conformational structures, 27:327
definition of, 32:333
of glycoprotein structure, 27:301-34 I
in plants, 44:382
protein-carbohydrate linkages in,
27:3 18-323
purity criteria for, 27:309-314
stability of, 27:340
types of, 27:305-307
Glycofuranoses, occurrence in nature, 21: 139
Glycofuranosides, 2 1:95- 142
conformation of, 21 :96
formation in acidic methanol, 21:101, 105
hydrolysis by acids, 21: 128, 130-1 3 I
kinetics of formation of, 21:106, 108
melting points and specific optical rotations
of, 21:140-141
methyl, synthesis of, 27:4
methyl 2-deoxy-, thermal polymerization of,
21:476
oxidation o f glycol groups in, 21: I32
polymerization of, 21:138
preparation from dithioacetals, 21:l 12-1 13
structure of, 21: 127
synthesis by Koenigs-Knorr reaction and
other methods, 34:277-283
Glycofuranosylamines, 21: 122
Glycogen
a-amylase action on, 23:3 17, 324
mechanism of, 23:328
affinity chromatography adsorbent, 39:419
arsenolysis of, 23:355,357
P-amylase action on, 23:317, 324
biosynthesis of, 26:326,376-382
as carbohydrate-reserve in yeasts, and
synthesis of, 32:230
carbon-I3 nuclear magnetic resonance
spectra of P-limit dextrins, 38:3940
chromatography of, 25:9
circular dichroism, 45:89
crystallography of, 22:478
degradation by P-amylase, 30:288
to o-glucose with glucoamylase, 30:281
dog-liver, structure of, 32:5
end-group assays, 35:8
237
enzymes in structural analysis of,
30:302-332
enzymic degradation of, 3:25 1-3 10,
17:407430,30:285-302,33:4
enzymic synthesis of, 17:371407
fungal, 41:69
as fungal component, 23:370
gel chromatography of. 25:42
hydrogen bonding. Raman and infrared
spectral study of, 44:29
hydrolysis by dextranglucosidases, 30:395
isolation, purity, and structure of, 30:4-5
laser-Raman spectroscopy, 44: 83
molecular structure of, 12:261-298
during Mycobacteriurn srnegrnatis growth,
30:255
phosphorylase action on, 23:352,355
reaction with concanavalin A, 35: 169-1 7 1
separation from guaran, 35:277
solubility in liquid ammonia, 27:91
solubilization by methyl sulfoxide, 27: 109
structure of, 26: 1 6 , 3 5 5
fine structure, 30:309-326
from sweet corn, structure of. 32:5
Glycogen synthetase, 26:377-38 1
Glycoglycerolipids, 44:387
Glycol, laser-Raman spectroscopy, 44:83
a-Glycol, rotamers, orientations of,
45:215-216
Glycolaldehyde
in aqueous solution, 42:30, 323-324, 327,
338
carbon monoxide elimination by radiation,
37: 14
2-cyclohexyl-2-phenyl-(R)-(-)- and (S)-(+)-,
preparation of, 27:219
D-, phosphate hydrate, carbon-I3 nuclear
magnetic resonance spectroscopy, 41:53
enzymic determination of, 30:282-283
formation, 51:280-281
in formose reaction, 29:183-184
gas-liquid chromatography of, 28:95
radiation chemistry, 37:32-33
reaction with, 1,3-dicarbonyl compounds,
45: 13
separation from glyceraldehyde as
trimethylsilyl oximes, 28:3 1
Wittig reaction with, 27:288
Glycol groups, oxidation of, in
glycofuranosides, 21: 132
238 SUBJECT INDEX
Glycolic acid
aminoalkyl and 3-piperidinyl esters,
preparation and anticholinergic potency
of, 27:209
2-(2-furyl)-, resolution of racemates, 40: 1 13
glucopyranosyl-, mass spectrometry of,
30:38
Glycolic-2-d acid, preparation and
configuration of, 27: 142
Glycolic-2-t acid, preparation and
stereochemistry of, 27: 141
Glycolipids, 44:342,387,51: 169-235,
53:397-398, see also Glycopeptidolipids;
Neoglycoconjugates, glycolipid-based
of acid-fast bacteria, 16:207-238
animal, occurrence, 39:308
structure determination, 39:309
from arthropods, 44:421422,436
biosynthesis of, 26:408,442455,39:3 10
from brachiopods, 44:42 1
in cellulose biosynthesis, 26:330
from coelenterates, 44:410411,436
distribution in marine invertebrates, 44:436
Dolichos biflorus lcctin in study of, 3 5 2 3 1
from echinoderms, 44:422434
class Asteroidea, 44:429
class Echinoidea, 44:422428
class Holothurioidea, 44:434
f.a.b.-mass spectrometry, 45: 54-5 8
from freshwater bivalves, 44:4 1 W 2 1
fucose-containing, 39:307-3 1 1
gas-liquid chromatography of bacterial,
28:47,50
giycosyl, composition, 51:172-173
glycosyl residue
anomeric and ring configurations,
51: 1 7 4 176
sequences, 51:173-174
hydrolysis with hydrochloric acid, 46:266
individual, separation, 44:395
isolation and fractionation, 51: 171-172
from marine bivalves, 44:415416
from marine worms, 44:411
methanolysis of, and gas-liquid
chromatography, 2 8 5 1
methylation analysis by mass spectrometry,
29:66
methylation-linkage analysis, 51: 173
from mollusks, 44:411421
class Bivalvia, 44:415421
class Cephalopoda, 44:421
class Gastropoda, 44:412
class Loricata, 44:412
in mycobacteria, 30:235
native, antigenicity, 51:229-23 1
neutral, from Asferoides, 44:429-430
other biological properties, 51:23 1-235
permethylated, mass spectrometry, structure
analysis, 38:394-395
pyruvic acetylated, f.a.b.-mass spectrometry,
45: 56 - 5 7
of rice bran, 44:413
from sponges, 44:409410,436
sterol-containing, in plant kingdom,
37:328-331
structural analysis, methylation techniques,
38:389416
structures, 51:175, 177-203
acyl substituent location, 51: 198-200
glycopeptidolipids, M. avium complex,
51: 179-188
historical prespective, 51:175, 177-179
phenolic, containing phenolphthiocerols,
51:200-203
trehalose-containing lipo-oligosaccharides,
51: 188-198
substrates, fucosyltransferases, 39:322-324
synthesis, 50: 151-152
trehalose-containing, 30:254
f.a.b.-mass spectrometry, 4 5 5 7
trifluoroacetates, gas-liquid chromatography
of, 28:55
from tunicates, 44:434-435
Glycols
cyclic 1,2-, periodate oxidation of, 33:93-94
on-column silylation of, 30:45
oxidation with lead tetraacetate, 33:93-96
a-Glycol units, oxygen-oxygen distance of,
45~215-216
N-Glycolylneuraminic acid, synthesis, 49:201
Glycolysis
control of, and Pasteur effects, 32: 168-1 73
in tumor cells, 33:4
Glycolysis aldolase, synthesis, 49: 190-1 94
Glycopeptide-N-glycosidase, 44:239
Glycopeptide n-heptyl esters, lipase-catalyzed
cleavage, 50:306-307
Glycopeptides, 23:406,24:3 14,50:277-307,
52: 167-168
a-o-mannosidase
 SUBJECT INDEX
action on, 28:420
as structural reagent for, 28:437445
amino acid sequences in, 27:333
p-eliminative degradation and structure of,
29:254
binding to proteins, 50:298-299
carbohydrate identification in, 25433
carrying o-glycosyl group
at C-terminal of peptide,I3C-NMR
chemical-shift data, 43:30
at N-terminal of peptide,I3C-NMR
chemical-shift data, 43:29
complex
interactions with Gd3+and Mn*-,
47: 155-158
ionic, liquid chromatography, 46:45-49
concanavalin A-reactive, from calf
thymocytes, 35325
containing 2-acetamido-N-(~-aspart-4-oyl)-2-
deoxy-b-o-glucopyranosyl-amine
residue, enlongation of peptide chain,
43~152-154
containing N-glycosyl linkages intact,
structural analysis, 43: 11-21
structural analysis, 43: I S 2 1
'
containing 0-glycosyl linkages, intact, i(:
NMR structural analysis, 43:3&45
containing unusual carbohydrate-protein
linkages, structural analysis, 43:4449
deamination and structure of, 31:77
enzymes as tools, 50:303-306
in glycoenzyme characterization, 27:3 14,
319
interaction with concanavalin A, 35: 187
with lectins, 35140
lactosamine importance, 50:73
lectin-reactive, from human erythrocytes,
35319
from tumor cells, 353277333
L-fucose-containing, 39:306
liquid chromatography separation, 46:47-
48
mass spectrometry, structure analysis,
38:394395
methanolysis of, 28:18-19
methylated, liquid chromatography
separation, 46:48
molecular weights of, 25:447452
N-acylated, liquid chromatography
separation, 46:48
239
from neuronal cells. lectins in isolation of,
35:326
0-glycosylated, structural analysis, 43:2 I -
44
pea Iectin-reactive, structure, 3 5 3 2 1
peptide composition of, 24:445
prechromatographic purification of, 46:20
preparative liquid chromatography, 46:60
sialylated, liquid chromatography separation,
46:48
solid-phase, 50:299-303, 306
synthesis, 49:221, 50:277-307
by solid-phase procedure, 43:151-153
in urine, 25:41&415
N-Glycopeptides, 50:278-287
2-acetam~do-2-deoxy-~-~-glucosyl-~-
asparagine linkage, 50:278-283
selective deprotection and peptide-chain
elongation, 50:283-287
3-O-Glycopeptides, L-serine or L-threonine,
50:287-298
3-0-glycosidic linkage formation,
50:287-294
selective deprotection methods, 50:294-298
Glycopeptidolipids, 51: 171
acyl substituent location. 51: 198-200
apolar C-mycoside, 51: 177-178
haptens, M. avium serovars, 51:2 19-220
M. avium complex, 51:179-188
hapten groupings, 51:179-181
from serovars 2 , 4 , 9 , 14,20,25, and 26,
51 :1 8 1- 184
from serovars 8 and 2 I , 51:1 85
from serovars 12 and 17, 51:184185
from other mycobacteria, 51: 186-1 88
polar antigenic, 51: 178
GIycophorin
glycopentapeptide 10, '3C'-NMRchemical
shift data, 45: I88
labeled, '3Cnuclear magnetic resonance,
45~169-198
N-terminus
di[ 13Clmethylaminogroups
"C chemical shift data. 45:189-192
titration data, 45: I89
peptides related to, pH-titration studies,
45192-194
stmctu re
effect of carbohydrate residues, 45: 197
effect of hydrogen bond, 45: 192
240 SUBJECT INDEX
Glycophorin (continued)
effect of neighboring glycosylation,
45: 191-1 92
role of lysine residues in determining,
45: 194
properties, 45: 170
reductively ['3C]methylated, pH titration
studies, 4 5 1 87-192
Glycophorin A, 45: 170
amino acid residues, 45: 172
amino acid sequence data, 45: 172-173
carbohydrate structure, 45: 172-1 73
I3C labels
chemical cleavage of glycoprotein for
assigning, 45: 178
enzymic digestion for assigning, 45: 178
on lysine and N-terminal amino acid,
distinction between, 45: 177-1 78
methods used for assignment, 45: 177-
178
partial-methylation assignment technique,
45: 178
pH-titration, 45: 178
deglycosylation, structural effects,
45184-186
dimethylated N-terminal species,
differentiation by pH studies,
45:182-183
display of MN blood group determinants,
45: 175
hlly reductively ['3C]methylated, I3C-NMR
spectra, 45: 186-187
functions, 45:170-171
inhibition of protein glycosylation, 40:339
intact, from heterozygous and homozygous
RBC, 45~178-186
labeling, reductive [13C]methylation
technique, 45: 175-195
drawbacks, 45: I77
method, 45175-177
NaCNBH, as reducing agent, 45: 176-
177
reaction scheme, 45: 176-177
side-reactions, 45: 176177
specificity, 45: 177
molecular weight, 45: 172
native and reductively methylated, aliphatic
region of proton-decoupled I3C-NMR
spectra, 45: 179-182
N-terminal proteins, I3C-NMR spectra in
various degress of glycosylation,
45:184-186
partial methylation studies, 45: 182-184
pH titration studies, 45: 182
as red cell receptor, 45: 170
structural analysis, 43:34-37
virgin and reductively methylated, circular
dichroism studies, 45: 178-1 79
Glycophorin A"
hydrogen bonding in, 45: 195
N-terminal structure, 45:194
reductively methylated, minor component,
45:181-182, 186, 197-198
Glycophorin AN,see Glycophorin A
Glycophorin B, 45: 170
amino acid residues, 45: 172-1 73
function, 45: 171
labeling studies of, 45: 195-197
relationship to results obtained for
glycophorin A, 45: 195-196
pH titration studies, 45: 196-197
relationship to results for glycophorin AN
and glyco-octapeptide AN,
45: 1 9 6 1 9 7
Glycophorin C, 45: I70
carbohydrate content, 45: 172
properties, 45: 172
Glycophorin glycopeptide, 45: 182
isolation, 45: 186
N-terminal di[13C]methylaminogroups I3C
chemical shift data, 45:189-192
titration data, 45: 189
pH dependence, 45: 187
production, 45: 186
reductively [I3C]methylated, pH titration
studies, 45: 187-192
Glycophorin-related glylcopeptides,
m~no[~~C]methylated, pH-titration
studies, 45: 192-194
Glycopranosyl oxocarbenium ion, 48:327
Glycoproteinosis, 37: 163
Glycoproteins, 43: 135-136,44:342-343,
52:167-168, see olso Glycans; Lectins
acetolysis and f.a.h.-mass spectrometry, as
screening method, 4550-5 1
a-o-mannosidase
action on, 28:420
as structural reagent for, 28:437445
in catabolism of, 28:436
amino acids of, 33:7
 SUBJECT INDEX
antifreeze, 40:35 1
antigenicity, effect of sugar side-chains.
40~352,355-356
basal-membrane, 43: 136
p-elimination
and degradation of, 31:213
reaction of, 25:427
biological and structural significance of,
27:337-34 1
biosynthesis, 25:467-472, 27:303, 328-337,
39:320-321
lipid-linked sugars as intermediates,
44:367-373
mechanism of, 26:456
carbohydrate-peptide linkages in,
25:467472
carbohydrates
components of, 25:409414,469,477.
27:325
compositional analysis of, 46:56
cell-surface lectin-reactive, 35:205,3 17-
333
chemical and functional aspects, 37:3
I3'-NMR studies, 43: 1 4 9
complex, storage products derived from,
f.a.b.-mass spectrometry of, 45:62
compound I , from aspartylglucosaminuria,
'H-NMR spectroscopy. 41:2 19-224
compound 2, from fucosidosis, 'H-NMR
spectroscopy, 41:2 19-224
compound 3, from aspartylglucosaminuria
and Gaucher's disease, IH-NMR
spectroscopy, 41:219,225-226
compound 4, from fucosidosis, 'H-NMR
spectroscopy, 41:219,226-228
compound 5, from mannosidosis, 'H-NMR
spectroscopy, 41:219, 227-230
compound 6, from Sandhoff s disease, 'H-
NMR spectroscopy, 41:219,23 1-234
compound 7, from GM,-gangliosidosis, and
Morquio syndrome type B, 'H-NMR
spectroscopy, 41:219,232-233,
235-237
compound 8 , from asialo a,-acid
glycoprotein, 'H-NMR spectroscopy,
41:219,237-240
compound 9, from asialo a,-acid
glycoprotein 'H-NMR spectroscopy,
41:219,239-242
compound 10, from asiolo GM,-
24 I
gangliosidosis 'H-NMR spectroscopy,
41~219.232-233.242-244
compound I 1 , from GM,-gangliosidosis and
Morquio syndrome type B. 'H-NMR
spectroscopy. 41:219,232-233,
244246
compound 12, from GM,-gangliosidosis. 'H-
NMR spectroscopy, 41:219,233,
246-248
compound 13. from asiolo a,-acid
glycoprotein , 'H-NMR spectroscopy,
41:219,239,248-251
compound 14, from Sandhoffs disease, 'H-
NMR spectroscopy, 41 :2 19.254-257
compound 15, from Morquio syndrome type
B, 'H-NMR spectroscopy, 41:219,
256-259
compound 16, from chicken ovotransferrin,
'H-NMR spectroscopy, 41:219,
259-261
compound 17, from and. 18 from GM,-
gangliosidosis,'H-NMR spectroscopy,
41:219.261-264
compound 18. from GM,-gangliosidosis, and
Morquio syndrome type B,'H-NMR
spectroscopy, 41:2 19, 262-266
compound 19, from Morquio syndrome type
B, 'H-NMR spectroscopy. 41:219. 263,
26&268
compound 20, from Morquio syndrome type
B, 'H-NMR spectroscopy, 41:219,263,
267-268
compound 2 I . from sialidosis, 'H-NMR
spectroscopy, 41 :269-274
compound 22, from sialidosis, 'H-NMR
spectroscopy, 'H-NMR spectroscopy,
41:270-272,274-275
compound 23, and 24, from sialidosis and
new-born human meconium, 'H-NMR
spectroscopy, 41:27&272,275-276
compound 25, and 26, from sialidosis and
new-born human meconium, 'H-NMR
spectroscopy, 41:270. 273.275.
277-278
compound 27, and 28, from sialidosis and
new-born human meconium' H-NMR
spectroscopy, 41:270, 273.279,282
compound 29, form sialidosis and new-born
human meconium, 'H-NMR
spectroscopy. 41:270, 273, 279. 282
242 SUBJECT INDEX
Glycoproteins (continued)
compound 30, from sialidosis, 'H-NMR
spectroscopy, 41:270,273,279,281,
283
compound 3 1, and 32, from rabbit
serotransferrin, 'H-NMR spectroscopy,
41~270,283-287
compound 33, from human serotransferrin.
'H-NMR spectroscopy, 41:270,
283-288
compound 34, 'H-NMR spectroscopy,
41:270,284-289
compound 35, 'H-NMR spectroscopy,
41:270,289-293
compound 36, and 37, from sialidosis, 'H-
NMR spectroscopy, 41:270,297-298
compound 38, from sialidosis, 'H-NMR
spectroscopy, 41:270,297-298
compound 39, from sialidosis, 'H-NMR
spectroscopy, 41:270,298-300
compound 40, from sialidosis, 'H-NMR
spectroscopy, 41:270,298,300-302
compound 41, from sialidosis, 'H-NMR
spectroscopy, 41:270,300,302-305
compound 42, from human lactotransfemn,
'H-NMR spectroscopy, 41 :306-308,
3 l C 3 1 1,324-326
compound 43, from human lactotransferrin,
'H-NMR spectroscopy, 41:306-311,
324-326
compound 44, and 45, from horse-pancreatic
ribonuclease, 'H-NMR spectroscopy,
41:306-307,309-312,316
compound 46, from fucosidosis, 'H-NMR
spectroscopy, 41:306,313-3 18
compound 47, from fucosidosis, 'H-NMR
spectroscopy, 41:306,313-3 18
compound 48, from asialo a,-acid
glycoprotein and asialo ceruloplasmin,
'H-NMR spectroscopy, 41:306,
314-315,319-321
compound 49,50, and 5 1, from asialo a,-acid
glycoprotein, 'H-NMR spectroscopy,
41:306,314-315,321-324
compound 52, from human lactotransferrin
and human milk, IH-NMR
spectroscopy, 41:306,324-328
compound 53, from human-plasma
ceruloplasmin, 'H-NMR spectroscopy,
41:306,327-330
compound 54, from fucosidosis, 'H-NMR
spectroscopy, 41:306,330-332
compound 5 5 , from aspartylglucosaminuria,
IH-NMR spectroscopy, 41:33 3-337
compound 56, from aspartylglucosaminuria,
'H-NMR spectroscopy, 41:333,
336-338
compound 57, from aspartylglucosaminuria,
'H-NMR spectroscopy, 41:333,335,
337-338
compound 58, from aspartylglucosaminuria,
'H-NMR spectroscopy, 41:333,
337-339
compound 59, from aspartylglucosaminuria,
'H-NMR spectroscopy, 41:333, 337,
340-342
compound 60, from aspartylglucosaminuria,
'H-NMR spectroscopy, 41:333,337,
340-343
compound 61, from Gaucher's disease, 'H-
NMR spectroscopy, 41:344-347
compound 62, from Gaucher's disease, 'H-
NMR spectroscopy, 41:344,346-348
compound 63, from hen-egg albumin, 'H-
NMR spectroscopy, 41:344,346,
348-350,357,359-361
compound 64, from mannosidosis, IH-NMR
spectroscopy, 41:344, 350-35 1
compound 65, from mannosidosis, 'H-NMR
spectroscopy, 41:344,351-352
compound 66, from mannosidosis, 'H-NMR
spectroscopy, 41:344,351,353-355
compound 67, from mannosidosis, IH-NMR
spectroscopy, 41:344,351,355-357
compound 68,69, and 70, from
Waldenstrom's macroglobulinemia,lH-
NMR spectroscopy, 41:344,357-363
compound 7 I , and 72, from bovine
lactotransfemn 'H-NMR spectroscopy,
41~344,360-361,363-366
compound 72, from soybean agglutinin, 'H-
NMR spectroscopy, 41:363-365
containing unusual carbohydrate-protein
linkages, structural analysis, 43:4449
crystallographic structures, effect of sugar
side-chains, 40:354
deamination of, 31:236
deglycosylation, 47:200
desialylated, elimination, 40:220-223
diseases related to changes in, 25:472477
 SUBJECT INDEX
distribution and mobility, 35: 129
Dolichos biflorus lectin in study of, 35:23 I
enzymes with structure of, 27:301-34 I
f.a.b.-mass spectrometry, 45:58-65
formation in cell walls, 26:340
function of sugar side-chains, 40:350-353
of fungal origin, 23:367
gas-liquid chromatography of, 28:4344,48,
63
glycosylation site(s), 46:4748
heterogeneity in, 25:443447,477
history, 33:34
in host-pathogen interactions, 44:380
hydrazinolysis. 43:6-7
hydrolysis of, 28: 16-1 7, 86
with hydrochloric acid, 46:267
with ion-exchange resin in acid form,
46:268-269
hydroxyl-L-proline-rich, in plant cell-walls,
42298-300
interaction with concanavalin A, 35: 177- I79
with lectins, 35:140-141
lentil, 35: 194
isolation, 53:2 10-2 I 1
lectin-reactive, of erythrocyte membrane.
35~318-325
from tumor cells, 35328-333
lentil lectin-reactive, from pig lymphocyte,
35325
L-fucose-containing, 39:301, 304-307
L-fucose enzymic transfer, 39:3 18-322
lipid intermediates in biosynthesis of, 26:430
LTF-D, from lactotransferrin, antennae,
circular dichroism, 45: 120
metabolism and structure of, 25:407478
methanolysis, 28:19,46:257
for analysis of carbohydrates in, 46:258
trimethylsilylation, and gas-liquid
chromatography of, 2 8 5 2
molecular biology, 37: 157-223
future, 37:200-212
past and birth, 37: 158- 164
present, 37: 1 6 6 199
molecular weights of polypeptides from,
25447452
with multiple 0-glycosylation sites, 50:344
N-acetyllactosamine-type carbohydrate
chains, high-resolution proton magnetic
resonance spoectroscopy, 41:2 18-343
N-and 0-linked chains, peripheral
243
substitutions, 50:239-332, 325
NaOH- NaBH, treatment. 43:6-7
nature and occurrence of, 25:4074 I7
from neuronal cells, lectins in isolation.
35:326
N-glycosylated, complex oligosaccharide
structure, 43:17
containing N-glycosyl linkages
intact, structural analysis, 43: 11-21
structural analysis, 43: 10-2 I
occurrence and functions. 37:225-226
0-glycosylated, structural analysis. 43:2 I-
44
containing 0-glycosyl linkages, intact, ' 3 c -
NMR structural analysis, 43:3445
oligomannoside-type carbohydrate chains,
high-resolution proton magnetic
resonance spectroscopy, 41 :343-365
oligosaccharides
I3C-NMR spectroscopy, 42:219-220,
43~8-10
determinants. 50:3 1-345
backbones and core regions, N- and 0-
linked chains, secreted and plasma
membrane glycoprotein. 50:3 15-325,
3 16-322
conformations and molecular
recognition
determinants adjacent to protein moiety,
50~343-345
determinants distant from core,
50:332-342,333- 337,337-342
purification and profiling, 50:314-315
structural analysis methods, 50:3 1 1 -
314
OTF-C, from ovotranferrin, antennae,
circular dichroism, 45: 120
physicochemical properties, effect of sugar
side-chains, 40:355
pig submaxillary-gland, 25433,458
pituitary, D-XY~OSCin, gas-liquid
chromatography of, 28:67-68
in plants, 26:299,346-347, 42337-338
biosynthesis, involvement of lipid
intermediates in, 44:372
linkage between peptide and saccharide
moieties, 44:372
from platelet membrane, 35:325
proteolysis, 43:6-7
glycosylation effect, 403356-359
244 SUBJECT INDEX
Glycoproteins (continued)
proton nuclear magnetic resonance
spectroscopy of Carbohydrate chains in
structural analysis, 41:210-374
removal of oligosaccharide chain, 43:6-7
routing, secretion, recognition, and uptake,
glycosylation effects, 40:359-364
separation of partially sialated, 35:277
sheep suhmaxillary-gland, 25446
stability of, 27:340
STF-A, from serum transferrin, antennae,
circular dichroism, 45: 120
structural analysis, methylation techniques,
38:389416
structure, 26:455,33:8
of carbohydrate moieties of, 25:452467
liquid chromatography analysis, 46:4647
sugar side-chains, effect on conformation,
40~353-354
sulfated oligosaccharide chains, 'H-NMR-
spectral and mass spectrometric
analysis, 50:330-33 1
sulfate incorporation into, 25:470472
synthetic, see Neoglycoproteins
in urine, 24:436,440,33:6
Y and T antennae, circular dichroism studies,
45:118-120
0-Glycoproteins, 43:136
Glycopyranose
3-acetamido- 1,2,4,6-tetra-O-acetyl-3-deoxy-
p-D-, acetoxonium rearrangement of,
26:161
OI-D-, conformation of, 26:77-78
OL-L-, conformation of, 26:77-78
2-amin0-2-deoxy-cw-o~-carba-,48:63
1,6-anhydro-p-~-,conformation of,
26: 1 1 6-1 17
p-D-
conformational inversion in, 26:67
conformation of, 26:75-76
1,2:4,6-di-O-henzylidene-~~-~-,
conformations of, 26: 120
1,2-0-( 1-aminoethyhdene)-a+-,
conformation of, 26: 1I8
penta-0-acetyl-
a-D-,acetoxonium rearrangements of,
26:146, 149
p-0-
acetoxonium rearrangements of, 26: 146,
149
rearrangement in hydrogen fluoride,
26: 182
D-, rearrangement in aluminum chloride-
phosphorus pentachloride, 26: 194
penta-0-benzoyl-p-D-, benzoxonium
rearrangements of, 26: 15 1
tetra-0-acetyl-
6-deoxy-6-iodo-o, acetoxonium salts,
26:157-158
3-O-methyl-o-, rearrangement in hydrogen
fluoride, 26: 184-185
6-O-methyl-~-,acetoxonium salts,
26: 157-158
6-O-p-tolylsulfonyl-~-,acetoxonium salts,
26: 157-1 58
1,3,4,6-tetra-O-acetyl-2-O-methyl-a-o-,
rearrangement in hydrogen fluoride,
26: 184
1.3,4,6-tetra-O-henzoyl-2-O-methyl-~-~-,
rearrangement in hydrogen fluoride,
26: 183
tetra-O-henzoyI-3-O-methyl-o-,
rearrangement in hydrogen fluoride,
26: 185
3,4,6-tri-0-acetyl-1,2-O-isopropylidene-cr-
D-, conformation of, 26: I 19
Glycopyranose peracetates, proton nuclear
magnetic resonance spectra, 29:26
Glycopyranoses, selective esterification of,
33:25
Glycopyranosides
alkyl, conformational effect of aglycon on,
26:95
1.2-cis- and 1,2-trans-, mechanism of
preparation by Koenigs-Knorr reaction,
34~272-277
ethylboronates, preparation, 35:41
hydrolysis of, 21:130-131, 137, 25:437
rate constants and kinetic parameters for,
22:66-67
indolyl, acid-catalyzed decomposition in
deuterium oxide and in water, 24:29
kinetics of formation of, 21:106, 108
methyl CX-D-, hydrolysis rate of substituted,
22:208
methyl 4,6-O-henzyhdene-o-, p-
toluenesulfonylation of, 33: 14
selective esterification of, 33:25
synthesis
of 1,2-cis-, 34:25&272
 SUBJECT INDEX
of 1,2-trans-, 34:246-256
and history of, 34:245-246
Glycopyranosiduronic acids, D-, acid-catalyzed
hydrolysis, 36:83-86
proton magnetic resonance spectroscopy,
36:86-88
GIycopyranosy lamine
2-acetaido-N-(~-aspart-4-oyl)-2-deoxy-p-o-, tritium labelling of, 29:350
linkage, 43:13&156
2-acetamido-N-(~-aspart-4-oyl)-2-deoxy-P-
D-, synthesis, 43:138-139
Glycopyranosyl derivatives, tetra-0-
acetyl(benzoy1)-o-, carbon- 13 nuclear
magnetic resonance spectroscopy, 41:SO
Glycopyranosyl fluorides, cyclization of, 34:3 1
Glycosamin, deamination of, 25: 18 I
Glycosamines, 1-hydroxy-o-, reactions with
ammonium hydrogencarbonate,
50:282-283
Glycosaminoglycans, 46:7
alkaline cleavage, 43:85
p-eliminative degradation of, 29:239. 244
biosynthesis of, 26:432439
circular dichroism, 45: 1 17-1 18
composition, 49:241
analysis, 4 6 5 5
crystalline, Fourier-transfomi infrared
spectroscopy, 44:6 1
detection of, 29:401
formation in cell wall by Golgi bodies,
26:340
gas-liquid chromatography of, 28:48-49, 54,
75,79
hydrolysis of, 28: 14
isolation of carbohydrates from, on
analytical-scale columns, 46:60
laser-Raman spectroscopy, 44:82
nomenclature, 43:56
optical rotation, 43:66
periodate oxidation, 43:95
in plants, biosynthesis, 44:373-375
proton magnetic resonance spectroscopy of,
27:41
repeating disaccharide units, 43:53-55
separation, 43:60-6 I
structure, 43:52-53,49:241-242
crystal bibliography, 33:399403,
35~381-385,36:327-329,
40:392-395
disaccharide units, 49:240-241
245
enzymic analysis, 44: 198-2 I7
sulfated, as activators of enzymes in
trehalose biosynthesis, 30:243
gas-liquid chromatography of, 30:36
synthesis, 49:256
synthetic, sulfated. 43: 108
titration, 43:62
vibrational spectra, isotopic substitution
studies, 4 4 5 5
Glycosaminoglycuronans
oliogosaccharides, liquid chromatography
separation, 46:48
reactions with carbodiimides, 29:348
sulfated oligosaccharides, chromatographic
separation of. 46:49
Glycose-based terms, 52: 177
Glycosenes, 45:4
Glycoseptanosides, synthesis of, 34:283
Glycoses, UDP-, biosynthesis of, 42:3 16
Glycosidases, 39:304, 324,42:383,
44:147-148,231-233,46:270
action on oligosaccharide, I3"-NMR
spectroscopic analysis, 43:48
activity of, 28:402
in cell walls, 42:337
classification of, 42:384
from different sources, 44: 149
effect on-a-ri-mannosidase activity, 28:409,
438
glycoside hydrolysis exogenously,
39:353-378
glycosphingolipid catabolism, 40:268
Helferich's work on, 45:4-5
history, 33:4
isolation and purification, 40:269-270
lectins and, 42:309, 337
pyranosyl transfer with, 49:232-233
specificities. 40:285
transfer reactions catalyzed by, 49:23 1-233
uses of, 25:462467
yeast, 39:350
Glycosidation
of I .6-anhydrohexopyranoses, 34:64
benzylated 0-galactosyl
trichloroacetimidates, 50:53-55
halide-ion catalyzed, 34:266
mechanism of, 34:272-277
methods, oligosaccharide synthesis,
52: 179-1 82
246 SUBJECT INDEX
Glycosidation (continued)
of sugars in methanol, 27:97
Glycoside-cuprammonium complexes,
6: 107-1 34
Glycosides, 52:51, 132-135
acetals, hydrolysis of, 34204
acetolysis of, and deacetylation of, 22: 19
from acetylated glucosyl
trichloroacetimidates, 50:41,4344
alditol, sweetness-structure relationship,
45:275-276
of aldohexose-containing oligosaccharides,
I3C-NMR data for, 42:211-212
alkali-sensitive, 9:59-95, 39:6
allyl, as affinity chromatography adsorbents,
39:420,427429
aminoalkyl, as affinity chromatography
absorbents, 39:420,423424,43 1
of amino sugars, trifluoroacetyl derivatives,
gas-liquid chromatography of, 28: 114
aryl, photolysis, 38:142, 147
aryl, times to half value for hydrolysis of,
22:83
associations of abilities of yeasts of utilize,
32:222-226
benzoylated, mass spectra of, 29:47
benzoylation of, 23:249
biosynthesis of, 26:439442
bitterness, 45:3 18
bond cleavage, 48: 128,326
boronates, acetates and benzoates, 35:53
preparation, 35:4548
properties, 35:72-76
C-alkylidene, branched-chain sugar synthesis
by addition to, 42:91-95
cardiac, 1:147-173
o-fucopyranosides, 39:302
perchloric acid in hydrolysis of, 28: 16
the sugars of, 17:65-120
catabolism of, 32: 183-209
chlorodeoxy, formation during sulfonylation,
28:255
1,2-cis-, of 2-amino-2-deoxy sugars,
preparation of, 34968
cleavage with bases, 34:2&3 I
complex, qualitative motional description,
51:97-102
crystal structures of, 25:90
deoxy, hydrolysis of, 22:54-55, 60
enzymic in vitro syntheses, 30:6
ethyl, sweetness-structure relationship,
45:275
fermentation, 50: 10-1 1
flavonoid, hydrolysis of, 28: 15
formation, 53:124, 126-129
from dithioacetals, 32:66-70
hydrolases, 48:3 19-384
active-site-directed inactivation, 48:370
anomeric specificity, 48:329-330
catalytic efficiency, 48:323-325
inhibition
access of solvent water to active site,
48:38&38 1
carhoxylate and proton-donating groups
at active site, 48:378-379
generalizations and exceptions,
48:383-384
ionic strength effects, 48:380
sequence homologies around, 48:38 1
slow, tight-binding inhibitors and
transition state, 48:382-383
substrate distortion and catalysis,
48:382
irreversible inhibitors, 48:362-364
conduritol epoxides, 48:364-371
electrophiles with reactive halogen
substituents, 48:375-377
glycosyl isothiocyanates, 48:377-378
glycosylmethyltriazenes,48:373-375
sugar-related aziridines, 48:37 1-373
mechanistic information from X-ray
crystallography, 48:325-326
reversible inhibitors
aldonolactones and 5-amino-5-deoxy-
lactams, 48:327-333
aminocyclitols, 48:347-348
cyclic sugar analogs having imino
group, 48:335-341
2-deoxy- and 2-deoxy-2-fluoro-
glycosides, 48:359-362
o-glycals, 48:349-359
glycosylamines, 48:333-335
glycosyl fluorides, 48:357-359
indolizine alkaloids, 48:34 1-344
polyhydroxypyrrolidines,48:344-
347
pseudosubstrates, 48:348-349
slow onset, 48:340
hydrolysis of
acid-catalyzed, 22:25-108
 SUBJECT INDEX
effect of aglycon on, 22:7 I
of ring size on, 22:42
effect of halogeno groups on, 28:305
Koenigs-Knorr synthesis of, 21:275
large-scale preparative liquid
chromatography, 46:62
linkages, 46:250
acetolysis, 46:252, 269-270
with activating group at @-position.
cleavage, 46:255
cleavage, 46:250-25 1
hydrogen fluoride, 47:168
liberation of Wand 0-linked
carbohydrate chains, 46:255-256
enzymic hydrolysis, 46:270-27 1
formolysis, 46:252,269-270
free energy of hydrolysis, 37:287
hydrolysis
correction factors, 46:254
internal standard, 46:254
liberation of neutral monosaccharides
during, 46:252-25 3
recoveries from, 46:255
lability, 47: 178, 180, I89
sugar residues, 47:194-195
methanolysis, 46:252, 259
deamination prior to, 46:256
recoveries from, 46:255
reductive cleavage, 46:27 1
synthesis, 46:250
total hydrolysis with acid, 46:259-269
liquid chromatography, pre-column
derivatization procedures, 46:68
low basicity, 48:32 1-322
from mannosyl trichloroacetimidates, 5 0 5 8 ,
62-65
mercaptalation of, 32:28
mercuric cyanide in synthesis of, 21:278
methyl
acetates, gas-liquid chromatography of,
28:54, 118,30:82
gas-liquid chromatography of,
285-56,30:5&71
methylated (fully), gas-liquid
chromatography of, 28: 118
separation by gas-liquid
chromatography, 30:22-24
trifluoroacetates, gas-liquid
chromatography of, 28:55, I 12
trimethylsilyl ethers, gas-liquid
247
chromatography of, 28:43.5 1-54,
115-1 18,30:25-26,SO-81
acid-catalyzed anomerization of, 24:43
ofcommon sugars, 12:157-187
gel chromatography of, 2 5 3 2
mass spectrometry and analysis of,
29~50-51
of oligosaccharides containing galactose
and glucose, ' T - N M R data for,
42:212-213
of reducing sugars, composition in
methanol, 42:61
selective esterification of. 33:37
sweetness-structure relationship, 45:274
times to half values for hydrolysis of,
22:61
of xylose oligomers, "C-NMR data for,
42~213-216
methyl anhydro-, carbon-13 nuclear
magnetic resonance spectroscopy, 41:57
methyl ethers, taste properties, 45262
methyl ketoses, carbon- 13 nuclear magnetic
resonance spectroscopy, 41:48
3-methyl-I -naphthyl, in mass spectrometry
of disaccharides, 30:40
methyl 2(or 3)-amino-4,6-0-benzylidene-
2(or 3)-deoxy-a-o-, proton magnetic
resonance spectra, iterative analyses of,
27:78
Meystre-Miescher modification in synthesis
of, 21:277
molecular weight determination, 21:274
in neoglycoprotein preparation, 37:252
nitro
acylation of, 24: 1 I5
synthesis, 40: 106
nitrophenyl, carbon- 13 nuclear magnetic
resonance spectra, 41:48
non-enzymic hydrolysis, 48:320-323
0-,synthesis, 50:296-297
oxidation of 4,6-0-benzylidene, by N-
bromosuccinimide, 22: 198
oxidation to uronic acids, 36:69
oximino, 24:208
oxygen catalysis, protonation by hydrated
magnesium ions, 52:461462
p-aminophenyl, as aftinity chromatography
adsorbents, 39:419421,431
enzymic synthesis, 39:429430
synthesis, 39:421423
248 SUBJECT INDEX
Glycosides (continued)
of the parsley plant, 4:57-74
peracetylated, mass spectrometry of, 29:46
permethylated methyl, mass spectra of, 29:43
permethylated oligosaccharide, mass
spectrometry of, 29:84-89
phenolic, trimethylsilyl derivatives, gas-
liquid chromatography of, 28:54, 118
phenyl
carbon- 13 nuclear magnetic resonance
spectra, 41:48-49
of the common sugars, 12: 157-187
1-seleno-p-o-, alkaline cleavage of, 34:28
photosensitive protecting groups,
46~182-187
plant, trimethylsilyl derivatives, gasliquid
chromatography of, 28: 118
as plant-growth substances, 21:408,413
preparation of, 3 3 5 5
preparative liquid chromatography, 46:60
radiolysis and radical-induced scission,
37:15,51-53
rate of formation of, 21:108
reaction with lectins, 35140
with phenylboronic acid, 3 5 3 2
related to blood-group determinants, I3C-
NMR data for, 42:2 17-2 19
of Salmonella oligosaccharides, I3C-NMR
data for, 42:222-223
steroid, gas-liquid chromatography of, 28:53
sweet
bonding to taste-bud receptor sites, 455279
structural features, 45289
sweetness-structure relationship, 4 5 2 7 4 2 7 6
synthesis of,21:21,491,25:164,34:243-244
with D-ribohranosyl group, 31:4
synthetic, as plant-growth substances,
21:413,415
taste, effect of aglycons on, 45245
thio, synthesis, 4O:lOl-104
l-thio-
as affinity chromatography adsorbents,
39:420421
p-, laser-Raman spectroscopy, 44:8 1
preparation, 36: 101
thio-
carbon-13 nuclear magnetic resonance
spectroscopy, 41:65
trimethylsilyl derivatives, gas-liquid
chromatography of, 28: 1 18
transport into yeasts, 32: 157-159
trimethylsilylated, mass spectra of, 29:47-50
2,3-unsaturated, 24:2 13
utilization by yeasts, 32:224, 233
entry into cell, 39:379-381
hydrolyzed inside plasmalemma,
39:378-397
hydrolyzed outside plasmalemma,
39~353-378
oxygen requirement, 39:397401
structure and hydrolysis, 39:349-353
vicinal proton-carbon coupling constants,
51:49
I ,2-hans-Glycosides, synthesis, 48: 108
3-0-Glycosidic linkage formation, 50:287-294
1-0-acetyl activation, 50:292-293
electrophile-induced lactonization of
glycosyl4-pentenoates, 50:293-294
glycosyl fluorides, 50:290
Koenigs-Knorr methods, 50:287-289
1-thioglycosides, 50:290-292
trichloroacetimidate method, 50:289-290
Glycosiduloses, nucleophilic addition to, for
branched-sugar synthesis, 42:78-9 1
Glycosid-3-uloses, preparation, 35:46
Glycosiduronase, from Flavobacterzum
heparinurn. 43: 72-73
Glycosiduronic acids, 36:66-96
of animals, 9: 185-246
circular dichroism spectra, 36:88-90
hydrolysis of, in xylans, 36:238-239
ofhr-hydroxy compounds, 36:131-132
optical rotatory dispersion, 36%
poly, of plants, 1:329-344
preparation by Fischer method, 36:74
by Helferich method, 36:74
by Koenigs-Knorr and other methods,
36~75-79
oxidative methods, 36:67-74
reactions, 36:82
and related compounds, 36:57-134
steroid derivatives, preparation, 36:77-78
sugar intermediates in synthesis, 36:59-66
1-thio-, isolation from biological materials,
36:102-103
preparation, 36:96-103
Glycosones, 3-deoxy-, see Glycosuloses, 3-
deoxy-
Glycosphingolipids, 24:381433,40:235-286,
44:387
 SUBJECT INDEX
abbreviations, 40:241-244
(2-aminoethyl)phosphonic group,
44~397-398
(2-aminoethy1)pliosphoricacid group bound
to mannose, 44:398
biosynthesis of, 24:394,26:442445,
39:3 I8,40:244-268
enzyme preparation and enzyme assay,
40:245-247
of globo and isoglobo series, 40:249-25 1
of lacto and neolacto series, 40:250,
252-253
in pathological conditions, 40:265-266
in virus-transformed cells, 40:266
in vitro, 403266-268
in blood group ABH, I, I, Lewis
characterization, 45:55
blood group B-active
digestion with a-o-galactosidase followed
by Smith degradation, 45:48
structure determination of permethylated
derivative, by f.a.b.-mass
spectrometry, 45:48
carbohydrate chain structure
chemical analysis, 44:399402
determination, 44:399409
enzymic analysis, 44:408409
mass spectrometry, 44:402406
NMR spectroscopy, 44:406408
physicochemical analysis, 44:402408
catabolism, 40:268-286
with P-linked galactose, 402744276
enzyme preparation and enzyme assay,
40:269-271
with a-linked galactose, 40:279-280
protein activators of enzymic hydrolysis,
40:281-285
classification, 40:238-244
composition of, 44:396-398
distribution, in marine invertebrates, 44:436
enzymic hydrolysis, protein activators,
40:281-286
f.a.b.-mass spectrometry, 4527-28, 54-56
molecular ion species, 45:42
fatty acids, 44:396-397
composition determination, 44:399
from freshwater bivalves, 44:4164 I7
fucose-containing, 44:42 1
mannose-containing, 44:420,438
in humans
249
chronic myelogenous leukemia cells,
characterization, 45:55
embryonal-carcinoma cells,
characterization, 45: 55
granulocytes, characterization, 4 5 5 5
identification, 40:267-268
isolation, 44:392-394
mammalian, 44:387-388
mannose-containing, from insect,
characterization, 45:56
from marine bivalves, 44:415416
marine invertebrate, 44:387
[2-(methylaniino)ethyl)]phosphonic group,
44:397-398
monosaccharides, 44:397
N-acetylgalactosamine-containing,
structures, 50:84, 92
nomenclature, 24:383,40:237-238.24 1-244
occurrence, among marine invertebrates,
44:39 1-392
permethylated
f.a.b.-mass spectrometry, 45:37, 54
mass spectrometry, 44:404
NMR spectroscopy, 44:406
of sea snail, 44:412
separation, 44:394395
sphingosine bases, 44:396, 398-399
structure, 40:236-244
determination. 44:398409
2 5 -sugar residue
f.a.b.-mass spectrometry, 45:54
isolated from rabbit erythrocyte membrane
sequence of, 45:48
after enzymic degradation with a - ~ -
galactosidase, 45:49
Smith-degradation product, predicted
sequence, 45:49
sulfate-containing, 24:403
synthesis, lactosamine importance, 50:73
trimethylsilylation of, 28:28
verbrate, composition of, 44:389-390
Glycosuloses
anhydro-I ,3-dideoxy-, synthesis by Wittig
reaction and properties, 27:284-288
3-deoxy-, 22:239,279
and the degradation of carbohydrates,
19: 18 1-21 8
intermediates in 2-furaldehyde formation
in sugar dehydrations, 28: 177-178
6-deoxy-, synthesis of, 29:294
250 SUBJECT INDEX
Glycosuloses (continued)
derivatives, radical-mediated brominations,
49:54-57
reactions in which carbonyl groups are
converted into asymmetric centers,
27: 193,204
reaction with ammonia, 25345
Glycosyl
glycolipid composition, 51: 172-1 73
residues
anomeric and ring configurations,
51: 174176
sequences, 51: 173-174
units, conjugation to protein, 51:204206
Glycosylamines, 10:95-168,23:209,211
carba-
enantiomeric, synthesis, 48:6&65
inhibitory activity, 48:88-89
synthesis, 48:52-59
condensation of acid chloride with, 43:
146
coupling with aspartic acid
carbodiimide reagent, 43: 136-144
2-ethoxy-N-(ethoxycarbonyl)-1,2-
dihydroquinoline reagent,
43:144146
miscellaneous methods, 43: 149- 151
mixed anhydrides and anhydrides,
43: 147- 149
Woodward Reagent K, 43: 149
formation in reaction of sugars and ammonia,
25:333
glycosidase inhibition, 48:333-335
hydrolysis of, 22:37,60
mutarotation of, 24:47
N-acyl-
as affinity chromatography adsorbents,
39:420,426
structure determination of, 31:102
N-[~-aspart4(0r1)-oyll-
mono- and-di-0-glycosyl-, properties,
43:187-189
properties, 43:182-186
nomenclature, 52: 137-139
N-phenyl-, mass spectrometry of, 30:43
as plant-growth substances, 21:413
polarography of, 29:153
synthesis of, 25: 166
(Glycosy1amine)uronic acids, 36: 120-13 1
Glycosyl6-aminohexyl diphospbates, as
affinity chromatography adsorbents,
39:424426
Glycosylation
acetylated 0-galactosyl
trichloroacetimidates, 50:53, 56-57
acety lated 0-mannopyranosyl
trichloroacetimidates, 50:58, 66-67
aldonolactones, 50: 179-181
of 1,6-anhydrobexopyranoses,34: 159-161
azidosphingosine derivatives, with
trichloroacetimidates, 50:4 I , 4 5 4 8
carbon, by condensations with carbanions,
33: 145-1 53
with organometallic and related agents,
33:142-145
ceramides, by trichloroacetimidates,
50:49-5 1
chitobiose derivatives, 50:81,89
by 0-Gal groups, 47:157
effect on structure of protein, 43:3 1-34
0-fucopyranosyl trichloroacetimidates,
inverse procedure, 50:98, 104-107
galactosamine trichloroacetimidates,
50:98-102
0-galactosyl trichloroacetimidates, with
sphingosine derivatives, 50:58-59
0-glucosyl trichloroacetimidates, 50:3940
glycopeptide synthesis, 50:303-306
glycosyl esters of nucleoside pyrophosphates
in, 28:391-397
glycosyl fluorides, 48: 103-104, 107-108
hydroxyl groups, 47: 170
of L-serine or L-threonine derivatives,
43:15&-172
alkyl orthoacetates, 43:159-160
by condensation with (2,l -d)-2-oxazoline
derivatives, 43: 156-1 58
Helferich-Wedemeyer procedure,
43:167-171
Koenigs-Knorr method, 43:160-171
of phenylboronates, 3 5 5 5
protein, 37: 183-1 87
biological effects, 40:350-379
inhibition by sugar starvation, 40:346
inhibition effect on cell differentiation,
40:366-369
inhibition effect on viruses, 40:369-373
inhibitors, 40:32 1-350
lipid pathway, 40:287-321
sidedness, signal theory, and theory of
 SUBJECT INDEX
membrane-triggered folding,
40:3 19-321
reaction mechanisms, 44:278, 309, 342,384
in plant glycoprotein biosynthesis, 44:37 I
ribofuranoside, 53:174
selenoglycosides in, 53: 167-1 70
sites
isolation, 46:47-48
separation of, 46:4748
solvent effects, 50:35, 39
steps, 50:26
with transferases, 49:2 18-23 1
galactosylation, 49:2 19-224
glycosylation, 49:23 1
sialylation, 49:223-23 1
trichloroacetimidates of 2-azido-2-deoxy-i>-
mannose derivatives, 50:98, I03
Glycosyl azides, 16:85-103
C-Glycosylbenzene esters, radical-mediated
brominations, 49:59-60
Glycosyl carboxylates, base-catalyzed addition,
50:116
Glycosylceramide, in pearl oyster, 44:4 I5
C-Glycosyl compounds
naturally occurring, 18:227-258,
20:357-369
nomenclature, 52: 139-140
N-Glycosyl compounds, Helferichs work on,
45:5
Glycosyl cyanide esters, radical-mediated
brominations, 49:57-59
0-Glycosyl derivatives
-L-serine and -L-seryl, properties,
43: 190-196
-L-threonine, properties, 43: 197-199
synthetic
base-catalyzed elimination, 43: 175-1 78
enzymic reactions, 43: 179- 180
hydrolysis with acid, 43:178-179
mass spectra, 43: 180-1 8 I
NMR spectra, 43: I80
optical rotatory dispersion and circular
dichroism spectra, 43: 18 I
properties, 43:181-201
reactions, 43: 175-180
Glycosyl di-o-fructose dianhydrides, 52:254
I3C NMR spectra, 52:259
dianhydride components, 52256-257
optical rotations and melting points, 52:255
Glycosyl donors, 52: 186-1 87,53:170-177
25 I
Glycosyl esters
cis-,53: 126
of nucleoside 5-pyrophosphates.
28:307-399
in plant cell-wall biosynthesis, 42:315-323,
338
Glycosyl fluorides, 16:85-103
cleavage, 48:358-359
glycoside hydrolase inhibition, 48:357-359
3-0-glycosidic linkage formation, 50:290
preparation, from glycals, 38:229-237
stability, 47: I72
synthesis, 38: 199-204,48:94-121
affinity of silicon, 48: 107
C-arylglycosyl derivatives, 48: I 19
BF, catalyst, 48: 108
cellulose treatment with HF, 48:97
chitin treatment with HF, 48:98-99
condensation reactions, 48: 109-1 10
enzyme-catalyzed reactions, 48: 12 I
o-fructose treatment with HF, 48:97-98
glycosylations, 48:103-104, 107-108
C-glycosyl compounds, 48: 116-1 18
inulin treatment with HF, 48:97-98
Mukaiyama condensation methods,
48: I 0 4 1 07
Noyori procedure, 48: 107
from 0-protected free sugars or 1 -0-acyl
sugars, 48:10&-101
per-0-acyl displacement, 48:9&95
from phenyl thioglycosides. 48: 100
physical and chemical properties.
48:119-121
polysaccharide treatment with HF. 4 8 9 6
protected, 48: 122-123
o-ribofuranosyl fluorides, 48: 101
treatment
with HF, 48:95-96
with pyridinium poly(hydrogen
fluoride), 48: 102
Glycosylfructoses, treatment with
hydrogen fluoride, 52:230
pyridinium poly(hydrogen fluoride), 52:
229
Glycosyl group, effect on rate of hydrolysis of
pyranosides, 22:49-50
Glycosyl halides, 51:7-8, 10
acylated, preparation of, 27:3
esters, radical-mediated brominations,
49:60-61
252 SUBJECT PJDEX
Glycosyl halides (continued)
in situ generation from thioglycosides,
52: 184-185
nomenclature, 52: 136-137
solvolysis of, 22:38
and their derivatives, 10:207-256
thioglycosides preparation, 52: 18I
C-Glycosylheterocycle esters, radical-mediated
brominations, 4 9 5 9 4 0
CX-D-G~YCOSYI hydrolases, specificities of
purified, 32:195-196
N-Glycosylic linkage, cleavage, 46:255
Glycosylic phosphate, lipid A backbone,
50:221-222
Glycosyl imidates, base-catalyzed addition,
50:114, 116
Glycosyl isothiocyanates, glucosidase
inhibition, 48:377-378
0-Glycosyl linkage, 43:4
distinguishing from N-linkages, 43:6
model compounds, 43:21-34
Glycosylmethyltriazenes, glucosidase
inhibition, 48:373-375
Glycosyl nucleotides
in biosynthesis of polysaccharide chains of
bacterial polymers, 44:280
primary, 44:280-283
in bacteria, 44:281
secondary, 44:280-281
GI ycosyl oxides, base-catalyzed addition,
50:114
Glycosyl4-pentenoates, electrophile-induced
lactonization, 50:293-294
Glycosyl phosphates
anomeric-oxygen activation, 50: 116
preparation of, 3 2 9
synthesis of, 31:4
Glycosyl piperidine carbodithioates, acetylated,
thioglycosides preparation, 52: 183
Glycosyl region, lipid A backbone, 50:2 18-22 1
Glycosyl residues
nomenclature, 52: 125
in plant cell-wall polymers, 42:274,276
sequencing of, 42:27&277
Glycosyl sulfonates, base-catalyzed addition,
50:116
Glycosyl sulfones, as glycosyl donors,
52: 199-200
Glycosyl sulfoxides, as glycosyl donors,
52: 199-200
Glycosyl thiocyanates, thioglycosides
preparation, 52: 183
Glycosyltransferase, 39:3 18,40:25 1,44: 150,
306,343
acceptor specificities, 40:246, 267-268
in bacterial polysaccharide chain assembly,
44:310-311
biosynthetic, specificity, effects on structure,
44:244
blocking, 40:266
glycosphingolipid biosynthesis, 40:245-
247
membrane-bound, 44:283,305
in plant cell-wall biosynthesis, 42:3 16
0-Glycosyl trichloroacetimidates, reactions
with N-, S-, C-, and P-acceptors, 50: 11I ,
114-1 15
C-Glycosyluronic acids, synthesis and
reactions, 36: 133-134
Glycosyluronic nucleosides, synthesis of,
42:232
Glycosyluronic residues in plant cell-wall
polymers, 42:276
Glycosyl xanthates, thioglycosides preparation,
52: 183
Glycotriosyl ceramide, synthesis, 48: 107
Glycoyl a-phosphate, lipid A substituents,
50:226-227
Glyculose derivatives, radical-mediated
brominations, 49:54-57
Glyculoses, 48:288-289
Wittig reaction with, 27:231
Glyculosonic acids, 48:295-298
3-deoxy-
in polysaccharides and glycoconjugates,
31:187
synthesis by Wittig reaction, 27:267,
274
Glyc-2-ulosonic acids, 3-deoxy-, periodate-
thiobarbituric acid assay, 38:238,327
Glycuronans, 24:296,323
(aminodeoxyg1yco)-, acidic, in human urine,
24:436
p-eliminative depolymerization of,
29~245-252
crystal structure bibliography, 33:403
decarboxylation of, 28:186, 188,46:306
dehydration of, 28: 188
high-temperature transformation of,
46~305-307
 SlJBJECT INDEX
hydrolysis, 46:265
in marine algae, 46:307
reaction with carbodiimides, 29:347
Glycuronic acids, 48:293-295
alkaline degradation of, 28:206
circular dichroism, 45: 102-105
decarboxylation of, 28: 186, 190
degradation of, 28: 166, 168
1-esters, 36:10&1 19
nucleosides, 36: 126-131
Glycyl azide, N-(benzyloxycarbonyl)glycyl-,
in selective esterification of adenosine,
33:45
Glycyphillin, taste properties, 45:280
Glycyrrhetic acid, 45:287
18P-Glycyrrhetic acid, o-glycopyranuronic
acid conjugates, preparation, 36: I09
Glycyrrhiza glabra L., 45:287
Glycyrrhizic acid, 45:287
Glycyrrhizin
structural features, 45:289
taste properties, 45:287-290
Glykergenic acid, sweetness, 45:290
Glyoxylic acid
phenyl-
esters with sugars, Grignard reaction with,
27:200
polarography of, 29:147
sodium salt, reaction with nitro alcohols,
40:106107
2-(2,3,5-tri-0-acetyi-P-~-nbofuranosyl)-,
preparation and use in synthesis of
showdomycin, 33:159, 167
Goepp, Rudolph Maximilian, Jr., obituary of,
3:xv-xxiii
Golden rod, polysaccharide from, antitumor
activity of, 32:253
effect on tumor cell volume and
vacuolization, 32265
Golgi apparatus, 26:469
biogenesis of matrix polysaccharides by,
26:339-342
in cellulose synthesis, 26:325,335,337
in glycoenzyme biosynthesis, 27:303, 330
polysaccharide biosynthesis in, 4 2 3 3 1-332,
334,336,338
Gomez-Sanchez, A,, 45: 13-14
Gonadotropin, 23466
a-o-mannosidase in structural studies of
human chorionic, 28:445
253
carbohydrate-peptide linkage in, 25:442
Gorse-seed extract, see Ulex europeus, I1
Cossypol, structure, 29:2
Gottschalk, Alfred, obituary, 33: 1-9
Gougerotin
antibiotic. 33:200
synthesis, 36:72
structure of, 42:229
Gracibioside, 39:302
Graminae, see also Cereals; Grasses
anatomy, 36:2 18-2 19
ferulic acid in, 42:315
hemicelluloses, 36:2 15-220
species, 36:2 18
Gram-negative bacteria
3-deoxy-o-ncmno-2-octulosonic acid
constituent, 38:324-325
lipopolysaccharides, 44:277
Gram-positive bacteria. cell-wall polymers,
44:277
Gram-staining process, study, 52: 12
Grandidentatin. gel chromatography of. 25:50
Granulation. of honey, 25:293
Granulocytes
normal, f.a.b. map of lactosaminoglycan
sample from, 45:3940
0-linked oligosaccharides, f.a.b.-mass
spectrometry, 4 5 5 4
permethylated ganglioside from, f.a.b.-mass
spectrometry, fragmentation observed
in, 45:54-55
Grape, development physiology of, 42334 I ,
344,363,371,378-380
Graphium, rhamnomannan. 41:89
Grasses
cultivars, 36:219
harvesting and storage, 36:220
hemicellulose-cellulose ratio, 36:253
hemicelluloses, 36:2 15-264
lignin and delignification, 36:222
xylans, structure, 36:229-249
Grasshoppers, gas-liquid chromatographic
analysis of constituents of, 28:62
Graviolbioside A, isolation of, 31: 146
Graviolbioside B, isolation of, 31:144, 146
Griessmayer-Aubry method, 47:234
Grignard reagents
in the carbohydrate series, 6:25 1-289
cyclic acetal cleavage, 39: 153
reaction with
254 SUBJECT INDEX
Grignard reagents (continued)
acyclic sugar derivatives for synthesis of
compounds containing asymmetric
benzylic carbon atoms, 27:217
a-0x0 esters of optically active alcohols,
27:199-201
asymmetric benzylic carbon atoms created
by, 27:213
conjugate-addition with a,P-unsaturated
carbohydrate esters, 27:202-204
with glycosuloses, new asymmetric
centers by, 27:204
oxirane aldoses, 25: 126, 137
in solvents containing carbohydrate
derivatives, 27: 193-195
in synthesis of 1-C-substituded
carbohydrates, 25241
in unsaturated carbohydrates preparation,
24:260,262
Grob fragmentation, 23: 156, 161
Ground state, anomeric effect, 47:118
Guanidination, in neoglycoprotein preparation,
37:245-246
Guanidine, nitroso-, research, 29:2
Guanidino group, participation in sugar
reactions, 22: 149
Guanosine
5 '-(a-o-galactopyranosyl pyrophosphates),
isolation of, 28:3 19
5 '-(a-o-glucopyranosyl pyrophosphate)
enzymic synthesis of, 28:338
role in biosynthesis, 32: 12
5 '-(a-~-mannopyranosylpyrophosphate),
enzymic and fermentation production
of, 28~339-340
occurrence and isolation of, 28:3 19
5 '-(a-o-mannopyranosyluronic acid
pyrophosphate), isolation of, 28:320
5'-(a-~-rhamnopyranosylpyrophosphate),
enzymic preparation of, 28:344
isolation of, 28:321
9-aminoacridine 5-iodocytidylyl-(3 ' 4 5 ')-,
hydrate, crystal structure, 43:302-304
5 ',8-anhydro-2,'3'-0-isopropylidene-8-
mercapto-, 24: 188
5 '-(P-L-fucopyranosyl pyrophosphate),
enzymic synthesis of, 28:343
5 '-(P-L-galactopyranosyl pyrophosphates),
isolation of, 28:319
5 '-(P-L-gulopyranosyluronic acid
pyrophosphate), isolation of, 28:320
8-bromo-
dihydrate, crystal structure bibliography,
30:459,31:370
2',5'-di-O-(methylsuIfonyl)-, 23:245
2',3 '-0-isopropylidene-5 '-0-
(methylsulfony1)-, displacement
reaction of, 24: 188
cadmium 5 ' -monophosphate octahydrate,
crystal structure bibliography, 37:4 16
copper 5'-monophosphate dodecahydrate,
crystal structure bibliography, 37:435
3',5'-cyclic monophosphate sodium salt
tetrahydrate, crystal structure
bibliography, 32:373
2'3'-cyclic phosphate, 22:314,357
3',5'-cyclic phosphate, 22:321, 360
hydrolysis, 39:61
2' -deoxy-
actinomycin complex dodecahydrate,
crystal structure bibliography,
30:460
5 '-,(a-o-mannopyranosyl pyrophosphate),
enzymic synthesis of, 28:340
3'-phosphate, 22:348
5'-phosphate, 22:308, 31 1,345
5'-phosphate disodium salt tetrahydrate,
crystal structure bibliography, 32:374
selective oxidation with chromium
trioxide, 33:99
6-thio, monohydrate, crystal structure
bibliography, 38:489490
5 ' -(6-deoxy-a-o-lyxo-hexopyranosyl-4-ulose
pyrophosphate), 28:322
5'-(2-deoxy-o-arabino-hexosyl
pyrophosphate), enzymic synthesis of,
28:338
5 ' -(6-deoxy-o-taIosyl pyrophosphate),
28:321
derivatives, diastereoisomeric, 46:28
5 '-(D-gbcevo-o-manno-heptosyl
pyrophosphate), occurrence and
isolation of, 28:320
5 '-(3,6-dideoxy-P-~-xylo-hexopyranosyl
pyrophosphate), isolation of, 28:321
diethidium 5-iodocytidylyl-(3 ',5')-, 27
hydrate 4 MeOH, crystal structure
bibliography, 38:502-503
dihydrate, crystal structure bibliogrpahy,
30:461
 SUBJECT INDEX
3,5-di-0-acetyl-N2-benzoyl-, preparation,
39:40
5 -(o-mannopyranosyluronic acid
pyrophosphate), from brown alga, 32:9
5 -(fructosyl pyrophosphate), occurrence of,
28:320
glycuronic acid conjugates, preparation,
36: 127
8-hydroxy-2,3 -0-isopropylidene-5-0-
(methylsu1fony)-, displacement reaction
of, 24: I88
8-iodo-, monohydrate, crystal structure
bibliography, 38:508
manganese 5 -monophosphate octahydrate,
crystal structure bibliography, 32:382
3.5-monophosphate,crystal structure
bibliography, 37:435
5-monophosphate copper complex, crystal
structure bibliography, 37:416
N 2 , N2-dimethyl-, crystal structure
bibliography, 30:463
N2-benzoyl-5-0-benzoyl-2-0-(4-
methoxytetrahydropyran-4-yl)-,
preparation, 39:37
N-benzoyl-2-0-(tetrahydropyran-2-yl)-, 5 -
phosphate, preparation, 36: I80
Nz-henzoyl-2,3,5-tri-O-benzoyl-, selective
deacylation, 39:3940
N7-[chloromercuri(II)]-, crystal structure
bibliography, 38:5 10
nickel 5 monophosphate octahydrate, crystal
structure bibliography, 32:382
N2-methyl-, monohydrate, crystal structure
bibliography, 38:516
occurrence and isolation of, 28:3 18. 32 1
2,3-U-isopropylidene-
p-toluenesulfonylation of, 24: 186
reaction with phosphoryl chloride, 28:239
5-(oligosaccharidepyrophosphates), 28:322
5-phosphate, 22:311,326, 328, 336
preparation, 35:54
5-phosphate trihydrate, crystal structure
bibliography, 31:370
5-phosphorocyclohexylamidate,in synthesis
of glycosyl nucleoside pyrophosphates,
28:346
phosphorylation of, 22:341
platinum ethylenediamine, mixed chloride
iodide salt dihydrate, crystal structure
bibliography, 34:375
255
5-pyrophosphase glycosyl esters, occurrence
and enzymic synthesis of, 26:355
5-pyrophosphate, esters of L-galactose and
o-mannose in red alga, 32:9
reaction with 2-acetoxy-2-methyl-propanoyl
halides, 33:85
selective etherification of, 33:70
selective oxidation of, 33:88
3 ,5-(sodium monophosphate) tetrahydrate,
crystal structure bibliography, 31:360
structure of, 28:309
3,5,6,8-tetramethyl-N1-methylphen-
anthroltnium 5-iodocytidylyl-(3+5),
methanolate, heptodecahydrate, crystal
structure, 43:305-306
5-tetraphosphate. in enzyme biosynthesis,
30:225
6-thio-, monohydrate, crystal structure
bibliography, 30:461
2,3,5-tri-O-acetyI-
N2-benzoyl-,selective deacylation, 39:40
6-O-(mesitylenesulfonyl)-, crystal
structure bibliography, 38:525-526
Guanosine 5-[copper(II)monophosphate],
tetrahydrate, crystal structure
bibliography, 38:508-5 10
Guanosine diphosphate: (1+4)-P-~-glucan
synthetase, cellulose biosynthesis, 41: 127
Guanosine 5-diphosphate, glycosyl esters,
44:280, see also Glycosyl nucleotides
Guanosine diphosphate-glucose. precursor to
cellulose biosynthesis, 41: 125-132
Guanosine diphosphate-glucose
pyrophosphorylase, cellulose biosynthesis,
41:126
Guanosine 5-( o-mannosyl diphosphate).
44:282; .see ulso Glycosyl nucleotides
Guanosine hydrobromide, hemihydrate. crystal
structure, 43:361-362
Guanosine 5-phosphate. trihydrate, crystal
structure, 43:321
Guanosine proflavine, 3-2 cytidylyl-(3, 5 )-,
hydrate, crystal structure bibliography,
38:527
8-Guanosin-8-ylguanosine, tetrahydrate, crystal
structure, 43:307-308
Guanylic acid, 22:312
2-deoxy-
3-phosphate, 22343
5-phosphate, 22:343
256 SUBJECT INDEX
Guar, galactomannan from seeds of, 31:245
Guaran
affinity chromatography adsorbent, 39:419
hydrolysis, 46:265
oxidation and acid hydrolysis of, 31:194
periodate oxidation of, 31:201,239
separation from glycogen, 35:276
structure, 35:349
Guaran sulfate, preparation of, 29:335
Guar galactomannan
solid film, circular dichroism, 45:9G91
structure, 35:349
Guar gum
industrial applications of, 31:307-3 12
solution properties of, 31:283
Guar seeds
a-D-galactosidase from, 35:364
P-o-mananase from, 35:367
enzymes in galactomannan degradation
during germination, 35:361
Gulal
4,6-O-benzylidene-n-, 24:20 1
3,4,6-tri-O-acetyl-~-,24:2 14
tri-0-acetyl-o-, 24:214
Gularic acid, 2,5-anhydro-o-, 25: 190
Gulitol
2-acetamido- 1,2-dideoxy- 1-nitro+-, 2
4:133
1 -amino- I-deoxy-D-, deamination of, 31:60
1,5-anhydro-
D-,25:237
from 1,5-anhydro-o-galactitoIin
hydrogen fluoride, 26: 173
L-, 25:237,245,250-251
2,6-anhydro-l-deoxy-l-nitro-o-, 24: 1 19
D-,preparation, 38:3 15
6-deoxy-1,2:3,4-di-O-isopropylidene-~-,
preparation of, 32:64
3.5-O-benzylidene-~-,preparation, 38:3 15
2,3-0-isopropylidene-~-, preparation,
38:315
Gulofuranose
5-acetamido-5-deoxy-~-,23: 176
1,6-anhydro-a-~-, crystal structure, 43:214
1,6-anhydro-a-~-,preparation of, 34: 153
1-(benzothiazo1-2-y1)-2,-3:5,6-di-O-
isopropylidene-L-, preparation, 38:3 I8
1-(1-benzylbenzimidazol-2-y1)-2,3:5,-6-di-
0-isopropylidene-L-, preparation,
38:318
1-C-( 1,3-Dithian-2-~1)-2,3:5,6-di-O-
isopropylidene-P-L-, 2-propanol solvate,
crystal structure, 43:347
1 -(chloroethynyl)-2,3:5,6-di-O-
isopropylidene-L-, preparation, 38:3 17
3-deoxy- 1,2:5,6-di-O-isopropylidene-3-C-
methyl-a-o-, synthesis of, 27:282
1,6:3,5-dianhydro-a-o-, crystal structure,
43:210-211
1 -(diethoxy- 1-propynyl)-2,3:5,6-di-O-
isopropylidene-r-, preparation, 38:3 17
2,3:5,6-di-O-isopropylidene- 1-
(phenylethyny1)-L-, preparation, 38:3 17
(pyridin-2-yl)-~-,preparation, 38:3 18
[(tetra-hydrop yran-2 -y10xy)- -propynyl]
1 -
L-, preparation, 38:317
1,2:5,6-di-O-isopropylidene-3-O-methyl-a-
D-,hydrolysis of, 34:203
1-( 1,3-dithian-2-yl)-2,3:5,6-di-O-
isopropylidene-P-L-, preparation,
38:321
I -ethynyl-2,3:5,6-di-O-isopropylidene-~-,
preparation, 38:37 1
3-0-benzyl- 1,2:5,6-di-U-isopropylidene-a-
D-
hydrolysis of, 34:203
selective hydrolysis, 39:15
2,3,5,6-tetra-O-benzoyl-~-, preparation,
38:316
Gulofi1ranose-4,6-lactone,3-O-acetyl-4-C-
carboxy-l,2-O-isopropylidene-5-O-p-
tolylsulfonyl-a-~-,crystal structure
bibliography, 38:471472
9-P-~-Gulofuranosyladenine, 50: 195
Gulonamide
2-acetamido-N-cyclohexyl-2-deoxy-3,-4: 5,6-
di-0-isopropylidene-D-, preparation,
38:309
D-, preparation, 38:299
2,3:4,5-di-O-carbonyl-6,6-dichloro-6-deoxy-,
preparation, 38:312
2,3:5,6-di-O-isopropylidene-~-, preparation,
38:301
L-, preparation, 38:299
N, N-dimethyl-D-, preparation, 38:300
N-allyl-D-, preparation, 38:300
N-(4-ethoxyphenyl)-~-,preparation, 38:300
N-(methoxycarbonylmethyl)-o-, preparation,
38:300
N-(methoxypheny1)-L-, preparation, 38: 300
 SUBJECT INDEX 257

4-0-(2-acetamido-2-deoxy-o- Gulono- I ~

galactopyranosy1)-L-, preparation, 6-lactam

38:3 I 1 6-amino-6-deoxy-~-,23: 164
3,5-O-benzylidene-~-,preparation. 38:30 1 preparation. 38:308
Gulonic acid L-, preparation of, 33:233
5-amino-5-deoxy-o~-,23: 139 4-lactone, 38:287-32 1
6-amino-6-deoxy-~-,preparation, 38: 308 5-acetamido-5-deoxy-~-,preparation,
5-amino-5,6-dideoxy-~~- 38:308
preparation, 38:310 alcoholysis, 38:301
synthesis, 40: 112 3,6-anhydro-~-,25:26 1
2,5-anhydro-o-, structure of, 33: 118-1 I9 preparation, 38:307
2,6-anhydro-6-deoxy-6-deoxy-6-phenyl-~-, biological role, 38:320
preparation, 38:307 D-
2-anilino-2-deoxy-o-, ammonium salt, crystal structure, 38:296
preparation, 38:308 mass spectra. 38:297
biological role, 38:320 synthesis, 38:287, 289, 294
D-, oxidation, 38:314 crystal structure bibliography, 30:
6-deoxy-6-[ 1,3-di(carboxypropyl)amino-~-, 448
preparation, 38:3 10 irradiation, 37: 123
6-deoxy-6,6-dipheny-~-,preparation, 38:3 10 synthesis, 36: 1 1
6-deoxy-6.6-sulfo-~-,preparation, 38:3 1 1 6-deoxy-6,6-bis(4,4-dimethyl-2,6-
3,5:4,6-di-O-benzylidene-~-, ethylestcrs, dioxocyclohexyl)-3,5-O-ethylidene-
preparation, 38:301 L-, preparation, 38:3 1 1
2,3 :4,5-di-O-carbonyl-6,6-dichloro-6-deoxy-, 6-deoxy-~-,preparation, 38:305
methyl ester, preparation, 38:3 12 6-deoxy-6-(2-isonicotinoylhydrazino)-6-
3,5:4,6-di-O-ethylidene-~-, preparation, S U ~ ~ O - D -preparation,
, 38:3 10
37:114 6-deoxy-~-,preparation, 38:305-307
2,3:4,5-di-O-methylene-~-, methyl ester, 2,3-di-O-acetyl-5,6-O-isopropylidene-~-,
preparation, 38:302 preparation, 38:32 1
L- 2,6:3,5-di-O-benzylidene-~-, preparation,
in L-ascorbic acid synthesis, 37: 1 19-125 38:304
oxidation, chemical, 37: 123-125 2,2' :5,6-di-O-isopropylidene-2-C-
fermentative, 37: 122-123 (hydroxymethy1)-L-
oxidation, 38:3 14 crystal structure bibliography, 38:456
preparation, 38:295 preparation, 38:313
preparation, and salts, 38:298-299 2,3:5,6-di-O-isopropylidene-2-C-
N-acetylchondrosaminido-r-, methylester, (hydroxymethy1)-L-, preparation,
preparation, 38:3 11 38:3 I3
3-O-P-~-glucopyranosyl-~-, preparation, 2,3:5,6-di-O-isopropylidene-~-
38:305 oxidation, 38:321
3-O-benzoyl-2,4,5,6-tetra-O-benzyl-~-, preparation, 38:302
preparation, 38:302 2,3 :5,6-di-O-isopropylidene-~-
2-O-methyl-~-,methyl ester, 38:3 1 I preparation, 38:302
preparation, 37:87, 113, 119-120 reaction with lithiated 1,3-dithiane.
2,4,5,6-tetra-O-benzyl-~-, preparation of. and 38:321
esters, 38:302 L-
3,4,5-tri-O-acetyl-2,6-anhydro-~-, methyl conversion into r-ascorbic acid,
ester, preparation, 38:307 37:124125
Gulonic phenylhydrazide, L-, preparation, irradiation, 37: 123
38:299 oxidation to L-ascorbic acid, 37: 123
258 SUBJECT INDEX
Gulono-I, (continued)
oxidation to L-ascorbic acid
enzymically, 37:123
preparation, 37537, 12C121
hydrolysis, 38:296,298
spectroscopic properties, 38:297
synthesis, 38:287-288,295
preparation of, 33:2 18
nucleophilic additions to carbonyl group,
38:3 17
3,5-O-benzylidene-~-,preparation, 38:303
3,5-0-benzylidene-6-O-trityl-~-,
preparation, 38:305
3,5-0-(2-chlorobenzylidene)-~-,
preparation, 38:303
3,5-O-ethylidene-~-,preparation,
38:303-304
2,3-O-isopropylidene-o-, preparation,
38:303
3,5-O-isobutylidene-~-,preparation,
38:303
5,6-O-isobutylidene-~-,preparation,
38:303
5,6-O-isopropylidene-o-, preparation,
38:302, 321
3,5-O-isopropylidenee-~-, preparation,
38:303
3,5-0-(2-methylbenzylidene)-~-,
preparation, 38:303
3,5-0-(3-methylbenzylidene)-~-,
preparation, 38:303
3-O-methyl-~-,preparation, 38:305
3,5-0-(2-methyoxybenzylidene)-~-,
preparation, 38:303
2-O-(tert-butyldimethylsilyl)-3,5-0-
isopropylidene-L-, preparation,
38:306
oxidation, 38:3 14
reactions, of hydroxyl groups, 38:302-305
reduction, 38:3 15-3 17
2,3,5,6-tetra-O-acetyl-1~-,preparation,
38:304
2,3,5,6-tetra-O-benzoyI-o-, preparation,
38:304
2,3,5,6-tetra-U-(trimethylsilyl)-o-,
preparation, 38:304
2,3,5-tri-O-(tert-butyldimethylsilyl)-~-,
preparation, 38:305
3,5,6-tri-O-(tert-butyldmethylsilyl)-~-,
preparation, 38:305
5-lactone, L-, formation, 38:296-297
Gulonolactone, 2-C-(hydroxymethyl)-~-,
2,2':5,6-di-U-isopropylidene-, crystal
structure bibliography, 38:456
Gulononitrile
2-amino-2-deoxy-o, N-derivatives,
preparation, 38:308
2,5-anhydro-3,4,6-tri-O-(p-nitrobenzoyl)-~-,
preparation, 38:3 1 1
2-deoxy-3,5:4,6-di-U-ethylidene-2-C-
methyl-L-, preparation, 38:3 12
2,3 :4,5-di-O-carbonyl-6,6-dichloro-6-deoxy-
DL-, preparation, 38:3 12
Gulopyranose
0.-D-, 45:74
2-amino- 1,6-anhydro-2-deoxy-p-~-,
preparation of, 34: 122
3-amino- 1,6-anhydro-3-deoxy-P-o-,
preparation of, 34:122, 126
1,6-anhydro-
p-D-
chiroptical properties of, 3 4 5 2
conformation of, 34:61
per-U-substituted, 34:77
2,3-phenylboronate, 34:93
preparation of, 34: 115
and triacetate, 34:89
p-toluenesulfonylation of, and 2,3-
phenylboronate, 34:81
reaction with hydrogen bromide and
bromine, 34:66
complexes, 3 4 5 4
2,3-dideoxy-2,3-epirnino-p-o-, preparation
and properties of, 34:13&13 1
2,3-di-O-p-tolylsulfonyl-@-~-, preparation
of, 3 4 s 1
2,3-O-isopropylidene-P-o-, as synthetic
intermediate, 34:90
D-, orientation of hydroxyl groups for, in
4 C , ( ~conformation,
) 4575
1,6:2,3-dianhydro-p-~-
crystal structure bibliography, 30:447
preparation of, 34:109, 113
1,2,3,4,6-penta-U-acetyl-a-~-, crystal
structure bibliography, 38:466
Gulopyranoside
2,3-anhydro-~-,48: 164
benzyl2-acetamido-2,4-dideoxy-4-dideoxy-
4-fluoro-6-O-trityi-u-o-, 48: 163
D-, benzyl2-acetamido-3-O-acetyl-2,4-
 SUBJECT INDEX 259

H- and
dideoxy-4-fluoro-6-O-trityl-01-, ' by o-gulono- 1,4-lactone reduction.
"F-NMR data for, 46: 1 19 3 8 ~ 15-3
3 16
2-deoxy-2-fluoro-p-~-,48: 132 preparation, 38:293-294
2-flUOrO-OI-D-, 48:13 1-132 halogen derivatives of, 22:217
methyl cx(and P)-D-, hydrolysis of, 22:45 synthesis of, 24:247
methyl 4-acetamido-4,6-dideoxy-01-~-, 6-deoxy-
23:187 ~-,21:173,178, 181
methyl 3-acetylation 3,6-dideoxy-a-~-, L-, 21:178
acetylation of, 33:30 preparation, 38:3 16
methyl 2,3-anhydro- 2,3-O-isopropylidene-~-composition in
OI-D-, 25~127,145-146 aqueous solution, 42:59
4,6-benzylidene-o-, 25: 116 4-thio-~-composition in aqueous solution,
methyl D-, effect of calcium chloride on 42:53
specific rotation of, 21:230 2,6-diamin0-2,6-dideoxy-o-, 22: 14 I
methyl 6 - d e o x y - a - ~ ~synthesis,
-, 40:h9 I ,2:5,6-di-O-isopropylidene-
methyl 2-deoxy-3,4,6-tri-O-p-tolylsufonyl-01- OI-D-, 24:247
D-, 23:272 D-, selective hydrolysis, 39: 15
methyl 4,6-O-benzylidene-, hydrolysis of, 2,3:5,6-di-O-isopropylidene-o-, preparation,
34:202 38:316
Gulopyranosiduronic acid, methyl p-0-, L-
ammonium salt, preparation, 36:73 derivatives of cyclic acetals, Table, 34:234
Gulopyranosse, 1,6-anhydro- preparation, 37: 109-1 10,38:290-29 1
p-D-, sulfonylation of, 23:252 synthesis of, 33:88
2,3-di-O-p-tolylsuIfonyl-~-u-, 23:252 2,3-O-isopropylidene-o-,preparation, 38:3 16
2,3,4-~-0-p-tolylsulfonyl-~-u-, 23:252 pyranose form, 42:63
Gulopyranosyl chloride, 6-deoxy-2,3-0- stability in solution, 42:26
isopropylidene-4-O-methyl-p-~-, reaction Guloseptanose, 4,5-di-O-acetyl- I ,2-0-
with base, 39: 147-148 isopropylidene-3-O-methyl-01-~-, crystal
Gulopyranosyluronic acid, P-L-, ester of structure bibliography, 31:3 53
guanosine 5'-pyrophosphate, isolation of. Guluronan, L-, crystal structure bibliography,
28:320 33:403
Gulopyranuronic acid, D-, methyl 01- and p- i.-Guluronan lyase, 44: 192-1 94
glycosides, preparation, 36:72 Guluronic acid
Gulose 2,3-diamino-2.3-dideoxy-~-, biosynthesis,
2-acetamido-2-deoxy-D- composition in 44:29&298
aqueous solution, 42:47, 67 01-L-, 47:24-25
2-amino-2-deoxy-u-, 22: 13 I , 14 I. 24: I 12 complexing. 47:32
derivatives, synthesis of, 22: 138 L-
3-amino-3-deoxy-o-, 22: 131 of alginic acid, 35:8, 10
2-amino-2,6-dideoxy-o-, 22: 141 biosynthesis, 44:296-298
3,6-anhydro-~-composition in aqueous Gum arabic, 22:5. 24:34&341
solution, 42:58 acetolysis of carboxyl-reduced, 31: 199
in aqueous solution, composition, 42:63 as a-L-arabinofuranosidase substrate,
OI-D-, effect of alkaline-earth metal salts on 42:390,392
specific rotation of, 21:230 antitumor activity of, 32:253. 266
D- structure, 24:343, 346, 41:8
calcium chloride complex, mutarotation enzymic analysis, 44:247
of, 23:34 Gums, 22:5,24:333-379
derivatives of cyclic acetals, Table, Acacia, 24:343-348
34:234 Acacia arubicu, 24:342, 345-346
260
Gums (continued)
Acacia drepanolobium, 24:345,348
Acacia elata, 24:348
Acacia karroo, 24:346
Acacia laeta, 24:348
Acacia laiifolia (ghatti), 24:354. 376
Acacia leiocarpus, 24:336, 340, 356
Acacia mearnsii, 24:34&345
Acacia nilotica, 24:344
Acacia nubica, 24:345-346
Acacia podalyriaefolia, 24: 348
Acacia pycnantha. 24:344-345
Acacia senegal, 24:344-345
Acacia seyal, 24:348
apricot-tree, 24:359
arabic antibodies, 53:242-246
Araucaria bidwillii, 24:339-340,35 1
blackthorn-tree, 24:359
British, structure of, 26:16
cereal, definition, 36:2 17
cherry, 24:354,359
cholla, 24:353
Citrus limonia (lemon), 24:342, 351
Cochlospermum gossypicum, 24: 365
Combretum leonense, 24: 336
polysaccharide from, 24:375,377
commercial, 13:265-287
consumption of natural, 36:268-270
damson, 24:354
Encephalarios longifolius. 24:359
gas-liquid chromatography of, 30:94
gel chromatography of, 2 5 3 8
golden-apple, 24:351
hydrolysis of, 46:263,265
in industry, 36:268-270
jeol, 24:353
Khaya, 24:336,351,361,363-365
Kuiira. 24:365
leiocarpan A, 24:356
lemon, 24:342, 351
mesquite, 24:341,349
Odina wodier, Roxb. (jeol), 24:353
Opuntiafulgida (cholla), 24:353
plant, constitution, 3 5 6
review, 3 5 8
structure, 35:9
ofplants, 4:243-291
polysaccharide, 53:411412
Prunus, 24:360
sapote, 24:371
SUBJECT INDEX
Sterculia, 24:361,365-369
Sterculia urens, 24:340
oligodsaccharides from, 24:368
structure, history, 41:3, 7
Virgilia oroboides, 24:360
Gum tragacanth, 24:336,353,361
antitumor activity of, 32:253-254,262,273
and pectinesterase activity, 33:329
Gutambuine, 46: 13
Gymneina sylvestre, sweet-taste inhibitors
from, 45:337
Gymnemic acids, as sweet-taste inhibitors,
45:33&339
Gymnosperms, cell-wall
composition of, 26:300, 302
formation in, 42:269
Gynocardin, 6-0- (p-bromophenylsulfony1)-,
crystal structure bibliography, 30:465
H
Haemophilus injluenzae
capsular polysaccharide-protein conjugate
vaccine, 41:198
capsular polysaccharides, end groups, 41: 185
structure, 41: 164-1 67
polysaccharide vaccine, 41: 195-1 96
Hakomori reaction, methylation of
carbohydrates, 30:12, 31:215, 230
Hall-Weber-Helfand model, 51:8 1-82, 122,
125
Haloalkanes, 53:35 7
Halobenzenes, 53:357
Haloformates, carbohydrate, decomposition of,
22:197
Halogenated carbohydrates, see Carbohydrates;
Sugars
Halogenation
of alcohols, 28:240
of carbohydrates with phosphorusbased
reagents, 33:77-80
cyclic acetal, 39:95-121
reagents causing migration of acetal
groups, 39:115-121
of 6-deoxyhexoses, 21: 182
1,4:3,6-dianhydrohexitols, 49: 149-150
of diazo compounds, 31:59-60
of glycals, 24:202
of nucleotides, 22:377
 SUBJECT INDEX
of polysaccharides, 29:348
selective, of carbohydrates, 33:72-86
of sulfonic esters of, carobhydrates, 23:268
Halogen nucleophiles, for oxirane aldoses,
25: 125
Halogeno carbohydrate, 4 5 4
2-Halogeno derivatives, nonselective
relaxation-rates, stereospecific
dependencies, 45: 152
Halogenohexopyranosyl fluorides, 2-deoxy-2-,
'H- and I9F-NMR data for, 46:129
Halogenoketonucleosides, synthesis of, 42:244
Halogenolysis
of dithioacetals, 32:72
of halogenated deoxy sugars, 25: 194
(Halogenomethy1ene)dimethyliminIum halides,
in synthesis of deoxyhalogeno sugars,
28:250
Halogenopentopyranosyl fluorides, 2-deoxy-2-,
'H- and lyFF-NMRdata for, 46:135-137
Halogen oxidation, see Oxidation, halogen
Halogens
addition to unsaturated sugars, 22: 193, 195
atom, effect on neighboring groups in
halogenated carbohydrates, 22:207
displacement of, in sugar derivatives, 25202
Halo(methoxyl)ation, of glycals, 24:203
Hamamelitol, in biosynthesis of clusianose,
37:3 19
Hamamelopyranoside, methyl f3-D-,preparation
of, 32:38
Hamamelose
composition
in aqueous solution, 4254, 134
in nonaqueous solution, 4 2 6 1
D-, carbon-I3 nuclear magnetic resonance
spectroscopy, 41:64
isolation of, 31: 136
L-, synthesis, 42:78, 81
natural occurrence of, 4269, 76
occurrence, 37:3 19-320
structure of, 42:70
synthesis of, 42:78, 80, 128
Hammett constant, 45:224-225, 303
Ham-Woolf plots, 51: 157
Hanganutziu-Diecher antigen, 50:339, 342
Hunsenula, 0-phosphonomannans, 36:302
Hansenulu cupsulutu Y-I842
phosphonomannan, 41:84
polysaccharide, 41 :77
26 1
Hunsenula holstii
phosphonomannan, 41:85-86
Y-2448, polysaccharide, 41:77
Hansenulu polymorphu, polysaccharide, 41:87
Hansenulu wingei, polysaccharide, 41:87
0-Hapten, 44:3 17
Hardegger, Emil, obituary, 38: 1-1 1
Hard-sphere exoanomeric algorithm, 47: 105,
50:333-3 35
Harmones, as glycoproteins, 25408
Hassid, William Zev, obituary, 32: 1-14
Haworth, Walter Norman, obituary of, 6: 1-9
Haworth method
cyclic monosaccharides, 52:6 1-63
of methylation of carbohydrates, 30: 1 I . 13,
15
Hayashi, H., 46:7
'H chemical shifts, isohexide derivative ring
system, 49: 108- 109
Heat of activation, of mutarotation of D-
glucose, 24:53
Heat of combustion, for levoglucosan, 34:52
Heat of dehydration, for levoglucosan, 3 4 5 2
Heat of evaporation, for levoglucosan, 34:52
Heat of formation, for levoglucosan, 34:52
Heat of pyrolysis, of cellulose, 23:447
Heavy water, reducing sugar composition in,
42:6344
Helferich, Burckhardt, 45: 1-6
awards, 45:2
career, 45: 1-2
education, 45: 1
mamage, 4 5 2
publications and patents, 45:6
research, 452-6
Helferich method
of glycosiduronic acid synthesis, 36:74
of 1-thio-P-o-glycopyranosiduronicacid
synthesis, 36:98
Heliunthus
coleoptiles, development physiology of,
42:358
D-fructose from, 22:232
Helichysoside, hydrate, 43:372
Helixpomatia lectin, see Snail, lectin
Helminthosporoside
and clones, effect on sugar-cane leaves,
37:321
isolation and structure, 37:320
Helminths, a-o-mannosidase in, 28:405
262 SUBJECT INDEX
Helveticoside, 21:308
Hemagglutination tests, for lectins, 35: 133, 140
Hemagglutinins, see Lectins
Hematoside, discovery, 40:235
Hemiacetals, 23:25
of aldehydo sugars, 25214
of 2,5-anhydroaldoses, 25:212
disaccharides
with, 52:149-150
without, 52:149-150
formation of, 42:30, 133
nomenclature, 52: 122-123
oligosaccharides
with, 52:153-154
without, 52: 151-153
sugar analogs having phosphorus in ring of,
42: 135-1 9 1
biological activity, 42:188-190
physical properties of, 42: 191
Hemicellulases
occurrence, purification, properties, and
mode of action, 32:277-352
of rumen micro-organisms, 32:344-346
Hemicellulose-lignin complex, from perennial
ryegrass, 36:260
Hemicelluloses, 46:300
antitumor activity of, 32:254-257,262
A and B from plant cell-walls, 42:310
biosynthesis of, 26:405
in cell walls of plants, 36:257-258
chemical composition of, 26:302
classification of, 32:278
definition, 32:278,36:216-218
effect on animal nutrition, 36:251
endospermic and non-endospermic, 36:220,
228
fractionation, 36:22&227
gas-liquid chromatography of, 28:62
gel chromatography of, 2 9 4 3
in grasses, 36:215-264
current views, 36:262-264
hardwood, 46:305
high-temperature transformation of,
46:305-307
from holocellulose, 36:223-225
isolation, 36:220-229
non-fermentable oligosaccharides, liquid
chromatography methods for, 46:52
in plants, 26:298,300,346,36:250-262,
42:268-269,27&275,287-292
biosynthesis, 42:321-322,331-332,337
bonding to cellulose, 42:306-307
in fruit ripening, 42:365, 378-379
interconnections, 42:3 1 1-3 12
tissue, gas-liquid chromatographic
determination, 28:60
polysaccharides, 46:305
problems, 35:8, 10
quantitative values, 36:25 1-262
of ryegrass, 36:258-262
softwood, 46:305
structure
chemistry of, 14:429468
features, 36:229-249
sugars in hydrolyzates of oats, 36:255-257
trimethylsilylation and gas-liquid
chromatography of, 28:42
of wood, 19~247-302,20:409483
Hemichordates, sialic acids occurrence, 40: 137
Hemiketals, nomenclature, 52: 122-123
Hemp, cell-wall studies on, 42:268
Hen egg-white lysozyme, 44: 195
Hen-ovalbumin glycopeptide, structure,
37:174, 179-180
Hen ovomucoid, complex glycans, f.a.b.-mass
spectrometry, 4560-62
Hen-ovotransfenin glycopeptide, structure,
37:176, 178-180
Henry reaction, 24: 12 1
for deoxynitroinositols, 24:lOO
for nitro-sugar synthesis, 24:68, 70
Hexonic acid, 3,4,5,6-tetra-O-acetyyl-2-deoxy-2-
diazo-o-arabzno-, methyl ester, irradiation,
38: 179
Hexopyranoside-4-uI0-2~,4-pyranose, methyl
2,3,6-trideoxy-2-C[ 1 , l -(ethylenedithio)-2-
hydroxyethyl]-a-~-treo-,crystal structure
bibliography, 38:442443
Heparanase, 43:99-100
cleavage of heparin, 43: 100-103
Heparan sulfate
biological activity, 43: 132-133
circular dichroism, 45: 117
crystal structure bibliography, 35:383,
36:329
depolymerization by nitrous acid, 31:75
disaccharide repeating units, 43:53-55
glycosidic linkage, 43:53
heterogeneous regions, structure, 43:72-74
hexosamine, 43:53,55
 SUBJECT INDEX
major uronic acid, 43:53, 55
N-acetyl-, p-eliminative degradation of,
29:243
periodate-oxidized, cleavage, 43:98-99
selective cleavage, 43:84-103
structure
enzymic analysis, 44:209-216
similarity to heaparin, 43:57-59
Heparan sulfate lyase, 43:102,44:210-214
Heparin, 24:291,25:11
acid hydrolysis, 43:8485
as activator of enzymes in trehalose
biosynthesis, 30:243
alkaline cleavage, 43:85-86
amide derivatives, preparation of, 29:348
amino acid content, 25:434,43:66
amino sugar content, 43:73-74
anticoagulant activity, 43:52,75, 1 1 8-1 19,
127
and charge density, 43: 130, 132-1 33
correlation with structure, 43:128-132
and degree of sulfation, 43: 129- I30
mechanisms, 43: 128
molecular weight dependence, 43: I32
as anticoagulant for blood, 29:336
antilipemic properties, 43: 127-128
antithrombin 111binding site, 52,86,120
structure, 43:75-79
antitumor activity of, and its salts, 32:257,
273
assays, 43:61
p-eliminative degradation of, 29:243-245
binding of Cu(I1) with, monitoring with
circular dichroism study, 45: I I8
binding to insoluble matrices, 43: 106
biosynthesis of, 26:434,437,43:56-59
Ca2' binding, 43: 1 15-1 16
carbohydrate chains in, 29460
carbon- 13 nuclear magnetic resonance
spectra, 38:72-74
characterization, 43:61-66
chromatographic methods, 43:6344
colorimetric methods, 43:61-62
electrophoretic methods, 43:63
optical rotation, 43:66
titrimetric methods, 43:6243
chemical modification, 43: 103-108
chemistry of, 10:335-368
circular dichroism, 45: 117
cleavage
263
with heparanase, 43: 102
with heparinase, 43:90, 100-103
commercial preparations, bleached, 43:6 1
complexation
with alkylammonium salts, 43:63
with antithrombin, 43:119-122
with basic biogenic amines and drugs,
43: I I7
with cationic dyes, 43:62-63, 116
with fibronogen, 43: 126
with lipoproeteins, 43: 123-124
with lipoproteinlipase, 43: 125-126
with plasmin, 43:126
with platelet factor 4,43: 124-125
with thrombin, 43:122
Cu2+binding. 43: 1 16
deamination
degradation of, 31:232,235
gas-liquid chromatography and, 28:76
D-glucoronic acid
configuration, 43:72-73
residues, 43:71-72
from different sources
biological activity, 43:67
physicochemical parameters, 43:67
Smith-degraded, fragmentation patterns,
43:98
disaccharide
repeating units, 43:53-55
structure. 39:240-241
divalent cation binding, 43: 114-1 16
effect on complement system, 43:126
fast- and slow-moving components, 43:82
fractions
affinity for antithrombin, 43533
characterization, 43:82-83
gas-liquid chromatography of hydrolyzates,
28:75, 78
gel chromatography of, 2 5 4 5
of degradation products of, 25:34
as glycosaminoglycan, 43:52-53
glycosidic linkage, 43:53
anomeric configuration, 43:70
heterogeneity, 43:52, 84
heterogeneous regions, structure, 43:71-
75
hexosamine, 43:53,55
structure, 43:6748
'H-NMR spectrum, 43: 1 11-1 12
hydrodynamic properties, 43: 113-1 14
264 SUBJECT INDEX
Heparin (continued)
hydrolysis of, trifluoroacetic acid in, 28: 16
infrared spectrum, 43:64
interaction
with cells and cell components,
43:126127
with coagulation proteinases, 43: 122-
123
with plasma protein, 43:117-127
isolation, 4 3 5 9 4 0
large-scale columns, 46:62
labeling, 43:105-106
with hydrogen isotopes, 27:138
r-iduronic acid in, 2 8 5 5
linkage region, 43:86-88
structure, 43:74-75
liquid chromatography, 43:64
macromolecular, 43 :56
major uronic acid, 43:53,55,69
Maurice Staceys work, 52: 1 1
molecular conformation, 43: 108-1 13
molecular weight, 43:80
nitrous acid deamination, 31:73-75,43:62,
8695
major fragments from, 43:89-95
nuclear magnetic resonance spectroscopy,
43:64-66
optical rotation, 43:7&71
oxidative hydrolysis of, 31: 190
partial deaminative cleavage, 43:89
periodate oxidation, 43:95-99, 104
physically separable species, 43S3O-84
physiological roles, 43: 132-133
as polyelectrolyte, 43:113-117
proton magnetic resonance spectroscopy of,
27:41
proton nuclear magnetic resonance spectra,
29:26
purification, 43:6061
Purity
assessment, 43:62
criteria, 43:66
quantitation, by photodensitometry, 43:63
radiolabelling of, by N-resulfation, 29:343
Raman spectra, 43:64
repeating units of, 26:432
selective cleavage, 43:84103
separation from other glycosaminoglycans,
43:6O-61
Smith degradation, 43:95-98
solvolytic desulfation, 43: 103
structural and sequence analysis of, 46:49,
57
structure of, 26:15,36:10,316
crystal bibliography, 33:401,35:382,
36:328-329
enzymic analysis, 44:209-216
main building blocks, 43:66-7 1
subfractionation, 43: 8 1-82
sulfated disaccharides, liquid
chromatography, 46:37
sulfur analysis, 43:66
supersulfated, 43: 104
tissue storage, 43:59
tritium labelling of, 29:350
ultraviolet spectrophotometry, 43:64
in urine, 24:443
Heparinase, 43:99- 100,44:21&2 14
cleavage ofheparin, 43:10O-103
Heparinoids, 43: 103-108, 128
preparation of, 29:342-343, 347
Heparin proteoglycan, 43:5657
molecular weight, 43:59
Heparin substitutes, polyglycose sulfates as,
21508
Heparin sulfate
composition, analysis, 4 6 5 5
crystal structure bibliography, 33:401
Heparitin
peptide compound, in urine, 24:444
proton magnetic resonance spectroscopy of,
27:4142
sulfate, 24:291
Heparitinase, see Heparan sulfate lyase
Heparitin lyase, see Heparan sulfate lyase
Heparitin sulfate, 2 5 4 7
as activator of enzymes in trehalose
biosynthesis, 30:243
carbohydrate chains in, 23460
deamination and structure of, 31:75
structure of, 26:433
Hepato-protective activity, of D-
glucohranosiduronic N-phenylthydrazide.
33:215
Heptasaccharide, synthesis, 49:228-229
Heptenitol, hydration, 48:355
Hept-5-enodialdo- 1,4-furanose
7-C-aryl- 1,2-O-cyclohexylidene-5,6-
dideoxy-a-o-xylo-, syntheses by Wittig
reaction, 27:247
 SUBJECT INDEX
3-0-benzyl- 1,2-0-cyclohexylidene-5,6-
dideoxy-a-o-xylo-, synthesis by Wittig
reaction, 27:244
Wittig reaction, with, 27:251
Hept-5-eno- I ,4-furanuronate
butyl3-0-benzoyl- 1,2-0-cyclohexylidene-
5,6-dideoxy-a-~-xylo-,synthesis by
Wittig reaction, 27:257
methyl 3-0-benzyl- I ,2-0-cyclohexylidene-
5,6-dideoxy-P-o-xylu-, synthesis by
Wittig reaction, 27:257
Hept-5-enofuranurononitrile
5-deoxy-1,2-0-isoproplidene-3-0-
(methylsulfony1)-a-o-xylo-, c/s-and
trans-, preparation of, 29:284
E-, and Z-6-fluoro- 1,2-0-isopropylidene-3-
0-methyl-a-o-xylo, preparation,
38:247
Hept-2-enonamidq 4,6:5,7-di-O-benzylidene-
2,3-dideoxy-o-ribo-, synthesis by Wittig
reaction, 27:256
Hept-2-enonate
ethyl 2-bromo-2,3-dideoxy-4,5:6,7-di-O-
isopropylidene-
D - ~ J O synthesis
-, by Wittig reaction.
27:257
L-urubino-, synthesis by Wittig rcaction,
27:257
ethyl 2-bromo-2,3-dideoxy-~-urabino-,
4,5,6,7-tetraacetate, synthesis by Wittig
reaction, 27:257
ethyl 3-deoxy-2-0-ethyl-4,5:6,7-di-0-
isopropylidene-o-aruhino-. synthesis by
Wittig reaction, 27:274
ethyl 2,3-dideoxy-o- and-L-arubino-.
synthesis by Wittig reaction, 27:254
ethyl 2,3-dideoxy-4,5 :6,7-di-0-
isopropylidene-L-urubino-, synthesis by
Wittig reaction, 27:254
ethyl 2,3-dideoxy-~-ribo-,synthesis by
Wittig reaction, 27:254
ethyl 4,6:5,7-di-0-benzylidene-2,3-dideoxy-
D-ribo-, synthesis by Wittig reaction,
27:254
methyl 2.3-dideoxy-3-C-(hydroxymethyl)-,
3 ',4,5,6,7-pentaacetate, synthesis by
Wittig reaction, 27:255-256
Hept-2-enono-l,4-lactone, 50: 167
Hept-2-enononitrile, 4,6:5,7-di-O-benzylidene-
2,3-dideoxy-o-ribo-, synthesis by W h i g
265
reaction, 27:256
Hept-6-enopyranose, 6,7-dideoxy- 1,2:3.4-di-0-
isopropylidene-a-o-guhcto-, synthesis by
Wittig reaction, 27:293
Hept-2-enose
4,6:5,7-di-O-benzyIidene-2,3-dideoxy- 1 -C-
phenyl-o-ribo-, synthesis by Wittig
reaction, 27:246
4,5 :6,7-di-O-cyclohexylidene-2,3-dideoxy-
uldehydo-o-xylo-, synthesis by Wittig
reaction, 27:245
aldehydo-L-aruhino-, synthesis by Wittig
reaction, 27:245
1-C-phenyl-L-urabino-, synthesis by
Wittig reaction, 27:246
Wittig reaction with, 27:252
Heptitols
acetates, gas-liquid chromatography of,
28:64, 128
acetylation of, 28:36
1 -amino-2,6-anhydro-
1 -deoxy-D-glycero-o-guh'to-,
deamination of, 31:51
1-deoxy-o-glycero-L-munno-,deamination
of, 31:52
1,7-deoxy-~-glycero-~-gaIacto-,
deamination of, 31:52
1-amino- 1-deoxy-D-g/ycero-u-
galacto-, deamination and cyclization of,
31:60
gulo-, deamination and cyclization of,
31:60
2,6-anhydro-. 25:248
anhydro-, and derivatives, 25:248, 28 1-
282
2,5-anhydro- 1-deoxy-
1-nitro-o-glycero-L-gluco-, 25:248
1-nitro-o-glycero-r-manno-,25:248
2,6-anhydro- 1 -deoxy-, 1-nitro-o-glycero-L-
manno-, 24:120
2,6-anhydro-3-deoxy-
o-galucto-, 23:73, 24:210, 25:248
0 - g l U C O - , 2 3 ~ 7 2 76.25~248
,
o-manno-, 23:72,76, 25:248
D-talO-, 23~73,24:210,25:248
2,6-anhydro-5-deoxy-, o-ultro-, 25:248
anhydrodeoxy-, characterization by X-ray
analysis, 23:86
2,6-anhydro-o-glycero-
0-gUlO-, 23~92-93, 110, 24:220
266 SUBJECT INDEX
Heptitols (continued)
L-manno-, 23:93,24:220,25:248
2,6-anhydro- 1,3:5,7-di-O-benzylidene-o-
glycero-r-manno-, selective hydrolysis,
39:20
2,6-anhydro-5,7-0-benzylidene- 1-deoxy- 1-
nitro-, 25248
2,6-anhydro-l,3-O-p-anisylidene-5,7-0-
benzyhdene-o-glycero-L-manno-,
selective hydrolysis, 39:20
1-deoxy-
D-glycero-o-galacto-, identity with ~ - a -
fucohexitol and 7-deoxy-o-g~ycero-o-
manno-heptitol, 32:79
1-nitro-o-glycero-L-manno-, dehydration
of, 33: 123
7-deoxy-, L-glycero-D-manno-,identity with
L-a-hcohexitol, 32:79
o-glycero D - ~ u ~ o24:68
-,
3,5:6,7-di-O-isopropylidene-~-glycero-o-
gulo-, selective hydrolysis, 39:23
glycero-gulo-, crystal structure bibliography,
37:379
1,3,4,5,7-pent-O-acety-2,6-anhydi-o-~-
glycero-o-gulo-, 23: 105
synthesis, 40:94
trimethylsilyl ethers, gas-liquid
chromatography of, 2 8 5 8
4,5,7-tri-O-acetyl-2,6-anhydro-
3-deoxy-~-gluco-,X-ray diffraction of,
23:254
3-deoxy-o-manno-, X-ray diffraction of,
23:254
1-O-(p-bromophenylsulfonyl)-3-deoxy-~-
gluco-, 23~72,86
I -0-(p-bromophenylsulfonyl)-3-deoxy-~-
gluco-, crystal structure bibliography,
31:369
Heptodialdo-I,
6-deoxy- 1,2-0-isopropylidene-a-~-gluco-,
23:102
5,6-dideoxy- I ,2-~-ispropylidene-a-~-xyb,
23: 102
4-furanose-7,3-pyranose,5-O-acetyl-6-
deoxy- I ,2-O-isopropyhdene-a-o-
gluco-, nucleoside, and anomer, 23:
105
Heptodialdo- 1,4-furanose, 6-deoxy- 1,2-0-
isopropylidene-a-~-gluco-7-(trimethylene
dithioacetal), preparation of, 32:37
Hepto-3,5-dienofuranuronamide, frans-3,5,6-
trideoxy- 1,2-0-isopropyhdene-a-o-
glycero-, preparation of, 29:285
Hepto-3,5-dienohranurononitrile, 3,5-di-
deoxy- 1,2-0-isopropIidene-a-o-
glycero-, cis-and trans-, preparation of,
29:285
Heptodiulose, 4,5-0-isopropylidene-7-0-
(tetrahydropyran-2-yl)-,2-(trimethylene
dithioacetal), preparation of, 32:39
Heptofuranose
1,5-anhydro-2,3:6,7-di-O-isopropyIidene-p-
o-glycero-o-allo-, 24: 171
2,3:6,7-di-0-isopropylidene-5-0-
isopropylidene-p-D-glycero-D-gub-,
displacement reactions of, 24: 171
Heptofuranoside, methyl 2,3:6,7-di-0-
isopropylidene-p-o-glycero-L-faIo-,
24:171
Heptofuranuronic acid, 5-O-acetyl-3-0-benzyI-
6-deoxy-6-(formamido)- 1,2-0-
isopropylidene-L-glycero-
a-L-allo-, ethyl ester, crystal structure
bibliography, 38:475476
P - D - t d O - , ethyl ester, crystal structure
bibliography, 38:475
Heptofuranurononitrile
3-azido-3,6-dideoxy- 1.2-0-isopropylidene-
a-D-gluco-, double @-eliminationin,
29:285
6-deoxy- 1,2-0-isopropylidene-3,5-di-0-
(rnethykulfonyl)-a-D-ghco-, double p-
elimination in, 29:284
3,5,6-trideoxy- 1,2-0-isopropylidene-p-~-
fhreo-, preparation of, 29:29 1
Heptonamide
3-acetamido-2,3-dideoxy-4,5:6,7 di-0-
isopropylidene-L-arabino-,preparation
of epimers, 27:263
3,4,5,7-tetra-O-acety1-2,6-anhydro-o-
glycero-L-gluco-, anomeric equilibrium,
47:65
Heptonate, ethyl 2,3-(Nbenzylepimino)-2,3-
dideoxy-L-glycero-L-galacto-, 4,5,6,7-
tetraacetate, preparation of, 27:264
Heptonic acids
3-amino-3-deoxy-, deamination of, 31:60
7-amino-7-deoxy-, derivatives, synthesis,
39:63
o-glycero-D-gulo-, analytical high-
 SUBJECT LNDEX
performance liquid chromatography,
46:34
Heptono-l,44actone
o-glycero-D-gulo-, selective periodate
oxidation of, 33:94
3,5:6,7-di-O-isopropylidene-o-gul~~-,
selective hydrolysis, 39:23
Heptonolactones
gas-liquid chromatography of, 28:72
trimethylsilylation of, 28:28
Heptononitrile
2,3,4,5,6,7-hexa-0-acetyl-~-g/ycero-n-
gulucto-, ammonolysis of. 31:83-84
hexa-O-acetyl-D-glycero-D-gu/o-,
ammonolysis of, 31:83
2,3,4,5,6,7-hexa-0-benzoyl-~-glycrro-
o-gzrlo-, ammonolysis of, 31:84
L-manno-, ammonolysis of, 31:84
Heptonoyl cobalt tricarbonyl triphenyl-
phosphine, 2,3,4,6-tetra-O-acetyI-2,6-
anhydro-o-g!vcero-o-gulo-, 23: 1 I0
Heptopyranose
1,4-anhydro-2,3 :6.7-di-O-isopropyl idene-a-
D-glycero-D-ullo-,synthesis, 39: 168
D-glj,cero-P-o-gulo-,crystal structure
bibliography, 38:436
6,7-dideoxy- 1,2:3,4-di-O-isopropylidene-7-
(diethoxymethylsilyl)-a-o-gul[~~,to-.
synthesis of, 27:293
Heptopyranoside, methyl P-D-gl?icero-u-gtr/o-
oxidation, 36:73
selective periodate of, 33:94
Heptose
3-acetamido-3-deoxy-, 24: 112
3,6-anhydro-2-deoxy- 1-C-(p-
methoxypheny1)-o-xylo-, synthesis by
Wittig reaction, 27:285
4,7-anhydro-~-glycero-~-munno-, diethyl
dithioacetal, preparation of, 32:48
7-deoxy-
glycero-gulo-, synthesis, 40:95
L-glycero-L-gulacto-, 21: 178
2-deoxy-o-
galucto-. 24: 127,264
manno-. 24:264
6-deoxy-~-,from liposaccharide from
Pusteurellu pseudotuberculosis, mass
spectrum of, 29:54
D-glycero-D-gulacto-
hexaacetate and hexabenzoate,
267
ammonolysis of, 31:87
synthesis of, 27:294
D-glycero-D-gulo-
dithioacetals, reaction with sulfonyl
chloride, 32:48
effect of calcium chlorode on equilibrium
rotation of, 21:230-231
hexaacetate and hexabenzoate.
ammonolysis of, 31:87
hydrolysis of, 22:45
o-g/ycero-D-ido
composition in aqueous solution, 42:3 1,
35-36,65
2,3 :6,7-dI-O-isopropylidene-o-glycero-
o-gulo-, composition in aqueous
solution, 42:59
purification of, dithioacetal in, 32:6 1
o-gljlcero-D-man no-
ester of guanosine 5'-pyrophosphate,
28:320
synthesis, 41:8-9
D-glycero-L-ido-,synthesis of, 27:294
o-glycero-L-munno-
diethyl dithio acetal, reaction with sulfonyl
chloride in pyridine, 32:48
gas-liquid chromatography of, 28:59
hexaacetate and hexabenzoate,
ammonolysis of, 31:87
o-glycero-r-tulo-,47:39
2,6-dideoxy-~-munnu-,24:264
dithioacetals, physical constants of, and
peracetates, 32: 1 13
hexa-0-acety l-u/dehydo-D-glvcero-
D- gU/UCtO-
preparation of, 32:62
reaction with acetic anhydride in
pyridine or in sulfuric acid, 32:69-
70
L-gluco-, preparation of, 3 2 6 2
1,2,3,4,5,6-hexa-0-acetyl-7-O-trityl-~-~-
glycero-n-gulucto-, detritylation and
acyl migration in, 33: 106
2,3,4,5,6-penta-0-actyl-7-O-p-tolylsulfonyl-
aldehydo- D-glycero-D-gulo-,
rearrangement in zinc chloride-acetic
anhydride, 26: 194
4,5,7-tri-O-acetyl-2,6-anhydr0-3-deoxy-
uldehydo-o-
gluco-, 23: 86
manno-, 23:86
268 SUBJECT INDEX
Heptose aldehydrol, 1,2,3,4,5,6-hexa-O-acetyl-
7-O-p-toly lsulfonyl-aldehydo-o-glycerol-
L-manno-, rearrangement in zinc chloride-
acetic anhydride, 26: 194
Heptoseptanoside, methyl 5-7-0-benzylidene-
3-deoxy-2,4-di-O-methyl-3-nitro-,
24:133
Heptoses, 48:285-287
deoxy-, melting points and optical rotations
of, 26:288
gas-liquid chromatography of, 28:49,54
trimethylsilyl derivatives, gas-liquid
chromatography of, 28: 109
Heptosylamine, N-benzoyl-o-glycero-L-
manno-, preparation of, 31:87
Heptulopyranose
7-acetamido-7-deoxy-~-galacto-, 23: 178
2,7-anhydro-
p-0-
ultro-
acetylation of, 33:24
catalytic oxidation of, 33:87
alfro-, monohydrate, crystal structure
bibliography, 31:366
carbon-I 3 nuclear magnetic resonance
spectroscopy, 41:5 I
conformations of, and tetraacetates,
26:116
optical rotation and conformation of,
and acetates, 26:61
4-deoxy-4-nitro-~-o-u/lo-,24:95
4-deoxy-4-nitro-~-o-gulo-,24:95
1,3:4,5-di-O-methylene-p-~-ulfro-,
26:252
formation by mutarotation, 24:46
4,5-O-isopropy~idene-p-~-uho-, 26:252
structure and proton magnetic spectra
of, 26:227
3,4-O-isopropylidene-p-~-manno-, 26:253
5,7-O-ethylidene-a-~-ulfro-, 26:253
1,3,5-tri-O-acetyl-2,7-anhydro-~-~-altro-,
preparation of, 33:24
a-~-manno-2-Heptulopyranose,crystal
structure, 43:219-220
2-Heptulopyranose
2,7:4,5-dianhydro-P-o-dfro-, structure of,
34: I09
2,7:3,4-dianhydro-P-~-manno-, structure of,
34: 109
3,4,5-tri-O-acetyl- 1,7-dibromo-6-
(chloromethyl)-l,7-di-deoxy-au-o~-
ido-,crystal structure bibliography,
38:458--459
4-Heptulopyranose, 1,2:6,7-di-O-isopropyl-
idene-3-oxa-a-o-ribo-, 23:268
Heptulopyranoside
ol-D-glucopyranosyl4-amino-4-deoxy-p-~-
gluco-, 2 4 ~ 9 7
methyl 4-deoxy-4-nitro-a-o-gluco-, 24:97
Heptulopyranosidonic acid, methyl 4,5-di-0-
benzoyl-3,7-dideoxy-7-iodo-a-~-arabino-,
methyl ester, crystal structure of, 25:69
Heptulose
1-deoxy-o-
gulacto-, 48:354-355
gluco-, 48:356
5,7-dideoxy-~-xylo-,synthesis, 49: 194
2-Heptulose, I -deoxy-, preparation of, 31:51
3-Heptulose
uffro, composition in dimethyl sulfoxide,
42:68
o-alfro-
in aqueous solution, 42: 16,41
crystal structure bibliography, 30:451
1,2,4,5,6,7-hexa-O-(triemthylsilyl)-keto-,
28:25
trimethylsilylation of, 28:25
D-munno-, monohydrate, crystal structure
bibliography, 31:366
trimethylsily ethers, mutarotation, 42:23
Heptuloses, 49:28
a-0-ghCO-, conformation of, 23:30
a-o-gluco-2-, sweetness-structure
relationship, 49253-254
a-D-munno-, difference-circular dichroism
spectra, 4 5 8 1
ol-D-?nUnn0-2-,sweetness-structure
relationship, 45253-254
a-o-tul0-2-, sweetness-structure
relationship, 45253-254
2,7-anhydro-P-o-a~t-,cyclic acetals,
26:252
I-bromo-l -deoxy-o-galacfo-, 22: 197
1-chloro-1-deoxy-o-galacfo-, 22: 197
composition in solution, 42:29,40-12,66
cyclic acetals, 26:252
properties of, 26:275
ol-D-UhO-2-, sweetness-structure
relationship, 45253-254
0-UlfrO-, taste properties, 45254
 SUBJECT INDEX
deoxy, composition in solution, 42:4042
7-deoxy-o-a~tro-,taste properties, 45:254
1-deoxy-o-manno-, taste properties,
45:254-255
7-deoxy-~-galacto-.taste properties, 45:254
o-gluco-
in aqueous solution, 42: 17
hexaacetate, reaction with ethanethiol.
32:34
1,3-dideoxy-4,5:6,7-di-O-isopropylidene-o-
arabino-, diethyl dithioacetal,
preparation of, 32:59
o-manno-
conformation of, 23:32
as plant-growth substance, 21:4 I6
halogen derivatives of, 22:227
ido-, in aqueous solution, 42: 17
L-allo-, taste properties, 45:254
I.-gulucto-
conformational equilibria. 23:32
taste properties, 45:254
L-gluco-, taste properties, 45:254
5,7-0-ethylidene-keto-~-manno-, 26:253
3,4,5,6,7-penta-O-acetyl- 1-chloro- 1 -deoxy-
o-galaczo-, reaction with triethyl
phosphite, 28:285
trimethylsilylation of, 28:25. 28
Heptuloside, methyl a-oL-gluco-, synthesis,
40:7 1
a-Heptuloside, formation. 48:356
Heptulosonate, ethyl 3-deoxy-4,s-0-
isopropylidene-o-arabino-, synthesis of,
27:279
2-Heptulosonic acid, 3-deoxy-4-O-methyl-~-
arabino-, periodate-thiobarbituric acid
assay, 38:33 1-332
Heptulosonic acid 7-phosphate, 3-deoxy-n-
arabino-2-, 49:206-207
5-Heptylbarbituric acid, cyclodextrin inclusion
complexes with, 46:223-224
Hept-1 -ynitol
4,5-0-isopropylident-7-O-trityl-o-allo-,
cyclization of, 33: 130
4,5,7-tri-O-benzyl-o-allo-, p-toluene
sulfonylation of, 33: 129
Hept-5-ynofuranose, 1,2-O-isopropylidene-3-
O-methyl-6-pheny1, preparation,
38:246-247
Hept-6-ynofuranose, 6,7-dideoxy-1,2-0-
isopropylidene-
269
p-L-ido-, 24:260
ol-D-g/UCO-. 24~260
Herbicides
3-amino-S-triazole, 21 :399
benzoic acid derivatives, 21:407
carbamates and carbanilates. 21:403
chlorinated aliphatic acids, 21:402
I ,4:3,6-dianhydrohexitolsas. 49: 170
maleic hydrazide. 21:398
phenoxyacetic acids, 21:392
plant-growth substances as, 21:392
s-triazines, 21:406
for sugarcane, 21:422
urea derivatives, 21:404
Herdan relations, 47:375
Hemandulcidin, sweetness-structure
relationship, 45:295-296
Herpes infections, glycosylation inhibition
effect, 40:369-370
Herpesvirus- 1. adenine nucleoside activity
against, 42: I3 1
Hesperitin dihydrochalcone-4-yI p-D-
galactopyranoside, taste properties, 45279
Hesperitin dihydrochalcone-4-yI p-D-
xyloside. taste properties, 45:280
Heterocyclic compounds
formation by ammonolysis, 31:89, 12&125
lithiated. addition to aldonolactones.
50: 138-1 39
nitrogen, synthesis from saccharide
derivatives, 25:35 1 4 0 5
as solvents for sugars, 27: 107, 1 I I , I 17
from sugars and aqueous ammonia,
25:3 1 1-349
sulfur-containing, preparation of, 32:20
Heterogalactans, 23:410
Heteroglycans. hydrolysis of, 28: 14
Heteropolymolecular, defined, 24:337
Heteropolysaccharides, 23:403,411
p-eliminative degradation of, 29:238-252
biosynthesis of, 26:403439
branched, 41:95-100
galactan main-chains, 41: 100-101
o-mannan main-chains, 41:89-100
methylation of, 30: 12
properties of, of Cvptococcus and Tremella
species, 23:416
Heteroxylans, in plant cell-walls, 42:275
Heuser, Emil. obituary of, 15:l-9
Hevea brasiltensis, apiose from. 31: 139
270 SUBJECT INDEX
Heveaprenol, structure, 44:346
Hexadecanoic acid
ester of trehalose 2-sulfate, in
Mycobacterium tuberculosis, 30:236
methy ester, transesterification of methyl a-
o-glucopyranoside with, 33:44
2P-Hexadienedioic acid, 2,5-dimethoxy-6-oxo-
and dimethyl ester, 33:22,229
preparation of, 33:225
2,4-Hexadiene- 1,6-diol, substrate for sugar
synthesis, 40:26
2P-Hexadienoic acid, see Sorbic acid
1,4-Hexadien-3-one, I-chloro-, substrate for
carbohydrate synthesis, 40:27
3,5-Hexadien-2-one, 3,4,5-trihydroxy-, from
dehydration of D-fructose, 28: 176, 180
Hexafluoro-2-propanol, 1,1,1,3,3,3-, as solvent
for circular dichroism studies, 45:96-97
Hexahydro-exo-methylenepolyprenol,structure,
44:346
Hexahydropolyprenol, structure, 44:346
Hexakis(cyclohexylammonium) myo-inositol
hexasulfate, hydrate, 43:370
Hexanal, 2,6-diethoxy-4-0~0-,diethyl acetal,
24:218
Hexanedioate, dimethyl (+)-3,4-dihydroxy-, p-
elimination of diacetate and
dimethanesulfonate of, 29:235
1,6-Hexanediol, cyclic phenylboronate,
preparation, 35:35
2,4-Hexanedione, formation of, 46:3 18
1-Hexanethiol
odor of, 32: 17
reaction with L-arabinose, 32:22
Hexanoic acid
amylose ester, preparation of, 29:330
2-ethyl-,l -ester with b-D-glucuronic acid,
36: 104
1-Hexanol, cyclodextrin inclusion complexes
with, 46:222-224
Hexanone, 1,6-dihydroxy-2-, dimerization
products, 52:228-229
2-Hexanone, 6-hydroxy-, acyclic form in
aqueous solutions of, 42:30
HeXa-O-~-D-glUCOpyranOSyl-D-glUCitOlS
isomeric, liquid chromatography separation,
46:4142
preparative liquid chromatography, 46:60
Hexasaccharide, from human milk, acetolysis
of, 31:199
Hex-2-enamide, N,N-dimethyl-2,4,6-tri-O-
24:263
benzyl-3-deoxy-~-thero-,
Hex-4-enaro-6,3-lactone,4-deoxy-2,5-di-O-
methyl-L-threo-, methyl ester, preparation
of, 33:202,219,221
1-Hexene
-o-ribo- 1,3,4,5,6-pentol, 3,6-anhydro-4,5-0-
isopropylidene- 1-S-methyl- 1-thio-,cis-
and trans-, synthesis by Wittig reaction,
27:27 1
-~-ribo-3,4,5,6-tetrol,1-C-nitro-, tetraacetate,
21:304
- D - x ~ ~ o1,3,4,5,6-pentol,
- 3,4:5,6-di-O-
cyclohexylidene- I -0-methyl-, synthesis
by Wittig reaction, 27:271
-~-arabino- 1,3,4,5,6-pentol
3,4:5,6-di-O-cycIohexylidene- 1-0-methyl-
, synthesis by Wittig reaction,
27:271
3,4:5,6-di-O-isopropylidene-l-O-methyl-,
synthesis by Wittig reaction, 27:271
3,4:5,6-di-O-isopropylidene-
1-0-p-tolyl-,
synthesis by Wittig reaction, 27:271
3,4:5,6-di-O-isopropylidene- 1-S-methyl-1-
thio-, synthesis by Wittig reaction,
27:271
tetraacetoxy-trans- 1-nitro-, conformation of
o-arabino, D-xylo. and D-ribo-, 26:72
3,4,5,6-tetrol, 3,4:5,6-di-O-isopropylidene-~-
arabino-, synthesis by Wittig reaction,
27:234
2-Hexene, 1-(2,3,5-tri-O-benzoyl-P-~-
ribofuranosy1)- preparation of, 33: 162
D-arabino-Hex- 1-enitol, 1,2-dideoxy- 1,l-
difluoro-3,4:5,6-di-O-isopropylidene-, 'H-
and I9F-NMR data for, 46: 159
Hex- 1-enitol
1,5-anhydro-
3-C-butyl- 1,2,6-trideoxy-~-auabino-,
synthesis, 39: 142-143
D-arabino-
dehydration (theoretical) of, 28: 184
3,4,6-tri-O-acetyl-2-deoxy-2-
thiocyanato-, 44: 144
2-deoxy-o-arubino-, as inhibitor of a - ~ -
mannosidase activity, 28:420
2-deoxy-o-&xo-, mercaptalation of,
32:28
4,6-0-benzylidene-2,3-dideoxy-3-
(iodomethy1)-o-arabino-, proton
 SUBJECT INDEX
magnetic resonance spectroscopy of,
27:29
4,6-0-benzylidene-2,3-dideoxy-3-
(iodomethy1)-o-ribo-, proton
magnetic resonance spectroscopy of,
27:29
4,6-O-benzylidene- 1,2,3-trideoxy-3-C-
(iodomethy1)-o-arabino-, preparation
of, 28:306
4,6-0-benzylidene- 1,2,3-trideoxy-3-C-
(iodomethy1)-D-ribo-,preparation and
methanolysis of, 28:305
4,6-0-benzylidene- 1,2,3-trideoxy-3-C-
methylene-o-erythro-, preparation of,
28:306
1-C-butyl-3,4: 5,6-di-O-cycIohexylidene- 1,2-
dideoxy-o-qlo-, synthesis by Wittig
reaction, 27:236
1-C-p-anisyl-3,4:5,6-di-O-cyclohexylidene-
1.2-dideoxy-
D - x ~ ~ o - ,synthesis
by Wittig reaction.
27:236
~-arabino-,synthesis by Wittig reaction,
27:236
2-cyano- 1,2-dideoxy-3,5:4,-6-di-O-
etbylidene-L-xylo-, preparation, 38:
313
I ,2-dideoxy-
1,l -bis(ethylsulfonyl)-o-urabino-,
formation of, 32:86
1-C-hexyl-L-urabino-, synthesis by Wittig
reaction, 27:231
1-C-pentyl-L-arubino-, synthesis by Wittig
reaction, 27:237
3,5:4,6-di-O-ethylidene- 1-C-nitro-L-.Yyh-,
preparation, 38:3 12
3,4:5,6-di-O-isopropylidene-o-thrro-,
24:26 1
3,4,6-di-O-acetyl- 1,5-anhydro-2,3-di-deoxy-
isothiocyanato-o-ribo-3-, 44: 142
3,4:5,6-di-0-cyclohexylidene-l,2-dideoxy- 1-
C-
hexyl-o-$0-, synthesis by Wittig
reaction, 27:236
hexyl-L-arabino-, synthesis by Wittig
reaction, 27:236
methyl-o-qb, synthesis by Wittig
reaction, 27:236
methyl-L-arabino-, synthesis by Wittig
reaction, 27:236
21 1
1-naphthyl-1.-urubino-, synthesis by Wittig
reaction, 27:236
pentyl-o-xylo-, synthesis by Wittig
reaction, 27:236
pentyl-L-arabino-, synthesis by Wittig
reaction, 27:236
phenyl-o-xylo-, synthesis by Wittig
reaction, 27:236
phenyl-L-arubino-, synthesis by Wittig
reaction, 27:236
(p-nitrophenyl)-o-.rylo-, synthesis by
Wittig reaction, 27:236
(p-nitropheny1)-L-arubino-,synthesis by
Wittig reaction, 27:236
propyl-L-arubino-, synthesis by Wittig
reaction, 27:236
1,2:4,5-di-O-isopropylidene-3-O-methyl-o-
urabino-, synthesis, 39: 145
6-0-acetyl- 1,5-anhydro-3-azido- 1,2,3-
trideoxy-4-0-(2,3,4.6-tetra-O-acetyl-a-
o-g~ucopyranosy~)-o-ribo-, synthesis,
39:242
3,4,5,6-tetra-O-acetyyl-
1-deoxy- 1 -nitro-D-rib, proton magnetic
resonance spectroscopy of, 27:23
1-deoxy- I -nitro-o-qlo-, proton magnetic
resonance spectroscopy of, 27:23
1,2-dideoxy-l,I-bis(ethylsulfony1)-o-
urubino-, preparation of, 32:83, 85
1,2-dideoxy- I -nitro-o-arabino-, proton
magnetic resonance spectroscopy of,
27:71-72
1,2-dideoxy-l-nitro-o-xylo-, proton
magnetic resonance spectroscopy of,
27:12, 11
2,3,4,6-tetra-O-acetyI- 1,5-anhydro-~-
arabino-
alkaline degradation of, 28:205
crystal structure, 43:235-236
3,4,6-tri-O-acetyl-
1,5-anhydro-o-, conformation of, 26: 122
1,5-anhydro-2-deoxy-~-arabino-, crystal
structure, 43:228
1,5-anhydro-2-deoxy-o-arabino-, reaction
with lead tetrafluoride, 25: 196
I ,5-anhydro-2-deoxy-2-isothiocyanato-~-
arubino-, 44: 142
2-(N-acetylacetamido)- 1,5-anhydro-2-
deoxy-o-arabino-, crystal structure
bibliography, 38:432,464
272 SUBJECT INDEX
Hex-1 -enitol (continued)
2-(N-acetylacetamido)-1,5-anhydro-2-
deoxy-D-bxo-, crystal structure
bibliography, 38:464-465
2-(N-acetylacetamido)- 1,5-anhydro-2-
deoxy-o-xylo-, crystal structure
bibliography, 38:465466
Hex-2-enito1, 1,3,4,5-tetra-O-acetyI-2,6-
anhydro-L-threo-, dehydration of, 28: 184
reaction with hydrogen bromide, 28:266
Hex-3-enitol
3-4-dideoxy-1,2:5,6-di-O-ispropylidene-
trans-D-
erythro-, 24:230
thero-, 24:230, 261
1-0-benzoyl 1-4-deoxy-2,3:5,6-di-O-
isopropylidene-o-thero-, 24:261
6-0-benzoyl-3-deoxy-l,2:4,5-di-0-
ispropyhdene-o-threo-, 24: 158
Hex-4-enitol
1-5-anhydro-2,3,4,6-tetra-O-benzoyl-~-
thero-, 24:254
1,5-anhydro-2,3,6-tri-O-benzoyl-4-deoxy-~-
erythro-, 24:254
2,3,6-tri-O-acetyl-I ,5-anhydro-4-deoxy-~-
threo-, 24:254
Hex-5-enitol
2,5-anhydro-l -S-benzy1-6-deoxy-3,4-di-O-
(p-nitrobenzoy1)- 1-thio-D-xylo-, 24:252
2,3,4-tri-O-acetyl- 1,-5-anhydro-6-deoxy-~-
xylo-, 24:259
Hex-1-enitols, 1,5-anhydro-2-deoxy-
, I ,6anhydrohexoses from, 34:4748
Hex-2-enno- 1,5-lactone, 4,6-0-benzylidene-
2,3-dideoxy-o-
eiythro-, 24: 1 13
thero-, 24: 1 14
Hex-4-enodialdo-l,5-pyranoside, ethyl 4-
deoxy-2,3-di-O-methyI-a-~-threo-,
preparation of, 31:222
Hex-4-eno- 1,6-dialdo-l,5-pyranoside
methyl 4-deoxy-6-nldehydo-aY-~-threo-,
preparation of, 29:272
methyl 2,3-di-O-acetyl-4-deoxy-
6-aldehydo-P-o-erythro-, preparation of,
29:271
P-L-threo-, reactions of, 29:300
Hex-2-enofuranose
2-acetamino-2,3-di-deoxy-5,6-0-
isopropylidene-a-o-erythro-, crystal
structure bibliography, 37:385
3-deoxy-2-O-methyl-P-~-erythro-,24:238
3-dexoy-2,5,6-tri-O-methyl-o-erythro-,
24:23 1
Hex-3-enofuranose
a-D-eVthro-, 3-deoxy- 1,2:5,6-di-O-
isopropylidene-, synthesis, 44: 139
3-deoxy- I ,2:5,6-di-O-isopropylidene-
a-D-erythro-, 22: 180, 24:246
o-erythro-, 21:163
Hex-5-enofuranose
6-deoxy-6-fluoro- 1,2-O-isopropyldene-3-0-
methyl-6-(methylphenylamino)-a-~-
qdo, preparation, 38:246
D-eiythro-, 3,5,6-trideoxy-6,6-difluoro- 1,2-
O-isopropylidene-a-
I3C-NMR data for, 46: 176
'H- and I9F-NMR data for, 46:154
5,6-dideoxy- 1,2-0-isopropylidene-
a-D-
irradiation, with 1,3-dioxolane, 39530
X J ~ O - ,24~255
0x0 reaction with, 23:lOl
reaction with iodine azide, 28:271
reaction with iodine azide with iodine
trifluoroacetate, 28:271
reaction with iodine a i d e with silver
trifluoroacetate and iodine, 28:272
xylo-, and acetate, synthesis by Wittig
reaction, 27:234, 293
xylo-, photochemical addition with 1,3-
dioxolane, 38: 118-1 19
3-o-Ct-D-XylO-, 24:255
5,6-didoxy-6,6-difluoro- 1,2-0-
isopropylidene-3-O-methyl-a-~-xy~o-,
preparation, 38246
o-ribo-, 5,6-dideoxy-6,6-difluoro-1,2-0-
i~opropylidene-O-methyl-a-,'~C-NMR
data for, 46: 176
D-XY~O-, 1,2-O-isopropylidene-5,6-dideoxy-
6,6-difluoro-3-O-methyl-a-, H- and
I9F-NMR data for, 46: 154
L - ~ ~ x o5,6-dideoxy-6,6-difluoro-
-, I ,2-0-
i~opropyIidene-3-O-methyl-f3-,'~C-
NMR data for, 46: 176
3-0-acetyl-5,6-dideoxy-1,2-0-
isopropylidene-
a-D-XY~O-, reaction with nitryl iodide,
28:270,299
6-C-nitro-a-~-xylo-,24:256
 SUBJECT INDEX
6-nitro-a-o-xylo-, preparation of, 28:2
99
3-0-benzyl-5,6-dideoxy-1,2-0-
isopropylidene-
cU-D-X,VlO-, 24~255
a - ~xylo-,
- synthesis by Wittig reaction,
21:293
3,5-0-benzylidene-6-deoxy- 1,2-0-
isopropylidene-, C U - D - X ~ ~ O22:202
-.
2.3,5-tri-O-acetyl-l,6-anhydro-P-~-urnhino-,
preparation of, 34: 156
Hex-3-enofuranoside, 4,6-dichloro-4.6-
dideoxy-a-o-galactopyranosyl1,4,6-
trichloro- 1,3,4,6-tertradeoxy-2.3-di-O-
sulfo-P-D-g[ycero-, physical properties
of, 33:294
dideoxy-2.3-di-O-sulfo-a-~-
galactopyranosyl 1,4,6-trichloro-
1,3,4,6-tetradeoxy-P-~-g[ycero-.
preparation of, 33:261
Hex-4-enofuranoside, methyl 5,6-dideoxy-2,3-
0-isopropylidene-P-n-eryfhro-, reaction
with bromine in chloroform or carbon
tetrachloride, 28:269
Hex-5-enofuranoside
5,6-dideoxy-2,3-O-isopropylidene-P- v-riho-, Hex-2-enopuranoside
preparation of, 31:56
D-riho-, methyl 5,6-dideoxy-6,6-difluoro-
2,3-O-isopropylidene-a-
13C-NMR data for, 46: 176
'H- and I9F-NMR data for. 46: 154
methyl 5,6-dideoxy-
2,3-di-O-p-to~ykulfony~-a-~-arabino-,
reaction with iodine trifluoroacetate,
28:273
with nitryl iodide, and with iodien
azide, 28:270-27 I , 299
6-nitro-2,3-di-O-p-tolylsulfonyl-a-~-
arubino-, preparation of, 28:299
2,3,4,6-tetra-0-acety~-a-~-glucopyranosyl
1,3,4-tri-0-actyl-6-deoxy-P-o-/hre~~-
preparation of, 33:264
reduction of, 33:266
2-Hexenoic acid, cis-4,5-epoxy-, resolution,
40:114
4-Hexenoic acid
3(R)-hydroxy-3(R)-methyl-, preparation,
40:114
trans-3-hydroxy-3-methyl-, methyl ester.
precursor for sugar synthesis, 40:2 I
273
Hex-5-enonic acid
3,4-di-O-acetyI-2.6-anhydro-5-deoxy-o-~yxo-
, methyl ester, preparation, 36:61
3,4.5-tri-0-acetyl-2,6-anhydro-o-lyxo-.
methyl ester, preparation, 36:61. 78
Hex-2-enono- I ,4-Iactone
2-acetamido-2,3-dideoxy-
o-erythro-, crystal structure bibliography,
38:437
D-threo-, crystal structure bibliography.
37:380
5,6-O-isopropylidene-~-threo-. crystal
structure bibliography. 38:44044 I
o-erythro-. see u-Erythorbic acid
I -threo-, see Ascorbic acid, I.-
2-mesyslates, 50: 167
2-O-benzyl-3-deoxy-~-threo-. preparation of,
33:220-22 I
Hex-2-enono- 1,j-lactone
2,4-di-0-benroyl-3,6-dideoxy-i.-eryrhro-,
50: 164
2,4,6-tri-0-benzoyl-3-deoxy-1~-erythro-,
synthesis. 49:90-91
Hex-2-enono- 1,5-lactone, 2,3,4,6-tetradeoxy-
m-glycero-. see Parasorbic acid
cholesteryl4.6-di-0-acetyl-2,3-dideoxy-a-o-
erythro-, 24:215
6-deoxy- 1,2:3,4-di-O-isopropylidene-a-~-
galactopyranos-6-yl4,6-di-O-acetyl-
2,3-dideoxy-a-o-etyhro-, 24:2 15
4,6-di-0-acetyI-2,3-dideoxy-i~ervthro-hex-
2-enopyranosyl4,6-di-O-acetyI-2,3-
dideoxy-o-ecvthro-. 24:2 16
ethyl 4,6-di-O-acetyl-2,3-dideoxy-a-~-
erythro-, 24:2 15
methyl 2-azido-4,6-0-benzylidene-2.3-
dideoxy-a-n-eythro-, 24:244
methyl 4,6-di-U-acetyl-2,3-dideoxy-a-o-
erythro-, 24:232
threo-, 24:215
methyl 4,0-acetyl-2,3,6-trideoxy-3-C-
methyl-L-threo-, 24:246
methyl 4,6-O-benzylidene-
3-cyano-2,3-dideoxy-a-~-y!~rhro-,
24:246
3-deoxy-2,S-methyI-2-thio-a-o-ey/hro-,
24:244
3-deoxy-2,S-phenyl-2-thio-a-o-enThro-,
24:244
274 SUBJECT INDEX
Hex-2-enopuranoside (continued)
2,3-dideoxy-a-~(andP-D)-eryfhro-,
24:232,244-245,249
2,3-dideoxy-a-o(and P-o)-ihreo-, 24:
232
2,3-dideoxy-3-C-nitro-cr-o-erythro-,
24:243
2,3-dideoxy-3-C-nitro-cY-o-threo-, 24:
243
2,3-dideoxy-3-C-nitro-P-~-eyZhro-,
24:242
2,3-dideoxy-3-phenylazo-0~-~-eythro-,
24:243
2,3-dideoxy-2-pyrroIidinyl-c~-o-eyihro-,
24:244
Hex-2-enopyranoglycan,2,3-dideoxy-6-0-
trityl-a-D-eythro-, bromination in
methanol and silver acetate, 28:268
Hex- 1-enopyranose
tetra-0-acetyl-I-deoxy-
D-
arabino, 0x0 reaction with, 23:93
0x0 reaction with, 23:92
D-~YXO-, 0x0 reaction with, 23:93
1,2,6-trideoxy-3,4-di-O-p-nitrobenzoyl-o-
ribo-, 21:299
Hex-2-enopyranose
2-acetamid0-2,3-dideoxy-o-thero-, 24:244
1,6-anhydro-2,3,4-trideoxy-P-~~-g~cero-,
preparation and epoxidation of, 34:48
4,6-di-0-acetyl-2,3-dideoxy-o-eythro-,
24:216
4,6-di-0-benzoyl-2,3-dideoxy-o-eyihro-,
24:216
3-0-acetyl- 1,6-anhydro-2,4-dideoxy-P-~-
glycero-, preparation of, 34: 103
1,2,4,6-tetra-O-acetyl-3-deoxy-
p-D-eythro-, 24:222
o-eyihro-, conformations of anomers,
24:241
tetra-O-acetyI-3-deoxy-c~-o-eyihro-
conformation of, and p-D anomer, 26:
123
0x0 reaction with, 23:94-95
1,2,4,6-tetra-O-acety1-3-deoxy-0~-~-ihreo-,
24:223
tetra-O-acetyl-3-deoxy-c~-~-Zhreo-, 0x0
reaction with, 23:99
1,4,6-tri-U-acetyl-
2,3-dideoxy-a-o-fhreo-, 24:2 14
2,3-dideoxy-~-eyihro-,24:2 13
2-(N-acetylacetamido)-2,3-dideoxy-a-o-
threo-, crystal structure bibliography,
37:399
2-(N-acetylacetamido)-2,3-dideoxy-~-
ihero-, 24:243
2,4,6-tri-0-benzoyl-3-deoxy-
L-ihreo-. 24:240
l-O-(trichloracetyl)-a-o-eyfhro-,24:
223
Hex-3-enopyranose
1,6-anhydro-3,4-dideoxy-P-~~-eyfhro-,
synthesis, 40:49
4-0-acetyl- 1,6-anhydro-2,3-0-
isopropylidene-p-D-ihhveo,preparation
of, 34:98
Hex-5-enopyranose
1,2,3,4,-tetra-O-acety~-6deoxy-~-~-xylo-,
hydrogenation of, 33:265
6-deoxy- I ,2:3,4-di-O-isopropyIidene-p-~-
arabino-
formation of, 28:246
preparation by irradiation, 28:304
Hexenopyranoses, 1,6-anhydro-, preparation of,
34: I45
Hex-2-enopyranoside
D-eyfhro-, 2,3,6-trideoxy-6-fluoro-a-
ethyl 4-0-acetyl-, 'H- and l9F-NMR data
for, 46: 134
methyl 4-O-acetyl-, 'H- and 19F-NMR
data for, 46: 134
ethyl OL-D-
eyihro-, 4,-deoxy-6-O-(methylsulfonyl)-
4-thiocyanato-, 44: 144
ihreo-6-azido-2,3,4,6-tetradeoxy-4-
thiocyanato-, 44: 144
2,3,4-trideoxy-6-0-(methylsulfonyl)-4-
thiocyanato-, 44: 144
ethyl 4,6-di-0-acetyl-2,3-dideoxy-a-o-
eryihro-, reaction with lead
tetrafluoride, 25: 196
ethyl 4-0-acetyl-
2-,-3-dideoxy-6-0-p-tolylsulfonyl-cu-o-
erythro-, fluorination, 38:206
2,3,6-trideoxy-6-fluoro-cu-~-eyihro-,
preparation, 38:24 1-242
ethyl 6-0-benzoyl-2,3,4-trideoxy-4-iodo-c~-
D-ihreo-, crystal structure bibliography,
37:395
ethyl 4-0-benzyI-2,3,6-trideoxy-6-fluoro-a-
 SUBJECT INDEX
o-erythro-, preparation, 38:209
ethyl 2,3,6-trideoxy-6-fluoro-a-~-e~~i~th~o-.
preparation, 38:242
methyl 4,6-0-benzylidene-2.3-dideoxy-.
22:204
methyl a-o-erythro-2,3-didexoy-, synthesis,
44:135
4,6-0-benzylidene-2,3-dideoxy-,
synthesis, 44: 135
methyl 3-deoxy-2,4,6-tri-0-methyl-o-
evythro-, conformation of, 26: 123
methyl 4,6-di-U-acetyl-2,3-dideoxy-P-~-
threo-, preparation of, and a anomer,
28:292
methyl 4-0-benzyl-2,3-dideoxy-6-O-trityl-a-Hex-4-enopyranoside
o-erythro-, reaction with hydrogen
bromide-acetic acid, 28:269
methyl 4,6-O-benzylidene-
2-bromo2,3-dideoxy-a-o-threo-
preparation of, 28:293
3-deoxy-P-o-e~~fhro-, preparation of.
28:286
2,3-dideoxy-a-o-erythro-, 25: I39
bromination of, 28:267
dehydration of, 28: 184
preparation of, 28:253,292,31:66
reaction with nitryl iodide, iodine azide,
or nitrosyl chloride, 28:273
with Simmons-Smith reagent, 28:305
2,3-dideoxy-a-~-fhreo-,preparation of,
28:292
2,3-dideoxy-P-~-erythro-, preparation of,
28:292
2,3-dideoxy-P-o-threo-, preparation of,
28:292
methyl 2,3,6-trideoxy-
a-D-eiythro-, preparation of, 28:292
a-DL-erythro-, synthesis, 40:32,67,69
a-oL-threo-, synthesis, 40:67, 69
a-L-erythro-, synthesis, 39: 142- I43
P-DL-erythro-, synthesis, 40:67, 69
P-DL-threo-, synthesis, 40:67
5-0-(2,3,4-tri-0-acetyl-6-deoxy-a-o-
glucopyranosyl)-P-o-eryfhro-,
synthesis, 39:242-243
Hex-3-enopyranoside
alkyl 3,4-dideoxy-, synthesis, 40:52
benzyl 2,3,4,6-tetradeoxy-a-~~-glyc'rro-,
synthesis, 40:53-54
ethyl 0-eryfhro-, 2,3,4,6-tetradeoxy-2-
275
isothiocyanato-6-O-(methylsulfonyl),
44: I42
ethyl r,-threo-, 2,3,4,6-tetradeoxy-2-
isothiocyanato-6-0-(methylsulfonyl),
44: 142
methyl 4,6-O-benzylidene-
P-o-erythro, preparation of, 28:293
2-bromo-2,3-dideoxy-a-~-fhreo-, 24:249,
253
2,3-dideoxy-a-o-givcero-, 24:236,249
methyl 3,4.6-trideoxy-
a-oL-eythro-. synthesis, 40:74
a-DL-threo-. synthesis, 40:74
derivatives, 24:250
o-fhreo-. methyl 3-benzamido-2,3,4,6-
tetradeoxy-2-fluoro-a-, 'H- and I9F-
NMR data for, 46: 127
L-threo-. methyl 2-benzamido-3-0-benzyl-
2,4.6-trideoxy-6-fluoro-~-. 'H- and IyF-
NMR data for, 46:127
methyl 2-benzamido-3-O-benzyl-2.4.5,6-
tetradeoxy-6-fluoro-P-~-threo-,
preparation. 38:222
methyl 4,6-dideoxy-2,3-0-isopropylidene-P-
L-eryrhro-, 23:277,24:254
methyl 2,3-di-O-benzyl-4,6-dideoxy a-D-
thero-, 24:253
Hex-5-enop yranoside
P-o-fructofuranosyl 6-deoxy-a-o-x.ylo-,
reduction of, 33:265
o-urubino-
methyl 3-benzamido-4-O-benzoyl-2,3,6-
trideoxy-2-fluoro-a-, I3C-NMR data
for, 46: 171
2,3,6-trideoxy-2-fluoro-2-a-
benzyl 3-azido-. 'H- and I9F-NMR data
for, 46:126
benzyl3-benzamido-, 'H- and "F-NMR
data for, 46: 127
methyl 3-benzamido-, 'H- and "F-
NMR data for, 46: 127
methyl 3-benzamido-4-O-benzoyl-,
'H- and "F-NMR data for, 46:
I27
methyl 4-0-benzoyl-3-
trifluoroacetamido-, 'H- and I9F-
NMR data for, 46:127
methyl 6-deoxy-
a-o-arubino-, hydrolysis of, 28:291
276 SUBJECT INDEX
Hex-4-enopyranoside (continued)
@-D-,hydrolysis and rearrangement of,
28:291
2,3-0-isopropylidene-4-0-
(methylsulfonyl)-a-o-r.rxo-,
instability of, 29:292
methyl 2,3,4-tri-0-acetyl-a-~-xylo-,
reduction of, 33:265
1,3,4,6-tetra-O-acetyI-@-o-fructofuranosyl
2,3,4-tr-O-acetyl-6-deoxy-a-~-xylo-
preparation of, 33:263
reduction of, 33:265
1,3,4,6-tr-0-benzoyl-6-deoxy-a-~-threo-
hex-5-enofi1ranosyl2,3,4-tr-0-benzoyl-
6-deoxy-a-~-xylo-,preparation of,
33:264
Hex-4-enopyranosideuronate
methylbenzyl2,3-di-0-benzyl-4-deoxy-a-~-
threo-, stereochemistry in preparation
of, and spectra, 29:268,270
methylbenzyl4-deoxy-a-~-threo-,
stereochemistry in preparation of,
29:269
methyl 2,3-di-O-benzyI-4-deoxy-@-~-threo-,
ultraviolet absorption spectrum and
optical rotatory dispersion spectrum of,
29:260
Hex- I-enopyranosid-3-ulose, 2,4,6-tri-0-
acetyl-1-thio-D-erythro-, 49:39
Hex-2-enopyranosid-4-ulose
methyl 2,3-dideoxy-@-o-glycero-
preparation of, 28:293-294
synthesis, 41:lO
methyl 2,3,6-trideoxy-
CI-DL-, reduction, 40:67
@-DL-, reduction, 40:67
L-glycero-, synthesis, 40: 117
Hex-3-enopyranosidulose,methyl 3,4-dideoxy-
6-O-methyl-a-o-, (and @-D)-glycera-,
24:239
Hex-4-enopyranosiduronicacid, methyl 4-
deoxy-@-L-threo-,methyl ester, 24:252,
255,28:206
Hex-2-enopyranos-4-ulose,I ,6-anhydro-2,3-
dideoxy-@-D-glycero-,synthesis of,
34: 103
Hex-3-enopyranos-2-ulose
1,6-anhydro-3,4-dideoxy-@-~-glycero-,
formation during pyrolysis of starch and
cellulose, 34:42, 103
synthesis of, 34: 103
3-O-acetyl-l,6-anhydro-4-deoxy-~-~-
glycero-, preparation of, 34:96
Hex-2-enopyranosylamine, N, N-diethyl-2,4,6-
tri-O-acetyl-3-deoxy-o-erythro-, 24:222
Hex-2-enopyranosyl chloride, 2,4,6-tri-0-
acetyl-3-deoxy-a-o-erythro-, 24:240
Hex-2-enopyranosyl dimethylphosphonate, 4,6-
Di-O-acetyl-2,3-dideoxy-a-~-erythro-,
crystal structure, 43:229-230
Hex-2-enopyranosyl fluoride
3-deoxy-a-~-erythro-
2,4,6-tri-O-acetyl-, 'H- and "F-NMR data
for, 46: 134
2,4,6-tn-0-benzoyl-, IH-and 19F-n.m.r
data for, 46: 134
4,6-di-O-acetyl-2,3-dideoxy-o-erythro-,
24:216
2,4,6-tri-0-acetyl-3-deoxy-~-ribo-,
preparation, 38:230
Hex-3-enopyranosyl fluoride, 3,4-dideoxy-o-
glycero-
6-0-acetyl-2-ulose, 'H and "F-NMR data
for, 46: 134
6-O-benzoyl-2-ulose, IH and I9F-NMR data
for, 46: 134
Hex-3-enopyranosylylose,fluoride, 6-0-acetyl-
3,4-dideoxy-o-glycero-, preparation,
38:230
Hex-4-enopyranuronate, r)-deoxy-~-threo-,
metabolism and @-eliminativedegradation
of, 29:253
Hex-2-enopyranuronic acid
1,4-di-0-acetyl-2,3-dideoxy-a-~~-
erythro-, butylester, synthesis, 40:49
threo-, butyl ester, synthesis, 40:49
3-O-methyl-~-eryfhro-,methyl ester,
24:241
Hex-2-enose
cis- and truns-3-deoxy-o-, by alkaline
degradation of 2,3,4,5-tetra-O-methyl-
D-gluCoSe, 28~202
3-deoxy-2,4,5,6-tetra-O-rnethyl-~-erythro-,
24:263
3-deoxy-2,4,5-tri-O-methyl-o-erythro-,cis-
and trans-, 24:263
4,6-di-O-acetyl-2,3-dideoxy-~-erythro-,
formation and degradation of, 28:204
(E)-4,5,6-tr-O-acetyl-2,3-dideoxy-aldehydo-
D-efythro-, synthesis, 39: 1 14
 SUBJECT INDEX
1,2,4,6-tetra-O-acetyl-3-deoxy-ol-u-erythro-, Hexitol-4,6,6-d3, 1,5-anhydro-4-deoxy-
24:240
4,5,6-tri-O-benzoyl-3-deoxy-2-S-etIiyl-2-
thio-, preparation of, 32:63
Hex-3-enose
3-deoxy- 1,2:5,6-di-O-isopropylidene-a-
erythro-, 0x0 reaction with, 23: 100
3-0-acetyl-1,2: 5,6-di-O-isopropylidene-u-~-
erythro-, 24:247
Hex-5-enose
5-deoxy- 1,2-0-isopropylidene-6-O-trityl-n-
D-XylO-, 24~256
2,3,4-tri-O-acetyl-5,6-di-deoxy-~-,ry/o-,
diethyl acetal, irradiation, 39:95
Hex-2-enoside
ethyl ,4,6-di-O-acetyI-2,3-dideoxy-u-o-
evthro-, 0x0 reaction with, 2 3 9 3
methyl 4,6-di-O-acetyI-2,3-dideoxy-
a-o-erythro-, 23: 110, 112
P-o-erythro, 23: 1 10
methyl 2,3-dideoxy-4,6-di-O-
(methykulfonyl)-cx-D-
erythro-, displacement reactions of,
24: 164
/hreo-, displacement reactions of. 24: 164
Hex-5-enoulofuranose, 6-deoxy-2,3-0-
isopropylidene-P-o-/hreo-, 24:25 1
Hex-3-enousulose, 3,4-dideoxy-5,6-di-O-
methyl-D-glycero-, 24:263
Hex-5-enufuranose, 1-2-O-isopropylidene-a-
D-, 25: 162
Hex-5-enulofuranose, 6-deoxy-2,3-0-
isopropylidene-P-o-treo-, preparation of,
28:29 I
Hex-5-enulopyranose, 5-deoxy-2,3-0-
isopropylidene- 1-O-(tetrahydropyran-2-
yl)-P-D-threo-, synthesis, 39: 145
Hex-4-enulopyranoside, methyl 1,3-0-
benzylidene-4,5-dideoxy-a-~-g!vc.ero-.
24:249
Hex-3-enulopyronose, 3-0-acetyl- 1,2:4,5-di-O-
isopropylidene-P-o-g[ycero-, 26:276
Hex-3-enulose
3,4-dideoxy-o-g!vceroo; 24:230,26 I
1,3,4-trideoxy-o-glycero-, synthesis by
Wittig reaction, 27:245,290
Hex-4-enuronic acid, 4-deoxy-~-/hreo-,
biosynthesis, 44:296-298
Hex-4-enurono-6,3-lactone, aldehydo-L-threo-,
synthesis, 37: 1 16
277
o-arabino-, 23:80-8 I
L-xylo-, 23:80-81
Hexitols
acetals of, 7: 137-207
acetates, gas-liquid chromatography of,
28: 127-128
aminodeoxy-, synthesis of, 29:8
anhydrides of, 5:191-228
1,4-anhydro-. selective catalytic oxidation of,
33:oo
1,5-anhydro-
o-deoxy- 1,2-C-(dichloromethylene)-3,4,6-
tri-O-methyl-D-g/vcero-o-ido-,
24:2 12
2-deoxy-~-arubino-,preparation by
hydrogenolysis o f levoglucosan,
34:69
4-deoxy-o-aruhino-, 2356, 74,91
4-deoxy-o-lyxo-, 23:69,76
4-deoxy-~-ribo-,23:69, 76
4-deoxy-~-.xylo-,23:66, 74,91
2-deoxy-3-O-~-tolylsulfonyl-o-arabino-,
23:26 1
4,6-0-benzylidene-2-deoxy-3-O-p-
tolylsulfonyl-o-nrabinu-, hydrolysis
of. 23:261
preparation of, 31:3
1 ,6-anhydro-, 25:245
2,5-anhydro-, 1 deoxy-1 , I -difluoro-o-
arabino-. 'H- and I'F-NMR data for,
46:151
riho-. 'H- and l9F-NMR data for. 46:
152
3,4,6-tn-O-acetyl-, 'H- and I9F-NMR data
for, 46: 152
3.6-anhydro-, I ,2-dideoxy-4,5-0-
isopropylidene-[I-ribo-. synthesis of,
27:281
anhydro-, 25236-247, 215-278
catalytic oxidation of, 25:261
ring opening of, 25:256
uses
biological, 25268
industrial, 25:267
3-benzamido-4,5-di-O-benzoyl- 1,2,3.6-
tetradeoxy-D-urabino-, preparation of,
32~77
I , I -bis(benzamido)-6-U-benzoyl- 1 -deoxy-
D-, preparation, 39:31
278 SUBJECT INDEX
Hexitols (continued)
C-alkylated and C-arylated unsaturated,
physical properties of, 27:239-241
catalytic oxidation of, 33:88
1-(6-chloropurin-9-yI)-l-S-ethyl- l-thio-o-
glycero-o-ido-, crystal structure
bibliography, 38:454,493494
conformation of, 25: 105
2-deoxy-
D-arubino-, reaction with butanal, 39:27
DL-ribo-, synthesis, 40: I09
4-deoxy-o-, acetates, gas-liquid
chromatography of, 28:63
3,6-diacetamido-4,5-di-O-acetyl- 1,2,3,6-
tetradeoxy-D-ribo-, 22: 163
dianhydro-, 25:245-247
circular dichroism spectra of, 25254
and derivatives, 25:279-280
1,2-dideoxy-
1-(diethylphosphono)-3,4:5,6-di-0-
isopropylidene-o-arubino-, synthesis
of, 27:297
1-nitro-D-ribo-, 21 :305
3,6-dideoxy-, L-lyxo-, preparation of,
29:289
5,6-dideoxy-
or-ribo-, synthesis, 40: 1 I0
1,6-imino-, 23: 157
4.6-di-0-acetyl- 1,5-anhydr0-2,3-dideoxy-o-
erythro-, 24:2 13, 22 1
gel chromatography of, 2 5 3 1
1,3,4,5,6-penta-O-acetyI-, 2-deoxy-o-
arubino-, preparation from dithioacetal,
32:75
2,3,4,5,6-penta-O-acetyI-
1-deoxy- 1-C-furfirrylidene-o-gluco-,
synthesis by Wittig reaction, 27:237
1-deoxy- 1-0-9-fluorenylidene-o-gu~ucto-,
synthesis by Wittig reaction, 27:237
1-0-1O-anthranylidene-l-deoxy-o-
galacto-, synthesis by Wittig
reaction, 27:237
selective periodate oxidation of, 33:95
separation, 47:37
and some of their derivatives, 4:211-241
sweetness-structure relationship, 45295
synthesis of, 2:107-114
trianhydro-, 25247
and derivatives, 25279-280
2,3,4-trideoxy-o~-glycero-, 1-diethyl-borinate
5,6-ethylboronate, selective cleavage,
39:54
trimethylsilyl ethers, gas-liquid
chromatography of, 28:57
3,4,6-tri-0-acetyl-1,5-anhydro-2-deoxy-o-
arubino-, 24:221
Hex-~-en-3-ulose, l-deoxy-2-methoxy-4,6-di-
0-methyl-o-, preparation of, 31:221
HexNAc cleavages, 4 5 5 4
HexNAc residues, permethylated molecules
containing, linkage-site-specific, 45:52
Hexo- 1,
6-deoxy- 1,2-0-isopropylidene-cw-o-xylo-,
23: 102
4-furanos-5-ulose,N-acetyl-3-0-benzyl-6-
deoxy- I ,2-0-isopropy~idene-cu-~-q\ylo-,
5-hydrazone, 23: 139
Hexobarbital, cyclodextrin inclusion complexes
with, 46:223-224
Hexodialdo- 1,4-furanose,5-(benzylamino)-1,2-
0-cyclohexylidene-5-deoxy-~-c~o-,
23:141
Hexodialdo-1,5-pyranose,1,2:3,4-di-0-
isopropylidene-cu-o-galacto-
and hydrate, 2 5 2 14
reaction with 2-lithio-2-methyl- 1,3-dithiane,
32:39
Hexodialdo- 1.5-pyranoside
o-gluco-, preparation of, 28:286
ethyl 2,3,4-tri-~-methyl-a-o-gluco-,
degradation of, 31:222
methyl, hydrolysis of, 31:193
methyl-P-D-glum-, hydrolysis of, rate
constants and activation energies for,
22:70
methyl 4-0-methyl-P-D- gluco-, hydrolysis
of, rate constants and activation
energies for, 22:70
Hexodialdose
a-o-gulucto-, ester of uridine 5'-
pyrophosphate, preparation of, and 6-
tritiated derivative, 28:344
o-gluco-, preparation of, 33:218
o-munno-,1,6-bis(diethyl dithioacetal),
oxidation of, 32530
mercaptalation of, 32:25
Hexo-2,5-dienonate, methyl 4-0-acetyl-2,6-
anhydro-3,5-dideoxy-o-glycero-,
29:281
Hexodiulose, 4-deoxy-o-glycero-2,3-, 46:292
 SUBJECT INDEX
2,3-Hexodiulose
1-deoxy-o-erythro-, 25:343
alkaline degradation of, 28:196
dehydration of, 28: 194
from D-fructose dehydration, 28: 1 79- I80
preparation of, 28: 168-1 69, I94
4-deoxy-o-g~cero-,25:343
preparation of, 28: 168-169
2,5-Hexodiulose
1,4:3,6-dianhydro-o-rhreo-, 25:26 1
o-threo-, 22:284
composition in aqueous solution, 42:38
dehydration of, 28: 186
preparation, 37: 140
L-threo-, dimer, crystal structure
bibliography, 37:387
Hexodiulosonic acid, o-thre0-2,5-, 46:34
composition in aqueous solution, 42:40
2,3-hexodiulosonic acid, threo-, polarog-raphy
of o-phenylenediamine condensation
products, 29: 154
2,5-Hexodiulosonic acid, o-threo-
methyl ester, preparation, 37: 143
reduction, 37: 145
preparation, 37: 137-140, 145-146
reactions, 37: 142-143
reduction, 37:14&145
structure, 37:141-142
2,3-Hexodiulosono- 1,4-lactone, L-thrro-.2-( p -
bromophenyl)hydrazone, crystal structure
bibliography, 37:386
Hexofuranose
1,5-anhydro-, formation of, 34:88
1,6-anhydro-, 7:37-52
(6-acetamido-2,3-di-O-acetyl-5,6-dideoxy-
P-D-xY~o-,preparation of, 34: 15 1
analogs, 34: 146-1 5 1
complex formation with, 34: 154
and derivatives, Table, 34: 177
formation and preparation of, 34388.
151
by pyrolysis of monosaccharides,
34:46
properties of, 34: 153-1 55
reactions of, 34: 155-1 57
5,6-anhydro-, 25: 160-163, 179
3,6-anhydro-5-deoxy- 1,2-0-isopropylidene-
~-D-I$o-, 23:241
preparation of, 28:271
3-C-(chlorofluoromethylene)-3-deoxy-
279
1,2:5,6-di-O-isopropylidene-a-~-
ribo-, cis- and trans-, preparation.
38:247-248
xylo-, cis- and trans-. preparation,
38:247-248
D-
3-deoxy-3-C-(difluoromethylene)- 1,2:,5,6-
di-0-isopropylidene-a-
ribo-. IH- and I9F-NMR data for,
46:141
xylo-. 'H- and "F-NMR data for,
46:141
3-deoxy-3-C-(fluoromethylene)- 1,2:5,6)-
di-0-isopropylidene-a-, ribo-, 'H-
and IyF-NMR data for, 46:140
3-deoxy-3-C-(fluoromethylene)-I .2:5,6-
di-0-isopropylidene-a-, xylo-. 'H-
and "F-NMR data for, 46: 140
L-ribo-
3-acetamido-2,3,5,6-tetradeoxy-5-
fl~oro-@-,'~C-NMR data for, 46: 17 I
3-acetamido-2,3,5,6-tetradeoxy-5-
fluoro- l-O-(4-nitrobenzoyl)a-, P-
'H- and I9F-NMR data for, 46: 128
methyl 3-acetamido-2,3,5,6-tetradeoxy-
5-flUOrO-P-, IH- and I9F-NMR data
for, 46: 128
1 -0-acetyl-2.3,5,6-tetra-O-henzoyl-4-
deoxy-4-fluoro-P-
galacro-, 'H- and I9F-NMR data for,
46: 143
gluco-, 'H- and "F-NMR data for,
46: 143
2-deoxy-, 2-fluoro-, IH- and "F-NMR data
for, 46:99
3-deoxy-
3-C-(difluoromethylene)- 1,2:5,6-di-O-
isopropyhdene-a-o-rzbo-,
preparation, 38:249
3-C-(difluoromethylene)-l,2:5,6-di-0-
isopropyhdene-a-o-xv[o-,
preparation, 38:249
3-C-(fluoromethyl)-I ,2:5,6-di-0-
isopropylidene-cu-D-ribo-,cis- and
trans-, preparation, 38:247-248
3-C-( fluoromethyl)- 1,2:5,6-di-0-
isopropylidene-a-o-xylo-,cis- and
trans-, preparation, 38:247-248
3-deuterio- 1,2:5,6-di-O-isopropylidene-a-
o-ribo-, preparation of, 28:303
280 SUBJECT INDEX
Hexofuranose (continued)
3,3-diiodo- 1,2:5,6-di-O-isopropylidene-a- Hexofuranosiduronic acid, methyl 5-deoxy-2,3-
o-ribo-, preparation of, 28:279
1,2:5,6-di-O-isopropylidene-a-o-ribo,
selective hydrolysis, 39: I 5
1,2:5,6-di-O-isopropyIidene-3-C-
methylene-a-D-ribo-, preparation by
Wittig reaction, 27:235
3-fluorO-, 'H- and I9F-NMR data for,
46:99
5-deoxy-
o-x~~o-, 21:169, 171
derivatives, preparation of, 33:232
5-fluOrO-, 'H- and 19F-NMRdata for,
46:lOO
1,2-O-isopropyhdene-ol-~-xy~o-, 21: 168,
23:275
preparation of, 28:271
1,2-O-isopropylidene-6-0-
(methykulfonyi)-a-D-xylo-, 23:241
1,2-O-isopropylidene-6-O-p-tolylsulfonyl- 5-deoxy-o-xylo-, preparation of, 33:232
Ci-D-XylO-, 23~241
6-deoxy-, 6-fluoro-, IH- and I9F-NMR data
for, 46: 100
5,6-dideoxy- 1,2-O-isopropylidene-6-nitro-a-
o-qlo-, 24:99
Hexofuranoside
2,3-anhydro-, 25: 177
5-deoxy-5-fluoro-, 'H- and I9F-NMR data
for, 46: 100
h-deoxy-6-fluoro-, 'H- and 19F-NMR data
for, 46: 100
methyl 3-acetamido-2,3,5,6-tetradeoxy-5-
fluoro-D,L,-ribo-
a anomer, 13C-NMR data for, 46: 17I
P anomer, ')C-NMR data for, 46:128, 172
methyl 6-amino-5,6-dideoxy-2,3-0-
isopropylidene-P-o-, ribo-, deamination
of, 3 1 5 7
methyl 3,6-anhydro-, sweetness-structure
relationship, 45:274
methyl 2-deoxy-o-arubino-, 21: 114,309
methyl 5-deoxy-2,3-O-isopropylidene-~-~~- 4-amino-2,3,4,6-tetradeoxy-o~-erythro-
ribo-, synthesis, 40: 109
methyl 5,6-dideoxy-2,3-isopropylidene-P-
oL-ribo-, synthesis, 40: 109
methyl 5,6-O-cyclohexylidene-3 -deoxy-2-C-
methyl-P-o-ribo-, acetal cleavage by
Grignard reagent, 39: 154
Hexofuranosid-2-ulose, methyl I-deoxy-3-C-
methyl-P-o-ribo-, synthesis, 40: 123
0-isopropyhdene-P-DL-ribo-, methyl
ester, synthesis, 40:109
Hexofuranos-3-ulose, 1,2:5,6-di-O-
isopropylidene-
a-o-ribo-
acetal cleavage by Grignard reagents,
39: 154
ketenic dithioacetal from, 32:44
D-, proton magnetic resonance spectra,
analyses of, 2 7 s I
Hexofuranos-5-ulose
1,6-anhydr0-2,3-0-isopropylidene-~-o-lyxo-,
preparation of, 34: 156
6-deoxy-o-, synthesis of, 29:294
Hexofuranosyl fluorides
I3C-NMR data for, 46:165-167
IH- and "F-NMR data for, 46:97-98
Hexofuranurono-6,3-lactone
5-deoxy- 1,2-isopropylidene-o-qlo-,
preparation of, 33:226
5-deoxy- 1,2-O-isopropylidene-a-~-xylo-,
preparation of, 28:303
1,2-O-cylohexylidene-5-deoxy-o-xylo-,
preparation of, 33:226
Hexoglycosuloses, 1,6-anhydro-, conformation
of, 34: 100
Hexokinase, 25269
enzymic activity in liver metabolism,
34:326
in formose sugar separation, 29: 178
halogenated sugars and, 22:209
hexose extraction from formose mixture by,
29:225
immobilization, 49: 1 8 6 1 8 7
specificity, fluorinated carbohydrate effect,
38:281
Hexonamide, 3-amino-3,4,6-trideoxy-r-q10-,
synthesis, 40: 120
Hexonic acid
preparation of, 30: 151
2,5-anhydro-4-deoxy-
3,6-di-O-(p-nitrobenzoyI)-o-ribo-,
preparation of, 33:142
D-ribo-, preparation of, 33: 142
2,3,4,5-tetra-O-acetyl-6-chloro-6-deoxy-,
ethyl ester, preparation of, 28:239
 SUBJECT INDEX
3,4,5,6-tetra-O-acetyl-2-deoxy-o-urubino-,
methyl ester, preparation of, 31:59
Hexonic acids
2,5-anhydro-, in synthesis of C-nucleosides,
33:117
diazo-, preparation of, 31:59
Hexonolactone, 4,6-dideoxy-~-ribo-,synthesis,
40:119
Hexono- 1,4-lactone
2,5,6-tri-O-acetyl-3-deoxy-~-riho-. 50: 176
tri-0-acetyl-2- deoxy-o-arabino-,
preparation of, 32:57
Hexononitrile, 3,4,5,6-tetra-O-acetyl-2-deoxy-
2-(phenyhmino)-~-araabino-,24: 1 14
Hexopyranoid systems, p-elimination in
unsaturated, 29:28 1
Hexopyranose
3-acetamido-2,3,6-trideoxy-o~-arahrno-, see chiroptical properties of, and aminodeoxy,
Acosamine, N-acetyl-
aminodeoxy, carbon-I3 nuclear magnetic
resonance spectroscopy, 41:54
3-amino-2,3,6-tridexoy-3-C-methyl-~~-l.vxu-, cleavage of, by acid, 34:63-69
see Vancosamine
l,f-anhydro-, 25: 163-167
1,5-anhydro-, 4-0-benzyl-3-bromo-2.3-
dideoxy-p-o-ribo, preparation of,
28:269
1,6-anhydro-
acetalation of,34:89-93
acetates, Table, 34: 16&-165
acetylation of, 34:83
alkylation of,34534
aminodeoxy, preparation of, 34:98
table, 34: 173-174
amino derivatives, properties and reactions
of, 34:126-129
analogs, 34:146-151
p-D-,25: 172-173
p-o-allo-, taste properties, 45:270
p-o-altro-, taste properties, 45:270
p-o-galacto-, taste properties, 45:270
p-o-glum-, taste properties, 45:270
P-D-~u~o-, taste properties, 45:270
P-D-idO-, taste properties, 45:270
p-o-manno-, taste properties, 45:270
p-o-talo-, taste properties, 45:270
carbon-I3 nuclear magnetic resonance
spectroscopy, 41:5 I
conformations of, and triacetates,
26:116
28 1
2-deoxy-p-o-urabino-, taste properties,
45:270
2-deoxy-p-~-]yxo-,taste properties,
45:270
2-deoxy-P-o-ribo-, taste properties,
45:270
interatomic oxygen-oxygen distances,
45~272-273
2-O-methyi-p-o-gluco-, taste properties,
45:270
proton spin-lattice relaxation, 45: I53
sweetness-structure relationship, 45:269
benzoylation of, 34:82
2-brom0-2,3,4-trideoxy-P-o~-,preparation
of, 34:48
3-C-(cyanomethyl)-2,3-dideoxy-~-~-ribo-,
preparation of, 34: 140
deoxyfluoro, and deoxy derivatives,
34~52-53
chromatography of, 34:62
complexes, 34:54-55
conformation of, 34:51
dehalogenation and desulfurization of,
34:141
deoxy
formation and preparation, 34: 140-143
properties and reactions of, 34:143-145
Table, 34:175-176
2-deoxy-P-arubino-, sweetness-structure
relationship, 45:269
deoxy-p-o-
conformation of, 26: 1 16
optical rotation and conformation of,
and acetates, 26:6 I
3-deoxy-(3-~-arabino-,21: 160
preparation of, 34: I40
3-deoxy-P-o-ribo-, preparation of, 34: 140
2-deoxy-P-o-xylo-, preparation of, 34: 140
3-deoxy-p-o-,ryk1-
preparation of, 34: 140
p-toluenesulfonylation of, 34:s 1
selective esterification of, 33:24
4-deoxy-p-~-arabino-,preparation of,
34:140
2-deoxy-P-lyxo-, sweetness-structure
relationship, 45:269
4-deoxy-4-diazo-2,3,-0-isopropylidene-P-
D-/,VXO-, preparation of, 34:98
282 SUBJECT INDEX
Hexopyranose (continued)
3-deoxy-2-0-p-to~ykuIfony~-P-~-xylo-,
preparation of, 34:81
4-deoxy-2-0-p-toly~su~fonyl-P-~-xylo-,
preparation of, 34: 141
2-deoxy-l(6)-thio-P-o-arabino-,
preparation of, 34:146
dideoxy, and trideoxy, table, 34:175-176
dideoxy, synthesis of, 34:141
2,4-d~deoxy-2-fluoro-~-o-xylo-,
preparation of, 34: 135
epimines and amino epoxides of,
34: 129-13 1
etherification and esterification of,
34: 74-7 6
formation
by mineral acids, 34:34-37
by mutarotation, 24:46
and preparation of, 34:26-49
fragmentation processes, 34:62
glycosylation of, 34: 159-1 6 1
halogeno derivatives, 34: 131-136
infrared spectroscopy of, 3 4 5 6
isopropylidene derivatives, Table VII,
34:171
mass spectrometry of, 34:62
methanesulfonylation of, 34232
mono- and di-0-substituted derivatives,
Table VI, 34: 1 6 6169
nitrogen analogs, 34:121-131, 149
nucleophilic substitutions in, 34:85-87, 92
oxidation (partial) of, 34:93-96
partially substituted, 34:78-85
periodate oxidation of, 34: 104-107
per-0-substituted, 34:77-78
polymerization of, 34:69-74
properties of, 3450-63
proton magnetic resonance spectroscopy
of, and conformation, 34:56-61
p-toluenesulfonylation of, 34530
pyrolysis of, 34:69
reactions of, 34:63-107
with boron tribromide or trichloride,
34:68
with trifluoromethanesulfonic acid,
34~87-88
reductive cleavage of, 34:69
structure of, 34:50-51
synthesis of, 34:75, 145
from acrolein, 34: 1 12
thio derivatives, 34: 136-139
2,3,4-trideoxy-
P-o-glycero-
chiroptical properties of, 3 4 5 3
preparation of, 34: 146
P-DL-glycero-
acid cleavage of, 34:64
polymerization of, 34:74
preparation from acrolein, 34:48
reductive cleavage of, 34:69
structure of, 34:26
unsaturated, preparation of, 34: 145-146
6-azido-4-0-benzoyl-2,3,6-trideoxy-2-
fluoro-o-ribo-
a anomer, 'H- and 19F-NMR data for,
46: 126
P anomer, 'H- and I9F-NMR data for,
46: 126
C-C and C-0 bond-lengths in, 44:14-15
cyclization of 6-C-substituted, 34:33-34
D-, peracetylated, carbon-13 nuclear
magnetic resonance spectroscopy,
41:49
2-deoxy-
2, 2-difluoro-D-arabino-
a anomer, 'H- and I9F-NMR data for,
46: 149
p anomer, 'H- and I9F-NMR data for,
46: 149
a-o-arabzno-, ester with uridine5'-
pyrophosphate, fermentation
production of, 28:341
C U - D - ~ ~ X O ester
-, with uridine 5 ' -
pyrophosphate, fermentation
production of, 28:341
a-o-arabino-, tetraacetate, 21: 146
o-arabino-, proton nuclear magnetic
resonance spectra, 29:33-34
D(OT L)-arabino-, tetraacetate, mass
spectrum of, 21:62
2-fluoro-, IH- and I9F-NMR data for,
46~85-89
3-deoxy-, 3-flUOrO-, 'H- and I9F-NMR data
for, 46:90-92
4-deoxy-, 4-flUOrO-, 'H- and I9F-NMR data
for, 46:92-94
6-deoxy-, 6-fluoro-, 'H- and I9F-NMR data
for, 46:95-96
deoxyhalo, carbon-13 nuclear magnetic
resonance spectroscopy, 4154-55
 SUBJECT INDEX
derivatives, proton spinlattice relaxat ion
rates, 45: 153
2,4-diamino-2,3,4,6-tetradeoxy-o-aruhino-,
synthesis of, 28:283
1,6:2,3-dianhydro-, 25:131-134
cleavage of, with ammonia, amine, and
azide ions, 34:122-125
4-deoxy+-~~-lyxo-,ring opening. 40:45
4-deoxy-P-o~-ribo-,reaction with
butyllithium, 34:49
preparation of, 34: 107-1 12
1,6:3,4-dianhydro-, 25:13 1-134
cleavage of, with ammonia, amine, and
azide ions, 34:122-125
preparation of, 34:107-112
dianhydro-
and derivatives, Table, 34: 172
hydrogenation of, reductive cleavage of,
34:141
oxidation of, 34: 100
properties of, 34: 112-1 15
reactions of substituted, 34:120-12 1
of unsubstituted, 34: 1 17-1 19
2,6-dideoxy-
P-D-ribo-, crystal structure bibliography,
38:425426
4-C-acetyl-~-xylo-,component of
quinocycline B and isoquinocycline
B, 35:92
4-C-( 1-hydroxyethyl)-L-xylo-, component
of quinocycline A and
isoquinocycline A, 35:9 1
3-C-methyl-o~-riho-,see Mycarose
3,6-dideoxy-
a-D-arabino-, see Tyvelose
a-o-ribo-, see Paratose
CY-D-XJJ~O-, ester of cytidine pyrophosphate,
isolation of, 28:3 16
P-D-arabino-, see Ascarylose
P-L-x~~o-, ester with guanosine 5'-
pyrophosphate, 28:32 1
DL-arabino-, synthesis, 40:33
DL-ribO-, synthesis, 40:33
4,6-dideoxy-, 3-O-methyl-~~-xylo-. see
Chalcose
2,4-di-O-acetyl- 1,6-anhydr0-3-deoxy-P-r,-
arabino-, preparation of, 34: 137
esters, 5-bromides from, 49:48
hydrogen bonding, Raman and infrared
spectral study of, 44:29
283
keto-, conformations in solution, 26:85
with one amino group, I3C-NMR data for,
42:210
optical rotation and conformation of, and
triacetates. 26:61-62
per-0-acetyl- 1,6-anhydro-P-o-, carbon- 13
nuclear magnetic resonance
spectroscopy, 41:5 1
2,3,4,6-tetradeoxy-4-( dimethylamino)-D-
eiythro-, 23: 155
tetra-0-acetyf-o-deoxy-a-D-urubino-,
anomerization of, 24:43
1,3,4,6-tetra-O-acetyI-2-deoxy-~-~-arabino-,
rearrangement in hydrogen fluoride,
26: 187
1,3,4,6-tetra-O-benzoyl-2-deoxy-~-o-
arahino-, rearrangement in hydrogen
fluoride, 26:185
thio, carbon-13 nuclear magnetic resonance
spectroscopy, 41:54
1,3,4-tri-0-acetyI-2,6-dideoxy-2,2-difluoro-
L-~J'XO-, 48: 182
3,4,6-trideoxy-3-(dimethylamino)-~~-xylo-,
see Desosamine
3.4,6-tri-O-acetyl- 1-0-benzoyl-2-deoxy-2-
bromo-o-, derivatives, nonselective
relaxation-rates, stereospecific
dependencies, 45: 152
Hexopyranosid-2,4,6-0-benzylidene-o-,
nucleophilic reactions of, 42:86
Hexopyranoside
2,3-anhydro-, 25:141-150, 171
4,6-O-benzylidene-. 25: 134-141
3,4-anhydro-, 25: 141-150, 171, 175-176
3,6-anhydr0-4-deoxy-a-o-xylo-
hexopyranosyl 3,6-anhydro-4-deoxy-a-
o - x ~ ~ otaste
- , properties, 45:270
3,2'-anhydro methyl 2,6-dideoxy-4-0-(3,6-
dideoxy-a-o-ribo-hexopyranosy l)-a-~-
lyxo. crystal structure, 43:343-344
benzy12,6-dideoxy-a-o~-
lyxo-, synthesis, 40:54
ribo-, synthesis, 40:54
2-deoxy-
a-o-urabino-, rate constants for hydrolysis
of, 22:83
2-fluoro-, 'H- and I9F-NMR data for,
46:85-89
3-deoxy-3-fluoro-, IH- and "F-NMR data
for, 46:90-92
284 SUBJECT lNDEX
Hexopyranose (continued)
4-deoxy-4-fluoro-, 'H- and I9F-NMR data
for, 46:92-94
6-deoxy-6-fluoro-, IH- and "F-NMR data
for, 46:95-96
derivatives, fluorinated, 'H- and "F-NMR
data for, 46:135
2,3'-didehydro-5-methyl-2H-l,2,6-
thiadiazin-3-yI4,6-di-O-acetyl-2,3-
dideoxy-a-u-ribo-. I , 1-di-S-oxide,
crystal structure, 43:364-365
o-ribo-
methyl 6-azido-4-O-benzoyl-2,3,-6-
trideoxy-2-fluoro-P-, IH- and "F-
NMR data for, 46: 126
methyl 4-O-benzoyl-6-bromo-2,3,6-
trideoxy-2-fluoro-P-, 'H- and I9F-
NMR data for, 46: 135
methyl 4,5-0-benzylidene-2-deoxy-3-C-
[(ethoxycarbonyl)-(fluoromethyl)]-a-
o-ribo-hexopyranoside
(R) isomer, I3C-NMR data for, 46:172
(S) isomer, I3C-NMR data for, 46:172
esters, radical-mediated brominations,
49~62-64
ethyl 2,3-anhydro-4,6-dideoxy-
a, P-DL-1~x0-, 25: 146
DL-ribo-, 25: 146
ethyl 2,4-bis(acetamido)-2,3,4,6-tetradeoxy-
P-D-urabino-, preparation of, 28:284
ethyl 2,3-dideoxy-
a-o-erythro-, 21:193
a-o-threo-, 21:194
6-O-p-tolysulfonyl-a-~-erythf-o-,23:241
ethyl 2,3,6-trideoxy-
6-fluoro-a-D-erythro-
4-O-acetyl-, 'H and I9F-NMR data for,
46:135
4-O-benzyl-, IH and I9F-NMR data for,
46: 135
4-O-sulfonyl-c~-o-etythro-, displacement
reactions of, 24: 163
4-O-sulfonyl-a-o-threo-, displacement
reactions of, 24: 163
ethyl 3,4,6-trideoxy-3-(dimethylamino)-a-
oL-arabino-, synthesis, 40:4&47
methyl, 4,6-dideoxy- 1,2-0-isopropyl-idene-
a-o-xylo-, conformation of, 34:200
methyl 3-acetamido-2,3,6-trideoxy-
a-o-arubino-, carbon-1 3 nuclear magnetic
resonance spectroscopy, 41:65
3-C-methyl-4-0-methyI-P-r.-xylo, crystal
structure bibliography, 38:443444
o~-D-~Yxo-, carbon-I3 nuclear magnetic
resonance spectroscopy, 41:65
a-i,-ribo-, carbon-I3 nuclear magnetic
resonance spectroscopy, 41:65
methyl 5-amino-5-N-benzoyl-4,5-didexoy
ribo-, synthesis, 40:lOl
methyl 4-amino-2,3,4,6-tetradeoxy-
a-o~-erythro-,synthesis, 40: 106
P-rx-etythro-, synthesis, 40: 106
methyl 3-amino-2,3,6-trideoxy-P-o-L-xylo-
carbon- I3 nuclear magnetic resonance
spectroscopy, 41:65
methyl 2,3-anhydro-, 25: 173-1 75
methyl 3,6-anhydro-
a-D-
4-chloro-4-deoxy-a-o-g~1ucto-, taste
properties, 45270
4- deoxy-a-o-xylo-, taste properties,
45270
a-D-gluco, taste properties, 45:270
D-,carbon-I3 nuclear magnetic resonance
spectroscopy, 41:5 1
methyl 2,3-anhydro-4-deoxy-6-O-methyl-a-
DL-
lyxo, synthesis of, 28:295
ribo-, preparation of, 28:295
methyl 2,3-anhydro-4-dideoxy-6-O-methyl-
~ - D L - ~ ~ x o25:
- , 120
methyl 4,6-0-benzylidene-3-deoxy a-D-
urabino-, 21: 160
methyl 2,6-bis(acetamido)-2,3,4,6-
tetradeoxy-a-DL-, synthesis, 40:35
methyl 3,6-bis(acetamido)-2,3,4,6-
tetradeoxy-a-DL-threo-, synthesis,
40:18
methyl 2,3-C-(aminomethylene)-4,6-0-
benzylidene-2,3-dideoxy-a-~-manno-,
synthesis (attempted) of, 27:299
methyl 2,3-C-[(aminomethyl)methylene]-
4,6-0-benzylidene-2,3-dideoxy-a-~-
manno-, synthesis of, 27:298
methyl 6-chloro-4,6-dideoxy-a-~-xylo-,
preparation of, 28:302
methyl 6-chloro-3,4,6-trideoxy-a-~-erythro-,
preparation of, 28:302
methyl 4-(cyanomethylene)-4-deoxy-2,3-0-
isopropylidene-6-O-methyl-a-~-lyxo-,
 SUBJECT INDEX
crystal structure bibliography, 34:358
methyl deoxy, carbon-13 nuclear magnetic
resonance spectroscopy, 41:56--57
methyl 2-deoxy-
a-D-
lyxo-, p-toluenesulfonylation of, 33:30
ribo-, sweetness-structure relationship, methyl 2,3-di-O-acetyl-6-chloro-4,6-
45:271
a-o-urubino-, hydrolysis of, 22:54
P-D-arabino-, 21:149,302
3-C-methyl-a-~-ribo-,carbon- 13 nuclear
magnetic resonance spectroscopy,
41:65
3,6-di-O-p-tolylsulfonyI-a-o-~~~0-.
23:248
a-o-ribo-, 21: 150
3,6-O-p-tolylsulfony~-a-o-arubino-.
23:240
methyl 3-deoxy-
P-o-ribo-, 21: 164
6-O-p-tolylsulfonyi-~-~xo-, 23:240
6-O-p-tolylsulfonyl-D-xylo-, 23:240
methyl 4-deoxy-
a-D-xylo-, sweetness-structure threshold,
determination, by triangular test,
45:245
6-O-p-tolylsulfonyl-a-~-~~o-, 23:240
methyl 2,4-diamino-2,3,4,6-tetradeoxy-a-~~-
arubino-, synthesis, 40:34
methyl 2,3-dideoxy-
3-C-[(methoxycarbonyl)methyl]-o-rib~~-,
preparation of, 27:262
3-C-methylene-a-~-erythro-,synthesis by
Wittig reaction, 27:235
methyl 2,6-dideoxy-
3,-C-methyl-a-o-ribo-, 23:272
a-o-ribo-, 23:271
a-L-arabino-, 24:210
3-C-rnethyl-3-O-methyl-a-~-ribo-, 23:272
3-C-methyl-3-O-methyI-~-ribo-, carbon-
13 nuclear magnetic resonance
spectroscopy, 4 1 6 5
3,4-di-O-methyI-a-o-arabino-, 23:270
3,4-di-O-p-to~y~su~fony~-a-~-xyb. 23:
272
methyl 3,6-dideoxy-
~ - D - T ~ o acetylation
-, and
methanesulfonylation of, 33:30
P-o-ribo-
hydrogen bonding, Raman and infrared
285
spectral study of, 44:29
preparation of, 28:301
P-D-xY~o-,23:272
methyl 4,6-dideoxy-
a-o-xylo-.preparation of, 28:302
3-O-methyl-o-xylo-, 23:75,273
dideoxy-a-o-xylo-, preparation of,
28:303
methyl 4,6-O-alkylidene-o-, 2,3-dinitrate,
selective denitration, 39:56
methyl 4-0-benzoyl-6-bromo-
6-deoxy-a-~-,preparation of, mechanism
of, 28:276
2,6-di-deoxy-3-C-methyl-3-O-methyl-a-~-
,I$o-, synthesis, 39:99
2,6-di-deoxy-3-C-methyl-3-O-methyl-a-~-
urahino-, synthesis, 39:99
2,3,6-trideoxy-a-o-eryfhro. preparation of,
28:283
methyl 4-O-benzoyl-6-chloro-, 2,3,6-
trideoxy-a-D-erythro-, preparation of,
28:302-303
methyl 4-0-benzoyl-2,3,6-trideoxy-6-iodo-
a-o-ewthro-, preparation of, 28:283
methyl 2-0-benzyl-4.6-dideoxy-3-C-(2-
methyl- 1,3-dithian-2-yl)-P-o-ribo-,
preparation of, and 3-epimer, 32:38-39
methyl 4.6-0-benzylidene-
a-D-,reaction with N-bromosuccinimide,
28:276
carbon-1 3 nuclear magnetic resonance
spectroscopy, 4 1 5 3
2,3-C-(cyanomethylene)-2,3-dideoxy-a-o-
manno-, synthesis of, 27:299
D-, 2,3-dinitrate, selective denitration,
39:56
3-deoxy-a-o-lyxo-, 25: 121
3-deoxy-u-o-ribo-, 23:276
3-deoxy-P-~-ribo-,23:276
2-deoxy-3-C-methyl-ar-~-urubino-.
preparation of, 27:242
2-deoxy-3-O-(methylsulfonyl)-a-~-ribo-,
displacement reactions of, 24: 163
3-deoxy-2-O-p-tolysulfonyl-a-o-ribo-,
displacement reactions of, 24: 163
2-deuteno-a-o-ribo-, proton magnetic
resonance spectra. 29: 16
2,3-dideoxy-a-o-erythro-, reaction with N-
bromosuccinimide, 28:283
286 SUBJECT INDEX
Hexopyranose (continued)
2,3-dideoxy-2,3-C-(formylmethylene)-a-
D-, synthesis of, 27:298
2,3-dideoxy-2,3-C-[(hydroxymethyl)-
methylene]-a-~-,manno-, synthesis
of, 27:299
2,3-dideoxy-2,3-C-[(methoxycarbonyl-
methylene)-a-D-munno-, synthesis of,
27:298
2,3-dideoxy-3-C-methylene-a-~-threo-, Hexopyranosid-3-ulose
synthesis by Wittig reaction,
27:234-235
2,3-dideoxy-2,3-C-vinylene-ol-o-manno-,
synthesis of, 27:299
2,3-di-O-methyl-a-~-,reaction with
butyllithium, 39: 140
fragmentation patterns of, 34: 194
methyl 3,4-0-(S)-benzylidene-2-6-di-deoxy-
a-D-ribo-, preparation of, 28:292
methyl 2,3,6-trideoxy-a-o-erythro-,
preparation of, 28:283
methyl 3,4,6-trideoxy-a-~-erythro-,
preparation of, 28:302
methyl 2,3,6-trideoxy-P-~-erythro-,
preparation of, 28:294
methyl 2,3,6-trideoxy-P-~-threo-,
preparation of, 28:294
methyl 3,4,6-trideoxy-3-(dimethylamino)-o-
xylo-, carbon-13 nuclear magnetic
resonance spectroscopy, 41:65
methyl 2,3,6-tri-0-acetyl-4-deoxy-a-o-xylo-,a-o-Hexopyranosid-4-doses nucleophilic
synthesis, 40: 113
replacement of primary hydroxyl groups with
methanesulfonyl chloride-N, N-
dimethylformamide complex,
33~261-263
1-thio-P-D-
aqueous, laser-Raman spectroscopy,
44:75
laser-Raman spectroscopy, 44:s 1
3,4,6-tri-0-acetyl-2-deoxy-P-~-arabino-, Hexopyranos-2-ulose, 1,6-anhydro-3,4-
synthesis, 44: 130
xylo-, methyl 3-C-cyano-2,6-dideoxy-3-0-
mesyl-0-methyl-P-L-, synthesis and
structure of, 42:9 1
Hexopyranosides
2-deoxy-P-o-arabino-, 50: 110-1 12
2,3-dideoxy-2-fluoro-, 'H and I9F-NMR data
for, 46:131-132
Hexopyranoside-3-ulose, methyl 2-0-acetyl-
4,6-0-benzylidene-a-~-ribo-, preparation
of, 33:92
Hexopyranosid-2-ulose
o-ribo-3-ket0, reductic acid formation from,
46:289
methyl-o-arubino-, reductic acid formation
from, 46:289
methyl 1-deoxy-3-C-methyl-P-~-ribo-,
synthesis, 40: 123
methyl P-o-ribo-, polarography of, 29: 145
methyl 2-bromo-2-deoxy-a-~-arubino-,3-
hydrate 3,3,4,6-tetraacetate, 25: 195
methyl 2-0-benzyl-4,6-dideoxy-P-~-erythro-
reaction with 2-lithio-2-methyl- 1,3-
dithiane, 32:38
methyl 4,6-0-benzylidene-2-O-p-
tolysulfonyl-a-D-ribo-,23:258
Hexopyranosi~-3-u~ose, methyl 4-deoxy-a-o-
erythro-, preparation of, 31:42
Hexopyranosio-4-ulose
methyl 3-deoxy-a-~-threo-,formation of,
31:43
methyl 2,3,6-tri 0-benzoyI-a-D-xylo-,
reaction with 1,2-ethanedithiol, 32:25
Hexopyranosid-3-dose 3-hydrate, methyl 2-
bromo-2-deoxy-a-~-arubino-,3,3,4,6-
tetraacetate, preparation of, 28:289
Hexopyranosiduloses, gas-liquid
chromatography of, 28:54
reactions of, 42:87
Hexopyranosiduronamides,degradation by
Weermann rearrangement, 31:237
Hexopyranosiduronic acid, methyl 4-deoxy-P-
L-urabino-, methyl ester, 21: 167
L-arabino-Hexo-l,5-pyranos-5-ulose, 5 (R)-5-
C-acetoxy-6-deoxy-6-fluoro- I ,2:3,4-di-0-
isopropylidene-P-, 'H- and 19F-NMRdata
for, 46: 142
dideoxy-, preparation of, 34: 103
0-isopropylidene-P-o-lyxo-,preparation and
reduction of, and hydrate, 34:91, 97
0-isopropyhdene-P-o-ribo-, acetylation of,
34:98
Hexopyranos-3 -dose
a-o-ribo-, ester of uridine 5'-pyrophosphate,
enzymic preparation of, 28:344
1,6-anhydro-P-~-
 SUBJECT INDEX
arabino-, dimers and acetals, 34:96
lyxo-, preparation of, 34:95
riho-, dimers, 34:96
xyfo-, dimers, and acetals, 34:96
1 ,h-anhydro4-deoxy-2-0-p-tolysulfonyl-~-
o-threo-, preparation of, 34: 103
1,6-anhydro-2,4-dideoxy-
P-o-glycero-
preparation of, 34: 103
reaction with 1,2-ethanedithiol, 32:24
2-fluoro-P-~-erythro-,'H- and "F-NMR
data for, 46: I 14
1,6-anhydro-2,4-di-0-p-tolylsulfonyl-~-u- Hexopyranosyl fluoride
ribo-, isomerization of, 34: 101
1,6-anhydro-2,3-0-isopropylidene-P- D-
arahino-, crystal structure, 43:238-
239
1,6-anhyldro-2,4-dideoxy-2,4-difluoro- P-D-
ribo-, reaction with phenylsulfur
trifluoride, 38:225
2,4-di-O-acetyl- 1,6-anhydro-P-~-l~.~o-,
preparation of, 34:96
Hexopyranos-4-ulose
1,6-anhydr0-3-C-(hydroxymethyl)-2,3-0-
isopropylidene-P-D-lyxo-, preparation
of, 34: 100
1,6-anhydr0-2,3-dideoxy- preparation of,
34: 103
1,6-anhydro-2,3-0-isopropyIidene-~-1~-1~~~~~-, 3,4,6-tri-O-benzoyl-a-, 'H- and IYF-
preparation and reduction of, 34:97-100
3-d, 1,6-anhydro-2,3-0-isopropyhdene-~-~-
fyxo-, preparation of, 27: 133
6-deoxy-a-o-lyxo-, ester with guanosine 5 ' -
pyrophosphate, 28:322
6-deoxy-a-~-xylo-,ester of cytidine 5 ' -
pyrophosphate, 28:318
of thymidine 5'-pyrophosphate, 28:323
3,6-dideoxy-a-~-erythro-, ester with cytidine
5'-pyrophosphate, 28:3 18
~-ribo-Hexo-pyranos-3-ulose hydrate, I ,6-
anhydro-2,4,-dideoxy-2,4-difluoro-P-, 'H-
and IyF-NMR data for, 46: 151
Hexopyranosuloses
1,6-anhydro-
preparation of, 34:9496
properties of, 34: 104
spectral properties of, 34: 104
preparation of, 34:93-104
Hexopyranosyl bromide
4-0-acetyl-3-bromo-2,3-dideoxy-6-O-p-
287
tolylsulfonyl-ol-u-arabino-,preparation
of, 28:264
3,4,6-tri-O-acetyI-2-deoxy-~-arabino-,
24:206
preparation of, 28:264
Hexopyranosyl chloride
2,2-dichloro-2-deoxy-ol-~-urabino-,
preparation of, 28:26 1-262
3,4,6-tri-O-acety-2,2-dichloro-2-deoxy-o-
arabino-, preparation of, 28:262
Hexopyranosyl ethylxanthate, 3,4,6-tri-0-
acetyl-2-deoxy-P-u-arubino-, 24:206
I3C-NMR data for, 46:160-161
2-deoxy-
u-arahino-
3,4,6-tri-O-acetyI-
a anomer, 'H- and IYF-NMRdata for,
46:131
P anomer, 'H- and I9F-NMR data for,
46:131
3,4,6-tri-O-benzoyl-a-, 'H- and "F-
NMR data for, 46: 131
D-~VXO-
3,6-di-O-benzoyl-a-, 'H- and IyF-NMR
data for, 46: 131
4,6-di-O-benzoyl-a-, 'H- and "F-NMR
data for, 46: 131
NMR data for, 46: 13 1
'H- and 1yFF-NMRdatafor,46:131-132
2,6-di-O-benzoyl-2-deoxy-
a-u-ribo-, preparation, 38:230
P-O-XJdO-, 26: I86
3,6-di-0-benzoyl-2-deoxy-a-~-ribo-, 24:2 17
4,6-di-O-benzoyl- 2.3-dideoxy-o-erythro-,
preparation, 38:230
'H- and I9F-NMR data for, 46:82-85
per-O-benzoyl-2-deoxy-a-o-
arabino-, synthesis, 38:203
lyxo-, synthesis, 38:201
poly-0-acyl-D-, proton magnetic resonance
spectroscopy of, 27:2 1
tri-O-acetyI-2-deoxy-a-u-, preparation,
38:234
Hexopyranosyl halide, 6-azido-4-0-benzoyl-
2,3,6-trideoxy-2-fluoro-o-ribo-
a bromide, 'H-and "F-NMR data for,
46: 126
chloride, 'H-and "F-NMR data for, 46: 125
288 SUBJECT INDEX
Hexopyranosyl halide, 6-azido-4-0-benzoyl-
2,3,6-trideoxy-2-fluoro-~-ribo-
(continued)
a iodide, 'H-and I9F-NMR data for, 46: 126
Hexopyranosyl nitrate, 2-deoxy-o-arabino-,
substituted, equilibrium composition,
47:6344
Hexopyranosylpyridine, 3-keto-arahino-,
synthesis of, 42:232
Hexopyranosyl streptamine, 2,6-dideoxy-O-
2,3-dideoxy-2-fluoro-ol-~-riho-, 48:224
Hexopyranuronates
@-eliminationin unsaturated, 29:281
conformations of, 29:256
deoxy, biochemical transformation of 4 3 -
unsaturated, 29:252
structure and conformation of unsaturated,
29:259
diaxial @-eliminationin, 29:265-271
in natural polysaccharides, 29:23 1
Hexopyroanoside, 3-amino-2,3,6-trideoxy-2-
fluoro-, derivatives
'H- and I9F-NMR data for, 46:123-125
N-containing synthetic precursors, 'H-and
I9F-NMR data for, 46:123-125
Hex-2(or 3)-enopyranose derivatives,
fluorinated, IH- and 19F-NMR data for,
46: 134
Hexosamines
gas-liquid chromatography of, 28:78-79
liquid chromatography, precolumn
derivatization procedures, 46:68
methylation of, in methyl sulfate and sodium
hydroxide, 30: 12
trimethylsilylation of, 28:29
trimethylsilyl derivatives, gas-liquid
chromatography of, 28: 143
Hexosaminidase
@-, isolation and characterization,
40~277-279
N-acetyl-P-D-, 44:204
and Tay-Sachs disease, 31:6
Hexosaminoglycans, bacterial, monosaccharide
composition, 47:174-175
Hexosans, polymerization of 2,3,4-tri-0-
substituted, 34:73
Hexos-2,3-diulose,4,6-dideoxy-glycero-,
21:191
Hexose C-nucleosides, 4-keto-lyxo-, synthesis
of. 42:232
Hexoses, 48:281-285
2-acetamido-
2-deoxy-, liquid chromatography methods
for analysis of, 46:33
2,4,6-trideoxy-, ester of uridine 5'-
pyrophosphate, isolation of, 28:327
acetamidodeoxy-
alkaline degradation of, 28:202
gas-liquid chromatography of, 28:80-82
0-trimethylsilyl derivatives, gas-liquid
Chromatography of, 28:143-144
4-0-acetyl-2,6-dideoxy-3-C-methyl-~-
arabino-, 21: 185
3-0-acetyl-2,6-dideoxy-~-lyxo-, 21: 184-1 87
acylamidodeoxy-, 1,2-oxazoline derivatives,
preparation, 31:4
acylated, gas-liquid chromatography of
trimethylsilyl derivatives, 28: 110
2-amino-
2-deoxycarba-, synthesis, 48:5943
enantiomeric, 48:6&67
2-deoxy-D-, preparation of, 24:9
2-dexoy-, trimethylsilylated, mass
spectrometry of, 29:47
3-amino-
2,3,6-trideoxy-o~-lyxo-, see Daunosamine
2,3,6-trideoxy-~-,composition in aqueous
solution, 42:48
5-amino-
5-deoxy-, 23: 131
deoxy-, composition in aqueous solution,
42:4849
6-amino-
1,6-anhydro-5,6-dideoxy-~-xylo-, 23:228
6-deoxy, composition in aqueous solution,
42:5 1
1,5,6-dideoxy-~-xylo-,23: 156
aminodeoxy-, in urine (human), 24:438-
439
1,6-anhydro-
5-deoxy-6-thio-o-xylo-, 23:229
4-0-benzyl-3-hrorno-2,3-dideoxy-o-
arahino-, 24:236
preparation of, 34:32
from 2,3-unsaturated hexopyranosides,
34:47
synthesis from acrolein, 34:49
3,6-anhydro-
composition in aqueous solution,
42:58-59
 SUBJECT INDEX
2-deoxy-o-arabino-, formation of, 28:202,
204
O-~JZO-, 23:266
3-benzamido-2,3,6-trideoxy-
D-xylo-,synthesis, 40: 1 17, I 18
L-, (4 isomers), composition in aqueous
solution, 42:61
5,6-O-carbonyl-2-deoxy-I ,3-di-O-p-
nitrobenzoyl-o-arabino-, 2 1 3 1 I
D-, 2-acetamidio-2-deoxy-, 46:3 1
dehydration of, 28: 176,209
2-deoxy-
o-arabino-, labeled, 48: 186-1 88
arabino-, liquid chromatography methods
for analysis of, 46:33
composition in aqueous solution, 42:35,
63
D-, polymer, 21:472
o-arabino-, 21:149, 157, 24:218, 25:191
alkaline degradation of, 28:202
effect on immunoglobulin secretion,
40:361
esters of uridine 5-pyrophosphate and
of guanosine 5-pyrophosphate,
enzymic synthesis of, 28:338
inhibition of lipid-linked
oligosaccharide formation,
40:327-331,378
nonselective spin-lattice relaxation
rates, 45: 148
proton spin-lattice relaxation rates,
45: 150
3,4:5,6-di-O-isopropylidene-~-arabino-,
diethyl dithioacetal, reaction with
butyllithium, 32:59
o-lyxo-, diethyl dithioacetal, preparation
of, 32:28
o-ribo-, 21:304,24: 127,264
in cancer chemotherapy, 21:145
methyl glycosides, synthesis of, 27:4
D - x ~ ~ o - 24:
, 127
in cancer chemotherapy, 21:145
r-arabino-, synthesis of, 27:280
lyxo-, furanose stability in solution. 42:28
ribo-, furanose stability in solution, 42:28
1,3,4,6-tetra-O-p-nitrobenzoyl-o-ribo-,
21:307
3-deoxy-
o-arabino-, 21:159, 164, 50:171
dimethyl dithioacetal, selective
289
benzoylation of, 33:4 1
DL-,synthesis, 40: 17-1 8
0 - l y X O - . 21:159
a - o - r i b , 21: 160, I64
o-ribo-, 21:159, 163
6-phosphate, 21:158
u - x ~ ~ o21~159,
-, 161, 163
dialkyl dithioacetals, selective
benzoylation of, 33:4 1
reaction with sulfonyl chloride, 32:48
4,5-O-isopropylidene-~-xylo-,
dithioacetals, preparation of, 32:54
ribo-, furanose stability in solution, 42:28
xylo-, composition in pyridine, 42:68
4-deoxy-
o-arabino-, 21:166
biosynthesis, 44:296-298
gas-liquid chromatography of, 28:63
0-xylo-. 21:166
synthesis, 39:63
5-deoxy-
o-ribo-, 21: 169
O-XY~O-, 21~168
1,2-O-isopropylidene-a-u-xv[o-, 24:256
6-deoxy-
5-c-methyl-o-xylo-, composition in
aqueous solution, 42:57-58
L-, biosynthesis of, 29:293
3-O-methyl-, from Rhodopseudomonas
capsulata lipopolysaccharide, 29:67
in urine (human), 24:438439
deoxy-
dithioacetals, physical constants of, and
peracetates, 32: 109-1 12
transport into Saccharomvces
cerevisiae, 32: I54
melting points and optical rotations of,
26~283-287
dexoy-, synthesis, 40: 17-1 8
u-galacto-
biosynthesis. 44:287-294
structure. 44:289
D-ghlCO-
biosynthesis, 44:287-294
structures, 44:289
2,6-diacetamid0-2,3,4,6-tetra-deoxy-o-threo-
diethyl dithioacetal, preparation of,
30:129
ethyl glycoside, synthesis of, 30: 127
5,6-diamino-5.6-dideoxy-,23: 13 1
290 SUBJECT INDEX

Hexoses (continued) synthesis, 41:8

o-arabino-,
2,4-diamino-2,3,4,6-tetradeoxy-, 1,2-O-isopropyhdene-o-xyio-, 21: 169
kasugamine structure, 30: 135 L-arubino-, 21:189-190, 193
2,6-diamino-2,3,4,6-tetradeoxy- synthesis, 41:8
in gentamicin and sisomicin, 29: 105 4,5-di-O-acetyl-2,6-anhydro-3-deoxy-
purpurosamines and, 30: 127 aldehydo-o-lyxo-, 23:91,25:214
2,4-diamino-2,4,6-trideoxy-, 23: 155 uldehydo-o-xylo-, 23:91,25:214
1,4:3,6-dianhydro-, formation during D - ~ x o -24:211
,
pyrolysis of starch and cellulose, 34:42 0-XylO-,24~211
2,2-dichloro-2-deoxy-o-arabino-, 4,6-di-O-acetyl-3-bromo-2,3-dideoxy-, (Y-D-

preparation of, 28:262 arubino-, 24:206

2,4-dideoxy- preparation of, 28:263
0-threo-, 24:212 2,6-di-O-benzoyl-3-deoxy- o-qlo-diethyl
synthesis, 40:41 dithioacetal, preparation of, 32:45
2,6-dideoxy- 3,4:5,6-di-O-cyclohexylidene-2-deoxy-
P-D-ribo-, see Digitoxose uldehydo-o xylo-, synthesis of, 27:278
3-C-methyL~arubino-, synthesis of, aldehydo-L-arabino-, synthesis of, 27:278
27:242 dithioacetals, physical constants of, and
D-arabino-, 21: 185-1 86, 308 peracetates, 32: 106-109
synthesis of, 27:4 o-manno-
DL-, synthesis, 40: 17 biosynthesis, 44:287-294
o-ribo- structures, 44:289
ester of uridine 5'-pyrophosphate, extraction from formose mixture by
isolation of, 28:326 hexokinase reaction, 29:225
1,3,4-tris(p-nitrohenzoate),preparation formation of furan compounds from,
of, 27:3 6:83-106
D - x ~ ~ o - 21:
, I86 high-temperature transformation
L-urubino-, 21: 186 acidic conditions, 46:284-291
L-lyxo-, 21: 184, 186 basic conditions, 46:291-295
4-O-methyl-~-xylo-,21:184185, 187 isotopic substitution, in i.r. and Raman
4-O-rnethyl-o-lyxo-, 23:27 1 spectra band assignments, 44:37
3,6-dideoxy- L-galacto-, biosynthesis, 44:294295
o-(and L ) - ~ x o - ,21: 190 ~-gltrco-,biosynthesis, 44:294-295
o-arubino-, 21:188-190,23:272,274, see L-munno-, biosynthesis, 44:294295
Tyvelose methylation analyses of, 30: 19-22
3-(dimethylamino)-P-~-ribo-,23:273 NMRspectroscopy,42:18
DL-, synthesis, 40: 17-1 8 2-(N-nitroso) acetamido-2-deoxy-
o-ribo-, 21:188-189,23:272, see Paratose alkaline decomposition of, to acetylenic
D-XJ~O-, 21:188-190,23:274 sugar derivatives, 31:71
L-ribo-, 21:190 stabilities of, 31:70
L-xylo-, 21:188, 190 3-0-acetyl-2,6-dideoxy-~-lyxo-, 23:27 1
periodate-thiobarbituric acid assay, 4-O-(dichloroisoeverninyl)-2,6-dideoxy-o-
38~335-336 arubino-. see Curacin
4,6-dideoxy- production of edible from formaldehyde,
D-XYlO-, 21:192 29:224
synthesis of, 28:300 proton nuclear magnetic resonance spectra
3-O-methyl-o-xylo-, 21: 191-1 92, of, spin decoupling method, 29:29
see+Chalcose pyrolysis of, 34:151-153
5,6-dideoxy- rearrangement in liquid hydrogen fluoride,
0-XylO-, 21:193 26: 176-1 88
 SUBJECT INDEX
saccharinic acids formed from, 46:29 I
2,3,4,6-tetradeoxy-4-dimethylamino-~-
erythro-, 24: 161
1,3,4,6-tetra-O-acetyI-2-deoxy-
Ol-O-lyXO-, 24:214
2-thiocyanato-a-o-manno-, 24:209
5-thio-, 23:216
2,3,6-trideoxy-
see
4-C-(2-hydroxyacetyl)-~-threo-,
Pillarose
3-C-methyl-4-0-methyI-3-nitro-~-ribo
L-arabino)-, 24:70
o-erythro-, 21:195, 197
3-(dirnethylamino)-4-0-(4-idobenzoyl)-~-
ribo-, dihydrate, crystal structure,
43:272-273
oL-erythro-, 21: 197
oL-threo-, 21: 197
o-threo-, 21:197
L-threo-, 21:195
3,4,6-trideoxy-3-(dimethylamino)-~-.~vlo-,
structure of desosamine, 28:299
3,4,6-tri-0-acetyl-2-deoxy-a-~-arabino-,
24:206
preparation of, 28:263
tr-O-acetyl-2-deoxy-~-arabino-diethyl
dithioacetal, dimethyl acetal from,
32:65
in urine (human), 24:438439
utilization by yeasts, 32:232
xylo-, 3-amino-2,3,6-trideoxy-C-methyl-~-
natural occurrence of, 42:73
structure of, 42:70-7 I
synthesis of, 42: 122
Hexose-2-t, 2-deoxy- D arabino-, preparation
of, 27: 137
Hexoside
2-Deoxy-o-arabino-, hydrolysis, 48:353
methyl acetamidodeoxy
gas-liquid chromatography of, 28:82-84
per-0-(trimethylsilyl) derivatives,
gasliquid chromatography of,
28: 144-145
methyl 4,6-0-benzylidene-
2-deoxy-a-o-ribo-, 21 :304
3-deoxy-a-o-ribo-, 21: 161-162
2,3-dideoxy-P-~-erythro-,21: 162
methyl 5,6-0-carbonyl-2-deoxy-3-O-p-
nitrobenzoyl-a-o-arabino-,21 :309
methyl 2-deoxy-
29 I
a - ~and-P-o-ribo-,
- preparation of, 34:281
3,5,6-tri-O-pni trobenozyl-
P-D-arahino-. 21:302
o-arabino-, 21:309
methyl 3-deoxy-P-o-xyh-, 21: 161
methyl 4-deoxy-P-o-.rylo-, 21: 161
methyl 4,6-0-benzylidene-2,3-dideoxy-P-~-
erythro-, 23:276
methyl 3,4,6-tri-0-benzoyl-2-deoxy-P-o-
arabino-, 21:297
(or Hexosid-3-dose
P-o-fructofuranosyl a-D-ribo-. from sucrose
microbial oxidation, 33:271
ethyl 2,3,6-tri-O-methyl-, isomers,
preparation of, 31:22 1
methyl 2,4,6-tri-O-methyl-a- and-P-n- ribo-,
degradation of, 31:221
Hexosid-4-ulose
methyl 2,3-di-0-ethyl-6-0-propyl-a-~-xyb
degradation of, 31 :22 1
as 1,3,4,6-tetra-0-acety~-~-~-fructofuranosy~
2,3,6-tri-0-acetykx-~-.~y~o-, preparation
of, 33:271
Hexosid-5-ulose, methyl 6-deoxy-2,3-0-
isopropylidene-a-D-lyxo-, 24:258
~-/yxo-5-Hexosuiopyranuronic acid, in mosses,
46:323-324
Hexosulose
o-arabino-, 22:245,284
mannonic acid from, 25:343
phenylosazone, 25:212
reaction with ammonia, 25:325
3-deoxy-, 26: 14
3-deoxy-o-en~irhro-,25:343,46:292
alkaline degradation of, 28: 196
in dehydration of o-fructose, 28: 179
preparation of, 28: 168- 169
reaction with ammonia, 25:325
structures of, 28: 171
trimethylsilylation
and gas-liquid chromatography of.
2858
and mutarotation of. 28:38
3,6-deoxy-~-erythro-,reaction with
ammonia, 25:325
3,4,5,6-tetra-O-acetyl-o-arahino-, I-(diethyl
dithioacetal), desulfunzation of. 32:77
Hexos-2-ulose
o-arabino-, from 2-amino-2-deoxy-o-
glucose radiolysis, 37:49
292 SUBJECT INDEX

Hexos-2-dose (continued) Hexosyl residues in plant cell-wall polymers,

3-deoxy-D- erythro-, formation. 46:3 1 0 - 42:276
31 1 Hexosyl-3-ulose, 5-4,6-dideoxy-a-~-glycero-,
3-deoxy-4,6-O-benzylidene, synthesis, 3-P-~-mycarosyl-1343-
39: 144 mycinosyllankamycin 1 1-(2-hydroxy-3-
L-qlo- methylbutanoic ester), monohydrate,
oxidation, 37: 1 1 1 monoacetonate, crystal structure,
preparation from iL-sorbose, 37: 109-1 12 4 3 ~ 2 1-272
7
Hexos-3-dose Hexulofuranose
3-deoxy-~-erythro-,21: 164 6-amino5,6-dideoxy-~-xylo-, 23: 142
2-deoxy-4,6-0-benzylidene,synthesis, 4,6-anhydro-
39: 1 39-1 40 1 -O-benzoyl-2,3-O-isopropylidene-a-~-
o-ribo-, polarography of, 29: 145 xylo-, preparation of, 28:290
1,2,5,6-tetra-O-acetyl-4-~-formy~-keto-~- 2,3-O-isopropylidene-a-~-xylo-, 24: 172
arabino-, synthesis, 39:83 6-deoxy-a-~-xylo-2-,crystal structure,
Hexos-4-ulose, D-threo-,1 -(dimethyl 43:21&215
dithioacetal), preparation of, 32:82 2,3 :4,6-di-O-isopropylidene- L-x~~o-
Hexos-5-dose oxidation to ~-xylo-hexos-2-ulose,
6-acetamido-6-deoxy-o-xylo-, composition in 37:llO
solution, 42:39 preparation from L-sorbose, in L-ascorbic
6-deoxy-o-arbino-, 21: 174 acid synthesis, 37:92-93
6-deoxy-o-xylo-, 24:256 4-0-acetyl- 1 -O-benzoyl-6-deoxy-6-iodo-2,3-
preparation of, 28:291 0-isopropylidene-a-L-xylo-, reaction
D - ~ X O - ,1 -(diethy1 dithioacetal) preparation with silver fluoride, 28:291
of, 32:82 1-O-benzoyl-6-deoxy-6-iodo-2,3-0-
Hexosulosonic acid, o-xylo-, calcium salt isopropylidene-a-L-, reaction with silver
dihydrate, crystal structure bibliography, fluoride, 28:290
31:364 2,3-O-isopropylidene-1,4,6-tri-O-
Hexosyl, 2-deoxy-a-~-arubino-,formation, (methylsulfonyl)-a-r-xylo-,
48:353-354 displacement reaction of, 24: 173
Hexosyl bromide 3-Hexulofuranose
5,6-O-carbonyl-2-deoxy-3-O-p-nitrohenzoyl- 1,2:3,4-di-O-isopropylidene-P-~-xylo-,
o-arabino-, 21:3 10 26:254
2-deoxy-3,4,6-tri-O-( p-nitrobenzoy1)- 1,2:5,6-di-O-isopropyiidene-a-~-ribo-,
a-o-arabino-, 21:301 23:267
a-o-lyxo-, synthesis of, 27:4 Hexulofuranoside
a-o-ribo-, 21:305,307 4,6-dichloro-4,6-dideoxy-
methanolysis of, 34:281 a-D-galactopyranosyl 3,4-anhydro- 1,6-
o-ribo-, synthesis of, 27:4 dichloro- 1,6-dideoxy-2,3-di-O-suIfo-
2,6-dideoxy-3,4-di-O-p-nitrobenzoyl-P-~- P-D-ribo-, physical properties of,
ribo-, 21:298 33:294
3,4,6-tri-O-benzoyl-2-deoxy a-o-arabino-, 2,3-di-O-sulfo-a-~-ga~actopyranosy~ 3,4-
21:297 anhydro- 1,6-dichloro-l,6-dideoxy-P-
Hexosyl chloride, 2-deoxy-3,4,6-tri-O-p- D-ribo-, preparation of, 33:261
ni trobenzoyl-a-D- 2,3-di-O-su~fo-a-~-ga~actopyranosy~
arabino-, 21:301 1,4,6-trideoxy-P-o-, preparation of,
ribo-, 21:305 33:261
Hexosyl purines, keto derivatives of, 42:232 4,6-dichloro-4,6-trichloro-, 1,4,6-tri-deoxy-
Hexosyl pyrimidines, keto derivatives of, 2,3-di-O-sulfo-P-o-, physical properties
42:232 of, 33:294
 SUBJECT INDEX 293

3-Hexulo-3,6-furanosidono- 1,4-lactone, methyl ascorbic acid, 37: 105-1 06

2-C-benzyl-a- ~-xylo-, crystal structure Hexulopyranosonic acid.-a-L-xylo-,
bibliography, 37:393 monohydrate, crystal structure
5-Hexulofuranosidurono-6,3-lactone, methyl D- bibliography, 34:349
xylo-, preparation of, 33:230 Hexulose, I -(Benzy lamino)- I -deoxy-o-rhreo-
Hexulofuranosonic acid, 2,3 :4,6-di-0- 2-, 46~320
isopropylidene- u-xylo-4-Hexulose, 1,3,-dideoxy- 1-fluoro-3-
WL-, monohydrate, crystal structure iodo- I ,2:5,6-di-O-isopropylidene-a-, 'H-
bibliography, 38:445 and "F-NMR data for, 46:159
L-xylo- 3-Hexulose
conversion to L-ascorbic acid, 37:96- 105 1,5-anhydro-2-deoxy-o-erythro-, preparation
preparation, in L-ascorbic acid synthesis, of, 31 :48
37~93-96 1 -deoxy-L-urabino-, synthesis, 41:9
uses, 37:96 4-0-benzoyl- 1,2:5,6-di-O-isopropylidene-
5-Hexulofuranurono-6,3-lactone,1,2-0- keto-u-urubino-, 26:254
isopropylidene-a-o-xylo- 6-0-benzoyl- 1,2:4,5-di-O-isopropylidene-
L-ascorbic acid preparation from, 332 19, keto-oL-xylo-, 26:254
232 synthesis, 41:9
preparation of, 33:230 1,2,5,6-tetra-O-acetyI-4-0-formyl-~-ribo-,
reaction with hydrazine or phenylhydrazine, 26:254
33:216 4-Hexulose. 3-deoxy-l -fluoro-3-iodo- 1,2:5,6-
2-Hexulopranose, I -(benzylmethylamino)-1 - di-O-isopropylidene-u;rylo-, preparation,
deoxy- 38:242
o-D-, lyxo-, crystal structure bibliography, Hexulose 1 -phosphate, 5,6-dideoxy-o-threo-,
38:460 composition in aqueous solution, 42:32
P-D-arabino-, crystal structure bibliography, Hexulose 6-phosphate furanoses, stability in
38:459 solution, 42:27-28
Hexulopyranose Hexuloses
4-deoxy-4-fluoro- 1,2-0-isopropy~idene-~-u- 5-acetamido-
xylo, preparation, 38:218 5-deoxy-, 23: 187
a-~-xylo-2-, crystal structure, 43:2 I7 5,6-deoxy-r.-xylo-, 23:188
1,2-~-isopropylidene-~-o-~.vb, 5-deoxy-i.-xylo-. 23: 188
preparation, 38:218 6-acetamido-
3-Hexulopyranose, 1,6-anhydro- 6-deoxy-, 23: 174
2,4-dideoxy-2,4-difluoro-P-~-,hydrate, 6-deoxy-~-xylo-,23: 178
preparation, 38:246 CX-D-~JJXO-, see Tagatose, a+-
4-0-benzyl-2-deoxy-2-fluoro-~-~-ribo-, a-o-xylo-, conformation of, 23:30
preparation, 38:246 a-~-xylo-, .see Sorbose, a - ~ -
Hexulopyranoside 6-amino-6-deoxy-, 23: 142
benzyl4-deoxy-4-nitro-a-~-xylo-, 24:97 composition in aqueous solution, 42:4849
methyl 5-amino- urubino-, composition in aqueous solution,
6-deoxy-xylo-, 23: 142 42:65
1,3-0-benzylidene-5-deoxy-a-~-.r~~lo-, P-D-arablnO-, see Fmctopyranose, P-0-
23:146 composition in aqueous solution, 42:30,
methyl per (trimethylsily1)- 3740,65
a-and-P-o-arubino-, mass spectra of, crystallography of, 2560
29:48 cyclic acetals, properties of, 26:274
a-and-P-L-xylo-, mass spectra of. 29:48 1-deoxy-
2-Hexulopyranosidonic acid,-a- ~-xylu-,methyl acyclic form in solutions of, 42:30
ester, preparation and conversion into L- hydrated carbonyl forms of, 42:3 I , 38
294 SUBJECT INDEX
Hexuloses (continued)
4-deoxy-, o-eiythro-, 21: 166
5,6-deoxy-, o-threo-, 21:193
5-deoxy-
o-erythro-, 21: 168
o-threo-2-, taste properties, 45:252
6-deoxy-
o-urubino-, 21:176
D-lyXO-, 21:176
L - x ~ ~ o21:174-176
-,
1,3-dideoxy-, o-erythro-, synthesis of, 27:4
1,2:4,5-di-O-isopropylidene-~-~-ribo-,
reaction with carbon tetrachloride-
triphenylphosphine, 28:247
1,2:5,6-di-O-isopropylidene-4-0-
(methylsu~fonyl)-o-urubino-3-, 23:258
D-lyXO-, 23~32,39
halogen derivatives of, 22:226
isopropylidene acetals, hydrolysis rates for.
26:204
keto-, conformation of, 26:73
~-xylo-,utilization by yeasts, 32:225
nucleosides of, reduction of, 42:254
trimethylsilylation, 28:25
and methyl glycosides, mass spectra of,
29:48, 50
xylo-, composition in aqueous solution,
42:65
2-Hexuloses
1-amino- 1,3-dideoxy-o-eiythro-, preparation
and deamination of, 31:50
3-deoxy-o-erythro-, preparation of, 31:50
sweetness-structure relationship,
45:253-254
Hexulosonates
3-deoxy-o-erythro-, from alginic acid,
29:252
3-deoxy-6-0-phosphono-~-eiythro-, from
alginic acid, 29:253
5-Hexulosonates
methyl tetra-0-acetyl-, conformation of,
26:73
methyl 2,3,4,6-tetra-0-acetyI-o-xylo-,
synthesis, 39233
2-Hexulosonic acid
arubino-, composition in organic solvents,
42:68
L-xylo-
conversion to L-ascorbic acid, 37:100, 103
esters, preparation, 37:97-98
methyl ester, cyclization to L-ascorbic
acid, 37:103-104
preparation, 37:89,97
preparation from L-gulono- 1,4-1actone,
37: 1 2 4 1 2 5
preparation, 37:89, 107, 130
by chemical oxidation of L-sorhose,
37: 106, 109
from o-galactose, 37: 146
from o-glucitol, 37: 112-1 15
from o-glucuronic acid, 37: 115-1 16
by fermentative oxidation of o-glucose,
37:127-129
by fermentative oxidation of L-sorbose,
37:108-109, 112
from L-glucuronic acid, 37:119-125
from L-idonic acid, 37:134-137
from ~-~yIo-hexos-2-ulose, 37:l I 1
from pectin, 37:147
L-xylo-, preparation, 38:288,3 14
3-Hexulosonic acid, 2,4,5,6-tetra-U-benzyl-r-
xylo-, benzyl ester, preparation, 38:3 14
5-Hexulosonic acid
D - ~ J X O - ,22:245,284
0-XylO-
calcium salt dihydrate, crystallography of,
2967
dehydration of, 28: 189
preparation from o-glucose, 37: 126-1 37
reduction, 37:129-133
salts, hydrogenation, 37:129-133, 136
sodium salt, structure, 37: 128-129
Hexulosonic acids
P-o-urubino-, calcium salt trihydrate, crystal
structure bibliography, 37:376
composition in aqueous solution, 42:37,
3940,66
D-urubino-, 22:245,284
2-, analytical high-performance liquid
chromatography, 46:34
calcium salt trihydrate, crystal structure
bibliography, 34:371
dehydration of, 28:188-189, 193
polarography of, 29: 171
3-deoxy-o-eiythro-, and ethyl ester,
synthesis of, 27:279
6-deoxy-6-fluoro-o-arabino-, 22:2 10
2,3:4,6-di-O-isopropylidene-~-xylo-,
preparation of, 29: 123-124
D-xy[o-5-. analytical high-performance liquid
 SUBJECT INDEX
chromatography, 46:34
L-xylo-
2-, analytical high-performance liquid
chromatography, 46:34
dehydration of, 28: 192
polarography of, 29: 147-149, 171
mass spectrometry of, 29:79
2-Hexulosono- 1,4-lactone, 3.6-anhydro-I -xyh-,
preparation, 38:3 14
Hexulosono- I ,4-lactone, 3,6-anhydro-i.-.~~,lo-,
25:261
Hexulosuronic acid
I -(benzylamino)- I -deoxy-o-arubino-2-,
46:320
1-deoxy- I -(dibenzylamino)-o-urabino-2-,
46:320
Hexuronic acids
analysis of, 28: 188
decarboxylation, 28: 186, 190,46:288-289
dehydration of, 28: 1 YO
derivatives
5-bromides from, 49:4344
radical-mediated brominations, 49:4245
formation of 2-furaldehyde from, 46:28Y
gas-liquid chromatography of, 28:7 1
history, 39:2
methyl ethers of, 9:131-148
nucleotide-linked, biosynthesis, 44:289-290
1,2-O-cyclohexylidene-5-deoxy-i~-xy~o-,
hydrazide, 23: 16 I
residues, reduction to hexose resides, 24:34 1
synthesis, 39:4
ultraviolet-absorbances of, 4 6 5 5
in urine (human), 24:438
5-Hexylbarbituric acid, cyclodextrin inclusion
complexes with, 46:223-224
4-Hexyn-l -al-3-ol, 3-methyl-, dimethyl acetal,
precursor for m-mycarose, 40: 14- I5
Hex- 1-ynitol, 1,2-dideoxy-o-uuuhino-, 24:224
Heyns rearrangement, 22:268,25:335.
337-338,46:308
Hibbert, Harold, obituary of, 16:l-1 1
High-mannose oligosaccharides, size-
fractionation of, 46:62
High mass, definition, 45:34-36
High-performance liquid chromatography,
46: 17-72, I8
alkylated (reversed-phase) silica gels,
46:27-30
amine-modified silica gels, 46:23
295
aminopropyl-bonded phase columns,
maintenance of, 46:24
aminopropyl-bonded silica gels, for
preparative purposes, 46:5Y
analytical separation, 46:3249
anion-exchange resins and silica gels. 46:30
automated fraction-collectors, 46:23
bonded-phase silica cartridges, 46: 19
boronic acid substituted silica gel, 46:3 1
cartridge-type filtration-units. 46:20
cation-exchange resin columns, 46:24-27
applications, 46:26
calcium-form, 46:2&27, 50-52
hydrogen-form, 46:25-26,50
lead-form, 46:26, 50-5 I
maintenance, 46:27
for preparative purposes, 46:59
silver-form, 46:26, 50
C,,-bonded silica-gel columns, 46:28-29, 59
column design, 46:2 1
column ovens. 46:22
column-packing equipment, 46:21-22
data systems, 46:22-23
degassing instruments, 46: 19
detectors, 46:22
diol-modified silica gel, 46:3 1
equipment for preserving column-life,
46: 19-20
filters, 46:20
fittings, 46:20
guard columns, 46:19
injectors. 46:20-2 1
instrumentation, 46: 18-23
ion-exchange resins, 46:3 1
in plastic cartridges, 46: I9
metal cation-carbohydrate complexes
applications, 47:40
mini-columns, 46: 19-20
phenyl-bonded phase, 46:28
post-column reaction-modules, 46:22
pre-columns, 46: 19, 27
preparative, solvent-delivery system, 46: 19
refractive-index detectors, 46: 18
reversed-phase columns, 46:24,29
reversed-phase silica-gel phases, 46:28
silica saturator columns, 46: 19
solvent-delivery systems, 46: 18-19
stationary phases, 46:23-3 1
sugars in solution, 49:22
switching valves, 46:20
296 SUBJECT INDEX

Hilbert-Johnson procedure, 23:211,222 folklore, 25:286

Hill reaction, inhibition of, 21:405 gas-liquid chromatographic analysis of,
Hirano, S., 46:4,6-7 28:48, 68
Hirase, Susumu, 46:1,9 granulation of, 25:293
Hirst, Edmund Langley, obituary, 35: 1-29 history, 25:285
Histamine, complexation with heparin, 43: 1 17 honeydew, 25:287,307-309
Histidine monosaccharides, 25:289-294
catalytic action on mutarotation, 24:32 nectar, 25:286
D-, favored conformation, 45:232 oligosaccharides
OL-, 45: 15 composition of, 25:295-298
histidyl-, catalytic action on mutarotation, origin of, 25:298-306
24:32 polysaccharides in, 25:306
Histidine pyridoxol pathway, 52:305 sugars of, 25:285-309
Histidine-2-thio1, DL-, 45: 15 uses of, 25:286
Histocompatability antigens, oligosaccharides, Honeydew, honey from, 25:287,307-309
liquid chromatography separation, 46:43 Honghelin, 21:286
Histone, calf-thymus, 25:444 Hormones
Histoplasma capsulatum, polysaccharide, effect on carbohydrate metabolism, 33:4
41 ~69-70 effect on glycogen synthetase activity,
Histoplasma farcinosum, polysaccharide, 26:378
41:70 ganglioside effect, 40:23 1
HMBC, 51:22 sex, effect on a-D-mannosidase activity,
HMQC, 51:22 28:434,437
'H-NMR spectroscopy, 43:7 Hormonocorticogonadotropin, structure,
Holocellulose 37: 185
hemicellulose from, 36:223-225 Horse gram, see Dolichos bijlorus
ryegrass, hemicelluloses from, 36:259 Horseshoe-crab lectin, isolation, purification,
Holoruthin A, 6-deoxy-~-glucosefrom, 21: and composition, 35:306
I73 Houssay, B., 46:12
Homarus americanus lectins, isolation, 35:3 13 2H-Pyran
Homogalacturonan from plant cell-walls, 2-alkoxy-5,6-dihydro-
42:285 chemical and physical properties,
interconnections of, 42305 40:3841
purification of, 42:276 cis-hydroxylation, 40:4142
structure of, 42:280 epoxidation, 40:4244
Homogeneous, defined, 24:337 synthesis, 40:35-38
Homonucleosides, preparation of, 32:73 cis-5,6-dihydro-2,5-dimethoxy-, preparation
Homopoly(deoxyribonucleotides),preparation, of, 28:296
36: 169-170 3,4-dihydro-
Homopolynucleotides, 22:360 2-(hydroxymethy1)-, preparation from
Homopolysaccharides acrolein dimer, 28:296
biosynthesis of, 26:37&403, 396 2-(methoxymethyl)-, bromomethoxylation
nomenclature, 52: 163 of, 28:295
Homoxylans, isolation, 36:229 selective acetalations with, 33:71
Honey in sugar syntheses, 40:30-35
chromatography of, 25:290-293,295 5,6 dihydro-
composition and analysis of, 25:289-293 2-methoxy-, reactions with 1,3-dibromo-
definition of, 25:287 5,5-dimethylhydantoin and with
enzymes in, 25:303 ethanesulfenyl chloride, 28:274
fermentation by yeasts, 32: 129 in sugar syntheses, 40:35-60
 SUBJECT INDEX
2-enoxy-5,6-dihydro-6-methyl-, preparation,
40:36
tetrahydro-, reaction with iodine
tris(trifluoroacetate), 40: 109
trans-5,6-dihydro-
6-(hydroxymethyl)-2-methoxy-,resolution
of racemates, 40: 113
2-methoxy-6-( methoxymethy1)-,
preparation of, 28:295
4H-Pyran, 2,3-dihydro-, halogenation of,
24:203
4H-Pyran-2-carboxylic acid
5,6-dihydro-3-hydroxy-4-0~0-, methyl ester,
formation of, 28: 185
3,4,5-triacetoxy-5,6-dihyro-,methyl ester,
dehydration of, 28: 185
2H-Pyran-2-methanol,3,4-dihydro-
cyclization of, 34:48
preparation of, 34:48, 145
4H-Pyran-4-one
2,3-dihydro-
3,5-dihydroxy-6-methyl-, from
dehydration of o-fractose, 28: 176,
179-180
3-hydroxy-2-(hydroxymethyl)-,24:2 18
3-hydroxy-2-methyl-, from o-fructose
dehydration, 28: 180
2( 1H)-Pyridinone
5-(2-deoxy-o-erythro-pentofuranosyl)-6-
hydroxy-, preparation of, 33: 179
6-hydroxy-5-o-nbofuranosyl-,preparation
of, 33:178-179
2( 1H)-Pyrimdinone
1-P-L-ribosyl-, dihydrate, crystal structure
bibliography, 38:504-505
4-ethoxy-5-methyl- 1-(2,3,5-tri-O-acetyl-4-
thio-o-ribohanosyl)-, 23:222
4-ethoxy- 1-(2,3,4-tri-O-acety1-5-thio-w
xylopyranosy1)-, 23:2 11
4-methoxy- I-P-o-ribohranosyl-, selective
methylation with diazomethane, 33:69
HSEA approach, 47: 105
HSQC, 51:22
2H-thiopyran, 5,6-dihydro-, carbohydrate
substrate, 40:38
Hudson, Claude Silbert, obituary of,
9:xiii-xviii
Hudson isorotation rule, 23:16, 185, 191,231
Human cerebral-cortex ganglioside,
hydrochloric acid hydrolysis, 46:267
297
Human chorionic gonadotropin glycopeptides,
structure, 37: 181
Human IgG glycopeptide, structure, 37: 178
Human milk, see Milk
Human plasma a,-acid glycoprotein,
deamination of, 31:236
Humectants, tobacco, gas-liquid
chromatography of, 28:97
Humic acids, spectral analysis and
identification, 44:24
Humus formation, carbohydrate transformation
in, 46:323-326
Hurlers syndrome, 45: 1 18
Hyaluronan, 52:370-378,421
3-fold helix, 52375-378
4-fold helix, 52372-375
segment, 52:371
Hyaluronate lyase, 44:204
Hyaluronate oligosaccharides, liquid
chromatography separation, 46:4849
Hyaluronates, crystal structure bibliography,
35:383-385
Hyaluronic acid, 24:29 I , 44: 198
in aqueous ethanol solvent at pH 2.5, circular
dichroism, 45:115-116
p-eliminative degradation of, 29:238, 241
biosynthesis of, 12:299-319,26:436
bovine nasal cartilage, 38:36,79
calcium and strontium salts, crystal structure
bibliography, 40:393-3 94
circular dichroism, 45: 1 13-1 15, 1 17
composition, analysis, 4 6 5 5
depolymerization by nitrous acid, 31:75
disaccharide repeating units, 43:53-55
gas-liquid chromatography of hydrolyzates
of, 28:78
gel chromatography of, 25:34,46
hexosamine; 43:53, 55
hydrazinolysis and deamination of, 31:78
major uronic acid, 43:53,55
model molecules, laser-Raman spectroscopy,
44~80-81
potassium salt, crystal structure bibliography,
33:402
proton magnetic resonance spectroscopy of,
27:4 I 43
repeating units of, 26:432
and salts. crytal structures of, 39384-385
sodium salt, crystal structure bibliography,
33:216
298 SUBJECT INDEX

Hyaluronic acid (continued) labeling of sugars with hydrogen

structure isotopes by, 27: I35
crystal bibliography, 33:401402,36:327, Hydrazinol ysis
40:393 of glucofuranurono-6,3-lactones,33:216
enzymic analysis, 44:203-205 N-deacetylation by, 31:78
and sequence analysis of, 46:57 regioselective, 39:40
synovial, 37:2-3 Hydrazones
synthesis and assay of, 27: 18 1 of o-fructose derivatives, 22:263
in urine, 24:443 as photosensitive protecting groups, 46:195
Hyaluronidase, 44: 199, 202,205 of sugars, 3:2344
testicular, heat stability of, 30:279 Hydroboration
transglycosylation activity, 30:276 of alkene sugars, 27:242
Hybrimycins, A and B, discovery of, 30:112 of sugar methanesulfonate, 23:268
and structure of, 30: 1 18 Hydroboration reaction, 21:168-169, 181
Hydantoin, 1,3-dibromo-5,5-dimetbyl-, reaction Hydrocarbon films, 1,4:3,6-dianhydrohexitoIs,
with 5,6-dihydro-2-methoxy-W-pyran, 49:171
28:274 Hydrocarbons, 53:352-353
Hydracrylaldebyde, from ethylene oxide, 23:63 aliphatic, as solvents for sugars, 27: 105
Hydracrylic acid methyl ester, from ethylene aromatic, as solvents for sugars, 27: 105
oxide, 23:64 Hydrocellulose, 25:6
Hydrangea,antimalarial alkaloid from, 29:2 gas-liquid chromatographyic analysis of,
Hydration, 44:87 28:74
of C-glycosylated alkenes, 27:241 Hydrochloric acid
Hydration shell, 44:87 as catalyst for hydrolysis of starch, 36:25
Hydrazine hydrolysis
1-benzyl- 1-phenyl-, 21: 147 of glycoconjugates with, 46:266
in degradation of polysaccharides, 31: 195 of polysaccharides, 28: 15
I,l-diphenyl-, in sugar chemistry, 21: I I recoveries of monosaccharides after,
lactone group reaction with, 50:155-157 46~260-261
1-methyl-1-phenyl-, in sugar chemistry, pH of aqueous solutions of, 46:252
21:11 Hydrochloric acid-magnesium chloride test, for
(p-bromopheny1)-, in sugar chemistry, 21: 11 sugar oxiranes, 25: 170
phenyl- Hydrocinnamic acid
derivatives, discovery by Fischer, 21:3, 10 P-methyl-. (+I, (-1, W-),and (SF(+),
reaction with preparation of, 27:202-203
a,6-unsaturated sugars, 27:249 cyclodextrin inclusion complexes with,
2,5-an-hydroaldoses, 25:2 12 46:222,224
(p-nitropheny1)-, reaction with bromodeoxy Hydrocolloids, commercial, polysaccharidic,
sugar, 28:287 13:265-287
in polarographic determination of Hydrofluoric acid, in hydrolysis of teichoic acid
carbohydrates, 29:152 polymers, 28: 16
reaction of anhydrous, with chlorodeoxy Hydroformylation, see also 0 x 0 reaction
sugars, 28:285 of 2-acetoxy-3,4,6-tri-~-acetyl-o-g~uca~,
(thiomethoxythiocarbony1)-, reactions with 24:220
ketoses, 22:267 of epoxides, 23:63
Hydrazine hydrate, deacylating agent, of glycals, 23:86,24:210
39:3940 of olefins, 23:61
Hydrazino compounds Hydrogen
carbohydrate, decomposition of, 22: 197 isotopes, hydride and proton exchange,
oxidation in alkaline deuterium oxide, 27: 156-1 62
 SUBJECT INDEX
intermolecular transfer, 27: 166
localization of proton movement,
27162-166
sugars labeled with, 27:127-190
substitution reactions, radical-mediated
brominations, 49:75-79
transfer to cofactor, 27:169
Hydrogen-abstraction reactions, by radiation,
37:18-19,65, 71-72
Hydrogenation
of a,@-unsaturatedacids, 27:261-263
catalytic, enonolactones, SO: 170-1 73
of nitro sugars, 24: 109
of nucleotides, 22:380
of unsaturated sugars, 27:241
Hydrogen atom abstraction, radical-mediated
brominations
regiochemistry, 49:67-68
stereochemistry, 49:7 1-72
Hydrogen bonding, see also Carbohydrates,
hydrogen bonding
bond lengths, 45219
in carbohydrates, 2956-57
effect on conformation, 23:30
in crystal structures, 25:98-101
in cyclic acetals, anomeric configuration and,
26:228
directional influence, in sweetness,
45:219-220
between hydrogen fluoride and hydroxyl
groups of sugars, 47: 169
infrared measurements and, for D-
glucofuranosidurono-6,3-lactones,
33:209-2 10
effect on selective esterification, 33: 15-1 9,
24,34,37,40,43, 204
in water and aqueous solutions, vibrational
spectroscopic studies, 44236
Hydrogen bromide
acetolysis and bromination of cyclic acetals,
39: 113-1 15
as catalyst in polymerization of sugars,
21:452
reaction with aldonolactones, SO: 134-136
Hydrogen chloride, catalysis of polymerization
by, 21:452,462
Hydrogen-deuterium exchange, 44:3 6
Hydrogen fluoride, S2:216
acyloxonium ion formation in liquid, 26: 132
in anhydridization of hexoses, 34:46
299
anhydrous
protonic activation of dihexulose
dianhydndes, S2:216-220
as solvent for carbohydrates, 27:93
glycoprotein deglycosylation, 47:200-20 1
glycosyl fluoride synthesis, 48:95-96
mechanism of reaction with carbohydrates,
47:168-173
polymerization in liquid, 21:445
polysaccharide degradation, 48:96
presence in reaction mixture of water, 47: 172
reaction with
cyclic acetals, 39: 1 17
tri-0-acetyl-D-glucal,24:2 I6
rearrangements of alditols and an-
hydroalditols in, 26: 173-175
of cyclitols in liquid, 26: 169
of monosaccharide esters in liquid,
26: 1 7 6 188
solvolysis, 47: 173-174
in methanol, 47: 195
sugar
polymerization, 47:202
removing from cell walls, 47:201
Hydrogen-ion concentration
effect enzyme kinetics, 23:292, 327
on phosporylase action, 23:355
mutarotation measurement by, 23:52
Hydrogen ions, catalysis of mutarotation by,
24: 17
Hydrogenolysis
of I ,6-anhydrohexopyranose ethers and
esters, 34:7475
of bicyclic acetals, 39: 133-135
bromodeoxyaldono-l,4-lactone, 50: I 73-1 74
of carbon-sulfur bonds of dithioacetals,
32:75-79
of cyclic acetals, 34:205,39:121-138
rate of reductive cleavage, 39: 122
reducing systems, 39: 135-136
regioselectivity, 39: 123-124
stereoselectivity, 39: 124-135
of cyclic orthoesters, 39:79
of levoglucosan, 34:69
of tri-0-acetyl-D-glucal, 24:2 13
unsaturated cyclic acetals, 39: 136-1 38
Hydrogen peroxide
action of carbohydrates and related
compounds, 19: 149-1 79
2-hydroxy-, 9:97-129
300 SUBJECT INDEX
Hydrogen peroxide (continued)
radioinduced, 51:27&277
reactions with radicals by radiolysis, 37:2 1
Hydrogen starch, moisture and degradation,
47:290
Hydrogen sulfide, as solvent for sugars, 27:94
Hydrogensulfite, thiamine cleavage,
52~271-272
Hydroglucan, antitumor activity of, 32:250,
267,271
Hydro(hydroxymethyl)ation, of olefins, 23:61
Hydrolases
carbohydrate, 27:305-307
nucleic acid, 27:307
Hydrolyses, monitoring with f.a.b.-mass
spectrometry, 45:4849,50
Hydrolysis
acetal, selective, 39: 14-24
of acetals, 22:30, 59, 113
acid, of glycofuranosides, 21: 128
acid-catalyzed, 47: 172
of D-glycopyranosiduronic acids, kinetics,
36~83-86
of starch, 36:29, 42
of glycosides, 22:25-108
alkaline, of methyl aldosides, 21: 137
of aminodeoxy 1,6-anhydrohexo-pyranoses,
34: 128
of carbohydrate boronates, 3550-52
of carbohydrate sulfonic esters, 23:259
for cleavage of glycosidic linkages, 46:252
of cyclic acetals of ketoses, 26:203
2-deoxy-~-arabino-hexoside, 48:353
dextrins, 47:301
of dithioacetals, mercury(I1) chloride in,
32:60-66
enzymic
of galactomannans, 31:256
glycosides, 48:323-324
of polysaccharides, 24:340
selective, 39:43
of starch, 36:31-34
structure and configuration effects, 50: 12
of furanosides, 22:39
a-D-glucopyranoside by glucoamylase,
50: 17-1 8
of glycosides, effect of aglycon on, 22:7 1
of glycosidic linkages in polysaccharides,
31:187
of glycosylamines, 22:37
of glycosyl esters of nucleoside 5-
pyrophosphates, 28:356-360
kinetics of, of cyclic monosaccharides,
23:209
a- and P-maltosyl fluoride, 48:358-359
mechanism of
of cyclic acetals, 34:202-205
of deoxyhalogeno sugars, 28:305
4-methylumbelliferyl P-o-ghcosides,
48:359-360
of nitro sugars, 24:118
non-enzymic, glycosides, 48:32&323
participation of carboxylate group, 48:379
of phosphate esters, 21:328
of polysaccharides, 22:85,24:337,28:14-23
of pyranosides, 22:27
of radicals a to lactol bridge by radiation,
37: 15
rates of, 22:91-106
of substituted methyl a-D-
glycopyranosides, 22:208
of sucrose, 22:31
effect of concentration on rate of, 22:41
of teichoic acids, 21:331,345-346,352
of I-thioglycosides, 22:35
of 5-thiopyranosides, 22:37
of 5-thioxylopyranosides, 24:50
Hydro(methoxycarbonyl)ation, of epoxides,
23:63
Hydronium ion, in mutarotation, 24:4 1,43
Hydroquinine, bitterness, 45320
Hydroxide ion, cyclodextrin inclusion
complexes with, 46:221
2-(2-Hydroxyacetyl)furan, 3 18 formation,
46:285-287
a-Hydroxy acids, cyanohydrin synthesis, 50:6
Hydroxyaldehydes
a-, 45:13
in aqueous solution, 42:29-30
hemiacetal formation, 42:30
D-, Helferichs work on, 45:3
8-(Hydroxyalkyl)adenines, 50: 153
Hydroxyalkylation, determination of,
29:315-316
a-Hydroxyalkyl radicals
elimination reactions, by radiation, 37: 1 1-12
radiation and reactions with nitrous oxide
and halides, 37:21-22
radical-radical reactions, 37: 17-1 8
Hydroxyaminolysis, regioselective, 39:40
 SUBJECT INDEX
4-Hydroxybenzoate ion, cyclodextrin inclusion
complexes with, 46:221
2-Hydroxybenzoic acid, cyclodextrin inclusion
complexes with, 46:223-224
3-Hydroxybenzoic acid, cyclodextrin inclusion
complexes with, 46:221
4-Hydroxybenzoic acid, cyclodextrin inclusion
complexes with, 46:221,223-224
m-Hydroxybiphenyl reagent for plant cell-wall
residues, 42:275
3-Hydroxybutanal, condensation, 49: I94
Hydroxy compounds
glycosiduronic acids, 36: 131-132
polyol products in formose, 29:209
Hydroxycyclopentylmethanol, 4-amino-3,3-
difluoro-2-, 48:152-153
2-Hydroxyethyl group, gas-liquid
chromatographic determination of, 30:35
Hydroxyethyl groups, from aminoethyl groups
by nitrosation, 31:71
Hydroxyfiran, 2-aceyl-3-, 46:320-32 1
a-Hydroxyketones, 45: 13
Hydroxyketones in aqueous solution, 42:29
hemiacetal formation, 4 2 3 0
temperature effects on, 42:33
Hydroxylamine
in polarographic determination of
carbohydrates, 29: 152
reaction with
glycosyl esters of nucleoside 5 -
pyrophosphate, 28:360-362
nucleotides, 22386
Hydrox ylation
of a,@-unsaturatedaldonic esters, 27:266
of unsaturated sugars, 27:24 I
Hydroxyl group
anomeric effects, solvent effects, 47:68-69
in dextrins, 47:303
effect on hydrolysis rates of acetals, 22:59
of pyranoid rings, 2255-56
glycosylation, 47: 170
lipid A backbone
position 4, 50:247-249
position 6 , 50:249-252
participation in sugar reactions, 22: I I2
photosensitive protecting groups,
46: 180-19 1
protecting groups for sugar, 36: 142-149
reactivity of primary, in sulfonylation,
23:240
30 I
of secondary, in sulfonylation, 23:244,
247
relative reactivities of, 8: 1 4 4 , 3 3 : 11-109
Hydroxyl ion, catalytic activity of, 24:24
4-Hydroxyl-~-threonine,pyridoxol
biosynthesis, 52:287
Hydroxy-r-proline
and D-glucose or r-rhamnose, high-
temperature transformation of, 46:3 15
in extensin, 42:270
glycoproteins in plant cell-walls, 42:298-
3 00
biosynthesis of, 42:322,372-373
cell-wall expansion and, 42352-355
interconnections involving, 42:307-309
inripening, 42:380-381
Hydroxyl radicals, 51:286
Hydroxymethylbutanoic acid, 2,4-dihydroxy-
2-, 46~305
Hydroxymethylpyrimidine,4-amino-2-
carboxymethyl-5-, decarboxylation,
52:303
C-(Hydroxymethy1)-scyllo-inositol,47: I 7
Hydroxymethyluridine, 2-deoxy-5-, crystal
structure, 43:3 19
y-Hydroxyvaleraldehyde, Helferichs work on,
452-3
Hydroxyvalidamine, 48:74
synthesis, 48:52-53
Hygromycin A, 24:258
structure of, 29:294
sugar component, preparation of, 28:291
Hygromycin B, isolation and structure of,
30: 133-1 34
Hygromycins, 21: 174
discovery of, 30: 112
identification of sugar component of, 32:78
Hyosamine. DL- and L-, synthesis of, 30: 134
Hyperuricemia, mechanism of o-fmctose-
induced, 34:322-324
Hypochlorous acid, in chlorinolysis of
glycosidic bond, 34:48
Hypophosphorous acid, 1,6-
anhydrohexopyranose cleavage by, 34:69
Hypoxanthine. 8-(2-deoxy-a-o-eythro-
pentofuranosy1)-, crystal structure
bibliography, 34:367
Hysteresis, 24:3 16
of agar gels, 24:277
of gels, 24:306
302 SUBJECT INDEX

I crystal
1(4),3(6)-(R,R)-di-S-oxide,
structure, 43:341
Idaric acid, 2,5-anhydro-o-, 25190 1,6-di-0-acetyl-2,4:3,5-di-O-methyl-ene-~-,
preparation of, 33: 119 22:15
ldono- 1,4-lactone, 2-amino-2-deoxy-~-, 1,6-di-O-benzyl-2,4:3,5-di-O-methyl-ene-~ ,
deamination of, 31:58 acetolysis of, 22:15
Iditol 1,2:5,6-di-O-isopropyIidene-o-,3,-4-
3-acetamido- 1,2:5,6-di-O-isopropylidene-~-, trithiocarbonate, acetobrominolysis,
22:133 39:114
1-amino-1,5-anhydro- I-deoxy-L-, 23: 137 di-0-isopropylidene-o ,monobenzoate,
preparation of, 34: 150 22:118
I-amino-l,6-anhydro- 1-deoxy-L-, 23: 156 1,2:5,6-di-O-isopropylidene-3,4-dithio-o-,
preparation of, 34: 150 acid hydrolysis of, 32:44
1-amino- 1 -deoxy-o-, deamination of, 31:60 2,4:3,5-di-O-methylene-~ , acetoiysis of,
1,4-anhydro-r-, catalytic oxidation of, 22:13
25261 L-, anhydridation of, 25:233
1,6-anhydro-r- 3,4-S-kopropylidene-3,4-dithio-o-,
crystal structure bibliography, 34:350 preparation of, 32:44
infrared spectrum of, 25250 tri-0-acetyl- 1,5-anhydro-5-deoxy-5-C-[(S)-
2,5-anhydro-~-,29243 phenylphosphinyl]-L-, physical
1,2-bis(acetamid0)-3,4,5-tri-O-acetyl-2,6- properties of, 42:191
anhydro- 1,2-dideoxy-o-, 23: 160 ldofuranose
crystallography of, 25:60 3,6-(acetylepimino)-3,6-dideoxy-1,2-0-
D-, 21:17 isopropylidene-P-L-, crystal structure
conformation of, 26:69 bibliography, 30:452
crystal structure bibliography, 30:450 5-amino-5-deoxy-l,2-0-isopropylidene-~-~-,
1,6-diamino- I ,5-anhydro-l,6-dideoxy-~-, 23:135
23:137 5-amino-3-0-benzyl-5,6-dideoxy- 1,2-0-
1,4:3,6-dianhydro- isopropylidene-P-L-, 23: 139
2,5-0-benzoyl-2,5-dithio-~-, 49: 153 3,6-anhydro-5-deoxy-5 -fluoro- 1,2-0-
D-, 25246 isopropylidene-
2,5-dideoxy-2,5-(dithiocyano)-~-, 49: 153 a-L-,proton magnetic resonance
2,5-di-O-p-tolylsulfonyl-r-, displacement spectroscopy of, 27532
reactions of, 24: 149 p-L-,preparation, 38:221
L-, 25:260,49:96 3,6-anhydro-5-deoxy-5-iodo-l,2-0-
catalytic oxidation of, 25261 isopropylidene-P-r-, preparation of,
infrared spectra of, and nitrates, 25:252 28:27 1
nuclear magnetic resonance spectra of, I ,5-anhydro-2,3-di-O-benzyl-6-O-trityl-a-~-,
and derivatives, 25254 24:171
2,3:4,5-dianhydro- 3,5-anhydro-l,2-0-isopropylidene-
D-, 24:168,49:124-125 p-L-,conformation of, 26: 122
proton magnetic resonance spectroscopy 6-O-trityl-p-~-,24:114
of, and esters, 27:64 5,6-anhydro- 1,2-0-isopropylidene-P-~-,
1.6-di-O-(methyIsulfonyl)-~-, cytostatic 25112
activity, 28:7 6-azido-5,6-dideoxy-5-iodo- 1,2-0-
2,5-dideoxy-2,5-diiodo-~-, 49: 149-1 50 isopropylidene-P-L-
2,5-di-O-acetyI-l,4:3,6-dianhydro- 1(4);3(6)- crystal structure of, 25:74,30:452
dithio-D- preparation of, 28:271
disulfoxide, crystal structure bibliography, S-(benzylamino)- 1,2-0-cyclohexylidene-5-
34:372 deoxy-L-, 23:141
 SUBJECT INDEX
3-0-benzyl-6-deoxy- 1,2-O-isopropylidene-
p-L-,21:180
5,6 bis(acetamido)-5,6-dideoxy-~-,23: I76
3-chloro-3-deoxy- 1,2:5,6-di-0-
isopropylidene-P-o-,conformation of,
34:201
D-, 3-deoxy-3-fluoro-
01 anomer, 'H- and 19F-NMR data for,
46:99
P anomer, 'H- and I9F-NMR data for,
46:99
3-deoxy-3-fluoro-
1,2:5,6-di-O-isopropylidene-P-~-,
preparation, 38:223
I ,2-0-isopropylidene-P-~-, preparation,
38:224
5-deoxy-2-fluoro-~-,48: 138-1 39
5-deoxy-5-iodo- 1,2-O-isopropylidene-6-0-
trifluoroacetyl-P-L, preparation of,
28:271-272
6-deoxy-1,2-0-isopropylidene-
P-L-,23:275
selective oxidation with chromium
trioxide, 33:99
5-C-phenyl-P-~-,preparation of.
27:21&2 16
5-thio-P-~-,23:2 17
5,6-diamino-l,6-anhydro-5,6-dideoxy-P-i.-.
23: 137
5,6-dideoxy-5,6-epithio- 1,2-0-
isopropylidene-P-L-, 25: 162
3,5-di-0-acetyl-6-0-benzoyl- 1-,2-0-
isopyopylidene-L-, 22: 120
5,6-di-O-benzoyl-3-deoxy-3-fluoro- 1,2-O-
isopropylidene-P-L-, preparation,
38:223-224
1,2:5,6-di-O-isopropylidene-c~-~-, hydrolysis
of, 34:203
L-
3,6-anhydro-5-deoxy-5-fluoro-
1,2-di-O-acetyl-,l-H- and l9F-NMR
data for, 46: 115
1,2-0-isopropylidene-P-,'H-and '"F-
NMR data for, 46: 1 15
3,6-anhydro-5-deoxy-5,6,6-trifluoro- 1,2- Idofuranurono-6,3-lactone
0-isopropylidene-P-
13C-NMR data for, 46:175, 177
'H-and "F-NMR data for, 46: 152, I58
5-deoxy-5-fluoro-
a anomer, 'IC-NMR data for, 46: 167
303
P anomer, I3C-NMR data for, 46: 167
data
1,2-0-i~opropylidene-P-,'~C-NMR
for, 46: 167
5-deoxy-5-fluoro- 1,2-O-isopropylidene-
@-, 'H-and I9F-NMR data for,
46: 100
N-acetyl-5,6-diamino- 1.6-anhydro-5.6-
dideoxy-P-L-, 23:137
2-0-acetyl- I ,6:3,5-dianhydro-a-i.-,crystal
structure, 43:220
3-O-acetyl-5,6-di-O-benzoyl- I ,2-0-
isopropylidene-I., 22: 1 19
6-0-benzoyl-3-deoxy-3-fluoro- 1,2-0-
isopropylidene-P-L-, preparation,
38:224
3-0-benzyl-5-
deoxy-5-hydrazino- I ,2-0-isopropylidene-
P-L-, 24: 156
S-benzyl-6-chloro-6-deoxy- 1,2-0-
isopropylidene-5-thio-P-t.-, 22: 1 93
1,2-O-isopropylidene-
P-L-, conformation of, 26: 120
5,6-dithio-P-~-,23:2 18
5,6-thionocarbonate, 25: 162
3,5,6-tri-O-acetyl- 1,2-O-isopropylidene-~-,
22: I20
Idofuranoside, methyl 3.6-anhydro-5-deoxy-5-
fluoro- 1.2-0-isopropylidene-P-~-,
preparation, 38:221
ldofuranosyl fluoride
L-, 2-O-acetyl-3,6-anhydro-5-O-benzoyl-
01 anomer, 'H- and "F-NMR data for,
46:l 15
P anomer, IH- and I9F-NMR data for,
46:115
2-O-acetyl-3,6-anhydro-5-O-benzoyl-P-~-,
synthesis, 38:203
Idofuranuronic acid, 3,5-di-U-benoyl- 1,2-0-
isopropylidene-P-r-, methyl ester,
preparation, 36:74
ldofuranuronic N,N-diethylamide, 5-azido-5-
deoxy- I ,2-O-isopropylidene-3-0-
(methylsulfony1)-@+-, crystal structure
bibliography, 38:46046 1
5-bromo-5-deoxy- 1,2-0-isopropylidene-P-~-
, debromination of, 28:304
5-deoxy-5-fluoro-P-~-
'H-and IyF-NMR data for. 46:116
1,2-0-benzylidene-
304 SUBJECT INDEX
Idofuranurono-6,3-lactone(continued)
I3C-NMR data for, 46: 170
'H-and "F-NMR data for, 46: 116
1,2-O-isopropylidene-
I3C-NMR data for, 46: 170
'H- and "F-NMR data for, 46: 116
1,2-0-isopropylidene-P-~-, preparation,
36:74
Idonic acid
2-amino-2-deoxy-o-, deamination, 25: 190,
31:58,33:119
2,4:3,5-di-O-benzyIidene-L-, preparation and
structure, 37: 129
L-, conversion into ~-xylo-2-hexulosonic
acid, 37:134-137
preparation, 37:108-109, 120, 129-133
Idono-l,5-lactam, 5-amino-5-deoxy-~-,23: 166
Idonolactone, 2-amino-2-deoxy-o-,
deamination, 25: 190,33:119
Idono- 1,4-lactone
3,6-anhydro-~-,25261
L-, irradiation, 37: 123
Idopyranose
OL-D-, 45:74
D-, orientation of hydroxyl groups for, in
4 C , ( ~conformation,
) 45:75
Idopyranose
2,3,4,-triamino- 1,6-anhydr0-2,3,4-trideoxy-
P-D-, preparation of, 34: 126
5-acetamido-
1,6-anhydro-5-deoxy-P-L-, 23: 175
2,3,4-tri-O-acetyl- 1,6-anhydro-5-deoxy-P-
L-, mass spectrum of, 23:204
6-acetamido-2,3,4-tri-0-acetyl-1,6-anhydro-
5-deoxy-P-~-,mass spectrum of, 23:203
a-D-
conformation in aqueous solution, 26534
pentaacetate
conformation of, 24:58
proton magnetic resonance spectroscopy
of, 27:23
6-amino- 1,6-anhydr0-6-deoxy-
p-L-, formation of, 34: 149
L-, 23: 156
2-amino- 1,6-anhydro-2- deoxy-P-o-,
preparation of, 34: 122
3-amino- 1,6-anhydro-3-deoxy-P-o-,
preparation of, 34: 122, 126
5-amino-l,6-anhydro-5-deoxy-P-~-, 23: 136
formation of, 34: 149
1,4-anhydro-
2,3-di-O-benzyl-6-O-trityl-P-~-,
24: 171
2,3,6-tri-O-methyl-i-, synthesis, 39: 165
1,6-anhydro-
p-0-
catalytic oxidation of, 33:90
per-0-substituted, 34:77
3-deoxy-3-fluoro-P-o-, specific rotation
of, 34: 135
3-deoxy-3-nitro-P-o-, preparation of,
34:105, 126
2,4-di (benzylamin0)- 2,3,4-trideoxy-3-
nitro-p-o-, preparation of, 34: 106,
126
2-Sbenzyl-2-thi-P-~-, preparation of,
34:136
5-(benzylamino)-5-deoxy-~-,23: 141
5,6-bis(acetamido)
1,6-anhydro-5,6-dideoxy-P-~-, 23: 176,
199-200
2,3,4-tri-O-acetyl- 1,6-anhydro-5,6-
dideoxy-P-L-, mass spectrum of,
23:205
carba-P-DL-, 48:34
5-deoxy-5-phosphino-and 5-phosphinyl-~-
bond lengths for pyranoid ring of, 42: 165
Cremer-People puckering parameters for,
42: 164
ORTEP representation, 42:163
synthesis and structures of, 42: 145-155
5.6 diamino- 1,6-anhydro-5,6-dideoxy-P-~-
formation of, 34: 149
mass spectrum of, 23: 176
2,6-diamino-2,6-dideoxy-~-, 23: 168
L-, 3-deoxy-3-fluoro-
01 anomer, 'H- and I9F-NMR data for,
46:91
p anomer, 'H- and I9F-NMR data for,
46:9 1
penta-0-acetyl-
OL-D-
conformation of, 26: 102
in solution, 26:87
preparation and conformation of,
26:149
5-thio-~-,23:217
1,2,3,4,6-penta-0-acetyI-a-~-, crystal
structure bibliography, 37:401
5-(phenylphosphinyl)-~-
mass spectrometry of, 42: 172-1 76
 SUBJECT INDEX
NMR spectroscopy of, 42: 165-172
X-ray crystallography of, 42: 161-1 65
phosphorus derivatives of, physical
properties, 42: 191
1,2,3,6-tetra-O-acetyl-a-~-,preparation by
acetoxonium rearrangement, 26: 149
1,2,3.4-tetra-O-acetyl-5,6-dideoxy-6-C-nitro- benzyl 2,3-di-O-benzyl-a-and-P-~-,
5-C-(phenylphosphiny)-P-~-,
methanolate, crystal structure. 43:253
2,3,4-tri-O- acetyl- 1,6-anhydro-P-o-
mass spectrum of, 23:203
reaction with trifluoromethanesulfonic
acid, 34:88
Idopyranose pentaacetate
a+-, nonselective spin-lattice relaxation
rates, 45: 148
Sol-Carba-a-L-, synthesis, 4834849
Idopyranoside
ethyl tetra-O-acetyl-a-~-,synthesis, 49:76
methyl 3-acetamido-3,6-dideoxy-a-i -.
acetylation of, 33:30
methyl OI-D-
conformation in solution, 26:84
2,3-di-O-benzyl-4,6-dideoxy-4-
thiocyanato-, 44: 145
methyl 5-benzamido-5-deoxy-, synthesis,
40:97-98
methyl 2-chloro-2-deoxy-a-~-,22: 190, 200
methyl 6 - d e o x y - a - ~ ~synthesis,
-, 40:70
methyl 3,6-di-O-benzoyl-2,4-di(N-
benzoylacetamido)-2,4-dideoxy-a-u-,
crystal structure bibliography, 38:483
methyl 4,6-O-benzylidene-
CY-D-
conformation in solution, 26:84
conformation of, 34: I99
hydrolysis of, 34:202
P-D-, conformation, 34: 199
in solution, 26:84
2-deoxy-2-iodo-a-~-,24:20 1
methyl 1,2,3,4-tri-O-acetyl-6-deoxy-~-1-,
preparation of, 33:265
methyl 2,3,4-tri-O-acetyl-6-deoxy-5-C-
methoxy-P-L-, preparation of, 29:293
~,3,4,6-tetra-O-acety~-~-~-fructofuranosyl
2,3,4-tri-O-acety1-6-deoxy-P-i
nuclear magnetic resonance spectra and
structure of, 33:276
physical properties of, 33:294
preparation of, 33:265
305
Idopyranosiduronatc, methyl [methyl 2.3-di-0-
benzyl-4-deoxy-P-1.-, preparation of.
29:260
ldopyranosiduronic acid
a-and P-L-,cycloheylanimonium salts,
preparation, 36:71
methyl
esters, preparation, 36:69
methyl a-and P-ri-, brucinium salts,
preparation, 36:72
ldopyranosyl bromide, 3,4-di-O-benzoyl-h-
bromo-6-deoxy-2-O-formyl-a-o-.
synthesis, 39: 120-1 2 I
ldopyranosyl chloride, tetra-0-acetyl-a-m,
acetoxonium salt, 26: I59
ldopyranosyluronic acid, I-. phosphate, and
dicyclohexylammonium salt of IX-L-,
preparation. 36:7 1
1.-Idopyranuronates, conformation of anomers,
29:266
Idopyranoside. methyl 1,2,3,4-tetrakis-
(acetamido)-2,3,4,6-tetradeoxy-ol-1i-,
23: 187
ldose
5-acetamido-
5-deoxy-L-, 23: 175
5,6-dideoxy-6-nitro-~-.23: I75
2-amino-, 2-deoxy-~-.24: 1 12
5-amino-
3,6-anhydro-5-deoxy-i.-, 23: 138
4-cyano-2-(2,3 ,S-tri-O-benzoyl-P-n-
ribofuranosy1)-, preparation of.
33: 185
5-deoxy-I -.23: 135
2-5-O-benzoyl-P-~-ribofuranosyl-4-
cyano-. preparation of, 33: I85
6-amino -
6-deoxy-o-, derivatives, preparation by
acyloxonium rearrangements, 26: 163
6-deoxy-t-, 23: I56
composition in aqueous solution, 42:51
5-thio-I 23:218
2,5-anhydro-
aldehydo-I.-, 25:206
L-, degradation of, mcchanism of, 28: 165
3-O-benzyl-6-O-~~-~olylsulfonyl-u/~e~~~~~-
I.-. dimethyl acetal, preparation of,
33:126
3-0-benzyl-6-O-p-tolylsulfonyl-~-.
dimethyl acetal, 25:203
306 SUBJECT INDEX
Idose (continued)
3,6-anhydro-, D-, 25: 140
5-(benzyloxycarbonyl) amino-5,6-dideoxy-3-
0-mesyl-L-, composition in aqueous
solution, 42:50
6-bromo-6-deoxy-~-,tetraacetate, 26: I 53
3-chloro-3-deoxy- I ,2:5,6-di-U-
isopropylidene-P-o-, preparation of,
28:247
5-C-methyl-~-,composition in aqueous
solution, 4257-58
D-
acyloxonium rearrangement, 26: 159
to o-glucose, 26: 146
composition in aqueous solution, 42:26,
29, 31,35,63
derivatives of cyclic acetals, Table,
34:222-223
halogen derivatives of, 22:217
isolation of, by mercaptalation-
purification-demercaptalation
process, 32: 100
nonselective spin-lattice relaxation rates,
45: I48
proton spin-lattice relaxation rates, 45: 150
purification of, dithioacetal in, 32:61
4-S-acetyl-6-deoxy-4-thio-, synthesis,
44:132
3-deoxy-, 3-fluoro-~-,preparation,
38:223-224
5-deoxy-, 5-fluoro-~-,synthesis, 48: 137-138
6-deoxy-
L-, 21~176,180
6-nitro-~-,24:98, 100, 1 18
2,6-diamino-2,6-dideoxy-
L-, 22~137
synthesis of, 30: 116
3,6-diamino-3,6-dideoxy-o-, 24: 147
5,6-diamino-5,6-dideoxy-~-, 23: 135
1,2:5,6-di-O-isopropyIidene-~-, selective
hydrolysis, 39: 15
or-synthesis, 40:93
L-
derivatives of cyclic acetals, Table,
34:222-223
preparation, 37:108, 133-134
rearrangement of, 28:5
synthesis of, 28:5,33:218,232
lack of crystalline form of, 42: 16
N-(aminoacy1)-, esterification of 5-
nucleoside derivatives with, 33:43
N-benzoyl-, benzoylation of carbohydrates
with, 33:4243
N-p-tolylsulfonyl-, selective sulfonylation
with, 33:43
N-(tri-0-methylgalloyl)-, selective acylations
with, 33:43
in solution, 49:3 1,35
2,3,4,6-tetraamin0-2,3,4,6-tetradeoxy-o-,
24: I47
5-thio-~-,23:2 I7
Idoside
methyl D-, 25:125
methyl 2X-benzyi-D-, 25: 125
a-L-Idosiduronase, 44:213-2 14
L-Iduronate sulfatase, 44:206
Iduronic acid
L-, 44:2
biosynthesis, 44296-298
colorimetric reaction, 43:61-62
from o-glucuronic acid by epimerization
in pyridine, 28:40
in heparin, 28:55,75
preparation, 36:74
synthesis of, 26: 15
4-0-methyl-~-,mass spectrometry of
trimethylsilyl derivatives, 30:38
Ilex puruguuriensis, 46: 13
Ilkovi 269; equation, in polarography, 29:135,
137
Imidazo[4,5-d] [ 1,3]diazepin-b(R)-ol, 3-p-0-
ribofuranosyl-6.7.8-trihydro-,crystal
structure bibliography, 32:383
Imidazole
5-amino-] -P-D-ribofuranosyl-
biochemical methods, 52:297-300
chemical synthesis, 52295-297
5-phosphate
derepression of thiamine synthesis,
52292-293
ring expansion, 52:293-295
preparation of specifically labeled
samples, 52:295-300
1,1-carbonylbis-, agarose activation for
affinity chromatography, 39:415416,
436
4-( o-arubino-tetrahydroxybuty1)-,
derivatives, 25:372-373
4(5)-(o-arubino-tetritol-1-yl)-, formation by
ammonolysis, 31:91
 SUBJECT INDEX
4(5)-(2-hydroxyethyl)-, formation by
ammonolysis, 31:90
4(5)-(hydroxyethy1)-, formation by
ammonolysis, 31:90-91
4(5)-(I-deoxy-glycerol-l-yl)-,formation by
ammonolysis, 31:90-91
4(5)-(~-xylitol-l-yl)-,formation by
ammonolysis. 31:90
4(5)-methyl-, formation by ammonolysis,
31:90-91
N-acyl-, for selective acylation of
carbohydrate, 33:4244
N -P-o-ribofuanosyl-, crystal structure
bibliography, 31:355
N-(trimethylsily1)-, trimethylsilylation with,
28:27
ring expansion, 52:293-295
sugar derivatives, 29315-318, 328, 336,
344,347,349,373
4(5)-(2,3,4-hihydroxybutyl)-,formation by
ammonolysis, 31:90-91
1-(tri-0-acetyl-a-D-xylopyranosy1)-, crystal
structure bibliography, 32:369
5-Imidazolecarboxamide, 4-amino-2-(2,3,5-tri-
0-benzoyl-P-o-ribofuranosy1)-,
preparation of, 33: 185
Imidazole-4-carboxamide, 5-amino- 1+-a-
ribofuranosyl-,5-phospbate, 22:374 Immunoadsorbents
5-Imidazolecarboxylic acid, 4-amino-2-(2,3,5-
tri-O-benzoyl-P-o-ribofuranosyl)-, ethyl
and methyl esters, preparation of,
33: 185
Imidazolide, (arylsulf0nyl)-, in nucleotide
formation, 36: 158
Imidazolidine, sugar derivatives, 25:367-
371
Imidazoline, sugar derivatives, 25:37 I
4-Imidazoline-2-thione
4-a-D-erythrofur-anosyl- 1-p-tolyl-, crystal
structure bibliography, 34:372
4-~-erythrofuranosyl-1 -methyl-, crystal
structure bibliography, 32:38 1
1-methy~-4-P-o-erythrofuranosyl-,crystal
structure bibliography, 34:353, 362
1-(p-chlorophenyl)-4-a-~-erythrofuranosyl-, oligosaccharides, liquid chromatography
crystal structure bibliography, 32:367
Imidazoline-2-thione
4-a-D-erythrofuranosyl-1-p-tolyl-, crystal
structure bibliography, 38:456457
4-P-~-erythrofuranosyl-1ptolyl-, crystal
307
structure bibliography, 38:457458
Imidocarbonates, of polysaccharides,
preparation of, 29:345
Iminium chloride, (chloromethy1ene)di-
methyl-. reaction with aldose oxiranes,
25:126
Iminium compounds
(alkoxymethylene)dimethyliminiumhalides,
reaction with alcohols, 28:254
(bromomethylene)dimethyliminium bromide,
in synthesis of bromodeoxy sugars,
28:250
(ch1oromethylene)dimethyliminium chloride,
in synthesis of chlorodeoxy sugars,
28:250,278
I ,5-Iminoalditols, glucosidase inhibition,
48:336, 338
2,2-Iminodiethanol, as matrix for f.a.b.-mass
spectrometry, 45:26
lmino group
in cyclic monosaccharides, 23: 119
cyclic sugar analogs with, 48:335-341
Immune system
fucose, 39:334-335
immunization, 53:212-2 13
natural immunity, 41:200-201
polysaccharide vaccines, 41: 191-197
polysaccharide derivatives as, 29:326-327,
375-383
preparation of, 31:323
Immunochemistry
dextrans in, 30:399404
in structure analysis of polysaccharides,
21:504
Immunodiffusion, agarose for, 29:329
Immunoelectrophoresis, 2-diethylaminoethyl
ethers of polysaccharides as media for,
29:323
Immunogenicity, sialic acids, 40: 176
Immunogens, azophenyl proteins, 37:232
Immunoglobulin D
isolation of carbohydrates from, on
analytical-scale columns, 46:60
separation, 46:4243
sialylated oligosaccharides, fractionation,
46:46
Immunoglobulin E, 44:232
Immunoglobulin G, production, 41:190, 197
308 SUBJECT INDEX
Immunoglobulin M
isolation of carbohydrates from on
analytical-scale columns, 46:60
oligosaccharides, liquid chromatography
separation, 46:4243
Immunoglobulins
a-o-mannosidase in structural studies of
human, 28:445
anti-carbohydrate myeloma, 31:326-346
antigenic markers on, 31:318
biosynthesis of, genetic control of, 31:317
carbohydrate linkage in, 25:42 I , 425,
26:46 I, 465
combining sites of, 31:3 18
dextran-antidextran systems, 31 :341
gas-liquid chromatographic analysis of,
28:72, 86
glycopeptides, liquid chromatography
separation, 46:48
as glycoproteins, 25:408
hydrolysis with hydrochloric acid, 46:266
interaction of homogeneous, with antigens,
3 1 ~ 3 1-323
2 I-ester with o-glucuronic acid,
m u r k myeloma, with polysaccharide
antigens, 31:3 13-346
molecular weights of, 31:316
myeloma, interactions with polysaccharides,
3 9 3 17
polyclonal, restricted, and monoclonal types
of cellular responses, 31:3 18-320
purification from ascites or serum,
31:323-325
secretion, effect of glycosylation, 40:36 1
structural effects, 40:354
structure of, 31:316317
Immunology
capsular polysaccharides, 41: 174-178
role ofcomplement, 41:187-189
of complex fucans, 39:3 1 1-3 16
lectins role in, 35:128
Immunostimulants, 48:13-I4
Inclusion complexes, 46:205-206
Indochrome A, synthesis of, 33: 169-171
Indochrome BI, synthesis of, 33: 170
Indochrome BII
structure of, 33:112-113
synthesis of, 33:169-171
Indochrome BIII, structure of, 33: I70
3-Indoleacetic acid, as reagent for o-fructose
estimation, 22:238
Indole-3-acetic acid, 21:377
effect on cell-wall polysaccharides, 21:381
on sugarcane, 21:424
role in fruit development, 42:344
lndole-3-butyric acid, effect on sugarcane,
21:424
lndolines
formation of, 46:317
I -(2,3,4,6-tetra-0-acetyl-P-~-
glucopyranosy1)-, proton magnetic
resonance spectrum, analysis of, 27533
Indolizine alkaloids, glucosidase inhibition,
48:34 1-344
Indol-3-ylacetic acid
I -ester of P-o-glucopyranuronic acid,
36: 108
of 3,4,6-tri-O-acetyI-2-0-
(trideuterioacetyl)-D-glucopyranose,
36:llO
5-hydroxy-, 1-ester of P-o-glucopyranuronic
acid, 36: 108
[N-(4-chlorobenzoyl-5-methoxy-2-methyl]-,
synthesis, 36: 104, 11 1
lndolyl glycopyranosides, acid-catalyzed
decomposition in deuterium oxide and in
water, 24:29
Indomethacin, 1-ester with o-glucuronic acid,
synthesis, 36: 104, 111
INDOR. see Proton nuclear magnetic resonance
spectroscopy
Induction, asymmetric, 50:2-7
discovery, 50:6-7
INEPT, 51:19, 21-22
Infection, see Bacteria, infection
Influenza virus
action on red blood cells, 33:4
red cell receptor, 45: 170
Infrared absorption spectra
of a,@-unsaturatedacids, 27:261
of a,P-unsaturated sugars, 27:248
of alkyl ald-3-enulosonates, 27:268
of anhydro-C-(p-methoxypheny1)aldosesand
anhydro- 1,3-dideoxy-ketoses, 27:286
of C-alkylated unsaturated sugars, 27:240
of deuterated sugars, 27: 149
of furan derivatives from sugars, 27:289
of thioenol sugars, 27:276
Infrared dichroism, 44:26-27
Infrared radiation, starch modification, 51:298
 SUBJECT INDEX
Infrared spectroscopy, 44:7-8, 16-22, 53:286
of 1 -acylamido sugars and 1,I-bisacylamido-
I-deoxyalditols, 31: 107
of anhydroalditols, 25:250-252
of I,6-anhydrohexopyranoses,3456, 63
anomer determination by, 23:41
band assignments, 44:36-39
isotopic substitution, 44:36-38
model-compound approach, 44:38-39
and carbohydrate boronate structure, 35:42
and carbohydrate chemistry, 19:2349
of carbohydrates, 12: 13-33
of cellulose on heating, 23:435
in conformational analysis, 26:54
of cross-linked celluloses, 29:354
of cyclic acetals, 26:227-229
1,4:3,6-dianhydrohexitols,49: 100- I02
of dithioacetals, 32:97
electro-optical parameters, 44:35-36
of fluorinated carbohydrates, 38:280
of formose, paraformaldehyde, and 1 J.5-
trioxane, 29: 18I
and gas-liquid chromatography, 30:43
and hydrogen bonding for D-
glucofuranosidurono-6,3-lactones,
33~209-210
of ketonucleosides, 42249-250
maturation measurement by, 23:s 1
noncomputer results, in analysis of
foodstuffs and biological samples.
44: 22-24
of reducing sugars in solution, 42:20
of sugar oxiranes, 25: 170
of sugars, 23:39,41
of sulfuric esters of carbohydrates, 23:255
Inhibine, in honey, 25:290
Inhibitors
of cellulose biosynthesis, 41: 143-1 44
of 3-deoxy-~-manno-2-octu~osonic acid
metabolism, 38:387-388
enzyme, 23:290,336,354
glycosylation, biological effects, 40:350-379
inhibition constants,
polyhydroxypyrrolidines, 48:345-346
for pectinesterases, 33:336
in plant pathology, 33:384
of protein glycosylation, 40:321-350
in unripe fruit, 33:382
Inline, carbon- I3 nuclear magnetic resonance
spectra, 38:72
309
Inorganic compounds. effect on reducing
sugars in solution, 42:33-34
Inosadiamines, di-N-acetyl-tetra-0-acetyl-.
24: 102
Inosamines
bromination with acetyl bromide, 33:85
deamination of. 31:29,3 I , 35,48-50. -39
paper electrophoresis, 36:6
synthesis of, 28:284
Inosine
5 -(a-o-glucopyranosyl pyrophosphate),
enzymic synthesis of, 28:338
5 -(a-u-mannopyranosyl pyrophosphate),
enzymic synthesis of, 28:340
5-(barium phosphate) hexahydrate, crystal
structure bibliography, 31:370
8-bromo-, crystal structure bibliography,
38:487488
5-bromo-5 -deoxy-2,3-0-isopropylidene-,
preparation of, 28:247-248
cadmium 5 -monophosphate dodecahydrate,
crystal structure bibliography, 34:375
S-chloro-5-deoxy-2,3-O-isopropylidene-,
preparation of, 28:247
cis-platinumdiammonio 5-monophosphate
sodium salt 16 hydrate crystal structure
bibliography, 34:375
cobalt 5-phosphate heptahydrate, crystal
structure bibliography, 34:366
crystal structure, 31:360, 43:286-287
3:5-cyclic phosphate. 22:320
5-deoxy-S-iodo-2,3-O-isopropylidene-,
preparation of, 283247
and dihydrate, crystal structure bibliography,
30:460
5-(disodium phosphate) hydrate, crystal
structure bibliography, 31:370
2-(ethylthio)-S-methyI-, monohydrate,
crystal structure bibliography. 32:379
2,3-isopropylidene-S-O-p-tolylsulfonyl-,
24: 185
nickel 5-monophosphate heptahydrate,
crystal structure bibliography, 32:381
nickel 5-phosphate heptahydrate, crystal
structure bibliography, 34:366
5-0-acetyl-, selective chlorination with
triphenylphosphine and carbon
tetrachloride, 33:79
5-0-acetyl-3-chloro-3-deoxy-, preparation
of, 28:247
310 SUBJECT INDEX

Inosine (continued) DL- I-acetamido- I-deoxy-, bromination

2',3 '-0-isopropylidene- with acetyl bromide, 33:86
p-toluenesulfonylation of, 24: 185 DL-4-acetamido-1,2,6-tri-O-acetyl-3,5-
reaction with phosphoryl chloride, 28:239 dibromo-3,4,5-trideoxy-, preparation
with triphenylphosphine-carbon of, 33:85
tetrabromide, 28:248 DL- 1 ,4-dibromo- 1,4-dideoxy-, preparation
5'-phosphate, 22:325, 336 of, 33:86
5'-phosphate methanolate monohydrate, ~~-2,4-dibromo-2,4-dideoxy-, preparation
crystal structure bibliography, 32:375 of, 33:86
reaction with 2-acetoxy-2-methylpropanoyl 1~-3-O-methyl-,catalytic oxidation of,
halides, 33% 33:89
selective acetylation of, 33:33 ~-3-amino-3-deoxy-,deamination of,
selective alkylation of, 33:70 31:37
selective bromination with N- 1~-3,4-di-O-benzyl- 1,2-0-
bromosuccinimide and cyclohexylidene-, selective
triphenylphosphine, 33:78 benzylation of, 33:65
5'-(sodium phosphate) octahydrate, crystal 1~-2-O-methyl-,catalytic oxidation of,
structure bibliography, 31:370 33:89
2',3,'5'-tri-O-benzoyl-, selective deacylation, I L- 1,2,3,4-tetra-O-benzyI-, selective
39:39 benzylation of, 33:65
zinc 5 'monophosphate monohydrate, crystal 1L- 1,2,3,4-tetra-O-methyl-, benzoylation
structure bibliography, 32:382 of, 33: 14
Inosine 5'-(calcium phosphate), 6.5 hydrate, penta-0-acetyl-l -amino-I -deoxy-L-,
crystal structure, 43:315-316 deamination of, 31:49
Inosine 5 '-[copper(II) 2,2'-dipyridylamine cis-, 47:4, 8, 138
phosphate], tetrahydrate, 43:334 I3C-NMR
Inosine [copper(II) 5'-monophosphate], Cu2' effect, 47:142-143
monohydrate, crystal structure, Mn2+effect, 47:141-142
43~283-284 complex-formation, 47: 15
Inosine (diethylenetriamine) platinum (11) plots of '3C-(Te,)-'versusmetal-ion
dinitrate, monohydrate, crystal structure concentration, 47: 142-144
bibliography, 38523 stability constants, 47:29
Inosinic acid, 22:309 trihydroxyl pocket, 47:29
Inositol, myo-, proton nuclear magnetic cyclic acetals, selective esterification of,
resonance spectra, 29:2&27 33:39
Inosit01-2-'~C,myo-, 24: 100 (-)- l~-l-deoxy-l-fluoro-myo-, 48: 152
myo-Inositol calcium bromide pentahydrate, deoxynitro-, acetalation of, 24: 116
crystal structure bibliography, 31:349 derivatives, proton spin-lattice relaxation
Inositol-24, myo-, preparation of, 27: 132 rates, 45: 153
myo-Inositol magnesium chloride tetrahydrate, 1,4-dideoxy- 1,4-dinitro-neo-, 24: 104
crystal structure bibliography, 31:350 1,2:3,4-di-O-isopropylidene-
scyNo-Inositol monoorthoformate, 47: 1 5 5,6-dithio-neo-, conformation of, 26: 120
Inositols epi-, 24: 170
acetylation of, 28:36 1,2:5,6-di-O-isopropyIidene-, 3,4-di-O-p-
allo-, ~~-5-bromo-5-deoxy-, preparation of, tolylsulfonyl-L-chiro-, crystal structure
3396 bibliography, 30:455
bromination with acetyl bromide, 33:85 di-0-isopropylidene- muco-,-epi-, and-cis-,
carbohydrate substrates, 40: 108-109 conformations of, 26: 120
chiro- DL-
1-amino- 1-deoxy-, deamination of, 31:48 I-O-benzoyl-3,4,5,6-tetra-O-benzyl-2-
 SUBJECT INDEX
(bromomethy1)-myo-, 48: 148
1,2-0-cyclohexylidene-5-deoxy-chiro-.
48:28
1,2:3,4-di-O-isopropylidene-5-O-methyl-
epi-, carbohydrate substrate, 40: 108
myo-l-deoxy-3-nitro,24: 100
1,4,5,6-tetra-O-substitutedmyo-,
methanesulfonylation and p -
toluenesulfonylation of, 33: 14
electrophoresis in metal salt solutions,
21:232
epi-, 47:7, 138
(+/-)-2-(acetoxymethy1)- 1,3,4,6-tetra-O-
acetyl-, crystal structure bibliography,
31:354
conformation of crystalline, 26:8 1
crystal structure bibliography, 30:449
2-deoxy-2-methyl-, 47:8, 15
diamagnetic shifts, 47: 129
DL-,bromination with acetyl bromide.
33:85-86
~~-2-amino-2-deoxy-, bromination with
acetyl bromide, 33:85
DL- 1,2:3,4-di-O-cyclohexylidene-,
selective benzoylation and p -
toluenesulfonylation of, 33:39
DL-1,2:3,4-di-O-isopropylidene-, selective
benzoylation andp-
toluenesulfonylation of, 33:39
electron-spin relaxation, 47: 138- I40
penta-O-acetyl-2-amino-2-deoxy-~i -,
deamination of, 31:49
strontium chloride pentahydrate, crystal
structure bibliography, 38:432
T',/Te2 values, 47:140-141
gas-liquid chromatography of, 28:89
hexa-0-(trimethylsily1)-myo-, 28:90
interactions with Gd3+and Mn2',
47:137-144
L-, 3-amino-l,3,6-trideoxy-l-methoxy-6-
(methylamino)-chiro-, crystal structure,
43:222
labeling with hydrogen isotopes, 27: 137-
138
laser-Raman spectroscopy, 44533
1L-chiro-, 48:40
in liquid hydrogen fluoride, 26: 170-1 73
mass spectrometry of, 21:91,29:78-79
metal-ion size-requirement for binding,
47:138
31 1
muco-
2-amino-2-deoxy-, hydrochloride,
bromination with acetyl bromide,
33:86
1,3-bis(acetamido)-4,5,6-tri-O-acetyl- I,3-
dideoxy-, preparation of, 33:40
catalytic oxidation of, 33239
3-deoxynitro-, 24: 100
1,3-diamino-l,3-dideoxy-, acetylation of,
33:40
1,5-diamino- 1,5-dideoxy-. bromination of
N-acetyl derivative with acetyl
bromide, 33536
DL- I -acetamido- 1-deoxy-. bromination
with acetyl bromide, 33:86
D L - ~ -and-3 -0-acetyl- 1,4,5,6-tetra-O-
methyl-, acyl migration in,
33: 106-1 07
DL- 1,2:4,5-di-O-cyclohexylidene-
selective benzoylation of, 33:39
selective benzylation of, 33:65
DL- 1,2:5,6-di-O-cyclohexylidene-
selective benzoylation of, 33:39
selective benzylatioii of, 33:65
DL- 1,2-O-cyclohexylidene-, benzoylation
and p-toluenesulfonylation of, 33:39
DL- 1,3,4.5,6-penta-O-acetyl-, methylation
and acyl migration in, 33: 107
DL- 1,4,5,6-tetra-O-benzyI-, selective
benzylation of, 33:64
penta-O-acetyl-3-amino-3-deoxy-
deamination of, 3 1 5 0
phophatidyl-, selective deacetylation in
preparation, 39:34
myo-
a-D-galactosides, 37:3 16-3 18
occurrence in plant kingdom, 37:345
radiolysis and free-radical chemistry,
37:27, 30, 32
role in plant metabolism, 37:346
a-L-fucopyranosyl-, in urine, 39:330
2-amino-2-deoxy-, deamination of, 31:48
1- and 2-phosphate, phosphono migration
in, 33: 109
assay by yeasts, 32:22 I
calcium bromide pentahydrate, crystal
structure bibliography, 30:465
catabolism by yeasts, 32:2 19-22 1
confomiation of crystalline, 26:81
I (3),2-cyclic phosphate, hydrolysis, 39:60
312 SUBJECT INDEX
Inositols (continued)
and dihydrate, crystal structure
bibliography, 31:365
DL-
1-amino-I-deoxy-, deamination of,
31:37
I ,4,5,6-tetra-O-benzyl-3-0-methyl-,
selective acetolysis, 39:46
2-C-(fluoromethyl)-, 48: 165
hexa-0-benzyl-, selective acetolysis,
39:46
hexaphosphate, selective
dephosphonylation, 3 9 5 9
2-C-(hydroxymethyl)-, 47: 17
I.- I ,2-anhydro-, preparation of, 31:48
1,2,3,4,6-penta-O-acetyI-, preparation of,
31:71
penta-O-acetyl-4-amino-4-deoxy-,
deamination of, 31:37
1,3,4,5,6-penta-O-benzyl-, selective
acetolysis, 39:46
I-phosphate, from o-glucose 1-phosphate,
27: 167
2-phosphate monohydrate, crystal
structure bibliography, 32:360
in plants, 26:402
preparation of, and hexaacetate, 31:35
racemic carba-sugars from, 48:28-29
selective p-toluenesulfonylation of,
33:38
utilization by yeasts, 32: 147
neo-
1,4-diamino-l,4-dideoxy-, broinination of
N-acetyl derivative with acetyl
bromide, 33:86
oL-I-bromo-1-deoxy-, preparation of,
33:86
L- I -amino- 1-deoxy-, deamination of,
31:37
penta-O-acety1-2-amino-2-deoxy-,
deamination of, 31:49,71
O-a-o-galactopyranosyl-
(l-+l)-myo-, see Galactinol
( 1-+6)-O-a-o-ga~actopyranosy~-( 1+ 1)-
myo-, occurrence, 37:318
2-~-a-o-mannopyranosy~-6-0-[(2-amino-2-
deoxy-a-D-glucopyranosyl)-(1-+4)-a-o-
glucopyranosyluronic acid]-, 24:411
4-0- (6-arnino-6-deoxy-P-o-
glucopyranosyl)-3-0-methyl-(+)-,
synthesis and antibiotic activity of,
30: I53
paper chromatography, phenylboronic acid
in, 35:60
I ,3,4,5,6-penta-0-acetyl-myo-, sulfonylation
of, 23:238,250
1,2,4,5,6-penta-O-acetyl-3-O-p-
tolylsulfonyl-myo-, 23:238
per(trimethylsily1)-scyllo-,28:90
as plant-growth substances, 21:416
proton magnetic resonance spectroscopy of,
27:64
rearrangements in acetic acid-sulfuric acid,
26: I90
scyllo-
aminodeoxy-, deamination of, 31:35
deoxy-l -nitro-, 24: 100
penta-0-acetylaminodeoxy-, deamination
of, 31:37
radiolysis and free-radical chemistry,
37:27-28,30
sweetness-structure relationship, 45:241
1,4,5,6-tetra-O-acetyL
myo-, sulfonylation of, 23:238, 250
3-U-(methylsulfonyl)-myo-,23:250
2,4,5,6-tetra-O-acetyl- 1,3-di-O-p-
tolylsulfonyl-myo-, 23:238
tetra-0-a-o-galactosyl-myo-, occurrence,
37:318
tri-0-a-o-galactosyl-myo-, occurrence,
37:3 18
Inositol-2-r, myo-, degradation in higher plants,
27: 177
epi-Inositol x SrCI, x 5 H , , 47:24
hiosose-2
myo-, phenylosotriazole derivative, proton
magnetic resonance spectroscopy of,
27:64, 73
per (trimethylsily1)-myo-,28:90
Inososes
dithioacetals, oxidative degradation of, 32:84
myo-, 2-(diethyl dithioacetal), oxidation of,
32:84
as valienamine precursor, 42: 129
Inoue, Yoshiyuki, 46:3
Insects
a,a-trehalose in, 30:23 1, 234
a-D-mannosidase in, 28:405
sex-attractant, preparation of, 42:94
trehalase from, 30:248, 25 1
 SUBJECT INDEX 313

Insolubilization treatment with HF, 48:97-98

of antibiotics, 29:387 utilization by yeast, 39:361-366
of enzymes, 29:361-375 Inverse gated decoupling method, 51:72
by cellulose triazine derivatives. 29:349, Inversion in w-deoxy sugar synthesis, 21: 178
372 Invertase, 23:5, SO: 1 1
by cellulose xanthates, 29:346 activity in developing systems, 30:252
by imidocarbonates of polysacchaddes, amino acids of, 27:3 1.5, 3 17
29:373 carbohydrate components of. 27:326
by triazine-dyed polysaccharides, 29:352 in fruit climacteric, 42:364
of nucleic acids by polysaccharides. in honey, 25303
29:384-387 in human intestine, 34:287
periodate-oxidized starch derivative in, membrane-associated isozyme, in plants,
29:341 44:370
Institute of Bioorganic Chemistry, purification and carbohydrates of, 27:305
establishment, 48: 12 yeast, carbohydrate-peptide linkages in,
Institute of Microbial Chemistry, establishment, 2 5 4 19
48:X Invertebrates, a,-a-trehalose in. 30:23 I , 235
Insulin, 46: 1 1 Invertin, 50:8, 12
carbon-13, signals, 38:23 Invert sugar, 52:449
effect on glycogen synthetase activity, Iodide ion, cyclodextrin inclusion complexes
26:379 with, 46:22 1
glycosylation inhibition effect, 40:377 Iodination
receptor, 40:23 1 of alcohols, 28:260
Interferogram, 4 4 5 7 of nucleosides and nucleotides, 22:378
Interferon Iodine affinity, dextrins, 47:283-284,297-298
glycosylation inhibition effect, 40:373-374 Iodine azide, reactions with unsaturated
inactivation, 40:221 carbohydrates, 28:271
Interleukin 2, f.a.b.-mass spectrometry. Iodine fluoride, reaction with unsaturated
45:6465 sugars, 28:273
Intermediate neglect of differential overlap Iodine-starch complexes
approximation, 51:27-28 alcohol effects, 53:283
Interstellar solid material, infrared spectroscopy applications, 53:296-298
of, 44:3 1 chemical properties, 53:293--294,296
Intradex, dextranglucosidase degradation of, electrolyte efffects, 53:272
30:396 formation, 53:278-284
Intramolecular &-elimination, 47:248 history, 53:264266
Inulinase, 39:361-366 organic compound effects, 53:272-274
enzyme of Kluyveromyces fragilis. 32: I87 origins, 53:268-270
induction of, 30:262 physical properties, 53:284-292
Inulin fructotransferase, microorganisms and, preparation, 53:26&268
52 :2 14-2 15 protein effects, 53:272-274
lnulins solvent effects, 53:270-272
caramels, 52:222-223 state, 53:268-270
catabolism by yeasts, 32: 185, 233 structure, 53:274-278
o-fructose from, 22:232 Iodine trifluoroacetate, reaction with
dihexulose dianhydrides from, 5 2 2 1 7-2 I 8 unsaturated carbohydrates, 28:27 I
gel chromatography of, 25:42 Iodine tris( trifluoroacetate),reactions with
hydrolysis, 46:269 alkanes and ethers, 40: 109
structure, 35:7, 39:362 o-Iodobiphenylyl ethers, irradiation of
thermal activation, 52:222 carbohydrate. 38:187, 190-191
314 SUBJECT INDEX
Iodo compounds, irradiation of carbohydrate,
38:186-190
5-Iodocytidine, crystal structure, 43:276-277
Iodocytosine, I-(2-deoxy-2-fluoro-p-~-
arabinofuranosyl)-5-, biological activity,
48:24&248,254-255
Iodofluorination, of glycals, 38:234-235, 242
Iodo (methoxyl)ation, of glycals, 24:203
Iodouracil, 1-(2-Deoxy-2-fluoro-fi-o-
arabinofuranosyl)-5-, labeled, biological
activity, 48:255-256
Iodouridine, 5-amino-2, 5-dideoxy-5-, crystal I-Isocyanates, as precursors, 50:281-282
structure, 43:275-276
Ion-exchange chromatography of plant cell-
wall polysaccharides, 42:274-275
Ionization constants, of wand p-D-
glucopyanose, 24:25
Irideue luminarioides ethanol-extractable
carbohydrates of, 32:5
Iris, cell-wall studies on, 42:300
Iron
dextran-citrate complexes, gel
chromatography of, 25:50
dextrin as complexing agent, 47:327-328
Iron-D-glucitol-citrate complexes, gel
chromatography of,25:50
Iron-starch complexes, 53:326-327
Irradiated food, 37:75
Irradiation, of-o-fructose, 22:243
Irvine, James Colquhoun, obituary of, 8:
xi-xvii
Isbell-Horace S., 51:1-13
coauthors, 51:5
postdoctoral fellows and graduate students,
51:4
scientific achievements, 51:4-13
lseki N., 46:9
Islandic acid, 23:379
Isoamylase, 44:252-253
debranching of amylopectins and glycogens
by, 30:329,331
in hydrolysis of starch, 36:33
preparation and properties of, 30:29&297
specificity of, 30:268-269
lsoascorbic acid
crystal structure bibliography, 30:448,
31:348
D-, crystal structure bibliography, 30:448
Isobutoxycarbonyl chloride, in esterification of
thymidine, 33: 13
Isobutyl alcohol
solubility of o-glucose in, 27:98
as solvent in ammonolysis of benzoyl
groups, 31:102
lsochromene, 3,5-bis(acetoxymethyI)-7-nitro-,
24: 129
lsocitrate dehydrogenase, in glycolysis control,
32:169
Isocolchicine, mutarotation of, 23: 13
Isocrotonic acid, precursor for sugar synthesis,
40:4-7
Isocyanuric acid, 3,5-dimethyl- 1-(2,3,4,6-tetra-
0-acetyl-a-o-mannopyranosy1)-,crystal
structure bibliography, 38:472
Isocytidine, 5,6-dihydro-, monohydrate, crystal
structure bibliography, 37:412
Isocytosine, 5-b-~-ribofuranosyl-,preparation
of anomers, 33: 179
Isodesmosine, from urine peptide, 24:45 1
Iso-o-glucosamine, 22:277, 280
3-deoxy-, 22:280
Isodigitoxigenin, 21:280
Isodityrosine in cross-linkages of plant cell
walls, 42:382
Isodonal, taste properties, 4 5 3 12
Isoelectric focusing, agarose for, 29:329
Isoenzymes, amino acid components of,
27:315, 317
Isoflavones, as plant-growth substances, 21:410
Isofloridoside
occurrence, 37:3 12-313
photosynthesis, 37:360-361
physiological function in algae, 37:3 13
structure, 37:3 13
Isoglobotetraosylceramide, biosynthesis,
40:249
Isoglobotriaosylceramide, biosynthesis, 40:249
Isoglucal, formation of, 28:204
Isoglycans, structure, 37: 170
Isoglycoenzymes, structure of, 27:301
Isohexide
amino-substituted, 49: 15G15 1
derivatives
H chemical shifts, ring system,
49: 108-109
infrared data, 49: 101
dialkyl, 49: 140
esters, 49: 129-130
etherification, 49: 139
 SUBJECT INDEX
fragmentation, 49: 1 12-1 13
monoalkylated, 49: 139
mono- and di-amines, 49: 165
mono- and di-nitrates, 49: 133-134
nicotinic esters, 49: 162-163
nitrates, 49: 1 I 8
nitric esters. vasodilation, 49: 161-162
phosphorus-substituted, 49: 155
as plasticizers, 49: 168- 169
preparation, 49: 122-124
proton coupling constants, 49: 105
unsubstituted azido, 49:147
Isohumulone, taste properties, 45:3 13. 3 19-320
Isolactose, 21:31
Isolectins
of Bandeiraea simplicifolia I, 35:266
from haricot kidney-bean, 35:297
lentil, properties, 35: 190, 192
pea, 35: 197
of Phaseolus vulgaris. 35:294
Isolichenan, 25:9
antitumor activity of, 32:248-249, 259-260
fine structure of, 30:345
lichen, 41:75-76
structure, enzymic analysis, 44:265
Isolychnose
occurrence, 37:29 1,300
oligosaccharides. occurrence and structure,
37:304-305
structure, 37:301
Isomaltobiouronic acid, from dextrans, 30:408,
410
Isomaltodextranase, 44:258,260
Isomaltohydrolase, exo-. 44:258
Isomaltol
from dehydration of D-fructose, 28: 176,
179-180
preparation of, 28: 170, 176, I79
Isomalto-octaose, preparation of, 34:265
Isomalto-oligosaccharides
fluorinated, 48:22 I
preparative liquid chromatography. 46:60
Isomaltopentaose, in honey, 25:297
Isomaltose
acetolysis of, 22:21
p-, octaacetate, 23:264
preparation of, 34:256, 261
carba-, synthesis, 48:68-70
decomposition, 47:272
derivative, preparation of, 34:270-27 1
315
from dextrans by acetolysis and acid
hydrolysis, 30:378-379, 386
from dextrans by exocellular dextranases,
30:392
Fischers, 21:3 I , 444,464
gel chromatography of, 25:33
in honey. 25:295, 300
liquid chromatography methods for analysis
of, 46:33
preparation of, 34:266
structure, 26:16, 32: 192, 39:356
synthesis of, on light-sensitive, solid support,
46: 184, 186
utilization by yeasts, 32: 194-197
Isomaltose myeloma protein, 53:240-242
lsomaltotetraose
in honey, 25:297
preparation of, 34:266
Isomaltotriose, 51: I5 I
from dextrans, 30:380,392
gel chromatography of, 25:33
in honey, 25:297,300
liquid chromatography separation, 46:4 1
Isomaltulose, 22:230
in honey, 25:297,300
liquid chromatography methods for analysis
of, 46:33
monohydrate, crystal structure bibliography,
31:352
structure of, 32: 193
taste properties, 45:254-255
utilization by yeasts, 32: 194
Isomannide, 25:246
1,4:2,5:3,6-trianhydro-~-. 49:116
(IR)-l-H-Isomannide, 49: 120-122
Isomerases
for carbohydrates, 36:46
and hydrogen-isotope action on sugars,
27:156
I somerization
acetal, 39:26-28
of anhydroalditols, 25:258-26 1
anhydro-ring, 25: 127- I3 1
o-glucose-mfructose, kinetics, 36:48
mechanism, 36:49
of D-ghCOSe to n-fructose, nonenzymic
catalysis, 36:4345
Of-D-fructOSe and derivatives, 22:239
photochemical, 38: 121
of pyranosides to furanosides, 22:4
316 SUBJECT INDEX
Isomerization (continued)
in sweetener industry, 36:43-56
Isomers, relative abundance, 4759-7 1
aglycon character, 47:62-65
exo-anomeric equilibrium, 47:69-7 I
P-D-ribopyranose derivatives, 47:62
ring substituents, 47:66-67
solvent effect, 47:6749
P-D-xylopyranose derivatives, 47:61
P - D - x Y ~ o ~ ~halides,
~ ~ o s 47:62-63
Y~
Isopanose
in honey, 25:297,302
from pullulan by enzymic action, 30:302
Isoprenoid intermediates in biosynthesis of
bacterial polysaccharides, 42:324-325
Isopropyl alcohol, as solvent
in ammonolysis of benzoyl groups, 31: 102
for sugars, 27:96
Isopropylidenation, aldonolactones, 50: 127
Isopropylidene, formation of, 42: 133
2 ',3 '-0-Isopropylideneadenosine5 '-phosphate,
synthesis of, 46:203
Isopropylidene-a-o-glucofuranose
5-deoxy-5-fluoro-1,2-0-, 'H- and I9F-NMR
data for, 46: 100
1-0-acetyl-3-0-benzyl-2-deoxy-2-fluoro-
5,6-0-, IH- and I9F-NMR data for,
46:99
Isopropylidene-a-D-glucofumnose3-sulfate,
1,2-0-, oxidation, Garcia Gonzalez' work
on, 4 9 9
Isopropyhdene-a-o-mannofuranose, 2,3 :5,6-di-
0-
nonselective relaxation rates of H-5,
45~143-144
proton spin-lattice relaxation, 45: I57
2,3-0-Isopropylidene-o-ribono- 1,4-lactone,
50: 129
Isopropylidenegalactitol,1,6-dideoxy- 1,6-
diffluor0-2,3:4,6-di-O-, 'H and I9F-NMR
data for, 46: 159
Isopropylidene group, determination of, in
carbohydrates, 30:4
Isopropylidenesucrose tetraacetate, 2, I ':4,6-di-
0-,crystal structure, 43:260
Isopropylidenetubercidin,8,5'-anhydo-7-
bromo-8-hydroxy-2,' 3 '-0-,crystal
structure, 43:364
Isopropylideneuridine, 2,5 '-anhydro-2,'3 '-0-,
43:373
crystal structure, 43:363-364
2 ',3 '-0-Isopropylideneuridine5'-phosphate,
synthesis of, 46:203
Isopropyluridine, 2'-deoxy-5-, crystal structure,
43:292
Isopullulanase, 44:257
isolation and specificity of, 30:302
Isoquinocycline A, crystal structure of
hydrobromide and hydrochloride, 25:82
Isoquinocyclines A and 3, components of,
35:91
Isorotation, furanoid ring detection by, 21: 127
Isosaccharic acid, preparation of, 31: 18
Isosaccharinates, 25:341
lsosaccharinic acid
a-D-, calcium salt, crystal structure
bibliography, 31:364
from deoxyglycodiuloses by alkaline
degradation, 28: 196
Isosaccharosan, 47:244
Isosclerotan, structure analysis of, 30:369
Isosorbide, 49: 126
acylation, 49: 126-127
bis(tetramethy1phosphoroic diamide), 49: 132
diesters, cosmetics use, 49:168
5-[ I ,4-dihydro-3-(methoxycarbonyl)-2,6-
dimethyl-4-(2-nitrophenyl)-5-
pyridylcarbonyl], 49:115-116
disulfite, 49:164-165
ethoxylated monoesters, 49: 171
infrared spectra of, and nitrates, 29252
platinum-catalyzed oxidation, 49: 155-156
proton-proton coupling constants, 49: 104
syndnonimine derivatives, 49: 163
Isosorbide 2-acetate, 49: 128
Isosorbide 5-acylates, 49: 128
Isosorbide di(docosanoate), 49: 168-169
Isosorbide diheptanoate, 49: 168-169
Isosorbide dimethyl ether, 49: 167-168
Isosorbide dinitrate, 49: I 17
pharmaceuticals, 49: 161
Isosorbide di(octadecanoate), 49: 168-1 69
Isosorbide dipropanoate, 49: 167-168
Isosorbide mono(trans-docosenate), 49: 168,
171
Isosorbide mononitrates
'H-NMR data, 49: 106
pharmaceuticals, 49: 161
Isosorbide mono-oleate, 49:168-169, 171
Isosorbide mono(tetradecanoate), 49: 168
 SUBJECT INDEX
Isosorbide 2-nitrate, 49:134
Isosorbide 5-nitrate, 49:99, 117, 142
fragmentation, 49:113-114
Isosorbide phosphinite, monosubstituted,
49:132
Isosucrose, permethylation of, in liquid
ammonia, 27:93
lsothioc yanates
aryl, synthesis, 44:97
cellulose, synthesis, 44:97
cycloaddition of, 44:92
in neoglycoprotein preparation, 37:224-2
LJ
nucleophilic additions, 44:91
reaction with amino sugars, 45:1415
unsaturated, synthesis, 44:95-96
Isotopes
effect inenzymic reactions, 27:171-176
effect on mutarotation reactions, 24:28
determination of mechanism of reaction,
24:32
effect on reactions of glycosyl esters of
nucleoside pyrophosphates, 28:371-373
hydrogen, radiochemical and chemical
stability of labeled sugars, 27: 138
sugars labeled with, 27: 127-1 90
Isotopic tracers, see Tracers, isotopic
Isotrehalose, 21:32
Isovaleraldehyde, formed from L-leucine.
46:3 11
Isovaleric acid, from apiose, 31:137
Isoxazole-5-carboxamide, 343-0-
ribofuranosyl-, preparation of, 33: 184
Isozymes, 23:286
J of, 30: I80
Jack beans
lectin, isolation from, 35:137
meal,-a-o-mannosidase from, purification of,
28:410
residual activity of purified, 28:414
Japanese agar, structure, enzymic analysis,
44: 187
Japanese pagoda tree, see Sophoru japonica
Javose, 21: 173
Jeol gum, 24:353
Jequirity bean, see Ahrus precatorius
Jerusalem artichoke,-o-fructose from, 22:23 I
317
Jones, John Kenyon Netherton, bibliography,
41: 1 1-26
obituary. 41:l-26
Jones-Stockmayer model, 51:81, 118-1 19,
124-125
Josamycin, 48:9
Juniprenol, structure, 44:346
K
Kaempferol, derivative, as plant-growth
substance, 21:410
Kaempferor-3 P-glucoapioside, from Cicer
urietinum, 31:147
Kamaloside, 39:302
Kanamycin
3 -amino-3-deoxy-2 -r-glycero-,
preparation of, 30: 180
chlorinated, 28:226
crystal structure of, 25:8 1
3-deoxy-, synthesis of, 30: 185
discovery, 48:6-7
inactivation of, 30: 184
mass spectrometry of, 29:105
NK-1001 and NK1012-I, isolation of.
30: 123
selective phosphorylation with diphenyl
phosphorochloridate, 33:50
structuresof. 30:121-123, 188
synthesis of, 30: 1 12, 143
I ,2,4,6-tetra-O-acetyl-, deamination of,
31:29
Kanamycin A
3-amino-3-deoxy-,preparation of, 30: 180
h-amino-6-deoxy-, preparation and activity
configuration of, 30:188
3-deoxy-, synthesis and antibacterial activity
of, 30: 165
6-deoxy-6-hydrazino-, preparation and
activity of, 30: 180
fluorinated analogs, 48:224-228
hepta-O-acetyl-tetra-N-(2,4-dinitrophenyl)-,
preparation of, 34:263
inactivation of, 30: 187
6-N-acetyl-, inactivated, 30: I73
1-N- (~-4-amino-2-hydroxybutyryl)-.
minimum inhibiting concentrations of,
30:222
318 SUBJECT INDEX
Kanamycin A (continued)
N-methanesulfonate derivatives. preparation
and activity of, 30:179
6-N-methyl-, preparation and activity
against resistant bacteria, 30: 173
3-O-methyl-, synthesis and antibacterial
activity of, 30: 165
3-phosphate
nuclear magnetic resonance spectrum of,
30: 189
structure of, 30: 187
preparation of, 34:262
synthesis of, 30: 156-1 58
tetra-N-alkyl and aralkyl derivatives,
preparation and activity of, 30: 179
tetra&( p-chlorobenzy1)-, activity against
Pseudomonas, 30: 179
Kanamycin B
3-deoxy-, minimum inhibitory
concentrations of, 30:22 1
3,4-dideoxy-
1-N-acyl derivative, activity against
resistant bacteria, 30: 174
adenylylation of, 30:206
minimum inhibitory concentrations of,
30:221
synthesis and activity against common
and resistant bacteria, 30: 169
synthesis of, 30: 185
6-N-methyl-, minimum inhibitory
concentrations of, 30:22 I
preparation and activity against resistant
bacteria, 30: 173
selective benzoylation of, 33:40
monoadenylyl-3,4-dideoxy-, trihydrate,
30:206
1-N-acyl derivative, activity against resistant
bacteria, 30: 174
1-N- (~-4-amino-2-hydroxybutyryl)-,
minimum inhibitory concentrations of,
30:222
1-N- (~-4-amino-2-hydroxybutyryl)-3,4-
dideoxy-, minimum inhibitory
concentrations of, 30:222
preparation of, 34:262
synthesis of, 30:158
Kanamycin C
preparation of, 34:262
synthesis of, 30:142, 159
Kanamycin monoselenate monohydrate, crystal
structure of, 25231
Kanamycin monosulfate monohydrate, crystal
structure of, 25531
Kanamycin-neomycin acetyl transferase
and inactivation of kanamycins, 30: 184
origins of, 30:208-211
Kanamycin-neomycin phosphate transferases
history and activity of, 30:186-196
and inactivation of antibiotics, 30: 185-208
and inactivation of kanamycins, 30:184
phosphorylations with, 30: 196-199
in Pseudomonas aeruginosa, and
phophorylations by, 30: 199-204
purification of, 30: 193
in Staphylococci, 30:204
Kanosamine
configuration, 51:2 15
from kanamycin A, 30: 12 1
preparation of, 34:262
Kanosaminide, methyl N-acetyl-2,4,6-tri-O-
acetyl-a+-, synthesis, 40:72
K-antigens, 38:324,35&357,361-365
Karabinos, Joseph Vincent, obituary, 36:9-13
Karasawa, I., 46:3
Karplus equation, 24:265, 45:126,49:104
and conformational analysis, 33:206
in conformational analysis, 26:57, 111
in localization of hydrogen isotopes,
27: 144-145
and proton magnetic resonance spectroscopy,
21:35
Kashimura, N., 46:6-7
Kasugamine, synthesis of, 28:283,30: 152
Kasugaminide
methyl, preparation of, 30: 15 1
methyl D-, synthesis, 40: 1 14
methyl DL-
crystal structure of, 25535
synthesis, 40:34
methyl N, N-diacetyl-a-, preparation of,
30: 152
Kasugamycin, 48:8
derivatives, preparation and antibacterial
activity of, 30: 181
diamino sugar component of, 28:283
discovery of, 30:112
hydrobromide monohydrate, crystal structure
bibliography, 31:368
isolation and structure of, 30:135-136
synthesis of, 30:15@152
 SUBJECT INDEX
Kasugamycinic acid, preparation of, 30: I35
Kasuganobiosamine, synthesis of, 30: 135,
151-152,40:35, 127
K-Carrageenan, 24:280,285
kcatinhibitors, 48:364
Kelp, algin from, antitumor activity of. 32:
257
Kerasin, 24:395,399
sulfate, 24:405
synthesis of, 24:401
Keratan sulfate, 29439, 44: 198-199
bovine nasal-cartilage, 38:36,79
carbohydrate chains in, 25:459462
crystal structure bibliography, 33:40 1
disaccharide repeating units, 43:53. -55
in glycoproteins, 2541 7
hexosamine, 43:53, 55
major uronic acid, 43:53, 55
mammalian, circular dichroism, 45: I 17
molecular weights of chains in, 2 5 4 5 I
proton magnetic resonance spectroscopy of,
27:41,43
shark sulfated, circular dichroism, 45: 1 I7
structure of, 26:433
enzymic analysis, 44:207-209
Keratan 6-sulfate, 52:383-384,427
Keratin fibers, hydrolysis of, with hydrochloric
acid, 46:267
Keratosulfates, gas-liquid chromatography of,
28~43,79
I-Kestose
I3C nuclear magnetic resonance spectra of,
33:277
crystal structure bibliography. 30:455.
32:370
crystal structure bibliogrpahy, 30:455
hendecaacetate, proton magnetic resonance
spectroscopy of, 27:30-3 1
in honey, 25295
synthesis of, 252301
Ketals, see also Acetals
nomenclature, 52: 123-124
Ketoaldonic acids, 52:51, 10&107
composition in aqueous solution, 42:41
Ketoaldoses, 52:5 1, 79-80
Ketoepoxynucleosides, synthesis of, 42:233
kero Forms of reducing sugars, 42:29-30
determination of, 42:2&22
2'-Ketofucosyl nucleosides, synthesis of,
42:238
319
Ketofuranose derivatives, mono-and
difluorinated
"C-NMR data for, 46: 174
'H- and "F-NMR data for, 46: 144-145
Ketoglycosyl nucleosides. unsaturated, 42:230
Ketohexose, reactions in anhydrous hydrogen
fluoride, 47:170
Ketohexose nucleosides
nucleophilic additions to, 42:257-258
stability of. 42245
synthesis of, 42:237-240
unsaturated, nucleophilic addition to,
42:258-260
Ketones, 53:36&367
aldonolactones, 50:127-130
conjugated, substrates for carbohydrate
synthesis, 40:26-27
protection of, 46: 195-198
reactions with
alditols, 39:2 1
carbohydrates, 38: 122-129
gulono-l,4-lactones, 38:302
hydrogen fluoride, 38:242-244
Ketonucleosides, 42:227-264
antitumor activity of, 42:262-264
biological activity of, 42:230-23 1, 261-264
definition of, 42:227
'H-NMR spectra of, 42:25&25 1
infrared spectra of, 42:249-250
nucleophilic additions to, 42:257-260
stability of, 42:245-248
in acidic media, 42:245-246
in alkaline media, 42:246-248
stereospecific reduction of, 42:252-257
structure and spectroscopic properties of,
42249-252
synthesis of. 42:23 1-244
epoxyketonucleosides, 42:240
from ketohexoses, 42:237-240
from ketopentoses, 42:233-236
oxidative systems in, 42:23 1-233
unsaturated ketonucleosides, 42:24 1-244
ultraviolet spectra of, 42:252
unsaturated, 42:241-244,251, 257, 263-264
nucleophilic additions to, 42:258-260
reaction with protein sulfhydryl groups,
42:264
stability of, 42:246
2'-Ketonucleosides, synthesis of, 42:237-238
4'-Ketonucleosides, synthesis of, 42:238-240
320 SUBJECT INDEX
5'-Ketonucleosides, synthesis of, 42:240
Ketopentose nucleosides, synthesis of,
42~233-236
Ketopyranoses, 47: 17-1 8
derivatives, fluorinated, 'H- and "F-NMR
data for, 46: 144
fluorinated, I3C-NMR data for, 46: 173
sweetness-structure relationship, 45:248-256
Ketoses
anhydro-l,3-dideoxy-, synthesis and
properties of, 27:284-292
anomeric, equilibria of, 23:30
in aqueous solution, 49:28-29
acyclic forms, 42:2 1
composition, 42:26-28,3742
NMR spectroscopy, 42: 18-1 9
temperature effects, 42:33
in bacterial polysaccharides, hiosynthesis,
44~301-302
branched-and straight-chain, in formose
formation, 29:213-215
carbon- 13 nuclear magnetic resonance
spectroscopy, 41 :48
catabolism by yeasts, 32:2 10, 2 16-2 17
circular dichroism, 45:79
classification, 52:75
configurational prefixes, 52:76-77
cyclic acetals, 26: 197-277
hydrolysis of, 26:203
stability of, 26:202
definition, 52:50
dehydration in acidic solutions, 28: 174-1 82
in alkaline solution, 28: 193-207
deoxy, in aqueous solution, 42: 17
NMR spectroscopy, 42: 18-19
I-deoxy-, 24:258
1,3-dideoxy-, preparation of, 32:59
disaccharides, large-scale preparative liquid
chromatography, 46:62
dithioacetals, degradative oxidation of, 32:84
physical constants of, and peracetates,
32:113-114
gas-liquid chromatography and mass
spectrometry of, 30:38
in honey, 25295
I-amino- 1-deoxy-, preparation and
deamination of, 31:71
keto hydration of, 42:31
liquid chromatography of, 42:24
methods for analysis of, 46:33
mass spectra of, 21:66
phosphorylated, in aqueous solution, 42:32
polarography of, 29:126, 128, 143-145
preparation of, 29:8,49:191-192
separation from aldoses, 32:24
synthesis of, 24: 1 1 1,26: 13
systematic names, 52:75-76
taste properties, 45:253-255
trimethylsilylation of, 28:24,42:23
trivial names, 52:75
2-Ketoses
acylesters, ammonolysis of, 31 :89
catalytic oxidation of, 33237
deoxy-, melting points and optical rotations
of, 26:289-290
Ketothionucleosides, synthesis of, 42:233
3'-Ketothymidines
protected, synthesis of, 42:233
synthesis of, 42:236
2'-Ketouridines
alkali effect on, 42:247-248
stereospecific reduction of, 42:252
synthesis of, 42:232
3 '-Ketouridines
alkali effect on, 42:247-248
synthesis of, 42:232
K-Furcellaran, 24:281
Kidney bean, cell-wall studies on, 42:271
Kidney-bean, extracts, effect on lymphocyte
division, 35: 130
Kikuyu grass, hemicellulose-cellulose ratio,
36:253
Kinases, alditol determination with, 30:282
Kinetics
of a-amylase action, 23:324
anomeric effect, 50:29
Koenigs-Knorr method, 50:2 1
3-0-glycosidic linkage formation,
50:287-289
of P-amylase action, 23:341
enzyme, 23:288
of glycofuranoside and glycopyranoside
formation, 21:106, 108
of hydrolysis of cyclic monosaccharides,
23:209
of mutarotation, 23: 16
parameters, 22:9 1-106
for acid-catalyzed hydrolysis of
glycosides, 22:26
for hydrolysis of disaccharides, 22:75
 SUBJECT INDEX
of maltose and derivatives, 22:77
of-@-D-glucopyranosides,2274
of pyranosides, 22:36,4849, 66-67
of phosphorylase action, 23:353
of thermal degradation of cellulosic
materials, 23:442443
Kinetin
effect on abscission and ripening, 21 :429
as plant-growth substance, 21:420
Kinins, 21:378
as plant-growth substances, 21:416
Kitaoka, S., 4 6 : 3 4
Kivirikko-Liesmaa reagent for plant cell-wall
residues, 42:275
Klebsiellu spp.
capsular polysaccharides
conformation and serological specificity,
41:179
mass spectrometry of, 29:55,90
K5 polysaccharide, crystal structure
bibliography, 36:330,40:398
K8 polysaccharide, crystal structure
bibliography, 36:330
K9 polysaccharide, crystal structure
bibliography, 40:397
K16 polysaccharide, crystal structure
bibliography, 40:397
K25 polysaccharide, crystal structure
bibliography, 40:397
K30 polysaccharide, crystal structure
bibliography, 40:396
K54 polysaccharide, crystal structure
bibliography, 40:398
K54 repeating-unit, f.a.b.-mass spectrometry,
45~65-66
K57 capsular polysaccharide, Smith
degradation of, 31:239
K57 polysaccharide, crystal structure
bibliography, 36:330,40:396
K63 polysaccharide, crystal structure
bibliography, 40:398
lipopolysaccharides, mass spectrometry of,
29:6?, 69-70,9 1,97
0 group 5 and 0 group 9, lipopolysaccharide
from, methylation analysis of, 30: 16
0 group 3 lipopolysaccharide, degradation of
acetylated, by oxidation with chromium
trioxide, 31:230
Smith degradation of, 31:208
0 group 5 lipopolysaccharide, Smith
32 1
degradation of, 31:208
0 group 7 lipopolysaccharide, Smith
degradation and methylation analysis of,
31:210
0 group 9 lipopolysaccharide, hydrolysis,
acidic, 31:191
K. pneumoniue, enzyme in E. coli from,
30~205-208
serotype 0 5 , 0-antigen polysaccharides,
f.a.b.-mass spectrometry, 4 5 6 6
type 9 capsular polysaccharide, degradation
by p-elimination, 31:217
type 28 capsular polysaccharide, degradation
of, 31:239
type 38 capsular polysaccharide, methylation
analysis of, 31:189, 191-192
type 47 capsular polysaccharide, degradation
by p-elimination, 31:218,220
of methylated, 31:225
type 56 capsular polysaccharide, hydrolysis
of methylated, 31: 192
type 59 capsular polysaccharide, degradation
of methylated, 31:225
Smith degradation of, 31:239
type 81 capsular polysaccharide, Smith
degradation of, 31:239
type 52 capsular polysaccharide degradation
of methylated, by @-elimination,
31:219
partial hydrolysis of methylated, 31 :192
Kloeckeru upiculutu
fermentation of o-glucose by, 32: 153
polysacchande, 41:74
Kloekeru brevis. phosphonomannan, 41:86
Kluyveromycesfrugilis
enzyme of, 32: 187
as protein source, 32: 128
Knoevenagel reaction, 24:262
Koenigs-Knorr reaction, 21:20, 275, 441,456,
23:264,26: 16,34:243-283
for glycosiduronic acid synthesis, 36:75-79,
91
glycosylation of anhydrohexopyranoses,
34: 166161
hexuronic acid, 39:5
history, 34:245
intermediates, 36:59, 62
selectivity in, 34:85
for steroid p-D-ghcosiduronic acid synthesis,
36~94-95
322 SUBJECT INDEX
Koenigs-Knorr reaction (continued)
in syntheses of aminoglycoside antibiotics,
30: 140
KOH-amylose, 52:34&347,41&411
Kojibiitol, 21:344
Kojihiose, 21:344, 22:2 I
a-, octaacetate, preparation of, 34:261
from dextrans by acetolysis and acid
hydrolysis, 30:378-379, 387
in honey, 25:295, 300
liquid chromatography methods for analysis
of, 46:33
Kojibiouronic acid, from dextran, 30:410
Kojic acid, 11:145-183
calcium salt, chelate structure of, 21:238
from ~-threo-2,5-hexodiuloseby
dehydration, 28: 186
Kojitriose, 21:344
Komano, T., 46:4,&7
Koutecky relation, of kinetic current in
polarography, 29: 137, 144
Krabbes disease, 40:27&276
Kratos HF-MS5O spectrometer, 45:36-37
Kuhn, Richard, obituary, 24: 1
Kuhn reaction
3-deoxy-o-manno-2-octulosonic acid
synthesis, 38:369-371
of methylation of carbohydrates, 30: 1 1, 16
L Lacto-neotetraose, 24:433
Labeling, of rafinose family oligosaccharides,
37:35 1-353
Labilomycin, 21: 172
Labilose, 21:172
occurrence, 39:28 1
synthesis of, 23:270
Laburnum alpinum lectin, 35:208
carbohydrate-binding specificity of, 35305
Lacquers
anhydroalditols for, 25:268
from copolymers of levoglucosan with
alcohols and ethers, 34:73
Lactal, hexa-0-acetyl-, fluorination, 38:232
a-Lactalbumin, 26:37 1
in lactose biosynthesis in mammary tissue,
32:10
Lactam rings, monosaccharides, containing,
23: 164
Lactams, from aldonolactone intramolecular
reaction, 50: 154-155
Lactase, 50: 12
Lactic acid
from o-glucose and ammonia, 25345
ethyl ester, as solvent for sugars, 27: 106
formation from hexoses, 28: I97
0-methyl-L-, preparation of, 32:79
Lactitol
1, I -bis(acetamido)-l -deoxy-, preparation of,
31:92
possible hydrogen bonding in, 45:27&277
sweetness-structure relationship, 45:275-276
Lactobucillus, dextran synthesis by, 30:373
Lactohucillus arabinosus, teichoic acid from,
21:334,361
Lactobacillus buchneri, teichoic acid from,
21:350
Lactobacillus casei, teichoic acid from, 21:34 I
Lactobionic acid-calcium bromide tetrahydrate,
crystal structure bibliography, 31:351
Lac tobiononitrile, octa-0-acetyl-, ammonolysis
of, 31:98
Lactoferrin, 44:233
Lactoglobulin, carhohydrate-peptide link-age
in, 25442
Lactol bridge, hydrolysis of a radicals by
radiation, 37: 15
Lactone group, reaction with hydrazine and
derivatives, 50: 155-157
Lactones
of aldonic acids, gas-liquid chromatography
of, 30:29
2-benzamido-4,6-0-benzylidene-2,3-
dideoxy-D-evythro-hex-2-enono-1 ,5-,
50: I63
of carbohydrate acids, gasliquid
chromatography of, 28:71-78
2,3-0-cyclohexylidene-~-rihono- 1,4-,
SO: 129-130
2,3-dideoxyhex-2-enonol,5-, derivatives,
50: 190
2,3-di-0-acetyl-2-C-methyl-~-erythrono-
1,4-, crystal structure, 43:222-223
electroreduction of, of polyhydroxy
carboxylic acids, 29: 125
epimerization of sugar, 21:175
fluorinated
I3C-NMR data for. 46:170
 SUBJECT INDEX
H-and I9F-NMR data for, 46: 116
nomenclature, 52: 105
polarography of, of sugar acids, 29: 162
as solvents for sugars, 27: 106
of sugar acids, 315
1,4,6-tri-O-acetyI- 1,3-0-(0- 1-carboxy-ethyl)-
P-~-glucopyranose-2,1-,crystal
structure, 43:239-240
ultraviolet-absorbances of, 46:65
I ,5-lactones, formation, 51:6
Lactonization, electrophile-induced, ;glycosyl-
4-pentenoates, 50:293-294
Lacto-N-tetraose, 24:7
Lactopyranoside
benzyl I-thio-, preparation from dithioacetal,
32:69
ethyl, preparation from dithioacetal, 32:69
Lactosamine
2-azido-2-deoxytrichloroacetimidates,
reaction with nucleophiless, 50:8 1. 85
as donors, 50:73,78-88
oligomers, synthesis, 50:8 I , 84
Lactosaminoglycans
f.a.b.-mass spectrometry, 4558-59
permethylated, f.a.b.-mass spectrometry,
45:38
Lactosan, synthesis of, 34: 159-1 60
Lactose, 16:159-206,21:28
01-
monohydrate, radiation-induced chain
reactions in crystalline, 37:69. 7 1-72
radiolysis and radical-induced scission,
3752
sweetness, 45:207
effect of infrared hydroxyl absorption
bands and hydrogen-bonding
strength, 45:217
2-acetamido-2-deoxy-, 24:8
4-acetamido-4-deoxy-a-, preparation of,
34: 162
analysis and identification, 44:22-23
in aqueous solution, inorganic ion effects,
42:34
P-
crystal structure bibliography, 32366
I ,2,6,2,3,4,6-hepta-O-benzoyl-,
ammonolysis. 39:3 1-32
6-0-benzoyl-, preparation, 39:32
sweetness, 49207,220
effect of infrared hydroxyl absorption
323
bands and hydrogen-bonding
strength, 4 5 2 17
binding to taste papillae. 45:329-330
biosynthesis of, 26:370-372
in mammary tissue, 32: 10
complex with calcium chloride and
methanol, 21:215
composition in nonaqueous solution, 42:61
dibenzyl dithioacetal, demercaptalation of,
3269
di-0-sialyl-, 2 5 3 5
in food, liquid chromatography separation,
46:52
1,2,6,2,3,4 ,6-hepta-0- benzoyl-P-,
ammonolysis of, 31:96
isomers, laser-Raman spectroscopy, 44: 80
3-keto-, polarography of, 29: 145
liquid chromatography methods for analysis
of, 46:33
mutarotation of, 23:12, 16,23, 24:24
N-acetylneuraminyl-, structure, 38:32
nonselective spin-lattice relaxation rates,
45: 149
nuclear magnetic relaxation study, 51: 100
octa-0-acetyl-, rearrangement in aluminum
chloride-phosphorus pentachloride,
26: 194
octa-0-acetyl-P-, ammonolysis of, 31:92
0-(N-acetylneuraminic acid)-(2r3)-a-.
24:425
3-0-(N-acetylneuraminyl)-, 24:8
polarography of, 29: 126
pyrolysis of, 34:45, 152
reaction with aqueous ammonia, 25x3 12, 315
reducing properties, 47:2 18,220
solubility in liquid ammonia, 27:91
in methanol, 27:95,97
stability constants, 47:30
structure, 39:359
crystal structure. 25:77
sweetness, 45:276
comparison to o-galactose, 45:247
synthesis, 41:9
thermodynamics of anomerization of a-and
P-, 2 4 5 I
6, I ,6-tri-O-p-tolylsuIfonyl-, 23:244
utilization by Candida inrerrnedia, 32: 183
by yeasts, 32:208-209
water loss, 47:2 18-2 19
Lactose antibodies, 53:23 1--233,235-236
324 SUBJECT INDEX
Lactose calcium bromide heptahydrate, crystal
structure bibliography, 31:352
Lactose calcium chloride heptahydrate, crystal
structure bibliography, 31:352
a-lactose hydrate, benzoylation of, 33:37
a-lactose monohydrate
C-C and C-0 bond-lengths in, 44: 15
crystal structure bibliography, 30:453
Lactose synthetase, 25:98,26:37 1
preparation of, 32: 10
Lactoside
benzyl penta-O-benzyl-4,6-0-benzylidene-
p-. hydrogenolysis regioselectivity,
39:130
methyl p-, benzoylation of, 33:37
Lactosylamine, N-acetyl-a-, and anomer,
preparation of, 31:92
Lactosyl bromide, 2,3,6,2,3,4,6-hepta-O-
acetyl-, reaction with pyridine, 39:32
Lactosylceramide, 44:437
biosynthesis, 40:248
catabolism, 40:274-276
in starfish, 44:429
Lactosyl fluoride, per-0-acetyl-a-, synthesis,
38:202
Lactotetraosylceramide
biosynthesis, 40:25 1-252
catabolism, 40:274-276
Lactotransferrin
bovine, glycoproteins (compounds 71 and
72), H-NMRspectroscopy, 41:344,
360-361,363-366
carbohydrate-peptide linkage in, 25:442
deamination of, 31:236
human, glycoprotein (compound 421, H-
NMRspectroscopy, 41 :306-308,
310-311,324-326
glycoprotein (compound 43), H-
NMRspectroscopy, 41:306-3 11,
324-326
glycoprotein (compound 52); H-
NMRspectroscopy, 41:306,324-328
Lactulose
composition
in aqueous solution, 42:65
in dimethyl sulfoxide, 42:68
conformational equilibria, 23:32
liquid chromatography methods for analysis
of, 46:33
synthesis of, 24:6
taste properties, 45:254-255
Lactulosucrose, as substrate for
dextransucrases, 30:423
Laminarabiose
in honey, 29297
0.19-hydrate, crystal structure bibliography,
38:447448
liquid chromatography methods for analysis
of, 46:33
octaacetate, gas-liquid chromatography of,
28:70
Laminaran, 25:9
carbon- 13 nuclear magnetic resonance
spectra, 38:48
carbon-13 signals, 38:23
in cell walls, 26:345, 349
permethyl-, mass spectrum of, 21:90
structure analysis of, 30:370
sulfated degraded antitumor activity of,
32:258
synthesis of, 26:324-325,32:11
Laminaranase, specificity of, 30:269, 277
Laminaran-exo-( 1+3)-p-~-glucanse, action
pattern of, 30:267,272
Laminaran sulfate, preparation of, 29:335
Laminarabiose, 21:464,22:2 1
Laminitol
natural occurrence of, 42:73,76
structureof, 42:71, 78, 80, 115
Lamport model for plant primary-wall
structure, 42:309
Lampteromyces japonicus, polysaccharide,
41:103
Lanceolarin, from Dalbergia lanceolaria,
31:147
Landsteiner hapten-inhibition technique, for
lectins, 35: 139
Langmuir, 53:381
Lankavose, 21 :190
Lanthanide ion
complex-formation, 47:20
coordination spheres, 47: 128
oxidation state, 47:129
Lanthanide metals, as shift reagents in proton
nuclear magnetic resonance spectroscopy,
29: 16-25
Lanthanide shift-reagents, in conformational
analysis of acetals, 34: 197
Larch
arabinogalactans
 SUBJECT INDEX
Barry degradation of, 31:203
hydrolysis of oxidized, 31: 194
cell wall studies on, 42:283-285
LasaNia papulosa, polysaccharide, 41:75
Laser-Raman spectroscopy, 44:8-9,67-85
advantages of, 44:73
applications, 44: 85
of carbohydrates, results, 44:75-85
of o-fructose solutions, 42:23
instrumentation, 44:70-73
sampling techniques, 44:70-73
Laspartomycin, inhibitor of protein
glycosylation, 40:342
o-Laudanine, 46: 13
Lauric acid, methyl ester, transesterification of
methyl a-o-ghcopyranoside with, 33:44
Laurusin, 25:243
Lead tetraacetate
action of, on the sugars, 14:9-61
in dimethyl sulfoxide as glycol-cleaving
agent, 31:202
oxidation of carbohydrates and glycols with,
33:95-97
Lead tetrafluoride, reaction with pyranoid
glycals, 25: 195
Lecithin, 53:388
Lectins, see also Isolectins
2-acetamido-2-deoxy-o-
galactose-binding, 35:226-254
glucose-binding. 35:206-226
a-o-mannosidase action of soybean, 28:445
antibody activity, 35: 147
anti-recognition glycoprotein, 40:220
applications in serological laboratories,
35: I29
arabinogalactan properties similar to. 42:287
binding function in plant cell-walls,
42~309-310,329-332,337-338
blood-group and carbohydrate-binding
specificities of purified, 35338-339
carbohydrate association, 35:340
carbohydrate-binding specificity,
35: 139-145,33 1-333
classification, 35:133, 141, 146
definition, 35: 128, 131
detection, 35: 133-136
o-galactose-binding, 35:254-277
o-mannose(D-ghxose)-hinding, 35: I 50-205
functions, 35: 146-149
in host-pathogen interactions, 44:380
325
interaction with cellular structure,
35:317-333
with glycosides, 35: 140
with polysaccharides, glycoproteins, and
glycolipids, 35: 140
isolation and purification, 35: 136-139
L-fucose-binding, 35:277-291
in life cycle of plant, 35: 148
neoglycoproteins as substrates, 37:268-269
nomenclature, 35: 145-146
physical and chemical properties,
35: 133-337
Plant a-D-galactopyranosyl-specific.
37:339-341
potato, 43:45,44:234
purification by affinity chromatography,
39:444445
red cell receptor, 45: 170
reviews, 35: 132
role in plant recognition systems,
44:379--381
sialic acid analysis, 40: 175
sources, 35: I39
soybean, 25:45 1
toxicity, 35:149
uses, 35: 129
Ledienoside, fucose-containing, 39:28 I . 302
Leguminoseae
chemotaxonomy of, 31:258
galactomannans, role in seeds of, 31:255
from seeds, 31:243,245,247-252
Lemieux effect, 45:264
Lemnaceae minor
apiobiose from, 31: 188
apiogalacturonan from cell walls of, 31: 151
Lemna spp., cell-wall studies on, 42:280-28 1
Lemon
cell-wall studies on, 42:278, 281
development physiology of, 42:362-363
Lens culinavis, see Lentil
Lens esculenra. lentil lectin from, 35: I93
Lentil
large-seed and small-seed, lectins from,
35: 193
lectin
carbohydrate-binding specificity, 35: 194,
20&205
hemagglutinating activity, 35: 190, 20 1
interaction with cellular structures, 35:317
with erythrocyte glycopeptide, 35:320
326 SUBJECT INDEX
Lentil (continued)
isolation, 35:137-138, 138, 190-196
properties, 35:138, 19G196
structure, 35: 190-192
Lentinan
antitumor activity, 32:247,269, 272, 38:5 1
effect of urea on, 32:260-261
carbon- 13 nuclear magnetic resonance
spectra, 38:51-52
crystal structure bibliography, 36:326,
40:390
fungal, 41:75
Lentinus edodes
a-r-arabinohranosidase of, 42:387
polysaccharide, 41:70,75
Lentinus lepideus, a-r-arabinofuranosidase of,
42:387
Leprosy, specific neoglycoconjugates,
51:20&2 10
Leptine, as beetle repellent, 24:6
Lettuce seeds, p-D-mannanase and germination,
35:371
Leucine, D-, favored conformation, 45232
Leucoagglutinin, purification and composition
of, from Phuseolus vulgaris, 35:295
Leucomycin, sugar component mycaminose,
28:297
Leuconostoc, dextran synthesis by, 30:373
Leuconostoc mesenterioides, 51: 135-1 37
action on sucrose, 32:7
alteman synthesis, by altemansucrase,
51:148
dextran
branch linkage synthesis, 51:159-162
synthesis
by dextransucrase, 51:148-149
two-site insertion mechanism,
51: 145-146
dextransucrase, acceptor reactions,
51:154-158
enzyme purification, 51:138-139
NRRL B-5 12 dextran, degradation of sulfone
derivative, 31:227
Leucopenia, 45: 171
Leucrose, 22:230,51:152
in honey, 25:295
liquid chromatography methods for analysis
of, 46:33
monohydrate, 43:37 1
Leukemia, treatment of, 22:213
Levans, 22:23 1
Fourier-transform infrared-difference
spectroscopy, 44:62
hydrolysis, 46:269
interaction with concanavalin A, 35: 175
mass spectrometry of, 29:54
plant, structure, 35:7
synthesis by Leuconostoc, 30:374
Levene, Phoebus Aaron Theodore, obituary of,
12:l-12
Levoglucosan
acetylation of, 34:83
2-amino-2-deoxy-
derivatives, preparation of, 34:3 1
preparation of, 34: 130
4-amino-4-deoxy-, preparation of, 34: 130
benzylation and tritylation of, 34:85
chiroptical properties of, 34:52
chromatography of, 34:63
cleavage of, by acid, 34:64-69
by hypophosphorous acid, 34:6849
by periodate oxidation, 34: 104
reductive, 34:69
by sodium hydrogen sulfite, 34:69
complexes, 34:93
formation by, 34:54-55
conformation of, and triacetate, 34:5 1
co-polymerization with alcohols and ethers,
34: 72
crystal structure bibliography, 30:448
determination of, 34:63
effect of flame retardants on pyrolysis of,
23:471
in flaming combustion, 34:26
formation from celluslose on heating,
23:43 1,433
glycidyl ethers, 34:76
heat action on, 34:52
heat of combustion formation, dehydration,
and evaporation, and vapor-tension data
for, 34:52
history, preparation, and uses of, 34:25,27
hydrogenolysis of, 34:69
infrared spectroscopy of, and derivatives,
34:56, 63
mass spectrum of, 21:81
methylation of, 34534
oxidation of, 34:94
partially substituted, 34:78
per-0-substituted, 34:77
 SUBJECT INDEX
polymerization of, 21:478,34:70, 1.59
preparation of, 34:27, 32-33
from acrolein, 34:4849
from monosaccharides, 34:46
production of, 2 2 4 9 8 4 9 9 , 501,34:3845
properties of, 34:50
p-toluenesulfonylation of, 34:80
pyrolysis of, 22:497,23:460462,34:69
structure of, 34:50
synthesis of, from Brigls anhydride. 34:29,
48
synthetic exploitation of, 34:79
1(6)-thio-, crystal structure bibliography,
38:423424
triacetate, acid cleavage of, 34:67
cleavage by dichloromethyl methyl ether
and zinc chloride, 34:68
formation of, 34:46
reaction with
antimony pentachloride. 34389
trifluoromethanesulfonic acid. 34:88
Shorygina reaction in ammonia, 34:78
tributyrate, tripropionate, tribenzoate, and
tristearate, reactions with titanium
tetrachloride, 34:67
Levoglucosenone, 44:4
Levulinaldehyde, a-hydroxy-, in dehydration of
2-deoxypentoses, 28:224
Levulinic acid, 46:296
from glycal dehydration, 28: 184
preparation of, 28:2 12-2 18
Lewis acids
as catalysts in C-glycosylations, 33: 158-162
copolymerization with 1 -6-anhydro- 2.3.4-
tri-0-methyl-P-u-, glucopyranose,
34:74
in degradation of acetals, 34:s
in diazomethane methylations, 33:61(-69
in flameproofing of cellulosic materials.
23:472
lanthanide shift-reagents in proton nuclear
magnetic resonance spectroscopy, 29: I8
Ievoglucosan complexes with, 3 4 5 - 5 6
in polymerization reactions. 34: 163
reaction with
cyclic acetals, 26:202
dialkyl dithioacetals, 32:60
rearrangements of saccharides in, 26: 192
Lichenan, 2 5 9
antitumor activity of, 32:248,249
327
carbon- I3 nuclear magnetic resonance
spectrum, 38:24,49-50
carboxymethyl ethers, preparation of, 29:3 19
enzymic degradation products of, 30:358
fine structure of, 30:357
levoglucosan from, 34:40
lichen, 41:75
0-(2-hydroxyethyl)-, preparation of, 29:3 15
structural analyses of. 30:353
structure, enzymic analysis, 44:273
Lichenanase, 44:273-275
Lichenase, preparation and specificity of,
30:351-352
Lichens
glucans, 41:75-76
polysaccharides, 41 :67-703
Licopodiirni swurus. 46: 13
Lidocaine, effect on glycosylation, 40:345
Light-scatteririg procedures, mucus
glycoproteins, 47:356-358
Lignin
in grasses and cereals, 36:222-224
in plant cell-walls, 26:300, 42:269
source of humus, 46:323
structure and origin of, 26:299
Lignocellulosic materials
fermentation products, 46:326
polysaccharides in, 46:306
Lignoceric acid, 24:410
Lilium longiflorum, trehalose 6-phosphate
synthetase in, 30:241
Lima-bean, see Phaseolus lunutus
Limonine, taste properties, 45:3 13
Limpet,-a-u-mannosidase, activation of,
28:417419
pH and activity of, 28:412
purification of, 28:411
Limulin, sialic acid analysis, 40: 175
Limuliis polyphemus lectin. see Horseshoe-crab
lectin
Linamarin, 21:23
biosynthesis of, 26:441
Ljncomycin
anhydrooctitols from, 25:249
carbon-1 3 nuclear magnetic resonance
spectroscopy, 41:65
chemical-ionization mass spectra of,
29:82-83
chlorination of, 28:225
crystal structure of, and hydrochloride, 25:85
328 SUBJECT INDEX

Lincomycin (continued) heptaacyl, 50:243

hydrochloride monohydrate, crystal structure hexaacyl, 50:24 1-242
bibliography, 31:368 as lipopolysaccharide endotoxic center,
migration of hexanoyl groups in, 33: 102 50:256-258
N-acetyl-, carbon- I 3 nuclear magnetic molecular shape, 50:253-254
resonance spectroscopy, 41:65 pentaacyl, 50:243-245
reaction with triphenylphosphinecarbon phase states, 50:258
tetrachloride, 28:247 phosphate and pyrophosphate, 48:3 14-
7(S)-chloro-7-deoxy- 315
crystal structure of, 2585 phosphate substituents, 50:225-227
hydrochloride monohydrate, crystal properties, 50:2 13-214
structure bibliography, 31:368 serology, 50:258-260
synthesis of, 28:282 structure, 50:260-261
Lincomycitol, anhydro-, 25249 chemical, 50:2 14-215
Lincosaminide, methyl 7 - d e o x y - a - ~ ~ - , primary, 50:214216
synthesis, 40:60 synthetic, 50:252
Lincosaminol, N-acetyl-3-4-O-isopropylidene-, tetraacyl, 50:244
25249 three-dimensional organization, 50:256-258
Linear models, mucin structure, 47:367-370 Lipid intermediates
(+)-Lineatin, synthesis, 50: 193 in biosynthesis of glycoproteins, 26:47 1
Lineweaver-Burk plot, 51: 157 of peptidoglycans, 26:427432
in enzyme kinetics, 23:289,292 in cellular biosynthesis, 41:132-135
Link, Karl Paul Gerhardt, obituary, 39: 1-12 Lipid-linked sugars, in plants
Linked-Atom Least-Squares analysis, 52:3 19 lipid moiety, 44:347-352
Linokic acid, in o-galactosylglycerides, 37:326 occurrence, 44:347
Linolenic acid, in D-galactosylglycerides, saccharide derivatives, 44:352-356
37:326327 structural aspects, 44:347-352
Lipase turnover, 44:356-358
in cultured cells, 40:377-378 Lipids
effect of sugar side-chain, 40:35 1 D-fruCtOSe effect on metabolism of,
Lipid A, 50:211-265 34~325-330
amphiphilic nature, 50:213 formation by yeasts, 32:219
amphoteric nature, 50:2 13 Lipid-starch complexes
antibodies, 50:259-260 characteristics, 53:385-386
antitumor activity of, 32:242-243 digestibility, 53:399400
backbone, 50:216225,260 functional properties, 53:396399
glycosyl region, 50:2 18-22 1 native, 53:386387
hydroxyl groups preparation, 53:387-388,390-392
position 4', 50:247-249,26 1-262 properties, 53:392-393,395
position 6', 50:249-252,262 structure, 53:392-393, 395
phosphate groups, 50:221-225 Lipooligosaccharides
principles and structures, 50:216 antigens, purification, 51: 171-172
structural elucidation, 50:2 17-2 I 8 trehalose-containing, 51:188-198
biosynthesis of, 26:409410 N-acylkansosaminyl-( 1 4 3 ) - ~ -
components, 48:308 fucopyranose disaccharides group,
conformation, 50:252-256 51:193
definition, 50:213 M.fortuitum, 51:195
endotoxic activity, 50:263-264 M.gordonae. 51:195-196
f.a.b.-mass spectrometry, 4557 M. kansasii, 51:188, 192-193
fatty acids, see Fatty acids M.malmoense, 51: 193-194
 SUBJECT INDEX
M. smegmatis, 51:197-198
M. szulgui, 51:194
M. tuberculosis, 51:196-197
structures, 51: 189-1 91
unknown Mycobacterium species,
51:194195
Lipopolysaccharides, 50:211-265, 53:254, see
also Lipid A
acid hydrolysis of, from Salmonella and
Yersinia, 31 :188
bacterial
L-fucose containing, 39:307-308
methanolysis, 46:258-259
biosynthesis, lipid intermediates in bacterial,
26:430
cell-wall, of Gram-negative bacteria,
26:409424
core oligosaccharide, 50:212
core region, 44:278
3-deoxy-o-manno-2-octulosonic acid
component, 38:324
effect on immune tumor response, 32:266
gas-liquid chromatography of, 28:49,
30:9498
gel chromatography of, 25:43
hydrolysis of, 28: 19
interaction with concanavalin A, 35: 179
Klebsiella
0-group 5, mass spectrometry, of, 29:67,
97
0-group 9, mass spectrometry, of.
29:69-70,91
0-group 10, mass spectrometry, of,
29:67
lipid A as endotoxic center, 50:25&258
methylation, ethylation, and propylation of,
30:15
methylation analysis, 38:352
Myxococcus fulvus, mass spectrometry of,
29:66
occurrence and linkages of KDO,
38:334-356
0-specific chain, 50:2 12
Pusteurella pseudotu berculosis, mass
spectrometry of, 2 9 5 4
from Proteus vulgaris, antitumor activity of.
32~241-242
Rhodopseudomonas cupsuluta, mass
spectrometry of, 29:67
Rhodopseudomonas viridis, mass
329
spectrometry of, 29:66
Salmonella, mass spectrometry of, 2 9 5 3
Salmonella &phi, mass spectrometry of,
29:63-65
serological determinants, 41: 177
structural principles, 50:211-212
structure of, 38:337,339,343-356
subunit of, from Salmonella typhimurium,
26:411
sugar composition, 38:341
of Veillonella, gas-liquid chromatography
and mass spectrum of, 30:36
Lipoprotein, desialylation, 40:22 1
Lipoproteinlipase. 43: 125-126
Liposaccharide, biosynthesis of bacterial,
26:439
P-Lipotropin, role, 37:2 14
Lipoxygenase in fruit climacterics, 42:365
Lippia dulcis Trev., 45:295
Liquefaction, 46:273-274,323
Liquid chromatography, 46: 17-1 8
accuracy, 46:63-64
combined techniques, 46:69-70, 72
detectability, 46:63-69
direct-detection methods, 46:65-66
electrochemical detectors, 46:65
flame-ionization detectors, 46:65-66
future trends in. 46:71-72
mass detectors, 4 6 5 - 6 6
polarimetric detectors, 46:66
post-column derivatization methods,
46:66-68
pre-column derivatization methods,
46:68-69
preparative, 46:58-63, 71-72
in analytical-scale equipment, 46:59-6 1
general aspects of, 4 6 3 - 5 9
in large-scale equipment, 46:61-63
sample recovery from columns, 46:59
refractive index detection, 46:64-65
stationary phases, 46:7 I
of sugars, pyranose form separation in,
42~23-24
triple-pulsed amperometry on platinum or
gold electrodes, 46:65
ultraviolet detectors, 4 6 5 5
Liquid chromatography-mass spectrometry,
46:69-70
Liquid chromatography-NMR spectroscopy,
46:69-70
330 SUBJECT INDEX
Lithium
butyl-, reaction with cyclic acetals, 34:49,
209
organic compounds, in synthesis of 1-C-
substituted carbohydrates, 25240
Lithium aluminum deuteride, for reduction and
deuteration of sugar derivatives, 27: 131
Lithium aluminum hydride
in 1,5-anhydrohexitols preparation, 31:3
effect of solvents on reduction of
carbohydrate sulfonic esters, 23:269
reaction with
complexes of, in presence of optically
active sugars, 27:195-199,216
sulfonic esters of dithioacetals, 32:52
reduction of chlorodeoxy sugars by, 28:303
reductive cleavage of 1,6-anhydrohexopy-
ranoses by, 34:69
Lithium borohydride, for reduction ofp-
toluenesulfonates and methanesulfonates,
33:217
Lithium borohydride-t, tritiation of sugars by,
27: 129
Lithium bromide, complex with sucrose,
21:223
Lithium chloride, complex with sucrose,
21:223
Lithium diisopropylamide, reaction with
acetals, 39: 145
Lithium divinylcyanocuprate, 1,4-conjugate
addition, 50:184-185
Lithium gellan, 52:386
Lithium iodide, complex with sucrose, 21:223
Lithium NAD' dihydrate, crystal structure
bibliography, 38527
Lithiumtrimethylsilyl acetate, C-1 elongation of
aldonolactones, 50: 144
Liver
D-fructose uptake by, 34:291
nucleotide pool in, effect of o-fructose on,
34:322-324
Lividomycins
A (ap,ap) conformation, 47: 120
5-amino-5-deoxy-, preparation and
antibacterial activity of, 30: 171
5-deoxy-, preparation and antibacterial
activity of, 30: 171
inactivated, 30: 191,203
minimum inhibitory concentrations of,
30:223
N-acylation of, 30:175, 177
1 -N- (1,-4-amino-2-hydroxybutyryl)-,
minimum inhibitory concentrations
of, 30:223
1-N- [(S)-4-amino-2-hydroxybutyryl]-,
preparation and antibacterial activity,
30:178
penta-N-(benzyloxycarbony1)-,preparation
of, 30: 192
penta-N-(benzyloxycarbonyl)-4',6':2 , 3 :
4,6-tri-O-isopropylidene-,5-
(diphenylphosphate), preparation of,
30:192-193
5-phosphate
structure of, 30:192,203
synthesis of, 30:193
sepharose 4B, preparation of, 30: 194
B, 48~229-230
discovery of, 30: 112
and structure of, 30:119-121
inactivation of, 30:190-191
Lividotriosamine, structure of, 30: 121
Lobry de Bruyn-Alberda van Ekenstein
transformation, 13:63-103, 25332,
28:161, 163, 168,46:281
of o-glucose, 46:303
in formose formation, 29: 180, 2 13
Lock and key concept, 50:9-13
Locust, cY,cY-trehalosebiosynthesis in, 30:238
Locust bean, galactomannan from, 31:242,
244-245
Locust-bean gum
conductivity of solutions of, 21:214
industrial use of, 31:307-312
solution properties of, 31:283
structure of, 31:272
Loguniuceae, polysaccharides from,
31:253-254
Loganin, crystal structure, 43:248-249
Log(c2) model, 51:79, 117-118, 125-126
Loliunr, see Ryegrass
Lone-pair orbitals
electron distribution and, 47:lOl-103
interactions in reactivity, 47: 1 19-1 23
orbital interactions, 47: 110
oxygen
distribution, 47: 109
interactions, 47:lll-I 12
p-type, 47: 109
 SUBJECT INDEX 33 1

through-space mechanism, 47: 122 2,5-anhydro-5-seleno-o-, dimethyl acetal,

Lopez Aparicio, F.J., 45: 13 23:232
Lorenzini jelly, gas-liquid chromatography of, mutarotation, 23:23
28:47 Lymphoblastic leukemia cells, adenine
Lossen reaction, for degradation of periodate- nucleoside activity against, 42: 13 I
oxidized polysaccharides, 31 :237 Lymphoblastoid cells, thioguanine nucleoside
of Salmonella lipopolysaccharide, 31 :2 1 I activity against, 42: 132
Lotus tetragonolobus lectin, see Asparagus-pea Lymphocytes
lectin desialylated, 40:221
Low-speed sedimentation equilibrium, mucus lectin-reactive glycoproteins from, 35:325
glycoproteins, 47:359-367 Lyoluminescence, of irradiated carbohydrates,
5-[(~-Phenylalanyl)amino]uridine, crystal 37:76
structure, 43:368 Lyxoside, methyl D-. acetylated. structure of,
Lubricants, 0-(carboxymethyl) cellulose as, 26:8
29:321 Lysine
Lucerne leaves, cell-wall studies on, 42:278, 5-hydroxy-~-
280 carbohydrate residues linked to, in
Lumazine glycoproteins. 26:456-458
6,7-dimethyl- 1 -P-o-ribofuranosyl-, crystal in glycoprotein linkages, 25:418
structure bibliography, 38:495;196 hydroxy-L-, in glycopeptide of urine, 24:450
6,7-dimethyl-N -P-D-ribofuranosyl-. crystal 5-O-P-~-galactopyranosyloxy-~-, linkage in
structure bibliography, 30:463 glycopeptides, 25:436
Lupin Lysogangliosides, analysis, 45:56
cell-wall studies on, 42:27 1, 309, 3 1 I , 3 13 Lysophosphatidylcholine, 53:386
enzyme from, in polysaccharide synthesis, Lysosomal-storage disorders, urine in
26: 324-3 25 liquid chromatography, 46:44
Lupinus luteus, a-L-arabinofuranosidase from, sialylated oligosaccharides, liquid
42:387 chromatography analysis, 46:4546
Lupoxes-A, taste properties, 45:3 13 Lysosomes
Lutean, structure, enzymic analysis, 44:275 glycosphingolipid catabolism, 40:269
Luteic acid, 52:8 of yeast cell vacuole, 32:141
fungal, 23:378 Lysosome theory. a-o-mannosidase activity
Luteolin, from Perroselinum crispum. 31: 143 and, 28:408
Lutes, 23:380 Lysozyme, 24:3 14, 26:371
Lyases, 44: 148 action on chitotriose, gel chromatography of
action pattern and specificity of, 33:367- products, 25:35
378 crystal structures of, and substrate
assay of, 33:380 complexes, 25:93-98
occurrence and formation of, 33:378 Lyxitol
purification of, 33:379 1-acetamido- 1-deoxy-L-, 23: I70
Lychee, development physiology of, 42:379 1-amino- I-deoxy-o-, deamination of,
Lychnose 31:60-62
occurrence, 37:291,301 2,5-anhydro-o-, 25:234
oligosaccharides 4-O-methyl-~-,22:115
occurrence, 37:306 2,3,4-tri-O-benzyI- 1,5,-di-O-p-tolylsulfonyl-
structure, 37:305 L-, solvolysis of, 24: 196
structure, 37:301-302 Lyxofuranose
Lycotetraose, 24:7 5-acetamido-5-deoxy-
Lyxose D-, 23~171
5-acetamid0-5-deoxy-o, 23: 170 1,2-O-isopropylidene-P-D-, 23: I7 I
332 SUBJECT INDEX
Lyxofuranose (continued)
1,5-anhydro-2,3-0-isopropyhdene-p-~-,
synthesis, 39: 168
conformation of, 34:201
5-deoxy-3-C-formyl-
p-~-,3'-(trimethylenedithioacetal), crystal
structure bibliography, 32:362,
34:357
1,2-O-isopropylidene-P-~-, 3 I-
(trimethylene dithioacetal), crystal
structure bibliography, 32:366,
34:358
L-
1-O-acetyl-2,3,5-tri-O-henzoyl-4-fluoro- Lyxopyranose
a-,l3C-NMR data for, 46:172
X-ray crystallography of, 42: 16 1
2,3-O-isopropyhdene-o-, synthesis, 39:74
tri-O-acetyl-4,5-dideoxy-4-C[(R)-
phenylphosphinyl]-cr-~-, physical
properties of, 42:191
2,3,5-tri-O-benzyl-~-,24: 194
Lyxofuranoside
ethyl 2,3-anhydro-5-0-(tetrahydropyran-2-
~I)-D-,25: 120
ethyl 2-S-ethyl-
1,2-dithio-o-, preparation of, 32:50
3-0-methyl- 1,2-dithio-o-, preparation of,
3250
methyl (Y-D-,21:122
conformation of, 21:98
crystallography of, 25:58,31:365
preparation from dithioacetal, 32:68
methyl 4-amino-4-deoxy-2,3-0-
isopropylidene-cu-D-, deamination of,
31:34
methyl 2,3-anhydro-~-,25: 1 16
methyl 3-deoxy-3-C-formyI-a-~-
hemiacetal, 24: 193
preparation of, 31:28
methyl 5-deoxy-3-C-(hydroxymethyl)-2,3-0- Lyxopyranoside
isopropylidene-P-DL-, synthesis, 40:82
methyl 5-0-benzoyl-2,3-0-isopropylidene-
(Y-D-,reaction with dibromomethyl
methyl ether, 39: 120
methyl 5-0-benzyl-a-o-, preparation of,
28:294
9-a-~-Lyxofuranosyladenine, 50:195
Lyxofuranosyl fluoride
D-
2,3-acetoxonium-5-0-acetyl-~-, 'H- and
"F-NMR data for, 46: 107
2,3-benzoxonium-5-0-benzoyl-a-, 'H-
and lyF-NMR data for, 46: 107
5-0-benzoyl-2,3-benzoxonium-(~-, 13C-
NMR data for, 46: 168
2,3,5-tri-O-acetyl-, 'H- and IYF-NMRdata
for, 46: 107
2,3,5-tri-O-benzoyl-
I3C-NMR data for, 46: 168-1 69
'H-and 19F-NMRdata for, 46:107
3,5-di-O-benzoyl-a, p-D-, 26: 179
1-p-o-Lyxofixanosyluracil, crystal structure,
43:277
5-acetamido-5-deoxy-cu-o-, 23: 171
(Y-D-, 45:74
conformation in solution, 26:85
tetraacetate, conformation in acetone-d,,
26:87
p-D-
conformation in solution, 26:85
reaction with sulfuryl chloride, 28:235,
33:76
p-L-,crystal structure bibliography,
38:4 1 9 4 2 0
D-, 1,3,4-tri-O-acetyl-2-deoxy-2-fluoro-a-,
IH- and I9F-NMR data for, 46:104
4-deoxy-4-(dimethylamino)-~-, 23: 151
tetra-0-acetyl-a- L-, crystal structure
bibliography, 37: 39 1
1,2,3,4-tetra-O-acetyl-5-[(benql-
oxycarhonyl) amino]-5-deoxy-a-o-,
conformation of, 26:89
tetra-0-acetyl-D-, rearrangement in hydrogen
fluoride, 26:179
tetra-0-benzoyl-a-D-, rearrangement in
hydrogen fluoride, 26: 179
1-thio-a-D-, tetraacetate, proton magnetic
resonance spectroscopy of, 27:28
benzyl a-D-, catalytic oxidation of, 33:89
D-, trifluoromethyI3,4-di-O-acetyl-P-,'H-
and I9F-NMR data for, 46: I04
methyl a(and P)-D-. hydrolysis of, 22:46
methyl c.-D-
reaction with sulfuryl chloride, 33:75
selective henzoylation of, 33:26
methyl (Y-DL-, synthesis, 40:67
methyl 4-amino-4-deoxy-a-~-,23: 15 I
methyl 2,3-anhydro-
 SUBJECT INDEX
synthesis, 40:68-69
a-DL-,
p-DL-, synthesis, 40:69
p-L-, 25: 154
D-, 25: 153
methyl p-DL-,synthesis, 40:68
methyl++-, 22:126
methyl D-, conformation in solution, 26:84
methyl 2,4-di-O-benzoyl-3-bromo-3-deoxy-
a-D-,synthesis, 39:112
methyl 2-O-benezoyl-3,4-di-S-benzoyl-3,4-
dithio-P-L-, 22: 141
methyl 4-O-benxoyl-2,-3-O-benzylidene-01-
D-, reaction with triphenylmethyl
fluoroborate, 39: 110-1 12
methyl 2,3-O-isopropylidene-01-~-
hydrolysis of, 34:204
in L-apiose synthesis, 31: 182
methyl 2.3-O-isopropylidene-4-O-p-
tolylsulfonyl-a-o-(or a - ~ ) - ,
displacement reactions of, 24: 191
methyl tri-0-methyl-a(and P)-D-, mass
spectra of, 21:60
methyl tri-0-acetyl-a+-, proton magnetic
resonance spectroscopy of, 27:28
methyl 2,3,4-tri-O-acetyl-5-amino-S-deoxy-
5-N-(methoxy)-, synthesis, 40: 100
methyl tri-0-benzoyl-a-D-, proton magnetic
resonance spectroscopy of, 27:28
Lyxopyranosyl chloride
01-D-, 2,3,4-tri(chlorosulfate), preparation and
reactions of, 28:235-237
2-chloro-2-deoxy-01-~-,2,4-di(chlorosulfate),
preparation of, 28:236
Lyxopyranosyl fluoride
D-
3,4-di-O-acetyl-2-deoxy-
2-bromo-, IH- and 19F-NMR data for,
46:135
2-iodo-, 'H- and IYF-NMRdata for,
46: I36
2,3,4-tri-O-acetyl-a-, IH- and IYF-NMR
data for, 46: 102
2,3,4-tri-O-henzoyl-a-, IH- and "F-NMR
data for, 46: 102
per-O-acetyl-2-deoxy-2-fluoro-p-~-,
preparation, 38:204
per-0-benzoyl-a-o-, preparation, 38:20 1
tri-0-acetyl-a, p-D-,26: 179
tri-0-benzoyl-
a,p-D-, 26: 179
333
a-D-, 26: 119
Lyxopyranosylmethane, bis(ethylsulfony1) a-
D-, triacetate, nuclear magnetic resonance
spectrum of, 25:252
Lyxose
2,s-anhydro-
D-
dialkyl dithioacetal, 25: 198
diisobutyl dithioacetal, 24: 175
3,4-di-p-tolylsulfonyl-~-, diisobutyl
dithioacetal, preparation of, 32:5 1
5-seleno-~-,dimethyl acetal, 25:205
5-thio-D-,dimethyl acetal, 25:205
p-L-
crystal structure bibliography, 31:363
taste properties, 45:242
5-bromo-5-deoxy-DL-,synthesis of, 28:304,
40:90
composition in nonaqueous solvents, 42:68
D-
in aqueous solution, 42:16
composition, 42:64.66
polarimetry, 42:22
derivatives of cyclic acetals, Table.
34:212
dialkyl dithioacetal, reaction withp-
toluenesulfonyl chloride, 25: 198
diethyl dithioacetal, partial
demercaptalation of, 32:67
diisobutyl dithioacetal, reaction with p -
toluenesulfonyl chloride, 3 2 3 1
dithioacetal
reaction with sulfonyl chloride in
pyridine, 32:48
selective esterification of, 33:4041
reaction with sulfuryl chloride, 33:76
synthesis of, 33:93
halogen derivatives, 22:2 16
nonselective spin-lattice relaxation rates,
45:148
polarography of, 29: 126
utilization by yeasts, 32:2 15
5-deoxy-~-,21: 177
5-deoxy-~-,21:17&177
preparation from dithioacetal of 6-deoxy-
L-galactose, 32:8S
3,4-di-O-acetyl-2,5-anhydro-
aldeh-ydo-o-, and p-nitrophenylhydrazone,
preparation of, 28:287-288
D-,(p-nitrophenyl)hydrazone, 25:202
334 SUBJECT INDEX

Lyxose (continued) sialic acid effect on structure, 40:2 18-220

dithioacetals,
2,4:3,5-di-O-benzylidene-o-,
preparation of, 32:53
DL-,synthesis, 40:8-9
L-
derivatives of cyclic acetals, Table, 34:212 Magnamycin, mycaminose sugar component,
synthesis of, 33:93
1-O-benzoyl-2,3,5-tri-O-benzyl-4-O-methyl-Magnesium ion
L-,methyl hemiacetal, 24: 194
4-O-methyl-o~-,composition in aqueous
solution, 42:45
4-S-methyl-4-thio-~-,dimethyl dithio-acetal,
preparation of, 32:35
5,5,5-hichloro-5-deoxy-~~-, synthesis, 40:92
3,4,5-tri-O-benzoyI-2-S-ethyl-2-thio-o-,
diethyl dithioacetal, dimethyl acetal
from, 32:65
Lyxose 2,3-carbonate, D-, composition in
aqueous solution, 42:59
Lyxose 5-phosphate, composition in aqueous
solution, 42:46
Lyxoside
methyl a-D-, selective periodate oxidation of, products of, 46:320,47:269-270
33:95
methyl 2,3-anhydro-cu-~-and-p-~-, 25: 150
methyl D-, catalytic oxidation of, 33539
Lyxurono- 1,4-lactone, 3,4-O-isopropylidene-~-, Maleic acid, 2-(2,3,5-tri-O-benzyI-p-~-
preparation, 38:3 14
M effect on sugarcane, 21:425
Muackiu umurensis lectins, isolation,
purification, and properties, 35:3 13
MacDonald-Fischer degradation
deoxy sugars by, 21:156, 178
of dithioacetals, 32:82
Muclura pornifem lectin, see Osageorange,
lectin
Mucracanthorhynchus. trehalose biosynthesis
in, 30:239
Macrodex, dextranglucosidase degradation of,
30:396
Macrodexhins, from glycogen, 30:3 14
a,-Macroglobulin, 44:23 3
Macrolide antibiotics, glycosidic, 3 5 8 1
Macromolecules
affinity chromatography, with
carbohydratebearing adsorbents,
39:405447
Macrophages
a-r-fucosidase activity, 39:334-335
immune action, 41: 187
Madinaveitia, A,, 4 5 1 0
28:297
effect on reducing sugars in solution, 42:33
inhibitor of cellulose biosynthesis, 41: 144
Magnetic field, Schrodinger equation,
51:23-24
Magnets, high-field, for proton nuclear
magnetic resonance spectrometers,
29:25
Maillard reaction, 14:63-134,22:272,46:3 1 I ,
3 18,47:255-256,52:458459
chromophoric products, 46:322
at elevated temperatures, 46:307
factors affecting, 46:307
mechanism of, 26: 14
non-nitrogenous products, 46:3 18-32 1
inhibition of bacterial growth by, 46:326
Maize, see Corn
Malarial parasites, red cell receptor, 45: 170
ribofuranosy1)-, methyl ester, preparation
of, 33:145
Maleic hydrazide
as plant-growth substance, 21:398
Maleylation, of lentil lectin, 35: 196
Malic acid, D-, fructose ester, 22:253
Malic-3-d acid, in determination of hydrogen
configuration in sugars, 27: 143
Malic dehydrogenase, in fruit climacteric,
42:365
Malic enzyme, in fruit climacteric, 42:364
Malignancy, fucose levels, 39:33 1
Malonaldehyde, formation, S1:280-28 1
from radicals from hydroxy compounds by
radiation, 37:16
Malonic acid
2-bromo-2-(2,3,5-tri-O-benzoyl-~-~-
ribofuranosy1)-, diethyl ester,
preparation of, 33: 151-152
2-(2,3 :5,6-di-O-isopropyhdene-a-~-and-p-~-
mannofuranosy1)-, diethyl esters,
preparation of, 33: 148
 SUBJECT INDEX
~r-tetrahydropyran-2-~1-, and diethyl cstcr.
preparation of, 33:145
2-formamido-2-~-glucopyranosyl-. dictliyl
ester, preparation of, 33: 146
2-(2,3-~-isopropylidene-~-lyxofuranosyi )-,
diethyl ester, preparation of, 33: 148
2-(2,3-O-isopropylidene-5-O-trityl-(3-1)-
ribofuranosy1)-, diethyl ester,
preparation of, 33: 152-1 53
2-(2,3,4,6-tetra-O-acetyl-p-~-
glucopyranosy1)-, and diethyl and
dibenzyl esters, preparation of,
33:146-147, 161
2-(2,3,4,6-tetra-O-benzyl-~-glucopyranosyl)-, methyl p-
diethyl ester, anomers, preparation of,
33: 147- 148
2-(2,3,5-tri-O-acetyl-a-~-and++
arabinofuranosy1)-, diethyl esters,
preparation of, 33: I52
2-(2,3,5-tri-O-benzoyl-a-~- and-@-I,-
ribofuranosy1)-, diethyl esters.
preparation of, 33: 150, 161
2-(2,3,5-tri-O-benzoy~-~-~-ribofuranosyl)-,
and dibenzyl ester, preparation of,
33: 162
Malonogalactan, 41:87
Maltal, hexa-0-acetyl-, synthesis. 39:242
Maltitol
I .I-bis(acetamido)-1 -deoxy-, preparation of,
31:93, 100
nonaacetate, degradation by oxidation with
chromium trioxide, 31:230
6-O-benzoyl-, ammonolysis, 39:3 I
per-0-(trimethylsilyl)ether, gasliquid
chromatography of, 28:58-59
structure, 45:276
sweetness-structure relationship, 45:275-
216
Maltobiouronic acid, from dextrans, 30:409
Maltodextrins
a-amylase action on, 23:3 15
from amylose, 23:3 18, 32 I , 323
salivary a-amylase action on, 23:3 19
Maltohexahydrolase, exo-, 44:254
Maltol
from u-fructose dehydration, 28: 180
5-hydroxy-, 22~284
by ~-threo-2,5-hexod1ulosedehydration,
28: 186
preparation, 37: 143
335
Malto-oligosaccharides
linear, preparative liquid chromatography,
46:60
liquid chromatography
large-scale preparative, 4 6 5 1-63
peak-area analyses, 4 6 5 4
4-O-methy1, degree of polymerization by
gas-liquid chromatography, 28:47
relative efficiencies, 51 :158- I 5 9
spectroscopic analysis, 44:23
Maltopentaose, 1-phenylflavazole acetate, mass
spectrometry of, 29: 1 0 1
Maltopyranoside
C-C and C C I bond-lengths in, 44:15
hydrogen bonding in; 25: 100
phenyl a-, crystal structure bibliography,
37:403
phenyl 6-deoxy-6-iodo-a-. crystal structure
bibliography, 37:402
Maltosamine
6-amino-6-deoxy-,synthesis, 39:24 I
6-azido-h-deoxy-,synthesis, 39:24 I
6,6-dichloro-6.6-dideoxy-, synthesis,
39:232
1,2,3,2,3,4-hexa-O-acetyl-6,6-di-O-trityl-,
synthesis, 39:219
N-acetyl-, synthesis, 39:240-24 1
N-benzoyl-, synthesis, 39:227, 239
per-O-methyl-
6,6-di-O-trityl-, synthesis, 39:223
h-O-trityI-, synthesis. 39:223
synthesis, 39:223
6-thio-, derivatives, synthesis, 39:244
Maltosan, synthesis of, 34: 158-159
Maltose, 21:30. 39:213-278
a-
crystal structure bibliography. 38:446-
447
1,2,3,2,3.4,6-hepta-O-acetyl-6-O-trityl-
, synthesis, 39:2 19
structure, 39:2 15-2 16
acceptor products, 51: 154
acetates and benzoates, properties,
39:266-267
acetolysis, 39:248
alkaline degradation, 39:247-248
6-a-maltotriosyl-, and enzyme specificity,
30:269
anhydro derivatives, properties, 39:272
336 SUBJECT INDEX
Maltose (continued)
1,6-anhydro-hexa-O-benzyI-, polymerization
of, 34: 163
aqueous, versus solid, laser-Raman
spectroscopy, 44:75
P-
I ,2,3,6,2,3,4,-hepta-O-acetyl-6-0-
trityl-, synthesis, 39:219
1,2,3,6,2,3,4,-hepta-O-acetyl-6-0-
trityl-a-D-, synthesis, 39:2 19
6-amho-l,6-anhydro-6-deoxy, synthesis,
39:241
1,6-anhydro-2,3,2,3,4,6,-hexa-0-
acetyl-6-thio-, synthesis, 39:244
1,6-anhydro-2,2-di-O-benzoyl-4,6-0-
benzylidene-, synthesis, 39:226
1,6-anhydro-2,3-di-O-benzoyl-4,6-0-
benzylidene-, synthesis, 39:226
1,6-anhydro-2-0-benzoyl-4,6-0-
benzylidene-, synthesis, 39:226
1,6-anhydro-4,6-0-benzylidene-
selective benzoylation, 39:225-226
synthesis, 39:237
1,6-anhydro-per-O-benzyl-,
polymerization, 39:244
1,6-anhyro-2,3,2,3-tetra-0-benzoyl-
4,6-0-benzylidene-, synthesis,
39:226
I ,6-anhyro-2,2,3-tri-O-benzoyl-4,6-0-
benzylidene-, synthesis, 39:226
crystal structure bibliography, 38:44&447
crystal structure of, 25:76
1,2,3,2,3,4,6-hepta-O-acetyl-,
synthesis, 39:225, 235
1,3,6,2,3,4,6-hepta-O-acetyl-,
synthesis, 39:224-225
2,3,6,2,3 ,4,6-hepta-@acetyl-,
synthesis, 39:223
1,2,3,2,3,4,6-hepta-O-acetyl-6-0-
methyl-, synthesis, 39:221
1,2,3,2,3,4,6-hepta-O-acetyl-3-0-
(methylsulfony1)-
desulfonylation, 39:230
proton nuclear magnetic resonance
spectroscopy, 39:252
synthesis, 39:229
1,2,3,2,3,4,6-hepta-O-acetyl-6-O-p- carboxylic derivatives, properties, 39:277
tolylsulfonyl-, synthesis, 39:229
I ,2,3,2,3,4,6-hepta-O-acetyl-6-9
acetyl-6-thio-, synthesis, 39:224
1,2,3,6,2,3,4,6-hepta-O-benzoyl-
ammonolysis, 39:3 1-32
synthesis, 39:225
1,2,3,2,3,4-hexa-0-acetyl-6,6-di-O-p-
tolylsulfonyl-, synthesis, 39:227
1,2,3,2,3,4-hexa-0-acetyl-6,6-di-O-
trityl-a+-, synthesis, 39:219
1,2,6,2,3,6-hexa-O-benzoyl, synthesis,
39:226
hydrogen bonding, Raman and infrared
spectral study of, 44:29
monohydrate, structure, 39:2 15-2 16
mutarotation of, 23:23
6-O-P-~-galactosyl-,synthesis, 39:244
6-0-benzoyl-
ammonolysis, 39:227
preparation, 39:3 1-32
octaacetate, preparation of, 34:261
octa-0-acetyl-
proton nuclear magnetic resonance
spectroscopy, 39:250-25 1
reaction with phosphorus pentachloride,
39:35,224
with piperidine, 39:224
selective deacylation, 39:28
synthesis, 39:215
octa-0-benzoyl-
ammonolysis, 39:3 1
selective debenzoylation, 39:226-227,
239
synthesis, 39:225
reaction with sulfuryl chloride,
39:23 1-233
selective benzoylation, 39:225-226
selective methanesulfonylation and p -
toluenesul fonylation, 39:227-229
structure, 39:216
synthesis of derivatives of, 34: 162
2,3,2,3-tetra-O-acetyl-1,6-anhydro-4,6-
di-0-(methylsulfony1)-, synthesis,
39:229
benzoylation of, 33:36
carba-, synthesis, 48:68-70
carbon-I3 nuclear magnetic resonance
spectroscopy of, and derivatives,
39:254-258
chemical ionization mass spectra,
39:261-263
complex-forming reactions, 39:245
 SUBJECT INDEX
cyclic acetals, properties, 39:273
decomposition, 47:272
dehydration of, 28: 169
deoxy derivatives, properties, 39:273
derivatives, tables of properties, 39:263-278
from dextrans by acetolysis and acid
hydrolysis, 30:378-379
electro-oxidation of, 29: 1 17
in food, liquid chromatography separation,
4652
gel chromatography of, 25:33
halides, properties, 39:269-270
1,2,6,2,3,4,6-hepta-O-benzoyI-~-,
ammonolysis of, 31:95
I ,2,2,3,3,4-hexa-O-acetyI-6,6-di-O-p-
tolylsulfonyl-P-, 23:241
and homologs, gas-liquid chromatography
of, 28:68
in honey, 25295,299
hydrolysis, 39:248
and fermentative oxidation, 37: 138
rate constants and kinetic parameters for,
and derivatives, 22:77
laser-Raman spectroscopy, 44:82
liquid chromatography methods for analysis
of, 46:33
mass spectrometry of, and derivatives,
39~258-263
methyl ethers, properties, 39:265
microbial oxidation, 39:246
nitrogen-containing derivatives, properties,
39:275-276
nonselective spin-lattice relaxation rates,
45: 149
octa-0-acetyl-P-, ammonolysis of, 31 :93.
100
octa-0-benzoyl P-, ammonolysis of, effect of
conformation on, 31:97
perbenzoate, ammonolysis of, 31:95
polarography of, 29: 126
polymer-forming reactions, 39:244
polymerization by hydrogen chloride, 21:463
in hydrogen fluoride, 21:446
proton nuclear magnetic resonance
spectroscopy, 39:249-253
p-toluenesulfonylation of, 33:36
pyrolysis of, 34:45, 159
course of, 47:273,276
radiolysis and radical-induced scission.
3752
337
reaction with
acetyl chloride or acetyl bromide, 22:23
aqueous ammonia, 25:3 13,3I5
selective-oxidation reactions. 39:246-247
selective tritylation of, 33:52
solubility in liquid ammonia, 27:91
in methanol, effect of calcium chloride on,
27:95
structure of, 25:4,32:192,39:214-215,356
sulfonates, properties, 39:267-268
sulfur-containing derivatives, properties.
39:276
sweetness. comparison, to D-glucose,
45247-248
synthesis of. 25:165,39:215-216
trimethylsilylation of. 28:24
trityl ethers, properties, 39:264
utilization by Torulopsis dufrilu, 32: I83
by yeasts, 32:146, 1944199,233
and associations of abilities, 32:223
vibrational spectra, isotopic substitution
studies, 44:54
volatile products from pyrolysis of, 22:505,
508
P-Maltose monohydrate
acetylation of, 33:36
crystal structure bibliography. 30:453,
38:449450
Maltoside
ci-
Lyxofuranose, S-deoxy-3-C-formyI-, P-
i.-,??-(trimethylene dithioacetal),
crystal structure bibliography. 39:22 1
methyl
synthesis, 39:217-2 18
synthesis, gas-liquid chromatography
in, 2 8 5 0
phenyl, heptaacetate, synthesis, 39:2 18
phenyl 3-O-methyl-, synthesis, 39:222
P-
benzyl, synthesis, 39:2 I8
benzyl 4,6-0-benzylidene-, selective [J-
toluenesulfonylation, 39:228
benzyl 6-trityl-. synthesis, 39:220
ethyl hepta-0-acetyl-1-thio, synthesis,
39:243
ethyl 1-thio-6-O-trityl-, synthesis, 39:220
methyl
reaction with sulfuryl chloride,
39:23 1-233
338 SUBJECT INDEX
Maltoside (continued)
selective benzoylation, 39:225-226
selective methanesulfonylation and p -
toluenesulfonylation, 39:227-228
structure, 39:215-216
synthesis, 39:217
methyl 3 ,6-anhydro-6-deoxy-, synthesis,
39:237
methyl 3,6:3,6-dianhydro-, synthesis,
39:237
methyl 6,6-dichIoro-6,6-dideoxy-,
synthesis, 39:234
methyl 6,6-di-O-p-tolylsulfonyl-,
synthesis, 39:228
methyl 2,4,6,2,3,6-hepta-O-acetyl-3-
azido-3-deoxy-, proton nuclear
magnetic resonance spectroscopy,
39:252
methyl 2,3,2,3,4,6-hexa-O-acetyl-,
synthesis, 39:235
methyl 2,6,2,3,4,6-hexa-O-acetyl-
oxidation to 3-keto derivative,
39:24&247
proton nuclear magnetic resonance
spectroscopy, 39:252
methyl 2,6,2,3,4,6-hexa-O-acetyl-3-
azido-3-deoxy-, synthesis, 39:230
methyl 2,6,2,3,4,6-hexa-O-acetyl-3-
bromo-3-deoxy-, synthesis,
39:23&237
methyl 2,3,6,2,3,6-hexa-O-acetyl-4-0- p-toluenesulfonylation of, 33:35
(methylsulfony1)-, proton nuclear
magnetic resonance spectroscopy,
39:252
methyl 2,6,2,3,4,6-hexa-O-benzoyl-,
synthesis, 39:226
methyl 2,3,2,3,4,6-hexa-O-methyl-,
preparation and oxidation, 39:222
methyl 4,6-O-benzylidene-
selective benzoylation, 39:225-226
selective p-toluenesulfonylation, 39:228
methyl 4,6-O-benzylidene-, synthesis,
39:237
methyl 3-O-(methylsulfonyl)-6-trityl-,
synthesis, 39:220
methyl 6-O-p-tolylsulfonyl-, synthesis,
39:228
methyl 2,3,2,3,4-penta-O-acetyl-6,-6-
di-0-(methylsulfony1)-, synthesis,
39:227
methyl 2,3,2,3,4-penta-O-acetyl-6-
deoxy-6-iodo-6-O-p-tolylsulfonyl-,
synthesis, 39:229
methy1,2,3,2,3,4-penta-O-acetyl-6,6-
dichloro-6,6-dideoxy-,mass
spectrometry, 39:258-260
methyl 2,3,6,2,3-penta-O-acetyl-4,6-di-
0-methyl-, mass spectrum, 39:261
methyl 2,6,2,3,6-penta-O-benzoyl-,
synthesis, 39:226
methyl 2,3,2,3-tetra-U-acety1-4,6-0-
benzylidene-6-O-p-tolylsulfonyl-,
synthesis, 39:228
methyl 2,2,3,4-tetra-O-acetyl-6,6-O-di-
p-tolylsulfonyl-, synthesis, 39:236
methyl 2,2,3,4-tetra-O-acetyl-3-O-
(methylsulfonyl)-6,6-di-O-trityl-,
proton nuclear magnetic resonance
spectroscopy, 39:253
methyl 2,6,2,3-tetra-O-benzoyl-4,6-0-
benzylidene-, synthesis, 39:226
methyl 2,6,2-tri-O-benzoyl-4,6-0-
benzylidene-, synthesis, 39:226
methyl 2,6,3-tri-O-benzoyl-4,6-0-
benzylidene-, synthesis, 39:226
p-bromophenyl, synthesis, 39:2 18
benzyl 0-, catalytic oxidation of, 33:XX
methyl p-
monohydrate, crystal structure, 2575,
31:368
reaction with sulfuryl chloride, 33:77
selective chlorination with
methanesulfonyl chloride, 33:8 1
with methanesulfonyl chloride-N,N-
dimethylformamide complex, 33:261
methyl 6,6-dichloro-6,6-dideoxy-P-,
preparation of, 33:X2
methyl 6,6-di-O-p-tolylsulfonyl-P-, 23:24 1
selective acetylation of, 33:37
properties, 39:263
Maltosyl bromide, 2,3,6,2,3,4,6-hepta-O-
acetyl-, reaction with pyridine, 39:32
Maltosyl chloride
6,6-dichloro-6,6-dideoxy-,
penta(chlorosulfate), synthesis, 39:232
3,6,2,3,4,6-hexa-O-acetyI-2-0-
(trichloroacety1)-0-, structure, 39:224
6-O-a-Maltosylcyclodextrins, synthesis,
48:116
 SUBJECT INDEX 339

01-and P-Maltosyl fluoride, hydrolysis. gas-liquid chromatographic analysis of,

48:358-359 28:48
Maltosyl halides, properties, 39:27 1 tissues
Maltotetraohydrolase, ex0 and endo action a-o-mannosidase in, 28:403,407
patterns, 44: 148 biosynthesis of lactose in, 32:lO
Maltotetraose subcellular localization of 01-D-
63-a-D-g~~COSy~-, structure Of, 30:304 mannosidase in, 28:405
substrate, 30:299 trehalase from, 30:249, 252
6s a-maltotriosyl-, and enzyme specificity, Mandelic acid
30:269 L-, cyclodextrin inclusion complexes with,
64-a-maltotriosyl-,from pullulan, 30:335 46:222,224
Maltotriosan, synthesis of, 34: 159 (R)-(-)- and (S)-(+)-,preparation of,
Maltotriose 27:201-202
63-a-~-glucosy~-, and glucosidase-transferase Mango, development physiology of,
action, 30:299 42~340-341. 347,361,363,369, 372,
from pullulan, 30:336 378-379
62-a-maltosyl-, structure of, 30:304 Manna, 25:287, 308
63-a-maltosyl-, and glucosidase-transferase Mannan, 52:33433 8
action, 30:299 acetate, conformation of, 29:33 I
63-a-maltotetrosyl-,from pullulan, a-D-
30:334335 (1~6)-acetate,circular dichroism, 45: 121
62-~-maltotriosyl-, and enzyme specificity, (I-+6)-benzylderivative, circular
30:269 dichroism, 45:122
I ,6-anhydro-l(6)-thio-~-, preparation of, antiparallel packing arrangement,
34: 170 52:335-336
gel chromatography of, 25:33 biosynthesis of, 26:394-398,430
in honey, 25:297 of bacterial, lipid intermediates in. 26:430
laser-Raman spectroscopy, 44:82 carbon-I 3 nuclear magnetic resonance
nonselective spin-lattice relaxation rates, Spectra, 39:200
45: 149 crystallography of, 22:458,465
pyrolysis of, 34:45 D-
structure of, 32:193,39:357 biosynthesis of, 42:323-325
utilization by yeasts, 32: 194195 crystal structure bibliography, 40:389
P-Maltotriose hendecaacetate, reaction with synthesis, in pants, 44:366
phosphorus pentachloride, 39:35 yeast cell-wall, structure, enzymic
6-0-a-Maltotriosylcyclomaltoheptaose. 46: analysis, 44:248-250
246 0-acetyl-, crystal structure bibliography,
Maltouronic acid, synthesis, 39:246 33:398
Maltulose oxidation of ivory-nut, with dinitrogen
composition tetraoxide, 29:346
in aqueous solution, 42:65 packing arrangement, 52:337-338
in dimethyl sulfoxide, 42:68 in plant cell-walls, 26:300,44:359
in honey, 25:295, 300 proton magnetic resonance spectroscopy of
liquid chromatography methods for analysis derivatives of, 27:40
of, 46:33 ( 1+4)-P-o-, enzymic analysis, 44: 165
taste properties, 45:254-255 structure of, 52:406
Mammals of green coffee bean, 26: I6
nerves X-ray diffraction pattern, 52:334-335
o-glucitol in, determination by gas-liquid yeast, 25:9
chromatography, 28:58 biosynthesis, 44:362-366
340 SUBJECT INDEX
Mannan (continued)
structural analysis by mass spectrometry,
29:46
Mannanase
P-D-, 44:167, 169, 179-180
A. niger, 44:170-171
action on galactomannans, 35350
activity, occurrence, and properties,
35~366-371
in biodegradative hydrolysis of
galactomannans, 31:256
endo-( l+4)-, 44: 165
exo-, 44: 165
eXO-( 1+4)-p-D-, 44:149
galactomannan reaction with, 31:272-273
OI-D-,exo-, Arthrobacter, 44:233
V-
amino acid composition of, 32:307
assay of, 32:304
definition, 32:299, 303
extraction from germinating seeds, 32:306
mode of action ofbacterial, 32:309-310
of fungal, 32:310-313
ofplant origin, 32:313-314
occurrence of, 32:300-304
physicochemical properties of,
32 :307-309
separation and purification of. 32:306-307
unit of activity of, 32:304-306
em-, induction of, 30:262
exo-a+-, activity of, 28:402,421
p-D-Mannan mannobiohydrolase, exo-, 44: 165
Mannans
P-D-(I h 3 ) - and P-D-(1+4)-linked, 23:397
branched-chain D-, carbon-13 nuclear
magnetic resonance spectra, 3 8 5 6 6 0 ,
64
from Candida species, 23:393
D-
antitumor activity of, 32:250-252, 261
in assay of v-mannanase activity, 32:305
formation in yeast cell-wall, 32:228
0-(carboxymethy1)-, antitumor activity of,
32:251-252
properties and antitumor activity of,
32:263
transfer of D-galactosyl substituents to,
44:172-173
in yeast cell-walls, 32: 139-140
fungal, 23:383
branched-chain, 41 :78-84
carbon-I 3 nuclear magnetic resonance
spectra, 41:78
linear, 41:77-78
gas-liquid chromatography of, 30:92
hydrolysis products from methylated, 23:388
I, crystal structure bibliography, 33:398
11, crystal structure bibliography, 33:398
interaction with concanavalin A, 35:173-1 75
linear D-, carbon-I3 nuclear magnetic
resonance spectra, 38:52-56
methylated, purificatyion by gel
chromatography, 30: 16
methylation analysis of, 30:25
protein complex with, 23:389
pyrolysis of, from ivory-nut kernels, 34:44
structure, from ivory nuts, 35:7
yeast, 23:386,41:82-84
acetolysis of, 31:197
methylation and gas-liquid
chromatography of, 30:22
Mannaric acid
2,s-anhydro-D-
dehydration of, 28: 166
preparation of, 31: 18
1,4:6,3-dilactone, p-eliminative degradation
of, 29:235
Mannaro- 1,4:6,3-dilactone
2,5-di-O-methyI-o-, reducing ability of,
33227
methylation with diazomethane, 33:202
Mannich condensation, 23:166
Mannide
p-, 25:246
D-, monooleate, as emulsifier in vaccine,
25:270
Manninotriose
formation, 37:357
occurrence and structure, 37:310
Mannitol
1,2,-O-isopropylidene-~-, synthesis of, 28:4
2-acetamido-
1,5-anhydro-2-deoxy-~-,24:225
1,2-dideoxy-l-nitro-o-, 24: 133
1,2-dideoxy-l-nitro-L-, 24:265
3,4,6-tri-O-acetyl- 1,5-anhydro-2-deoxy-o-,
24:225
2-amino- 1,5-anhydr0-2-deoxy-o-,
deamination of, 31:48
I-amino-1-deoxy-o-, deamination of, 31:60
 SUBJECT INDEX
I ,4-anhydro-
2,3-and-3,-5-0-benzylidene-o-, 25:265
D-, 29236
infrared spectrum of, 25:25 1
preparation of, 33: 121
sweetness-structure relationship. 45:257
di-0-benzoyl-o-, preparation of, 33: 120
3,5-O-benzylidene-o-, isomerization,
39:2&27
1,5-anhydro-
o-, 25237
preparation of, 33: 121
sweetness-structure relationship,
45:240, 249
2-S-benzyl-2-thio-o-, 24:209
sweetness-structure relationship,
45:240-241
taste properties, 45:254
2,5-anhydro-
D-, 24:193,25:194,208
preparation of, 31:20-22
I-deoxy-1,l-difluoro-o-, 22: 196,24:205,
25:196
preparation, 38:233
1,6-dichloro- 1,6-dideoxy-~-,25:257
1,3:4,6-di-O-methylene-o-, 23:277
2,6-anhydro-, 1-deoxy- 1,l-
bis(ethylsulfony1)-o-, preparation of,
32:86
3,6-anhydro-, D-, oxidative cleavage of.
25:209
3-benzamido-2,4,5-tri-O-benzoyl- I ,3,6-
trideoxy-o-, preparation of, 32:77
1,I-bis(benzamid0)-I-deoxy-o-, preparation
of, 31533, 86
1.6-bis[2-(chloroethyI)amino]-1,6-di-deoxy-
D-, dihydrochloride, synthesis and
antitumor activity of, 28:7
1-bromo- 1-deoxy-o-, crystal structure
bibliography, 32:380
1 -chloro-I-deoxy-o-, crystal structure
bibliography, 32:380
D-
anhydridation of, 25:233
B-form and K-form, crystal structure
bibliography, 31:365
catalytic oxidation of, 33:88
dehydration of, 33:121
selective chlorination with sulfuryl
chloride, 33:73
34 1
selective oxidation with mercuric
acetate, 33: 100
with sodium metaperiodate, 33:95
selective phosphorylation of, 33:50
conformation of, 26:69
crystallography of, 25:64
from o-fructose, 22:283
D-fructose from, 22:233
1,6-dideoxy- I ,6-difluoro-2,5-0-
methylene-, IH-and "F-NMR data
for, 46: 159
ester of adenosine 5'-pyrophosphate.
28:333
3,4-ethylboronate, preparation, 35:4 1
hexanitrate, selective denitration,
39: 57-58
1,2:5,6-tetrakis(diethylborinate)3,4-
ethylboronate, selective cleavage,
39:54-55
1,2:3,4:5,6-tris(ethyIboronate), selective
cleavage, 39:54
3,4-0-benzylidene- 1.6-dideoxy- 1.6-
difluoro-2,5-O-methylene-, 'H-, and
I9F-NMR data for, 46: 159
1,2,43,5,6-penta-O-acetyl-3-deoxy-3-
fluoro-, 'H- and "F-NMR data for,
46: 159
polysaccharide from, 32:5
in potato extracts, determination by
gas-liquid chromatography, 28:57
production by alkane-grown Cundida
zeylunoides, 32:234
radiolysis and free-radical chemistry,
37:27
sweetness-structure relationship, 45:295
1,2,5.6-tetrakis(diethylborinate) 3.4-
ethylboronate, preparation, 35:40
I ,2:3,4:5,6-triboronate, preparation, 35:40
1,2:3,4:5.6-tris(phenylboronate),crystal
structure bibliography, 38:477478
tris(phenylboronate), hydrolysis, 35:50
utilization by yeasts, 32: 146
I-deoxy-
I-C-methyl-r-, preparation of, 27:242
D-, identity with 6-deoxy-~-mannitol,
32:79
I -(2-methylhydrazino)-~-,preparation of,
29: 153
I-nitro-. 24:69
2-0-methyl-l-nitro-o-. 24: 130
342 SUBJECT INDEX
Mannitol (continued)
3-deoxy-, 3-fluoro-o-, 48: 164
6-deoxy-, 1,2:3,4-di-O-isopropylidene-o-,
preparation of, 32:63
2,5-diamino- 1,4:3,6-dianhydro-2,5-dideoxy-
D-,deamination of, 31:55
1,2:5,6-dianhydro-
D-, formation of, 28:287
3,4-di-O-isopropylidene-, sulfonylation of,
23:239
1,4:3,6-dianhydro-
2,-5-di-O-benzyl-o-, acetolysis of, 22: 16
D-, 49:96
monostearate, surface activity of,
25:255
preparation of, 33: 12 1
ring opening of, 25:256
sweetness-structure relationship,
45:257,274
taste properties, 45:270
di-0-benzoyl-o-, preparation of, 33: 120
2,5-di-O-benzyl-o-, acetolysis, 39:45
2,5-di-O-methyl-~-,infrared spectrum of,
25:25 1
2,5-di-O-(methyIsulfonyl)-o-,
displacement reactions of, 24: 150
2,5-di-O-p-toly~sulfony1-~-,displacement
reactions of, 24: 149
1,6-dibromo- 1,6-dideoxy-o-, 25:257
as antitumor agent, 28:287
crystal structure, 43:338
cytostatic activity, 28:7
1,6-dichloro- 1,6-dideoxy-~-,crystal structure
bibliography, 32:381
1,6-dideoxy-
I ,6-difluoro-o-, preparation, 38:2 11
2,5-0-methylene-o-, proton magnetic
resonance spectroscopy of, 27:65,73
3,5-di-O-acetyl- 1,6-dibromo- 1,6-dideoxy-
2,4-di-O-(metbylsuIfonyl)-o-,
cyclization by sulfonate displacement,
33:127-128
1,6-di-O-benzoyl-o-
dehydration of, 33:120
p-toluenesulfonylation of, 33: 128
1,6-di-O-benzyl-2,5-0-methylene-o-,
selective oxidation with dimethyl
sulfoxide-acetic anhydride, 33:93
1,2:4,5-di-O-isopropyIidene-
D-, selective hydrolysis, 39:23
3,6-di-O-(methylsulfonyl)-o-,
displacement reactions of, 24: 158
1,2:5,6-di-O-isopropyIidene-
~-,3,4-trithiocarbonate,acetobrominolysis,
39: 1 I 4
3-O-(methyIsu~fony~)-o-, oxidation of,
23:258
1,3:4,6-di-O-methylene-o-, 23:277
1,6-di-O-(methylsulfonyl)-o-, 23:239
cytostatic activity, 28:7
reaction with sodium methoxide, 33: 131
2,5-di-O-(methylsulfonyl)-o-, cyto-static
activity of, 22:213
DL-, 21:12-13
crystal structure bibliography, 38:432433
synthesis, 40:2
effect of alkali tetraborates on rotation of,
23:36
hexa-0-acetyl-o-, rearrangement in hydrogen
fluoride, 26: 176
liquid chromatography methods for analysis
of, 46:33
3-0-benzoyl- 1,2:5,6-di-O-isopropylidene-
D-, oxidation of, 26:254
4-O-(metbylsulfonyl)-o-
displacement reactions of, 24: 157
reaction with potassium fluoride,
38:22 1
2,4-O-benzylidene- 1,6-dibromo- 1,6-dideoxy-
3,5-di-O-(rnethylsu~fony~)-o-,
cyclization by sulfonate displacement,
33: I28
3,4-0-benzylidene-2,5-O-methylene-
D-, proton magnetic resonance
spectroscopy of, and derivatives,
27~65
1,6-di-O-p-tolylsulfonyl-o-, fluorination,
38:210
2.5-0-ethylidene- 1,3:4,6-di-O-methylene-~-,
proton magnetic resonance spectroscopy
of, 27:65
3,4,-O-isopropylidene-~-, selective
esterification with pivaloyl chloride, and
with benzoyl chloride, 33: 13
2,5-O-isopropylidene-1,3:4,6-di-O-
methylene-D-, proton magnetic
resonance spectroscopy of, 27:65
2,5-O-methylene-~-,sodium chloride, crystal
structure bibliography, 37:379
6-O-(tert-butyldimethylsily)- 1-0-(tert-
 SUBJECT INDEX
butyldiphenylsily1)-2,3:4,5-di-O-
methykne-o-, selective hydrolysis,
39:64
1-0-( tert-butyldiphenylsilyl)-2,3:4,5-di-0-
methyhe-o-, preparation. 39:64
1,2,5,6-tetra-O-acetyl-, 3,4-O-methylene-~-,
oxidation by chromium oxide, 39:83-84
1,3,4,6-tetra-O-acetyl-
2,5,-0-methylene-l, I , 6,6,-d4-o-,proton
magnetic resonance spectroscopy of,
27:73, 81
1-2,5-di-O-benzyl-o-, 22: 15
2,5-0-methylene-o-, crystal structure
bibliography, 38:462463
tetra-0-acetyl- 1,5-anhydro-o-, 24:22 1
rearrangement in hydrogen fluoride,
26: 174
2,3,4,5-tetra-O-benzoyl-, reaction with
phosphorus pentachloride, 28:239
1,2,5,6-tetra-O-benzoy1-3,4-0-
isopropylidene-o-, oxidation by
triphenylmethyl fluoroborate, 39:85
1,3,4,6-tetra-O-benzyl-o-, selective oxidation
with dimethyl sulfoxide-acetic
anhydride, 33:93
1,4:2,5 :3,6-trianhydro-
crystal structure bibliography, 34:346
o-, 25:247
3,4,6-tri-O-acetyl-2-acetyl- 1,5-anhydro-2-
thio-D-, 24:209
1,3:2,5:4,6-tri-O-ethyIidene-o-
conformation of 1,3-dioxepane ring in,
26: 1 14
proton magnetic resonance spectroscopy
of, 27:65
selective hydrolysis, 39:22
1,2:3,4:5,6-tri-0-isopropylidene-o-. selective
hydrolysis, 39:22
1,3:2,5:4,6-trI-O-methylene-o-
acetolysis, selective, 39:25
proton magnetic resonance spectroscopy
of, 27:65
selective hydrolysis, 39:22
Mannitol-I, I , 6,6,-d4,1,3,4,6-tetra-O-acetyI-
2,5,-0-methylene-o-, proton magnetic
resonance spectroscopy of, 27:73, 81
D-Mannitol diardenite, 43:333
Mannocarolose, 23:392
Mannofuranose
1,6-anhydro-P-o-
343
acetonation of, 34: 155
conformation of. 34:153-154
crystal structure bibliography, 30:448
preparation of, 34: 152
synthesis, 39: 163
p-D-
calcium chloride tetrahydrate, crystal
structure bibliography, 30:465
xCaC1, 4 H , , 47:22-23
2,3:4,6-di-0-cyclohexylidene-,a+-,
synthesis, 39:76
2,3:5,6-di-O-isopropylidene-
OL-D-, 51:105-106
acetobrominolysis, 39: 114-1 15
carbon-I 3 nuclear magnetic resonance
spectroscopy, 41:53
reaction with (p-methoxybenzoyl-
methy1ene)diphenylphosphorane.
33: 154-1 55
D-
acetolysis of, 22: 19
mass spectrum of, 21:77
selective oxidation with silver
carbonate-on-Celite, 33:97
2,3-O-cyclohexyhdene-a-o-, synthesis,
39:76
2,3-O-isopropylidene-o-
acetobrominolysis, 39:l 15
5,6-phenylboronate, preparation, 35:39
1,2-S-ethylene-5,6-O-isopropylidene- 1,2-
dithio-cr-r)-, crystal structure, 43:22?
1,5,6-tri-0-acetyl-2,3-O-isopropyl~dene-o-,
acetolysis of, 22:20
tri-0-acetyl- 1,2-S-ethylene- 1,2-dithio-a-~-,
preparation of, 32:57
3,5,6-hi-O-benzoyl-2-S-ethyl-2-thIo-o-,
methanethiolysis of. 32:32
Mannofuranoside
ethyl 2-S-ethyl- 1,2-dithio-a-~-, 25: 192
crystal structure bibliography, 30:452
preparation of, 31:65
ethyl 2-S-ethyl2-S-ethyl- 1,2-dithio-a-o-,
preparation of, 32:3 I , 56,67
ethyl 1,3,5,6-tetra-O-acetyI-2-S-ethyl-2-thio-
a,pa-, desulfurization by Raney
nickel, 32:?6-77
ethyl 3,5,6-tri-O-acetyI-2-S-ethyl- 1,2-dithio-
OL-D-, desulfurization by Raney nickel,
32:76-77
methyl OL-D-. 21:102, 122, 126
344 SUBJECT INDEX

Mannofuranoside (continued) structure bibliography, 37:390

kinetics of formation of, 21: 110 N- ( p-bromobenzyl)-6-deoxy-3-C-methyl-
preparation from dithioacetal, 32:68,70 2,3,4-tri-O-methyl-~-,crystal structure
methyl p-D- bibliography, 30:454
acetolysis of, 22:20 Mannonic acids
conformation of, 21 :100 2-amino-2-deoxy-o-, deamination of, 31:58,
preparation from dithioacetal, 32:68,70 33:119
methyl 6-deoxy-2,3-O-isopropylidene-5-O- analytical high-performance liquid
p-tolylsulfonyl-a-L-, displacement chromatography, 46:34
reaction of, 24: 156 2,5-anhydr0-~-,25~189
methyl 5,6-di-O-acetyl-P-~-,2,3-carbonate, dehydration of, 28: I66
preparation of, and a-Danomer, 34:279 preparation of, 31:18, 33:119
methyl 2,6-di-O-benzyl-a-o-, synthesis, D-, 25343
39: 127 preparation of, 29: 119
methyl 2,3 :5,6-di-O-benzylidene-a-~-, Mannonolactone, 2-amino-2-deoxy-o-,
hydrogenolysis regioselectivity, 39: 127 deamination of, 25: 189
methyl 6-O-trityl-a-o-, selective p - o-Mannono- I $lactone
toluenesulfonylation of, 33:35 inhibition of a-D-mannosidase activity by,
Mannofuranosidurono-6,3-lactone,methyl p- 28:419
D-, synthesis of, 33:232 preparation of, 25:4
Mannofuranosylamine, N-acetyl-a- and-p-D-, Mannono- 1,4-lactone
preparation of, 31:86 2-amino-f-deoxy-o-, deamination of, 3 1 5 8
Mannofuranosyl bromide D-, trimethylsilyl ether, gas-liquid
2,3 :5,6-di-O-isopropylidene-a-o-, reaction chromatography of, 28:7 I
with base, 39: 147 2,3 :5,6-di-O-isopropylidene-o-, oxidation,
5-0-acetyl-6-bromo-6-deoxy-2,3-0- 38:32 1
isopropylidene-a-o-, synthesis, 39: 1 15 D-Mannophosphoinositides, biosynthesis of,
Mannofuranosyl fluoride 26:453
D- Mannopyranan, a+-
3,5,6,-tri-O-a~etyl-2-O-rnethyl-P-,'~C- carbon-I3 nuclear magnetic resonance
NMR data for, 46: 166 spectra, 38:5460
2,3:5,6-di-O-acetoxonium-, IH- and I9F- structure, 41:80-81
NMR data for, 46:98 Mannopyranose
2,3:5,6-di-O-benzoxonium-, IH- and IYF- 2-acetamido-
NMR data for, 46:98 2-deoxy-P-o-, monohydrate, crystal
2,3 :5,6-di-O-isopropylidene- structure bibliography, 34:355
I3C-NMR data for, 46: 166 1,3,4-tri-O-acetyl-2,6-dideoxy-6-fluoro-o-,
IH-, and 19F-NMR data for, 46:98 48:2 10
2,3:5,6-tetra-O-acetyl- a-o-, 45:74
I3C-NMR data for, 46: 166 crystal structure bibliography, 37:378
'H-, and I9F-NMR data for, 46:98 ester with adenosine 5'-pyrophosphate,
2,3,5,6-tetra-O-benzoyl-a-, IH- and ''F- 28:315, 339
NMR data for, 46:98 with 2'-deoxyguanosine 5'-
2,3:5,6-di-O-isopropylidene-a-~-, synthesis, pyrophosphate, enzymic preparation
48:lOl-102 of, 28:340
per-0-benzoyi-a-D-, synthesis, 38:20 1 with guanosine 5 '-pyrophosphate,
D-Mannolipid, as intermediate in 28:319
polysaccharide biosynthesis, 42:323-324 with guanosine 5'-pyrophosphate,
Mannonamide enzymic preparation and fermentation
2,5-anhydro-6-0-benzoyl-o-, crystal production of, 28:339-340
 SUBJECT INDEX
with inosine 5'-pyrophosphate, enzymic
preparation of, 28:340
with thymidine 5 '-pyrophosphatc,
isolation of, 28:322
of uridine 5'-pyrophosphate, 28:325
sweetness-structure relationship, 45:239
taste properties, 45942
2-amino-
1,6-anhydro-2-deoxy-P-o-, preparation of,
34:131
2-deoxy-P-o~-carba-,synthesis, 48:60-6 1
4-amino-
1,6-anhydro-2-deoxy-P-o-
deamination of, 34: 128
preparation of, 34: 123, 131
1,6-anhydro-4-deoxy-p-o-, deamination
of, 31:40
4,6-dideoxy-~-,23: 155
1,2-anhydro-, 3,4,6-tri-O-benzyl-P-o-
polymerization, 39:208-209
synthesis, 39: 171-172
1,3-anhydro-, 2,4,6-tri-O-benzyl-p-i)-
polymerization, 39:207
synthesis, 39: 170
1,4-anhydro-, 6-deoxy-2,3-0-isopropylidene-
a-L-,synthesis, 39: 166
1,6-anhydro-
p-o-, 47:2 I
conformation of, 34:61
copolymer with tribenzyl ethers of
levoglucosan, 34:73
esterification of, 33: 14
per-0-substituted, 34:77
p-toluenesulfonylation of, 33:23
p-toluenesulfonylation of, 34:8 1
sweetness-structure relationship, 45:269
D-, formation of, 34:47
2,3-dideoxy-2,3-epimino-p-~-, preparation
of, 34:129, 131
2,3-0-benzylidene-p-~-,reaction with N-
bromosuccinimide, 39: 107
2,3-0-isopropylidene-P-~-, oxidation of,
34:97
2,3-0-isopropylidene-4-0-p-tolylsulfonyl-
p-O-,reactivity of, 24: 154
2,3-O-isopropylidene 4-thio-p-o-,
preparation of, 34: 136
2-3-O-isopropyhdene-~-thio-p-~-, 23:225
4-O-methyl-P-o-, p-toluenesulfonylation
of, 33:23
345
4-0-methyl- I-2-O-p-tolylsulfonyl-~-~-,
23:25 I
2-0-p-tolylsulfonyl-p-~-,preparation of,
34:8 I
2-O-p-tolylsulfonyl-~-~-, 23:25 1
3-S-benzyl-3-thio-o-, preparation of,
34:137
2,3,4-tri-O-benzyl-p-~-
polymerization, 39: 182, 187
synthesis, 39:163
p-D-
pentaacetate, from cellulose, 22:22
sweetness-structure relationship, 45:239
taste properties, 45:242
3,4,6-tri-O-acetyl,l,2-0-( 1-
benzyloxyethylidene) derivatives,
proton spin-lattice relaxation, 45: 158
3,4,6-tri-0-acetyl,l,2-0-(1-
methoxyethylidene) derivatives,
proton spin-lattice relaxation, 45: 158
OL-D-, 1,3,4,6-tetra-O-acety1-2-deoxy-2-
thiocyanato-, 44: 145
D-
2-acetamido-2-deoxy-, circular dichroism,
4595
2-acetamido-2,6-dideoxy-6-fluoro-
'H- and I9F-NMR data for, 46: 122
I ,3,4-tri-O-acetyl-, 'H- and I9F- NMR
data for, 46: 122
1.6-anhydro-3-deoxy-3-fluoro-p-
2,4-di-O-acetyl-, 'H- and 19F-NMR data
for, 46: I 14
'H-and I9F-NMR data for, 46: 1 14
axial hydroxyl group on C-2,47:66
2-deoxy-2-fluoro-
cx anomer
I3C-NMR data for, 46: 162
'H- and I9F-NMR data for, 46537
p anomer
"C-NMR data for, 46:162
'H- and I'F-NMR data for, 46:87
1,3,4,6-tetra-O-acetyI-, IH- and I9F-
NMR data for, 46:87
1,2,4,6-tetra-O-acetyI-cx-, IH- and "F-
NMR data for, 46:92
I ,3,4,6-tetra-0-acetyl-p-,13C-NMR data
for, 46: 162
1,4,6-tri-0-acetyl-3-U-methyl-, IH- and
"F-NMR data for, 46:87-88
3-deoxy-3-fluoro-
346 SUBJECT INDEX

Mannopyranose (continued) 0-o-glucopyranosyl-o-, octaacetate, from

a anomer cellulose, 22:22
')C-NMR data for, 46: 163 4,6-O-isopropylidene-~-, synthesis, 39:73
'H-and I9F-NMR data for, 46:92 1,2,3,4,6-penta-0-
P anomer acetyl-P-o-, ammonolysis of, 31:86
I3C-NMR data for, 46:163 nicotinoyl-P-o-, ammonolysis of, 31:89
'H-and I9F-NMR data for, 46:92 penta-0-acetyl-a-o-, rearrangement in
4-deoxy-4-fluoro- hydrogen fluoride, 26: 183
a anomer, I3C-NMR data for, 46: 164 per-0-trimethylsilyl-D-, mass spectrometry
P anomer, I3C-NMR data for, 46: 164 of, 29:48
hydrochloride, 2-amino-2,6-dideoxy-6- 2,3,4,6-tetra-0-acetl-a-~-,double p-
fluoro- elimination in, 29:283
a anomer, 'H-and I9F-NMR data for, tetra-0-acetyl-2- and-3-O-methyl-o-,
46:122 rearrangements in hydrogen fluoride,
P anomer, 'H-and I9F-NMR data for, 26: 184
46: 122 1,2,3,4-tetra-O-acetyI-P-o-,reaction with
orientation of hydroxyl groups for, in phosphorus pentachloride, 28:239
4 C , ( ~conformation,
) 45:75 tetra-O-acetyl-6-chloro-6-deoxy-~-o-,
6-deoxy a-L- 22: 184
crystal structure bibliography, 30:449 preparation of, 28:239
monohydrate, crystal structure 1,2,3,6-tetra-O-acetyI-4-0-(2,3,4,6-tetra-O-
bibliography, 38:430 acetyl-P-o-galactopyranosy1)-a+,
2-deoxy-2-fluoro-P-o- preparation of, 34: 162
crystal structure, 34:349, 38:280 tri-0-acetyl- 1,6-anhydro-P-o-, reaction with
preparation, 38:224 trifluoromethanesulfonic acid, 34:87
1,4:3,6-dianhydro-, D-, 49: 158 1,3,4-tri-O-acetyl-2,6-anhydro-~-,
I ,6:2,3-dianhydro- preparation of, 34: 129
p-D-, 25: 112-1 13 3,4,6-tri-O-acetyl- 1,2-0-
preparation of, and derivatives, 34: 108, ( 1-benzyloxyethylidene)-P-D-, 51:89
111, 113 (I-methoxyethylidene)-P-~-, 51:83,89
4-deoxy-4-fluoro-P-o-, preparation, crystal structure bibliography, 37:398
38:217 3,4,6-tri-O-benzyl-I,2-0-, (1-
4-0-benzyl-P-o-, rnethoxyethylidene)-P-o-,selective
conversion to 1,6-anhydro-2,3-di-O- acetolysis, 39:46
methyl-P-o-glucopyranose, 34:79 Mannopyranose pentaacetate
as synthetic intermediate, 34: 120 carba-a-DL-, 48:3 1
4-0-p-tolylsulfonyl-p-~-,as synthetic carba-P-L-, synthesis, 48:44
intermediate, 34:121 Mannopyranoside, 2-amino-2-deoxy-a-o-
2,3:4,6-di-O-isopropylidene-o-, synthesis, glucopyranosyl a-D-,48:72
39:73 Mannopyranosides
L- a-o-glucopyranosyl a-D-,preparation of,
2,6-dideoxy-2-fluoro 34:265
a anomer, 'H-and 19F-NMRdata for, aldehydo-o-, pentaacetate aldehydrol,
46:133 23:25
P anomer, IH-and I9F-NMR data for, alkyl and aryl, interaction with concanavalin
46: 133 A, 35: 188
1,3,4-tri-O-acetyl-a-, IH-and 19F-NMR P-D-, synthesis, 49:82
data for. 46: 133 benzyl2,3-di-0-benzyl-4,6-0-benzylidene-
6-0-a-D-xy~OpyranOSyl-D-, preparation of, a-D-,hydrogenolysis regioselectivity,
28:236 39: 128
 SUBJECT INDEX
benzyl exo-2,3:4,6-di-O-benzyIidenc-01-r)-,
hydrogenolysis and regioselectivity.
39: 132
D-
methyl 2-deoxy-2-fluoro-
4,6-di-O-acetyl-3-0-methyl-P-3
'H-and
I9F-NMR data for, 46238
3-0-acetyl-4,6-0-benzylidene-P-, ' H-
and I9F-NMR data for, 46388
3-0-benzoyl-4,6-0-benzylidene-, ' H-
and I9F-NMR data for, 46:88
4,6-O-benzylidene-P-, IH-and '"F-NMR
data for, 46:88
3-0-benzyl-4,6-0-benylidene-P-, 'H-
and I9F-NMR data for, 46:88
3,4,6-tri-O-acetyl-P-, IH-and '"F-NMR
data for, 46:88
methyl 6-deoxy-6-fluoro-
OI anomer, 'H-and I9F-NMR data for,
46:96
I3C-NMR data for, 46: 165
2,3-di-O-methyl-a-, IH-and "F-NMR
data for, 46:96
2,3-di-O-meth~I-,~~C-NMR data for,
46: 165
2,3-O-isopropylidene-a-, IH-and "F-
NMR data for, 46:96
2,3-O-i~opropylidene-,'~C-NMR data
for, 46: 165
trifluoromethyl3,4,6-tri-O-acetyl-2-
deoxy-2-fluoro-P-, 'H-and '"F-NMR
data for, 46:88
2,6-diamino-2,6-dideoxy-~-, 23:24 I
ethyl 3-amino-3,6-dideoxy-I-thio-B-i)-.
formation of, 32:22
ethyl 4-O-benzoyl-2,3,6-tri-S-ethyl- 1,2,3,6-
tetrathio-a-o-, preparation of, 32:33
ethyl l-thio-
P-0-,21:117
preparation of, 32:2 1
L-, trifluoromethyl 3,4-di-O-acetyl-2-,6-
dideoxy-P-, 'H-and "F-NMR data for,
46:133
methyl 2,3,-di-O-acetyl-4,6-O-benzylidene-
a-D-, reaction with N-
bromosuccinimide, 39:99
methyl 3-acetamido-
3-deoxy-6-O-p-tolylsulfonyl-cr-o-, 23:24 1
3,6-dideoxy-a-o-, acetylation and
methanesulfonylation of, 33:3 I
347
3,6-dideowy-6-O-p-toIyIsulfonyI-cu-~-,
23:241
methyl 6-acetamido-, 2,3,4-tri-O-acetyl-6-
deoxy-a-Dr-, synthesis, 40:72
methyl a-D-,21:458
acetolysis of, 22:20
2,3-and 4,6-phenylboronates and 2,3:4,6-
bis(phenylboronate), preparation.
35:48
methyl 6-deoxy-a-~-,2.3-
phenylboronate, preparation, 35:48
benzoylation of, 23:249
crystal structure bibliography, 30:45 1,
38:435
methylation of, 30: 15
methyl ethers, separation of, 30:2 I , 25
hydrolysis of, 22:3 I
trifluoroacetic acid in, 28: 17
preparation from dithioacetal and bromine,
32:70
reaction with sulfuryl chloride, 28:234,
33:74
relative reactivities of hydroxyl groups in,
33:.58
selectivc chlorination with
methanesulfonyl chloride, 33:8 1
selective esterification of, 33:28
selective methanesulfonylation of, 33:27
sulfonylation of, 23:248
synthesis, 40: I 13
2,3,4-tri-0-acetyl-6-deoxy-6-thiocyanato-,
44: 145
3,4,6-tri-O-acetyl-2-deoxy-2-thiocyanato-,
44: 14.5
methyl 2-amino-
2-deoxy-01-~-, deamination of, 31:4.547,
234
2-deoxy-P-~-,deamination of, 31:47
4,6-0-benzylidene-2,3-dideoxy-3-nitro-P-
D-, 24: 134
methyl 4-amino-
4,6-dideoxy-a-~-,deamination of, 31:3 1,
34
4,6-dideoxy-2,3-0-isopropylidene-c-~-,
deamination of, 31:34
methyl 2.3-anhydro-
01-D-, 23:106,25:145, 147
4,6-O-benzylidene OI-D-
crystal structure bibliography, 30:454
0x0 reaction with, 23: 106
34 8 SUBJECT INDEX
Mannopyranosides (continued)
4,6-O-benzylidene-o-, 25: 114, 141
methyl 2-anilino-4,6-0-benzylidene-2-
deoxy-a-o-, preparation of, 29:6
methyl p-D, 3,4,6-tri-O-acetyl-2-deoxy-2-
thiocyanato-, 44: 145
methyl 6-chlor0-6-deoxy-a-o-, 2,3,4-
tri(chlorosulfate), preparation of,
28:234,33:74
methyl 4-deoxy-2,3,-0-isopropylidene-4-C-
methyl-6-0-methyl-a-o-, synthesis of,
27:28 1
methyl 6-deoxy-
a-DL-, synthesis, 40:69
a-L-
catalytic oxidation of, 33:89-90
dibenzoylation of, 33:28
6-C-nitro-a- DL-, synthesis, 40:72
2,3-U-isopropylidene-a-~-, chemical shift
values for, 32:42
2,3-O-isopropylidene-4-0-
(methyhlfonyl)-a-o-, displacement
reactions of, 24: 189, 191
solvolysis of, 24: 194
2,3-0-isopropylidene-4-0-
(methy1sulfonyl)-a-L-, 23: 177
2,3-O-isopropylidene-4-O-p- tolylsulfonyl-
L-, displacement reactions of, 24:189,
191
methyl 2,3-diamino-2,3-dideoxy-p-~-,
24:136
methyl 4,6-dideoxy-4-iodo-2,3-0-
isopropylidene-a+-
iodine displacement, 28:282
preparation of, 28:242,282
methyl 2,3-di-O-acetyl-
4,6-O-benzylidene-a-o-, reaction with N-
bromosuccinimide, 28:283
6-azido-4-O-benzoyl-6-deoxy-a-o-,
preparation of, 28:283
4-O-benzoyl-6-bromo-6-deoxy-a-~-,
preparation of, 28:283
methyl 3,4-di-O-acetyl-, 6-deoxy-6-iodo-2-
0-p-tolylsulfonyl-a-o-, crystal structure
bibliography, 38:47047 1
methyl 4,6-di-O-acetyl-, a- DL-, synthesis,
40:70
methyl 2,3-di-0-benzoyl-6-deoxy-a-~-,
sulfonylation of, 23:237
methyl 2.3:4,6-di-O-benzylidene-a-o-
configuration of, 34: 196
hydrogenolysis regioselectivity, 39: 126,
133
irradiation, 39:92
preparation by acetal exchange,
34~187-188
reaction with N-bromosuccinimide,
39~103-106
with butyllithium, 39: 139-140
with triphenylmethyl fluoroborate,
39: I 12
selective hydrolysis, 39: 18
synthesis, 39:78
methyl 2,3:4,6-di-O-isopropyIidene-
a-D-, selective hydrolysis, 39: 18-19
D-, selective hydrolysis, 39:23-24
methyl 2,3 :4,6-di-O-(o-nitrobenzylidene)-a-
D-, irradiation, 39:91
methyl 4,6-ethylidene-3-0-p-tolylsulfonyl-a-
D-, 23:25 1
methyl 4-O-acetyl-6-deoxy-2,3-0-(~-
nitrobenzy1idene)-a-r-, irradiation,
39:89
methyl 2-0- and 3-O-acetyl-a-~-,acyl
migration in, 33: 102
methyl 2-0- and 3-O-carbamoyl-a-o-, acyl
migration in, 33: I02
methyl 4-0-benzoyl-
3-bromo-2,6-dichloro-2,3,6-trideoxy-a-o-,
dehalogenation of, 28:302
2,3-0-carbonyl-6-0-p-tolylsulfonyl-a-~-,
23:266
2,3,6-tri-S-ethyl- 1,2,3,6-tetrathio-a-o-,
preparation of, 32:33
methyl 3-O-benzoy1-4,6-U-benzylidene-a-o-
acyl migration in, 33:102
imidazole-catalyzed acyl migration in,
33:42
preparation of, 33:22
methyl 4,6-0-benzoyl-2,3-0-isopropylidene-
a-D-, reaction with dibromomethyl
methyl ether, 39: 120
methyl 4,6-O-benzylidene-
a-D-
acetylation of, 33:22
benzoylation with N-benzoylimidazole,
33:42
conformation of, 34: 199
hydrogenolysis regioselectivity, 39: 125
hydrolysis of, 34:202
 SUBJECT INDEX
selective benzylation of, 33:55
p-D-, acetylation of, 33:22
2-deoxy-2-C-methyl-3-0-methyl-n-.
carbon-I3 nuclear magnetic
resonance spectroscopy, 41 :65
2,3-dideoxy-2,3-di(phenylazo)-~u-n-.
crystal structure bibliography. 38:479
2,3-dideoxy-2,3-epithio-a-o-, 22: 158,
25:139
2-(o-carboxyphenylamino)-2,3-dideoxy-3-
nitro+-, and methyl ester, 24: 136
methyl 4,6-0-ethylidene-a-o-
2,3-dinitrate, selective denitration, 39:56
p-toluenesulfonylation of, 33: 14
methyl 2,3-~-isopropyhdene-a-~-
conformation of, 34:200
synthesis, 39:79
methyl 4,6-0-isopropylidene-a-o-, synthesis,
39:79
methyl 6-0-methyl-a-~-,
ethoxycarbonylation of, 33:30
methyl 4-0-methyl-2,3,6-tri-O-
(methylsulfony1)-a-o-. infrared
spectrum, 23:256
methyl 3-0-( p-nitrophenylsulfonyI)-a+,
solvolysis and ring contraction of,
24: 193
methyl 6-O-trityl-a-o, selective p -
toluenesulfonylation of, 33:27
methyl tetra-O-methyl-a-D-, mass spectrum
of, 21:61
methyl 2,3,4,6-tetra-O-acetyyl-, a-D-.crystal
structure bibliography, 34:372
methyl 2,3,4-tri-O-acetyl-, 6-bromo-6-deoxy-
OL-D-, preparation by Pinner reaction,
28:257
methyl 2,4,6-tri-O-acetyl-, 3-deoxy-3-nitro-
p-D-,dehydroacetylation of, 24: 129
methyl 3,4,6-tri-O-acetyI-
2-bromo-2-deoxy-a-o-, reaction with
sodium cobalt tetracarbonyl and
carbon monoxide, 28:293
2-deoxy-2-iodo-a-o-, reaction with
sodium cobalt tetracarbonyl and
carbon monoxide, 28:293
methyl tri-0-acetyl-
2-deoxy-2-bromo-a-o-, 0x0 reaction with,
23: 1 12
2-deoxy-2-iodo-a-o-, 0x0 reaction with,
23: 110
349
methyl 2.3,6-tri-O-benzoyI-, 4-0-acetyl-2-
bromo-2-deoxy-a-o-, displacement
reaction of, 24:161
methyl 2,3,6-tr-O-(methylsuIfonyl)-a-o-,
23:248
phenyl 2-acetamido-2-deoxy-6-0-p-
tolylsulfonyl-a-o-, 23:24 1
phenyl OL-D- and P-D-, l,h-anhydride
formation from, 34:29-30
2-S-ethyl-2-thIo-o-, preparation of, 32:3 1
4-thio-0-, 23:225
trifluoromethyl 3,6-di-O-acetyl-2-deoxy-2-
fluoro-4-0-(2,3,4,6-tetra-O-acetyl-p-D-
galactopyranosy1)-pa-, preparation,
38:232
trifluoromethyl 3,4,6-tr-O-acetyl-2-deoxy-2-
fluoro-p-o-, preparation, 38:23 1
2-0-hflyl-D-, 48: 125
tri-0-acetyl- 1.2-S-ethylene-1-2-dithio-a-o-,
preparation of, 32:57
Mannopyranosiduronic acid
methyl OL-D-
acid-catalyzed hydrolysis, 36:84
circular dichroism spectra, 36:90
methyl ester, preparation, 36:74
p-nitrophenyl a-D,preparation, 36:71
Mannopyranosylamine
a-DL-carba-, synthesis, 48:59,61
N-acetyl-a-o-, preparation of, 31:86
N-acetyl-P-o-, configuration of, 31: 104
N-benzoyl-u-, preparation of, 31:83, 122
2,3,4,6-tetra-O-benzoyI-p-~-% ammonolysis
of, 31:122
Mannopyranosyl chloride
WD-, 3,4,6-tri-O-acetyl-2-deoxy-2-
thiocyanato-, 44: 145
tetra-0-acetyl-a-r-, crystal structure
bibliography, 37:394
2,3,4,6-tetra-0-benzoyl-a-~-, crystal
structure bibliography, 38:48 1 4 8 2
3,4,6-tri-0-acetyl-2-chloro-2-deoxy-
a-D-,preparation of, 28:262
p-D-. preparation of, 28:261-262
tri-O-acetyl-6-deoxy-a-~-,crystal structure
bibliography, 37:387
Mannopyranosylh-erythritol, 4-0-p-o-, taste
properties, 45:275
Mannopyranosyl fluoride
Q-D-, reaction with sodium methoxide, 34:31
2-bromo-2-deoxy-P-o-. 22: 194
350 SUBJECT INDEX
Mannopyranosyl fluoride (continued)
o(-D-, polymerization of, 21 :458
D-
2-deoxy-2-fluoro-
P anomer, IH-and "F-NMR data for,
46: 146
3,4,6-tri-O-acetyI-, IH-and "F-NMR
data for, 46: 147
2,3-di-O-benzoyl-4,6-di-O-methyl, 'H-and tri-O-acetyl-2-chloro-2-deoxy-P-~-,
I9F-NMR data for, 46:84-85
2-0-benzoyl-4,6-di-O-rnethyl-a-, 'H-and
I9F-NMR data for, 46:85
3-0-benzoyI-4,6-di-O-methyl-P-, 'H-and
I9F-NMR data for, 46:85
2,3,4,6-tetra-O-acetyl-
')C-NMR data for, 46: 161
'H-and "F-NMR data for, 46:84
2,3,4,6-tetra-O-benzoyl-a-, IH-and I9F-
NMR data for, 46534
3,4,6-tri-O-acetyI-2-deoxy-
2-bromo-, 'H-and IyF-NMR data for,
46: 130
2-chloro-, 'H-and I9F-NMR data for,
46: 130
2-iodo-, IH-and I9F-NMR data for,
46: 130
3,4,6-tri-O-acetyl-2-O-rnethyl-a-
I3C-NMR data for, 46:161
IH-and "F-NMR data for, 46:132
2,4,6-tri-O-a~etyl-3-O-rnethyl-ol-,'~C- phosphate, preparation, 36:71
NMR data for, 46: 16 1
2-deoxy-
2-fluoro-P-~-,conformation, 48: 177
2-iodo-p-o-, 22:194
3,6-di-O-acetyl-, 2-deoxy-Z-fluoro-4-0-
(2,3,4,6-tetra-O-acetyl-P-o-
galactopyranosy1)-P-D-,preparation,
38:232
3,6-di-O-acetyl-, 4-0-(2,3,4,6-tetra-O-acetyI-
P-o-glucopyranosy1)-a+-,from
cellobiose, 26: 188
L-
I3C-NMRdata for, 46: 173
3,4-di-O-acetyI-2,6-dideoxy-2-fluoro-P-,
IH-and I9F-NMR data for, 46: 153
'H-and I9F-NMR data for, 46: 132
per-O-acetyl-2-
bromo-2-deoxy-a-~-,synthesis,
38:202-203
deoxy-4-fluoro-4-0-P-o-
galactopyranosyl-P-D-, synthesis,
38:204
3,4,6-tri-O-acetyl-2-brom0-2-deoxy-
24:204
a-D-,
crystal structure bibliography, 31:367
crystal structure of, 25:74
P-D-, crystal structure bibliography,
31:367
preparation, 38:237
3,4,6-tri-O-acetyI-2-deoxy-2-fluoro-P-~-
F-2 chemical shift, 38:257
preparation, 38:23 1
3,4,5-tri-O-acetyl-2-deoxy-2-iodo-a-~-,
24:205
o-Mannopyranosyl radicals, 49:72-73
O-a-D-MannopyranosyI-( 1-+3)-O-p-o-
mannopyranosyl-( 1+4)-2-acetamido-2-
deoxy-a-D-glucopyranose, crystal
structure, 43:253-254
0-Mannopyranosyl trichloroacetimidates
acetylated, glycosylation, 50:58,6&67
as donors, 5 0 : 5 8 , 6 M 7
glycosides and saccharides from, 50:58,
6245
reaction with, 50:58, 61
Mannopyranosyluronic acid, a-o-
ester of guanosine 5'-pyrophosphate.
28:320
Mannopyranuronic acid
p-D-, structure, 45: 102
1,2,3,4-tetra-O-acetyl-o, methyl ester,
preparation, 36:66
Mannosamines
4-deoxy, composition in aqueous solution,
42:47
trichloroacetimidates, as glycosyl donors,
50:98, 103
Mannose
2,3,4-,2,4,6, and 3,4,6-tri-O-methyl-o-, and
gas-liquid chromatography of
trimethylsilyl ethers of, 30:25
3-acetamido-
3-deoxy-o-, nitrosation of, 31:67
3,6-dideoxy-~-,mercaptalation of, 32:27
2-acetamido-2-deoxy-o-, crystal structure
bibliography, 32:381
a-D-
crystallography of, 25:61
 SUBJECT INDEX
2-(hydroxymethyl) derivatives, circular
dichroism, 4 5 7 9
sweetness, effect of infrared hydroxyl
absorption bands and hydrogen-
bonding strength, 4 5 2 1 6 2 I7
(Y-DL-, crystal structure bibliography, 3 I :365
2-amino-
3,h-anhydro-2-deoxy-o- derivativcs,
24: 1 76
2-deoxy-, deamination of, 33: 1 IS
2-deoxy-o-. 24: 1 12,208
deamination of, 25:187, 31:40-44
3-amino-
3-deoxy-o-
deamination of, 31:29
derivative, 22: I32
diethyl dithioacetal, preparation of,
32:22
preparation by acetoxonium
rearrangement, 26: 162
3,6-dideoxy-o-, diethyl dithioacetal.
preparation of, 3 2 2 2
6-amino-, 6-deoxy-u-
composition in aqueous solution, 42:5 I
preparation of, 28:283
1.6-anhydro-
p-0-
complexes, 34:54-55
from mannan pyrolysis, 34:44
D-, formation of, 34:36
2,3-anhydro-, D-
composition in aqueous solution,
4259-60
composition in nonaqueous solvents,
4261, 68
2,5-anhydro-
D-, 25:181, 185
degradation mechanism of, 28: 164- I65
dimethyl acetal and, 25212
mutarotation of, 25:2 I3
preparation of, 33: 1 15
reaction with phenylhydrazine, 25:2 12
4,6-O-benzylidene-u-, 25: 118. 188
4-O-(r-idopyranosyIuronicacid 2-sulfate).
D-, 6-sulfate, from heparin, 31:236
3,4,6-tri-O-methyl-aldehydo-~-,
mutarotation of, 25:2 14
2,25:5-anhydro-, D-, 2 5 1 8 1 , 185
degradation mechanism of, 28: 164-165
dimethyl acetal and, 2 5 2 12
351
mutarotation of, 25:2 13
preparation of, 31:18, 33: 115
properties of, and derivatives, 31:19
reaction with phenylhydrazine, 2 5 2 12
structure of. 31:9
and derivatives, 3 I : 19-2 1
3,6-anhydro-, 2.4-di-O-methyI-o-.
composition in aqueous solution, 42:58
2-azido-2-deoxy-o-, derivatives,
hichloroacetimidates, glycosylation,
50:98, 103
p-0-
bitterness, 45:322
crystallography of, 2561
sweetness-structure relationship, 45:248
3-benzamido-
3,6-dideoxy- D-, mercaptalation of, 32:27
2,4,5-tn-O-benzoyl-3,6-dideoxy-u-.
diethyl dithioacetal, hydrogenolysis
by Raney nickel, 32:77
composition in nonaqueous solvents, 42:68
IU-,48~282
absorptive rate by human jejunum, 34:289
derivatives, cyclic acetals, Table,
34:236238
pyrolysis of, 34:46. 152
2-acetamido-2-deoxy-, nonselective
spin-lattice relaxation rates, 45: I48
alkaline degradation of, 46:292
anomers. correlation between CH
orientation and vibrational
frequencies observed, 44:2 1
in aqueous solution, 42: I6
composition, 4226, 28. 3 I , 34,45,47,
63
inorganic ion effects. 42:34
polarimetry, 42: 17
calcium chloride complex, mutarotation
of, 23:35
catabolism of, 32: 173
catalytic oxidation of, 33:87
diethyl dithioacetal. selective
methylation of. 33:66
dithioacetals, selective esterification of,
33:40
reaction with sulfuryl chloride, 33:76
in cellulose structure, 26:326
complex formation with phenylboronic
acid, 35:49
structure. history, 35:5
352 SUBJECT INDEX
Mannose (continued)
diethyl dithioacetal, methylation of, 32:49
dithioacetals, hydrolysis of, 32:67
oxidation of, 32:84
oxidation by Acetobacter suboxydans.
32:82
preparation of, 32:21
2,6-di-O-methyl-, see Curamycose
dithioacetals, hydrolysis of, reaction with
sulfonyl chloride, 32:48
electro-oxidation of, 29:117
gel chromatography of, 2 5 3 2
glycoenzyme constituent, 27:302,307,
321
in glycoprotein of urine, 24:44 1,443
in glycoproteins, 25:413
guanosine 5-pyrophosphate ester in red
alga, 32:9
halogen derivatives of, 22:225
infrared spectrum of, 23:39
intramolecular hydrogen bonding in,
4 5 2 16-2 17
in keratan sulfate, 25:441
mercaptalation of, 32:2 1
methanolysis of, 28: 19
mutarotation and gas-liquid
Chromatography of, 28:40
nonselective spin-lattice relaxation rates,
45: 148
(p-bromophenyl)hydrazone,crystal
structure bibliography, 31:367
pernicotinate, ammonolysis of, 31:89
in plant cell-wall hydrolyzates, liquid
chromatography analysis, 46:55
polarography and reactions with
hydrazine, semicarbazide, and
hydroxylamine, 29: 152
polarography of, 29: 126
protein linkage with, 25:418
proton spin-lattice relaxation rates, 45: I50
radiation chemistry, 37:33
ring structure of, 23:4
solubility in methanol, 27:97
in trichloroacetonitrile, 27: 1 13
sweetness, 49220
synthesis, 40:2
trimethylsilyl ethers, mutarotation of,
42:22
utilization of, 32:21
2-deoxy-, i!-fluoro-o-, 48: 171
inhibition of lipid-linked oligosaccharides,
40:326,333-334
labeled
PET technique, 48:203
synthesis, 48:192-194, 198
preparation, 38:23 1-233
synthesis, 48:128-129
3-deoxy-, 3-flUOrO-D-, 48~164,183
composition in aqueous solution, 42:45
6-deoxy-
composition
in aqueous solution, 42:63
in dimethyl sulfoxide, 42:68
L-, see Rhamnose
determination of enantiomeric form, 46:66
2,3-diamino-2,3-dideoxy-o-, 24: 135-136
1,4:3,6-dianhydro-o-, 47:306
4,6-dideoxy-4-[(S)-2,4-
dihydroxybutanamidol-D-,47: 175-
176
3,4:5,6-di-O-isopropylidene-~-dithioacetals,
preparation of, 32:54
trimethylene dithioacetal, preparation of,
32:38
3,4-di-O-methyl-, mass spectrum, 38:399
3,6-di-O-methyl-, mass spectrum,
38:399400
2,3-di-O-methyl-~-,composition in aqueous
solution, 42:45
2,4-di-O-methyl-o-, synthesis and gas-liquid
chromatography of, 30:21
3,6-di-O-methyl-o-, synthesis and gas-liquid
chromatography of, 30:21
GDP-D-
in cellulose biosynthesis, 42:3 17-319
in polysaccharide biosynthesis, 42:323,
327
L-
derivatives, cyclic acetals, Table,
34:23&238
gel chromatography of, 2 5 3 2
synthesis, 40:2
liquid chromatography, 46:33,52-53
methylation analysis of, 30:20-2 1
methyl ethers
of D-, 8:217-230
periodate oxidation and gas-liquid
chromatography of, 30:34
6-O-(ol-~-ga~actopyranosyluronic acid)+-,
preparation of, 31: 194
 SUBJECT INDEX
6-O-a-o-xy~opyransoyh-,preparation of,
34:258
0-P-D-, glucopyranosyluronic acid-( 1-2)-
0-o-mannopyranosyl-( 1+4)-O-p-u-
glucopyranosyluronic acid-( 1+2)-u-.
24:355
2-O-P-o-glucopyranosyl-o-, 24:357
2-0-P-o-glucopyranosyluronicacid-n-,
24~354,359-360
3-O-~-arabinopyranosyI-o-, 24: 355
2-O-methyl-o-
composition in aqueous solution, 42:45
formation from dithioacetal, 32:68
nucleoside, preparation, 42:254
3-O-methyl-o-, from Klebsiella 0-group 5
lipopolysaccharide, 29:67
5-O-methyl-o-, composition in aqueous
solution, 42:4546
2,3,4,5.6-penta-O-acetyl-o-, diethyl
dithioacetal, oxidation of, 32:83
1,2,3,4,6-penta-O-benzoyl-a-o-,
ammonolysis of, 31536
3,4,5,6-penta-O-benzoyl-2-S-ethyl-2-thio-
aldehydo-n-,ammonolysis of, 31 :1 14
and phenylhydrazone, 21:lO
2-S-ethyl-2-thio-~-,25: 194
diethyl dithioacetal, crystal structure
bibliography, 31:353, 32:367
hydrolysis of, 32:67
nuclear magnetic resonance spectrum
and conformation of, 32:92
ethyl phenyl dithioacetal, identification by
mass spectrometry, 32:94
preparation of, 3 2 5 6
I ,3,4,6-tetra-O-acetyl-2,5-anhydro-u-
dimethyl acetal, 25:194
methyl hemiacetal, 25: 194
preparation of, 28:288
3,4,5,6-tetra-O-benzoyl-2-S-ethyl-2-thio-~-
diethyl dithioacetal (Brigl's compound),
dimethyl acetal from, 32:65
preparation of, 32:30, 31
ethyl phenyl dithioacetal, preparation of,
32:32
2,3,4,6-tetra-O-methyI-o-
acetate, and gas-liquid chromatography
of, 30:29
composition in aqueous solution, 42:45
1-thio-a-o-, 53:220-223
trimethylsilyl ethers of methylated,
353
gas-liquid chromatography of, 30:28
3,4,6-tri-O-acetyl-2,5-anhydro-o-, formation
by deamination, 31:22, 68-69
2,4,6-tri-O-acetyl-P-o-,methylation and acyl
migration in, 33: 104
3,5,6-tri-O-benzoyl-2-S-ethyl-2-thio-o-,
diethyl dithioacetal. preparation of,
32:32
3,4,6-tri-O-methyl-, and gas-liquid
chromatography of, 30:3 1
2,3,6-tri-O-methyl-o-, synthesis and
gas-liquid chromatography of, 30:2 1
2,4,6-tri-O-rnethyl-o-, gas-liquid
chromatography of, 30:3 1
synthesis and gas-liquid chromatography
of, 30:2 I
a-o-Mannose antibodies, 53:2 19-220
Mannose 2,3-carbonate, D-, composition in
aqueous solution, 4 2 5 9
D- Mannose kinas,. in metabolism of D-
fructose, 34:33 1
Mannosidase
OI-D-, 25:466,28:401445,44:209,234-236
A . nigev.44333
action on naturally occurring substrates,
28:437445
activation and inhibition of, 28:416420
activity, in certain mammalian tissues,
28:403
changes in iivo, 28:434-437
in molluscs, 28:405406
of plant seeds, 28:404
in sucrose homogenates of mammalian
tissues, 28:407
assay, 28:408
distribution in nature, 28:402405
in sucrose homogenates of mammalian
tissues, 28:407
effect of zinc2' and other cations on
activity of, 28:422,424431
epididymis, purification of, 28:411
residual activity of purified, 28:4 1 4 -
415
history, 28:401
inactivation by heat, 28:4 16
inhibition by swainsonine, 48:342. 344
jack bean, 44:232-233
purification of, 28:410412
residual activity of purified, 28:414
limpet, activation of, 28:417419
354 SUBJECT INDEX
Mannosidase (continued)
effect of chloride ion on activity of,
28:431432
purification of, 28:411
residual activity of purified, 28:415
metal analysis of fractions during
purification, 28:435
as metalloenzyme, 28:423, 433
PH
and activity of, 28:4 1 2 4 13
and stability of, 28:413416
in plant cell-walls, 42301. 376
purification of, 28:409412,424
residual activity of purified, after
incubation, 28:414415
specificity of, 28:420422
as structural reagent in ovalbumin,
28:437443
subcellular localization in manmialian
tissues, 28:405408
p-D-, 44:165, 168,209
assay, 28:408
for biodegradative hydrolysis of
galactomannans, 31:256
distribution in Nature, 28:420
in galactomannan degradation during
germination of seeds, 35:362,
366-371
occurrence, 35:372-375
and activity of, 28:420
in plant cell-walls, 42:301
purification, and properties, 35372-375
in carbohydrate degradations, 38:4 13
Mannoside
3-amino-3-deoxy-~-,derivative, 22: 132
methyl a-D-
periodate oxidation of, 33:95
phenylboronate, preparation. 3 5 3 8
methyl 4-0-benzoyl-2
3-O-carbonyl-6-deoxy-a-o-, 21 :295
3-O-carbonyl-6-deoxy-p-~-, 21:296
3-O-carbony~-6-O-p-to~y~sulfony~-a-~-, deoxy-2-thiocyanato-, synthesis, 44: 130
21:295
methyl D-, 25: 125
halogen derivatives of, 22:225
methyl 6-deoxy-6-O-sulfo-a-o-, 22203
methyl di-0-methyl-, gas-liquid
chromatography of trimethylsilyl ethers o-Mannuronan lyase, 44: 192
of, 30:25
methyl 4,6-O-benzylidene-
3-deoxy-3-(thiocyanato)-o-, 25: 139
2,3-epimino-o-, 22: 143
methyl 2,3,4,6-tetra-O-methyl-, effect of
volatility on methylation analysis of,
30:17
trimethylsilylation and separation of,
30:25
methyl 2,4,6-tri-O-methyl-, tri-
methylsilylation and separation by
gas-liquid chromatography of, 30:25
methyl 3,4,6-tri-U-methyl-, tri-
methylsilylation and separation by
gas-liquid chromatography of, 30:25
p-nitrophenyl-a-D-, hydrolysis, effect of
limpet a-D-mannosidase on,
28:4 18-41 9
by jack bean meal, 28:430
Mannosidosis
H-NMRspectroscopy, 45:63
glycoprotein (compounds 5), 41:219,
227-230
glycoprotein (compounds 64), 41:344,
350-351
glycoprotein (compounds 65), 41:344,
351-352
glycoprotein (compounds 66), 41:344,
351, 353-355
glycoprotein (compounds 67), 41:344,
351,355-357
structure of oligosaccharides of urine,
37:182, 190,205,209
Mannosylamine, N-benzoyl-o-, preparation of,
31:83, 86
Mannosyl bromide
4-0-benzoyl-2,3-carbonyl-6-deoxy-a-~-,
21:296
2,3,4,6-tetra-O-acetyyl-a-r-,21:29 I
2,3,4-tri-O-benzoyl-6-deoxy-a-~-, 21:290
Mannosylceramide, from freshwater bivalves,
44:420
ol-D-Mannosyl chloride, 3,4,6-tri-O-acetyl-2-
o-Mannosyltransferase, 44: I79
in cellulose biosynthesis, 42:3 18-319
GDP-, 44~244
Mannuronan, D-, crystal structure bibliography,
33:403
Mannuronic acid
2-acetamido-2-deoxy-o-, 41: 164-167
 SUBJECT INDEX
D-
of alginic acid, 35: 10
methyl ethers, synthesis, 35:11
derivatives, preparation, 36:66
gas-liquid chromatography of, 28:64
isolation of crystalline anomers, 39:3 4
on fungal polysaccharides, 23:412
L-, isolation of crystalline anomers, 39:3-4
~-Mannurono-6,3-lactone
mutarotation kinetics, 23:57
polography of, 29: I63
Mannurono- 1,4-lactone, D-, mutarotation of.
23:33
Marenzi, A.D., 46: 13
Marine microorganisms, bioactive products
from, 48: 14
Marini-Bettolo, G., 46: 13
Marrow, development physiology of, 42:380
Mascaroside ditmethanolate), crystal structure
bibliography, 38:479480
Mass fragmentography, 38:405.413,4 15
Mass spectrometry, 21:40,46:69
of acetals, 21:74, 79
of aldonic acids, 38:3 18
of aldoses and ketoses, 21:66
of amino sugars, 21:67,93
of 1,6-anhydrofuranoses, 34: 155
of 1,9-anhydrohexopyranoses, 34:62
of anhydro sugars, 21:93
of carbohydrate boronates, 35:41, 65 -70
of carbohydrate derivatives, 21:39-93.46
chemical-ionization, 29:43, 8 1-84
of methylated alditol acetates, 38:40 I 4 0 2
of cyclic acetals, 26:229-233
of degradation products of polysaccharides.
31:239
of 5-deoxy-5-phosphino- and 5-phospliinyl-
L-idopyranoses, 42: 165-1 72
of deoxy sugars, 21:204
of deuterated sugars, 27: 146, 149
of deuterio-labelled and unlabelled
compounds, 30:39
1,4:3,6-dianhydrohexitols, 49:l 10, I 12- I 14
of diastereoisomers, 30:39
of disaccharides, 21:69
of dithioacetals, 32:92-97
effect of substituents on, 21:54
extended mass-range, 45:37
of fluorinated carbohydrates, 38:253-255,
285
355
of formosc reduction products. 29:207
Fourier-transform. 45:36
future developments. 45:7 1-72
and gas-liquid chromatography in structural
studies. 30: 103-104
techniqucs of, 30:4345
glycolipids, 51:173-174
of hemicelluloses, 36:264
high mass, 45:35
high-voltage, double-focusing, sector. 45:36
instrumentation, 29:42
magnetic-sector, maximum mass range,
4536
maltose and derivatives, 39:258-263
of methylated monosaccharides, 29:3 I 1
in methylation analysis of alditol acetates,
30:30
for methylation completeness, 38:391
mucin oligosaccharide chains, 50:322-328
of nucleosides, 21:90
of oligosaccharides, 21:93, 50:3 12-3 13
partial, per-0-trimethylsilylated dihexulose
dianhydrides, 52:253
of partially methylated sugars, 38:398402
of permethylated glycolipids, 38:394-395
of polysaccharides. 24:338
polysaccharide structure determination by.
30:3745
principles of interpretation of, 21:43,45
scope and limitations of, 21:43
of sialic acids. 40:165-167
of sphingosines, 24:390
stereochcmistry and, 21:79. 92
of stereoisomers, 2 1 5 9
in structural analysis of natural
carbohydrates, 29:41-105
and structurc of cyclic acetals, 34: 192-194
of sucrose derivatives, 33:278-281
of sulfonic esters of carbohydrates, 23:254
of thioacetals, 21:93, 205-206
time-of-flight, 45:36
of tri-O-acetyl-o-glucal and other
unsaturated sugars, 24:2 19
Mass spectrometry-NMR spectroscopy. 45:70
Masuda, F., 46:6-7
Mate, 46:13-14
4-0-Methylglucuronoxylans
enzymic analysis, 44: 16 I
white willow, enzymic analysis, 44: 162
Matsushima, Y., 46:9
356 SUBJECT INDEX
Maturation
of glycans, 37: 188
raffinose family oligosaccharides during, of
plants, 37:358
Meadow-mushroom lectin, see Mushroom
lectin
Mechanism-based inhibitors, 48:364
Meconium
glycoproteins, expressing oncofetal antigens,
f.a.b.-mass spectrometry, 45:64
new-born human, glycoproteins (compounds
23 and 24), 'H-NMR spectroscopy,
41:270-272,275-276
glycoprotein (compounds 29), 'H-NMR
spectroscopy, 41:270,273,279,
282
glycoproteins (compounds 25 and 26), 'H-
NMR spectroscopy, 41:270,273,
275,277-278
glycoproteins (compounds 27 and 28), 'H-
NMR spectroscopy, 41:270,273,
277,280
Medlar, development physiology of, 42:37 1
Megalomycin A, 4-0-(4-iodobenzoyl)-,
dihydrate, crystal structure, 43:272-273
Megosamine, DL-,synthesis, 40:23, 25-26
Megosaminic acid lactone, synthesis, 40:23
Melamine resins, anhydrohexitols for, 25:267
Melanoidins
13C-and lSN-cp./massNMR spectra, 47:257
carbon types, 47:257-258
formation, 46:307,47:223-224, 257,
259-262
in ammonolysis, 31:89-91
mutagenicity, 47:269-270
nondialyzable, 47:256-257
oxidation, 47:256-257
precursors, 47:259
spectral analysis and identification, 44:24
structure, 47:256
Melanoma, 44:240
Melezitose, 2: 1-36
monohydrate, crystal structure bibliography,
32:381,37:404
solubility in methanol, effect of calcium
chloride on, 27:95
structure of, 8:277-290,32: 193,39:357
utilization by yeasts, 32:194
and associations of abilities, 32:226
Melibiase, in galactomannan degradation
during germination of seeds, 35:362-366
Melibiitol
1,l -bis(acetamido)-1 -deoxy-, preparation of,
31:94
sweetness-structure relationship, 45:275
Melibiononitrile, octa-0-acetyl-, ammonolysis
of, 31:98
Melibiose, 21:30
in honey, 25:295
liquid chromatography methods for analysis
of, 46:33
nonselective spin-lattice relaxation rates,
45: 149
occurrence, 37:309-3 10
octa-0-acetyl-, ammonolysis of, effect of
solvent on, 31: 100
octa-0-methyl-, ammonolysis of, 31:94
pyrolysis of, 34:45, 152
radiolysis and radical-induced scission,
37:52
reaction with aqueous ammonia, 25:313,
315
structure, 39:359
sweetness, comparison to D-galactose,
45:247
utilization by yeasts, 32:205-208,
39:374-378
a,P-Melibiose, monohydrate, crystal structure
bibliography, 37:388,38:448449
Melibiosylamine, N-acetyl-P-, configuration of,
31:105
Melizitose, in honey, 25:286,295, 301,308
Melon, development physiology of, 42:371
Melting points, of deoxy sugars, 26:279-296
Meningitis, capsular polysaccharide vaccine,
for infants, 41:195-197
Meningococcal disease, polysaccharide
vaccines, 41:193-195
Mental retardation, lysosomal enzyme and
glycopeptides in, 29474
Menthone, 53:367
Menthyl benzonylformate, mutarotation of,
23:12
Mephrobarbital, cyclodextrin inclusion
complexes with, 46:223-224
Mercaptalation
of carbonyl compounds, 32: 18
of deoxyhexoses, 32:23
effect of substituents on, 32:27-36
stereochemistry and, 32:20
 SUBJECT INDEX
Mercaptals, of aldoses, 21: 19
Mercaptans, reaction with aldoses, 21: I9
Mercaptolysis, of polysaccharides, 26: 13.
31:190,32:29
Mercurationdemercuration, of alkene sugars,
27:242, 280
Mercuric acetate, selective oxidation of alditols
with, 33:99
Mercuric chloride, in anhydridization of
hexoses, 34:47
Mercurie cyanide, in cardenolide synthesis,
21:278
Mercury compounds
crystal structure of methyl 2-
(chloromercuri)-2-deoxy-a-~-
talopyranoside, 25:75
organic, research, 29:2
Mercury(I1) chloride, reaction with dithiacetals,
32:61-70
Mercury salts, in Koenigs-Knorr reaction,
34:246,251-252
spiro-Mesenheimer complex, aryl migration
and, 33: 109
Mesitylenesulfonyl chloride, intermediate in
nucleotide formation, 36: 157
meso forms
aldaric acids, 52: 110-1 1 I
monosaccharides, 5 2 5 9
Mesogloia, antitumor activity of, 32:257
Mesquite gum, 24:341,349
Metabolism
of a,-a-trehalose, 30:227-256
of apiose, 31: 153-154
of auxins, 21:396
of carbohydrates, 2:119-160,33:4
use of isotopic tracers in studying,
3:229-250
3-deoxy-o-manno-2-octu~osonic acid.
enzymes, 38:378-387
Of D-frUCtallS, 34:315
o-fructose, 34:285-343
inborn errors of, 34:306-3 10
key enzymes in, 34:330-343
in micro-organisms, 34:3 10-343
o-fucose, 39:328-329
of o-galactose-containing oligosaccharides
and polysaccharides, 37:342-372
of domestic fowl, 30:6
of epithelial cells of intestine, effect of I)-
fructose on, 34:324
357
of ethanol, effect of o-fructose on,
34:3 17-322
of fat, 2:119-160
D-glucuronic acid in, 8:251-275
ofglycans, 37:182,218-221
of glycoproteins, 25:407478
inhibitors, for 3-deoxy-~-manno-2-
octulosonic acid, 38:387-388
i,-fucose, 39:327-328
of lipids. o-fructose effect on, 34:325-330
of marine algae, 32:5
in plants
auxin activity on, 21:387
polysaccharides, 37: 366-3 72
role of a,a-trehalose in, 30:254-256
of the sugar alcohols and their derivatives,
1: 175--l92
Metal cation--carbohydrate complexes, 47: 1-3,
see also Metal-sugar complexes
alduronic acids, 47:31-35
applications
cation-exchange resin columns, 47:3&40
electrophoresis, 47:35-36
high-performance liquid chromatography,
47:40
NMR spectroscopy, 47:4041
synthetic applications, 47:4142
thin-layer chromatography. 47:35-36
biological implications, 47:4243
cations, 47: 19-21
complexing sites, 47:12-19
a, e, a sequence, 47:12-13
alditols, 47: 13-14
syn-axial hydroxyl groups, 47: 15-1 6
dextran, 47:20
effectiveness of, 47:19
cis-inositol. 47: 15
ketopyranoses, 47: 17-18
methoxyl group replacing hydroxyl group,
47:14
crystalline complex structures, 47:22-26
a-o-allopyranosyl a-o-allopyranoside,
47:25
a-L-guluronic acids, 47:2&25
epi-inositol x SrCI, x 5H,O, 47:24
p-o-mannofuranose x CaCI, x 4H,O,
47:22-23
methyl o-glycero-a-o-gulo-
heptopyranoside x CaCI, x H,O,
47:23
358 SUBJECT INDEX
Metal cation-carbohydrate complexes
(continued)
methyl P-o-mannofuranoside x CaCI, x
3H,O, 47:23
in solution, 47:22
electrophorectic mobilities, in cupric sulfate
solution, 47:21
stability constants, 47:26-30
1: 1 and I :2 complexes, 47:27
cation-sugar complexes, 47:28
in methanol, 47:30
methods of determination, 47:27
reducing sugars, 47:29
Metal chelates, effect of pH on stability of,
28:422, 424
Metal hydrides
complex, reduction of D-
glucofuranosidurono-6,3-lactonesand
o-g~ucofuranurono-6,3-~actones with,
33:217, 220
ketonucleoside reduction by, 42:252
Metal ions, see also specific ions
binding site, 47:127
coordination spheres, 47: 128
diamagnetic species, 47: 129-130
interactions with carbohydrates, 47: 125-126
a, e, a sequence, 47: 127
m, p arrangement, 47: I27
selective-broadening technique, 47: 134
U-(amineothyl)cellulose in chromatography
of, 29:323
0-(carboxymethyl)cellulose in
chromatography of, 29:321, 349
oxidation states, 47: 129
paramagnetic species, 47: 130-1 35
quaternization of caramel, 47:232
Metallation, of sugars in liquid ammonia, 27:92
Metalloenzymes, 28:423,433
Metals
hydroxides, 53:3 14-3 16
nontransition, 53:322-326
transition, 53:326-327
Metal salts
cello-and malto-oligosaccharides in presence
of, f.a.b.-mass spectrometry, 45:70
reactions of 5-(hydroxymethyl)-2-
furaldehyde and, 47:252-253
Metal-sugar complexes
electrophoretic mobilities, 47:4-5
NMR spectroscopy, 47:5-11
syn-axial hydroxyl groups, 47:8
complexes
with diamagnetic cations, 47:6-9
with paramagnetic cations, 47:9-11
contact and pseudocontact shifts, 47:9-10
polyols, 47:5-6
screening constant change, 47:6
shifts, 47:5
optical rotation, 47: 12
paper electrophoresis, 47:3-5
stability constants, 47:28
thin-layer ligand-exchange chromatography,
47:5
Metaphosphates, as phosphorylating agents for
nucleosides, 22:333
Metaphosphoric acid, in selective
phosphorylation of carbohydrates, 33:47
Metasaccharinates, 2 5 3 4 1
Metasaccharinic acid
4-carbon, preparation of, 28: 195
from deoxyglycodiuloses by alkaline
degradation, 28: 196
Methacrylic acid, methyl ester,
copolymerization with 6,1',6'-tri-U-(p-
vinylbenzoyl)sucrose, 33:274
Methacrylic anhydride, reaction with 1,6-
anhydro-o-glucose 2,4-phenylboronate,
3555
Methane
bis(ethylsulfonyl)-(2,3,4-tri-U-acetyl-~-~-
ribopyranosy1)-, proton magnetic
resonance spectra, nonequivalence of
nuclei in, 27:63
C-a-oand C-P-o-galactofuranosylnitro-,
preparation of, 33: 124
C-OC-D and C-P-D-galactopyranosylnitro-,
preparation of, 33: 123
chlori(methoxypheny1)diphenyl-,selective
tritylation with, 33:53
chlorotriphenyl-, selective etherifications
with, 33:5 1
diazo-, reaction with aldehydo-aldose
acetates, 32:64
dibromo-, methylene acetals prepared with,
34: I89
dichloro-
complex
with anthracene and tetracyanoethylene,
structure of, 25:55
with tri-0-ethylamylose, crystal
 SUBJECT INDEX
structure bibliography, 40:385
as solvent for sugars, 27: 105
dipivalo-europium complex, in proton
magnetic resonance spectroscopy,
29: 17
nitro-
complex
with tri-0-acetylcellulose, crystal
structure bibliography, 33:397
with tri-0-ethylamylose, crystal
structure bibliography, 40:385
in nitro-sugars synthesis, 2458, 70
syntheses with, 6:291-3 18
(4-0-acetyl-2,3-0-isopropylidene-cu-1~-
lyxopyranosyl) bis (ethylsulfony I)-,
conformation of, 26: 1 18
[5-O-(bromobenzoyl)-2,3-0-isopropyl1dene-
a-D-ribofuranosyl]cyano-, crystal
structure bibliography, 38:467-468
trifluoro(fluor0xy)-, fluorinating agent,
38:230-233
Methanediol, 47:78-79
Methanesulfonates, photolysis of, 46: I9 1
4-Methanesulfonates. 48:63
Methanesulfonic acid
esters, Helferichs work on, 45:4
sulfonylation of carbohydrates by, 23:239
trifluoro-, reaction with I ,6-
anhydrohexopyranoses, 34:87-88
Methanesulfonic anhydride, sulfonylation of
carbohydrates by, 23:238
Methanesulfonylation
of I ,6-anhydrohexopyranoses, 34:X2
of hexopyranosides. 28:256
selective, 33: 14, 27
of maltose and derivatives, 39:227
Methanesulfonyl chloride
selective chlorination with, in N.N-
dimethylformamide. 33:XO-83
sulfonylation agent for sugars, 23:236
Methanesulfonyl chloride-NJ-dimethy I-
formamide reaction, 39:233-235
in selective replacement of primary hydroxyl
groups, 33:261-263
Methanethiol, reaction with D-ribose, 32:23
Methanethiolysis, of 3,5,6-tri-O-benzoyl-2-9
ethyl-2-thio-u-mannofuranose, 32:32
Methanol
complex with sodiocellulose, crystal
structure bibliography, 33:395
359
solubility of sugars in, effect of salts on,
2795
as solvent
in ammonolysis of benzoyl groups. 31 :102
for sugars, 27:96-97
sugar composition in, 42:61
Methanol-utilizing micro-organisms,
polysaccharides, 36:3 12-3 13
Methanolyses, monitoring with f.a.b.-mass
spectrometry, 45:48
Methanolysis
of carbohydrate sulfonic esters, 23:262
of cyclic acetals, 34:206
deacetylation in, 28:82
deacylation and, of polysaccharide aliphatic
carboxylic esters, 29:332-333
in degradation of polysaccharides, 31: 190
f.a.b.-mass spectrometry, 45:5 1
and gas-liquid chromatography, 30:36
of glucopyranosyl chlorides and bromides,
34:274-275
of glycofuranosyl bromides and chlorides,
34~279-281
of glycolipids and glycoproteins, and
gas-liquid chromatography. 28:5 1
ofglycopeptides and oligosaccharides, 28: 18
of glycosyl esters of nucleoside 5-
pyrophosphates, 28:358
of monosaccharides, gas-liquid
chromatography and, 28:54
of nitro sugars, 24: I 18
of pyranosides, 22334
structural analysis, 38:397
of 5-thiopyranosides, 22:37
of uronic acids, gas-liquid chromatography
and, 28:76
Methase, definition, 29: I74
Methionine
ethylene biosynthesis from, 42:343-344
inhibition of, 42:363-364
S-adenosyl-. selective methylations with,
33:66
Methoximes. of monosaccharides, gas-liquid
chromatography of trimethylsilyl
derivatives, 28:49. 110
Methoxyl group
anomeric effects. solvent effects, 47:68-69
determination of, in carbohydrates, 26: 15
Methoxymercuration, of glycals, 24:2 10, 220
Methoxymethanol, relative energies, 47:78-79
360 SUBJECT INDEX
2-Methoxyoxane
acetal segment, rabbit-ear effect interactions, 2-Methylallyl group, as protecting group, 39:52
47: 107-108
axial, exo-anomeric effect, 47:95
bond angle variation with torsional angle,
47: 100
conformers, solvent effect, 47:90-92
net atomic charges and dipole moments,
47: 103
torsional potential, 47534, 8 6 8 7
4-Methoxyphenacyl, photocleavage of,
46:20 1-202
N-(p-Methoxyphenyl)glycosylamines,liquid
chromatography, pre-column
derivatization procedures, 46:68
5-Methoxyuridine, 43:373
Methyl 3-acetamido-4-O-benzoyl-2,3,6-tri-
deoxy-2-fluoro-P-~-mannopyranoside,
48:232-233
Methyl 2-acetamido-2-deoxy-a-o-
glucopyranoside, circular dichroism, 45:96
Methyl 2-acetamido-2-deoxy-p-~-
galactopyranoside, circular dichroism,
45:96
Methyl 2-acetamido-2-deoxy-p-o-
glucopyranoside, circular dichroism, 45:96
in water and fluorinated alcohols, 45:97
Methyl 4-0-(2-acetamido-2-deoxy- p-D-
mannopyranosy1)-a-o-glucopyranoside,
synthesis, 49233
Methyl 2-acetamido-2,6-dideoxy-6-fluoro-a-~- of dextrans, 30:384-386
galactopyranoside, 48: 139
Methyl 3-acetamido-2,3,5,6-tetradeoxy-5-
fluoro-ribo-hexopyranosides,48: 155
Methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-
3,5-dideoxy-2-nonulosyl fluoride)onate
a-o-glycero-a-D-galacto-, I3C-NMR data
for, 46: 177
a-o-glycero-P-o-galacto-, "C-NMR data
for, 46: 177
Methyl [21-acetoxy-(18R)-l l p , 18-epoxy-3,20-
dioxopregn-4-en- 18-yl2,3,4-tri-O-acetyl-
a-D-giucopyranosid]uronate, crystal
structure, 43 :352-3 54
Methyl 5-acetoxy-teha-O-acetyl-a-L-
idopyranuronate, synthesis, 49:79-80
2'-C-Methyladenosine, 50: 195
Methyl aldofwanosides, cation-exchange
columns, retention volumes, 47:20
Methyl D-allosides, synthesis, 47:42
1-Methylallyl group, as protecting group, 3 9 5 2
Methyl 3-amino-2,3-dideoxy-2-ureido-p-
xylopyranoside, 43:37 1
Methylaminomethyluridine, 2-thio-5-,
dihydrate, crystal structure, 43:290
Methylamylose, 2,3,6-tri-O-, nonselective
spin-lattice relaxation rates, 45: 149
Methyl 2,3-anhydro-6-bromo-6-deoxy-40-(4,6-
di-O-acetyl-2,3-dideoxy-a-~-erythro-hex-
2-enopyranosy~)-a-o-a~~opyranoside,
crystal structure, 43:248
Methyl 2,3-anhydro-4-deoxy-4-fluoro-a-~-
lyxopyranoside, 48: 137
Methyl 3,6-anhydro-P-o-gIucopyranoside,
51:6,9
Methyl a-L-arabinoside, circular dichroism,
predicted and fragment spectra, 45:84
Methyl-P-D-arabinopyranoside,crystal
structure, 43:215
Methylated sugars, 48:300-302
Methylation, 53:61-62, see also
Permethylation
acyl migration during Purdie, 33: 103
analysis, 47:308-3 10
of 1,6-anhydrohexopyranoses,34:50
glycolipids, 51:173
of carbohydrate boronates, 35:42,55
of carbohydrate sulfonic esters, 23:266
carbon, of sugars, 35233
of dithioacetals, 32:47
effect on transport of monosaccharides into
yeasts, 32: 152
Hakomori method
for carbohydrates, 30: 12
for polysaccharides, 31:215
Haworth method for carbohydrates, 30: 1 1,
15
hemicellulose loss, 36:261
Kuhn method for carbohydrates, 30: 1 1, 16
of nucloeotides, 22:383
oligosaccharide of glycoconjugates analysis,
50:3 11-3 I3
of polysaccharides, 25:6,29:3 10-315,
36:239-240,264
selective
of cyclic acetals of carbohydrates, 33:54
of maltose derivatives, 39:220-223
sodium hydride in, 30: 12-13,53
 SUBJECT INDEX
Srivastava method for carbohydrates. 30: 1 I,
15
structural analysis, of glycoproteins and
glycolipids, 3k389-416
Smith degradation, 38:407408
in structural analysis, 3 5 5
of sucrose, 33:243-245
of sugars, 24:7,30:4, 1Q-18
history, 23: 1
in liquid ammonia, 27:93
technique, 46:214
Unrau methof for carbohydrates, 30: 13
C-Methyl7-azabicyclo[4.1.O]heptanes,
epimine-ring opening, 48: 168
Methyl 3-azido-4,6-O-benzylidene-2,3-
dideoxy-3-C-( fluoromethyl)-ol-o-urcrhino-
hexopyranoside, 48: 142
Methyl 2-azido-4,6-0-benzylidene-2,3-
dideoxy-2-C-(fluoromethyl)-P-~-riho-
hexopyranoside, 48: 142
5-Methylbarbituric acid, cyclodextrin inclusion
complexes with, 46:223-224
Methyl 2-benzamido-4,6-0-benzylidene-2-
deoxy-3-O-tosyl-ol-o-glucopyranos~de.
48: 166
2-Methylbenzofuran-5,6-diol, 46:290
3-Methylbenzoic acid, cyclodextrin inclusion
complexes with, 46:222,224
2-Methylbenzoquinone, formation, 46:294
4-Methylbenzoylacetic acid, cyclodextrin
inclusion complexes with, 46:223-224
Methyl [benzyl2-(benzyloxycarbonyl)a1nino-
2,3,4-trideoxy-5-fluoro-ol-o-erythm-hex-
3-enopyranosid]uronate I3C-NMR data
for, 46: I72
IH-and I9F-NMR data for, 46:116
Methyl 2,3-0-benzylidene-c~-~-
rhamnopyranoside, 51:9&95
Methyl 3-C-acetyl-4,6-0-benzylidene-2-deoxy-
a-o-ribo-hexopyranoside, crystal
structure, 43:243
Methylcellulose, 2,3,6-tri-O-, nonselective
spin-lattice relaxation rates, 45: 149
Methyl 4-chloro-3,4-didieoxy- 1,2:6,7-di-0-
isopropylidene-ol-o-erythro-hept-3-
enopyranos-5-uloside, crystal structure,
43:231
Methyl-chromone
3.8-dihydroxy-2-, formation, 46:290-29 1
3-hydroxy-6-(hydroxymethyl)-2-, 46:290
361
Methyl 2-C-(hydroxymethyIacetyl)-P-o-
ribopyranoside [methyl P-D-
hamameloside], crystal structure, 43:340
Methylcoumarin, 7-(3-0-carbamyl-5,5-di-C-
methyl-4-O-rnethyl-ol-r-lyxopyranosyl)-4-
hydroxy-3-[4-hydroxy-3-(3-methyl-2-
buteny1)-benzamidol-8-, monohydrate,
crystal structure, 43:35 1
N-( I -Methylcyclohexyl) sulfamate, three-
dimensional X-ray analysis of, 4 5 5 0 1
Methylcyclopent-2-en- 1-one, 2-hydroxy-5-,
formation, 46:294
Methylcytosine, I -(2-deoxy-2-fluoro-P-o-
arabinofuranosyl)-5-
biological activity, 48:248-249,255
synthesis, 48:238
Methyl 3-deoxy-a-o-manno-2-
octulopyranosidonic acid, circular
dichroism, 45: 107
Methyl 3-deoxy-P-o-manno-2-
octulopyranosidonic acid, circular
dichroism, 45: 107
Methyl 5-deoxy-5,5-ditluoro-~-ribofuranoside
3-O-benzyl-a-, 'H-and I9F-NMR data for,
46:156
2,3-0-isopropylidene-P-,IH-and I9F-NMR
data for, 46: 156
Methyl 2-deoxy-2.2-difluoro-3,4-0-
isoprop ylidene-D-erythro-
pentopyranosides, 48: 153
Methyl 4-04 deoxyfluoro-, galactopyranosy1)-
P-D-galactopyranoside, 48:2 13-2 14
Methyl 3-deoxy-3-fluoro-a-o-gulopyranoside,
'H-and I9F-NMR data for, 46:91
Methyl 2-deoxy-2-fluoro-P-o-ribo-
hexopyranoside, 4,6-0-benzylidene-3-
deoxy-, IH-and I9F-NMR data for,
46: I32
Methyl 5-deoxy-5-fluoro-~-ribofuranoside
2,3-di 0-acetyl-, IH-and I9F-NMR data for,
46:112
2,3-O-isopropylidene-, 'H-and "F-NMR
data for, 46: 1 12- 1 13
Methyl 4-deoxy-4-fluoro-P-o-
galactopyranoside, 48: 136,209-210
Methyl 6-deoxy-6-fluoro-4-0-cu-~-
galactopyranosyl-P-o-galactopyranoside,
48:213-214
Methyldextrantaose, 2,3,4-tri-O-, nonselective
spin-lattice relaxation rates, 45: 149
362 SUBJECT INDEX
Methyl 3,4-dideoxy-a-~~-threo-hex-3-
enopyranoside, crystal structure, 43:2 18
Methyl 3,6-dideoxy-3,6-difluoro-p-~-
allopyranoside, 48: 149
Methyl 4,6-dideoxy-4,6-difluoro-a-~-
galactopyranoside, 48: 149
Methyl 2,3-dideoxy-3-fluoro-~-eryrhro-
pentofbranoside, 48: 135
Methyl 3,4-didiexoy-3-(salicylidenedmino)-a-
L-erythro-pentopyranoside,crystal
structure, 43:343
Methyl 2,4-di-O-acetyl-3-deoxy-3-C-nitro-P-~- 01 and P pyranose anomers, circular
xylopyranoside, crystal structure.
43:22&227
Methyl 4,5-di-O-acetyl-2,3-dideoxy-a-~-lhreo- nonselective spin-lattice relaxation rates,
hex-2-enopyranoside, crystal structure,
43:226
Methyl 3,4-di-O-a-o-fructofuranoside, 52:445 U-Methyl-D-glucose polysaccharide
Methyl-2,3:4,5-di-O-isopropylidene-a-~-
glucoseptanoside, crystal structure,
43:233-234
Methylenation, aldonolactones, 50: 143-146
Methylene blue, 53:381, 383
Methylenitan
definition, 29: 173
synthesis, 40:2
Methyl 1,2-epoxy- 1-methylethanephosphonate,
synthesis and structure of, 42: 150
Methyl a-n-erythrofuranoside, 51:83. 89.94
Methyl ethers, 48:300-302
of the aldopentoses, 7:l-36,10:257-272
of 2-amino-2-deoxy sugars, 13: 189-214
of fucose, 7:l-36,10:257-272
of D-galactose, 6: 11-25, 10:273-282
of o-glucose, 5: 145-190
ofhexuronic acids, 9:131-148
of o-mannose, 8:217-230
of rhamnose, 7: 1-36, 10:257-272
Methyl(ethyl2,3,4-tri-O-acetylglucosid)-
uronate, 43:371
2-Methylformycin, 43:373
Methyl D-fructofuranosides, 52:445447
Methyl furanosides
conformation of, 42:27
synthesis, 47:42
Methyl D-galactofuranosyl-( 1+6)-P-u-
galactofuranoside, 50: 180
Methyl a-and P-o-galactopyranoside, Gd3
and Mn2+effect, 47: 15&152
Methyl P-D-galactopyranoside, 51:94
Methyl a-o-galactopyranoside
crystal structure, 43:339-340
monohydrate, crystal structure, 43:219
Methyl P-n-galactopyranoside, crystal
structure, 43:218-219
Methyl a-and P-D-glucopyranoside
aglycon orientations, 47:50-5 1
conformational energy, 47:88
Methyl a-o-glucopyranoside, 50: 16-1 7
circular dichroism, 45:87-88
Methyl o-ghcopyranoside, 51:89,94,96
dichroism, 45:80
circular dichroism-difference spectra, 45:8 I
45: 148
proton spin-lattice relaxation rates, 45: 157
f.a.b.-mass spectrometry, 4 5 2 - 2 3 , 58, 65
molecular weight, 45:21
mycobacterial, f.a.b.-mass spectrometry,
45:37
structure, 45:21-22
Methyl o-ghcoside, a and p pyranose
anomers, circular dichroism, 45:80
2-C-Methylglyceric acid, 46:303
Methyl D-glycero-a-o-gulo-heptopyranoside
calcium chloride, monohydrate, crystal
structure, 43:221
Methyl glycopyanosiduronic acids, circular
dichroism, 45: 102
Methyl glycopyranosides, circular dichroism,
45:96
Methyl a-glycoside, 47: 198-1 99
Methyl glycosides. 46:29
circular dichroism, 45:79
high-performance liquid chromatography of,
46:256
hydrogen bonding, 44: 15-1 6
perbcnzoylation of, 46:256
prcparative liquid chromatography, 46:60
1,2-cis-Methyl glycosides, 53:124, 126
Methylglyoxal, liquid chromatography,
46:53-54
Methyl a-o-gulopyranoside, 47: 10
Methyl a-o-gdoside, I3C-NMR structural
analysis, 43:4748
Methyl D-~~,vcero-a-o-gulo-heptopyranoside x
CaCI, x H,O, 47:23
Methylideneadenosine, 3 -(N-benzylamino)-3 I-
 SUBJECT INDEX
deoxy-0-2,' N'-, crystal structure, 43:329
4(5)-Methylimidazole, 47:267
Methyl iodide-methyl red test, for sugar
oxiranes, 25: 170
Methyl P-isomaltoside, synthesis, 4 9 5 3
Methyl P-lactoside, 51:114-1 15
Methyllithium, reaction with aldose oxirane,
25:139
Methyl a-o-lyxofuranoside, 47: 16
Methyl maltosides, large-scale preparative
liquid chromatography, 46:62
Methyl P-o-mannofuranoside x CaClz x 3 H,O,
41:23
Methyl a-o-mannopyranosiduronic acid,
circular dichroism, 45: 102- 104
3-0-Methylmannose dodecasaccharide,
complex with alkyltrimethylammonium
ions having decyl and hexadecyl as alkyl
chains, f.a.b.-mass spectrometry, 45:70
N-Methylmayserine, synthesis of. 42:96
Methyl methacrylate. copolymerization with
6,1'6'-tri-O-( ~-vinylbenzoyl)sucrose,
33:274
Methyl (methyl 4-deoxy-4-fluoro-a-o-
glucopyranosid)uronate, 'H-and "F-NMR
data for, 46: 1 16
Methyl a-nigeroside, crystal structure, 43:234
Methyl 3-O-a-o-glucopyranosyl-a-~-
glucopyranoside, crystal structure, 43:234
Methyl 4,6-O-benzylidene-2-deoxy-3-0-
[(methylthio)thiocarbonyl]-a-D-
arabinopyranoside, crystal structure,
43:240-24 I
Methyl 4,6-O-benzylidene-3-deoxy-2-0-
[(methylthio)thiocarbon y l ] - a - ~ -
arabinopyranoside, crystal structure.
43 :24 1-242
methyl 2,3-0-benzylidene-5,6-di-O-methyl-a-
D-, hydrogenolysis, 39: 127
Methyl 4,6-0-benzyIidine-2-deoxy-3-0-
[(methylthio)thiocarbonyl]-a-D-
ribopyranoside, crystal structure,
43:242-243
Methyl 3,4-O-ethylidene-P-~-
arabinopyranoside, 43:333
Methyl 3,5-O-isopropylidene-2-(methyl-3,5-0-
isopropy~idene-a-~-xylofuranosid-3-yl )-a-
o-xylofuranosid, 43:372
Methyl 4,6-O-methylene-o-hexopyranosides,
taste, 45:243
363
Meth,vlomonus. polysaccharides, properties,
preparation, and uses, 36:3 12-313
Methyl 2,3,4-0-phosphono-P-u-
ribopyranoside, crystal structure, 43:2 I2
Methyl 4,6-0-fR)-benzylidene-2,3-di-O-
methyl-a-o-glucopyranoside, crystal
structure, 43:24&245
Methyl 4,6-0-(R)-benzylidene-2,3-di-O-
methyl-P-o-galactopyranoside,crystal
structure, 43:245
Methyl orthoacetate. reaction with
ribonucleosides, 22340
Methyl 2,3,4-0-(thiophosphono)-o-
ribopyranoside, crystal structure,
43:2 12-2 I3
Methyl oxetane-2-carboxylate. 50: 193
a-Methylphenacyl, photocleavage of,
46:201-202
Methylphenylquinoline, 4-
(amidosulfonylmethyl)-6-methoxy-2-4-,
photodecomposition of, 46: 194
Methyl phosphate methanolate, 2,3-0-
sodiouridine 5'-, crystal structure
bibliography. 38:s 10-5 11
Methyl P-D-psicofuranoside, 47: I & I 7
Methyl p-(2,4.6-tridiexoy-2-guanidino-4-
ureido-a-o-glucoyranosylox y)-benzote,
hydrochloride, monohydrate, 43:372
Methylpyan-2-one. 3-benzoyloxy-6-,
50:165-166
Methyl pyranosides, circular dichroism, 45:85
Methyl a- and P-D-pyranosides, mean.
hemiacetal and acetal geometries, 47:72
2-Methylpyrazine, formation of, 46:3 17
Methylpyrimidine, 4-amino-5-hydroxymethyl-
2-, 52:268-269
Methylpyrrole
1 -Ethyl-2-formyl-5-, formation of,
46:3 13-3 14
2-formyl-5-(hydroxymethyl)-l-, 46:3 14
formation of, 46:312-3 14
Methyl quinate, selective esterification of,
33:40
Methyl 3-O-a-~-rhamnopyranosyl-a-u-
glucopyranoside, 51: 1 15- 1 16
Methyl a-o-ribofuranoside, 51:83,89
Methyl(SR)-tetra-O-acetyI-5-bromo-(3-~-
glucopyranuronate, synthesis, 49:43
Methylsucrose
1 ',6'-di-O-, sweetness, 45:264
364 SUBJECT INDEX
Methylsucrose (continued)
6,6-di-O-, sweetness, 45:264
4-0-, sweetness-structure relationship,
45:263
6-0-, sweetness, 45:264
0-,degradation, 52:447
Methyl sulfate
methylation of sugars by, history of, 23: 1
as solvent with sodium hydroxide for
methylation, 30: 12
Methylsulfinyl carbanion, in methylation of
carbohydrates, 30:12-13
Methylsulfonyl group, deshielding effect in
sugars, 27:283
Methylsulfonyloxy group, reactivity of,
24:139
Methyl sulfoxide
polymerization of sugars in, 21:449,
453454
purification of, 28:30
as solvent
in acetalation, 34: 186
in displacement reactions of carbohydrate
sulfonic esters, 24:141
for methylation of carbohydrates, 30: I 1
for sugars, 27:89, 108
for trimethylsilylation, 28:29
sucrate production in, 27:93
Methyl sulfoxide-sulfur trioxide, sulfation of
polysaccharides with, 29:335
Methyl tetra-0-acetyl-P-D-glucopyranuronate,
synthesis, 49:87
Methyl tetra-0-acetyl a-and P-
glycopyranosides, vicinal carbon-proton
coupling constants, 51:56
Methyl tetra-0-acetyl-P-L-xylo-
hexulopyranosonate, synthesis, 49:79-80
Methyl tetra-0-acetyl-a-L-idopyranuronate,
photobromination, 49:45
Methyl 6,6,7,7-tetradehydro-6,7-dideoxy-2,3-
0-isopropylidene-P-o-allo-
heptofuranoside, crystal structure, 43:342
Methyl 2,3,4,5-tetra-O-acetyl-a-o-
galactoseptanoside, crystal structure,
43:240
Methyl 2,3,4,5-tetra-O-acetyl-a-o-
glucoseptanoside, crystal structure, 43:345
Methyl 1,2,3,5-tetra-O-acetyI-P-o-
galactofhranuronate, 43:37 1
Methyl 2,3,4,6-tetra-O-(trideuterioacetyl)-a-o-
gIucopyranoside-2,3,4,6,6-d5, anomeric
forms proton spin-lattice relaxation,
45: 162
Methylthiazole, 2-carboxy-5-(2-
hydroxymethyl)-4-, synthesis and
transformations, 52:284-286
Methyl 5-thio-P-o-ribopyranoside(R)-S-oxide.
43:371
Methyl 5-thio-P-o-ribopyranoside(S)-S-oxide,
43:371
Methyl P-o-threo-2,5-hexodiulo-2,6-
pyranosonate 5-(dimethyl acetal), crystal
structure, 43:224
Methyl(tri-O-acetyl-a-~-xylo-
hexulopyranosy1)ate bromide, synthesis,
49:4243
Methyl triflate, 52: 187
Methyl 2,3,6-tri-O-acetyI-2,3:4,6-di-O-
benzylidene-7-(R)-P-cellobioside,crystal
structure, 43:266
Methyl 2,3,4-tr-O-(acetylglucosyl
bromide)uronate, 43:37 1
Methyl 2,4,6-tri-O-acety1-3-0-(2,3,4.6-tetra-O-
acetyl-~-o-glucopyranosyl)-~-o-
glucopyranoside, crystal structure,
43~350-351
Methyl 2,3,4-tn-0-benZOyl-P-D-
xylopyranoside, 43:372
crystal structure, 43:26 1-262
Methyl 2,3,4-tri-O-methyl-6-thio-a-~-
glucopyranoside (methyl 2,3,4-tri-O-
methyl-a-o-glucopyranoside) 6,6-
dithiocarbonate, preparation of, 28:283
Methyluridine, 2-deoxy-6-, crystal structure,
4 3 ~ 138-3 19
Methyl vinyl sulfone, selective etherifications
with, 33:6&67
Methyl P-xylobioside, vicinal carbon-proton
coupling constants, 51:54
Methyl a-o-xylopyranoside, circular dichroism,
45:85
Methyl P-u-xylopyranoside, 53:67
circular dichroism, 45:85
Methyl o-xylopyranoside, circular dichroism-
difference spectra, 45:8 1
Methyl+-xyloside, a and b pyranose anomers,
circular dichroism, 4 5 8 0
Methyoxynapthalene esters, 5-azido-4-
(hydroxymethy1)-1-, photocyclization of,
46:201
 SUBJECT N D E X
Mevalonic acid, inhibition of protein
glycosylation, 40:324
Mevinolinic acid, inhibition of protein
glycosylation, 40:324
Meyer, Kurt Heinrich, obituary of, 11:
xiii-xviii
Meystre-Miescher modification, of
Koenigs-Knorr synthesis, 21:277
Mg2+.exchange of Gd3' and Mn2' for, 47: 136
MGP, see 0-methyl-D-glucose polysaccharide
Micelles
critical concentration, dextrins, 47:30 1-302
orientation, 26:303
Mice tissue, water-soluble polysaccharids from,
antitumor activity of, 32:257
Michaelis-Arbuzov reaction
carbon-phosphorus sugars by, 28:285
in phosphorus sugar synthesis, 42: 139,
142-143, 145
Michaelis constant, 23:289
of a-amylases, 23:325-326
of P-amylases, 23:342
D-glycal hydration, 48:355
for pectinesterase, 33:333
of phosphorylases. 23:353,355
Michaelis-Menten kinetics, 51: 157
of D- fructose transport, 34:290-29 1
in enzyme kinetics, 23:288
Michael reaction, 24: 137
Michelson interferometer, 44:56-57
Micrasterias denticulata, cellulose biosynthesis
in, 42:332-336
Microanalysis
carbohydrate, 39:2
of sugars, 35:5
Microbial media, L-arabinitol and D-mannitol
metabolism in, gas-liquid chromatography
of, 28:57
Microbial polysaccharides, see Polysaccharides
Micrococcus lysodeikficus, biosynthesis of cell-
wall polysaccharides in, 42:323-325,330
Microfibrils
biogenesis by plasmalemma particles,
26:342-345
biosynthesis, 41:116-117
cellulosic
formation of, 26:326-331
morphology and biogenesis of, 26:298
new models, 26:312-319
orientation
365
of cellulosic, 41:123-125
mechanism of, 26:331-335,338
original concepts, 26:307-3 12
structure,41:111-116
terminal complexes, 41:119-121
uncoupling, 41:117
Micro-organisms
P-o-mannanase in, 35:366
o-fructose metabolism in, 34:310-3 14
di-o-fructose dianhydrides, 52:2 13-216
in enzyme production, 30:263
formose utilization by, 29:2 19-223
galactomannans in, 35:354, 376
Microsomes, -a-D-mannosidase in structural
studies of rat-liver, 28:445
Microtubules, in cell-wall formation,
26: 335-337-338
Microwave radiation, starch modification,
51:299-304
kinetics of heating, 51:299-300
Microwave spectroscopy, in conformational
analysis, 2 6 5 5
Mildiomycin, 42: 135
structure of, 42:17
Mildiomycin monobenzoate, heptahydrate,
43:374
Milk
a-o-mannosidase in cow's, 28:403
gas-liquid chromatographic analysis of,
28:48, 53, 81, 83
hexasaccharide from human, acetolysis of,
31:199
human, 24:7
complex, neutral oligosaccharides, liquid
chromatography. 46:44
glycoprotein (compound 52), 'H-
NMRspectroscopy, 41:306, 32&
328
oligosaccharides
f.a.b.-mass spectrometry, 45:70
preparative liquid chromatography,
4660
sialylated oligosaccharides, liquid
chromatography analysis, 46:4546
0-(carboxymethyl)cellulose as stabilizer for,
29:32 1
Mills, John Archer, obituary, 36: 1-8
Mills depiction, cyclic monosaccharides,
5253
Mining, plant galactomannans in, 35:342
366 SUBJECT INDEX
Miraculin, 45:290
sweetness, 45:213
as sweet-taste modifier, 45339
Misaki, A,, 46:9
Mitochondria, of yeast cells, 32:137, 141
Mitogenesis, lectin-induced, 3 5 2 9 1
Mitogenic activity
of Phytoluccu lectins, 35:309,3 1 1
of WisturiujZoribundu lectins, 3 5 3 11-3 12
Mixtures, analysis of
advantages of Fourier-transform infrared
spectroscopy, 44:58
by infrared spectroscopy, 4 4 5 8
Miyazaki, N.,46:6
Mn2+
effect on I3C-NMR
N-acetyl-cY-D-neuraminic acid,
47~162-163, 165
o-gluconamides, 47: 146, 148-149
cis-inositol, 47: 141-142
electron-nuclear relaxation methods,
47:136-140
exchange for CaZ+and Mg2' in biological
systems, 47: 134
epi-inositol electron-spin relaxation effect,
47:138-140
interactions
with complex glycopeptides, 47: 155-158
with inositol, see Inositols
with methyl a-and p-D-
galactopyranoside, 47: 150-1 52
medical uses, 47:135-136
Moenuronic acid
natural occurrence of, 42:73
structure of, 42:70
synthesis of, 42:120-121
Moffatt, J.G., 46:6
Molar response factors, in gas-liquid
chromatography, 30: 50-52
Molasses
cane, 3:113-128
cane final, composition of, 8:29 1-2 14
cane-sugar, composition of, 26: 15
caramel from, 47:221
polysaccharide, antitumor activity of, 32:257
Mold
gas-liquid chromatographic analysis of,
28:48
slime, trehalase in, 30:253
trehalose biosynthesis in, 30:239-24 1
Molecular biology, 26:297
Molecular connectivity index, 45229-230, 319
third-order, 45230
Molecular interactions, in aqueous solution,
44:9
Molecular mechanics, 47: 104-106
calculations, 44: 16
Molecular orbital calculations, 45:231
anomeric effect, see Anomeric effect
pyranose forms of sugar in solution,
49:22-23
solvent effect
u form preference, 47:92
2-methoxyoxane conformers, 47:90-92
solvophobic theory, 47:89
supermolecule quantum chemical
calculations, 47:89
Molecular sieves in ketonucleoside synthesis,
42:233
Molecular still, 22:500
Molecular structure, of glycogens, 12:26 1-298
Molecular weight
of asparagus-pea lectin, 35284
of castor-bean lectin, 39272
chemical-ionization mass spectra of
carbohydrates and, 29:82
of concanavalin A, 35152
determination
by gel chromatography, 25:21-30
of glycosides and cardenolides, 21:274
of polysaccharides, 21:494
by mass spectrometry, 21:44
of endo-o-galacturonanase, 33:346,362-364
of endopectate lyase, 33:379
of enzymes, determination of, 23:287
of fava-bean lectin, 35203
of galactomannans, 31:260-261,277-279
of glycopeptides from glycoproteins,
25447452
of lectins, 35:334,336
mass spectrometry and, of carbohydrates,
29:43
of Osage-orange lectin, 3 5 2 6 8
of pectinesterase, 33:339-341
of pectin lyase, 33:380
of polymers, determination of, 25: 14,22
of ricin, 35:271
for starch, determination of, 29:400
of UIex europeus lectin, 35289
of urine constituents, 24:438
 SUBJECT INDEX
Moles, Enrique, 45: 10
Mollusks
a-o-mannosidase activity in. 28:405406
glycolipids, see Glycolipids
sialic acids occurrence, 40: 136-137
Molybdate complexes, in conformational
analysis by circular dichroism, 26:63
Monellin
sweetness, 45:2 13,332
three-dimensional structure, 45:333 -334
Monensin, effect on glycosylation, 40:347
Moniliformis dubius. trehalose biosynthesis in.
30:239
Monoamine oxidase, amino acids of,
27:3 15-3 16
Monoaminohexoses, 48:290
Monobenzoylated isohexides. fragmentation,
49:113
Monoblephurellu elongutu, glycogen, 41:69
Monocarba-disaccharides, synthesis, 48:67- 73
Monocotyledonous plants
cell wall-bound enzymes in, 42:301-302
o-glucans from, 42:293-294
hemicelluloses of, 42:291-292
hydroxy-L-proline-rich glycoproteins of.
42:298-299
pectic polysaccharides of, 42:285, 287
polymer interconnections in cell walls of,
4 2 3 1 4 3 15
Mono-6-deoxy-6-fluorocyclomaltoheptose,
48:22 1
Monodeoxy sugars, taste properties, 45:260
Monoglycerides, 53:396-397
Monoglycosylceramide, from freshwater
bivalves, 44:417
Mononucleotides, 22:307-419; see also
Nucleotides
polymerization, 36: 169-1 70, 184
synthetic, 22:398416
Mono-0-methylsucrose derivatives, taste
properties, 45263
Monosaccharide isothiocyanates, 44:93- I23
I3C NMR, 44:139, 141
'H NMR, 44:139
reduction
by tributyltin hydride, 44: 123
by triethylphosphine, 44: 122
by triethyl phosphite, 44: 122
by triphenyltin hydride, 44:122
spectroscopic properties, 44: 139-1 4 I
367
UV spectra, 44: 139
Monosaccharides, 53:400405, see also
Aldoses
absolute or relative decomposition of, 46:259
acetates. gas-liquid chromatography of,
28:33,49
acetylated, gas-liquid chromatography of.
28:111
with acetylimino group in ring. 23:166
acid degradation, 52:457459
acid hydrolysis, losses, 46:259
acyclic, 'H-and l9F-NMR data for,
46: 158- I59
acyl esters, reaction with ammonia, 31:8 1-92
acylic, carbon-I3 nuclear magnetic
resonance spectroscopy, 4 1 5 9
alkali metal hydroxide adducts, 21:254
alkaline degradation, 52:449455
mechanisms, 5 2 4 5 I
reaction model, 52:453454
ammonolysis
of perbenzoylated, 39:30-3 1
products from acylated, 31:12&131
anomeric protons. nonselective spin-lattice
relaxation rates, 45: 148, 150
anomers
ct and p. 44: 19-20
center of chirality, 52:65
mixtures, 52:67
reference atom and configurational
symbol, 5 2 5 - 6 7
use of a and b, 52:68
biologically significant, carbon- 13 nuclear
magnetic spectroscopy, 41:6465
biosynthesis of, 11:185-262
bivalent and tervalent groups, 52:128
branched-chain
l3C-NMR data for, 46: 172-173
naming branches, 52: 101
numbering, 52: 10 1
parent choice, 5298-101
synthesis by Wittig reaction, 27:294
systematic names, 52:98
terminal substitution, 52: 100
trivial names, 5297-98
carbon- 13 nuclear magnetic resonance
chemical shifts, 41:28
carbon-I3nuclear magnetic resonance
spectroscopy, 41 :27-65
carbon- I3 signals, identification, 38: 1 9-22
368 SUBJECT INDEX
Monosaccharides (continued)
ceramide, 24:395,401
CH,OH group, possible dispositions of,
44: 18-19
circular dichroism, 45278-85
composition of bacterial
hexosoaminoglycans, 47: 174-175
configurational atom, 5257-58
configurational prefixes in systematic names,
52~58-59
conformational analysis, 44: 14
conformation and frequency calculations for,
method, 4451-52
conformationand tautomers, vibrational
spectra used to analyze, 44:25
crystal structure of, 2558-75
cyclic
conformationdepiction, 52:6344,68-69
conformations of chains, 52:64
enantiomers, 52:72
Fischer projection, 5259-60
Haworth projection, 52:6 1 4 3
hydrolysis of, kinetics of, 23:209
Mills depiction, 52:63
modified Fischer projection, 52:6M1
with nitrogen of sulfur in ring, 23: 115-232
ring shape notation, 52:69
ring size, 5259
unconventional Haworth representations,
52:63
variant notation, 52:69-72
D and L, use of, 5257
definition, 5250
deoxy fluorinated, I3C-NMR data for,
46: 172-1 73
derivatives, anomeric C-H bond, carbon-
proton coupling constants, 51:32-33
deuterated
preparation and position of deuterium,
27: 188-189
separation by trimethylsilylation,28:32
dithioacetalsof substituted,physical
constants of, and peracetates,
32: 118-123
of unsubstituted, and their peracetates,
physical constants of, 32: 102-1 15
dolichol-linked, biosynthesis, 40:288-299
electroreductionof, 29: 109-1 17
esters, rearrangement in liquid hydrogen
fluoride, 26:176-188
Fischer projection of acyclic forms,
525657
fluorinated
branched, IH-and I9F-NMR data for,
46: 142- I43
NMR spectroscopyof, 46:73-178
formation of phenolic compounds from,
46:295
furanoid, selective esterificationof,
33:31-35
selective etherification of, 3 3 5 9
gel chromatographyof, 2 5 3 1
glycoenzyme constituents, 27:302,307
glycosides, 52:132-135
glycosidic linkages, 47: 167-168
C-glycosyl compounds, 52:139-140
N-glycosyl derivatives, 52:137-139
glycosyl halides, 52: 136137
glycosyl residues, 52:125
high-performance liquid chromatography,
46:31
hindered rotation of acetyl group in,
containing acetamido in ring, 23:193,
197
honey, 25:289-294
hydrogen bonding, Raman and infrared
spectral study of, 44:29
hydroxyl groups, 44: 18
identification of partially methylated,
38:398402
interaction with concanavalinA, 35181-184
ionic, high-performance liquid
chromatography, 4633-37
isomolar solutions, and related reducing
disaccharides, comparison of sweetness,
45246247
isopropylideneacetals, in gas-liquid
chromatography, 28: 37
isotopic substitution and isotopic labelling,
52:91
kinetic currents of, and derivatives,
29:135-149
labeled, incorporation into polysaccharides,
27: 179
with lactam rings, 23:164
large-scale preparative liquid
chromatography, 46:62
laser-Raman spectroscopy,44:75-8 1
lectin-reactive,classification,35: 141
lipid-linked, in plants, 44:352-355
 SUBJECT INDEX
mass spectra of, 21:46
with acetamido in ring, 23:201
meso forms, 5259
methanolysis, 46:257-258
methylated, quantitation, 38:402407
mutarotation and mass spectra of, 2950
neutral, analytical high-performance liquid
chromatography,46:32-33
occurrence and structure of natural. book,
30:7
optical rotation, 5259
0-substituted, carbon-13 nuclear magnetic
resonance spectroscopy,4152-53
parent structure
choice, 5253
numbering and naming, 52:53-56
partially methylated, structural and sequence
analysis of, 4657
2-phenyl-l,2,3-osotriazolederivatives,
circular dichroism, 45:123
polarography of, 29:126135
preparation, for analysis, 47:174180
preparative liquid chromatography,46:60
proton magnetic resonance spectroscopy of,
27:21-30
proton nuclear magnetic resonance
spectroscopy of, and spectrometersfor,
29:25
pyranoid, selective acylation of, 33:1 9-31
selective etherification of, 3353
pyrolysis of, 34:4546
pyruvated, of bacterial origin, studied using
methanolysis, 46:259
qualitative motional description, 51:83,
89-105
C-H bond length, 51:92
''C spin-lattice relaxation times, 51:96
effective correlation times, 51:92
hexopyranoses, 51:94-96
oligosaccharides,complex glycosides, and
derivatives, 51:97-102
pentofuranoses, 51:95-96
polysaccharides, 51: 102-104
structural features, 51:93-94
quantitative motional description,
51:105-114
quinoxaline derivatives, polarography of,
29~157-162
racemates, 5259
radical ions, 52:131-132
369
radicals, 52:129
reactions of, with beta-ketonic esters and
related substances, 11:97-143
rearrangement of acyloxonium ions in,
26:146-168
replacement of
carbonyl oxygen by nitrogen, 52:89-90
hydrogen at non-terminal carbon atom,
52~87-88
OH at non-terminal, non-anomeric carbon
atom, 52:88
reversion of, to disaccharides,21:444
ring oxygen replacement by
carbon, 52:141-143
nitrogen or phosphorus, 52:140-141
selenoglycosides,52:136
structural and sequence analysis of, 46:57
structure, 35:5,7
as substituent groups, 52:125-128
sulfates, esters with uridine 5'-
pyrophosphates, 28:329
sulfur-or selenium-containing,23:206
synthesis of, 28:295-296
from 2,5-dihydrofurans, 40:61-74
from vinylene carbonate, 40:84-96
terminal substitution, 52:89
thioglycosides, 52:135-136
transport
into Rhodotorula glutinis, 32:155
into Sachharomycescerevisiae,
32:15&155
into yeasts and carriers, 32:150-157
within tissues and excretion in urine, 30:7
tri-and tetra-fluorinated
I3C-NMR data for, 46:177
'H-and I9F-NMR data for, 46:158
trifluoroacetyl derivatives, gas-liquid
chromatographyof, 28:112
trimethylsilylationand methanolysis of,
2854
and mutarotation of, 2838
solvents for, 28:30
himethylsilyl ethers, gas-liquid
chromatographyof, 28:4149,102-1 10
tritiated, preparation and localization of
tritium, 27:183-187
trivial names with systematic equivalents,
52:172-176
unequal substitution at non-terminal carbon
atom, 52:88-89
370 SUBJECT EVDEX

Monosaccharides (continued) Mountain-pine pollen, polysaccharides of,

unsaturated, 52:91 24:363
double bonds, 52:92-95 Mucilage, 22:5,24:333-379,44:375-376
triple bonds and cumulative double bonds, commercial, 13:265-287
52:95-96 constitution, 35:6
utilization by yeasts, effect of temperature cress-seed, 24:336-369
changes on, 32:230 galactomannan polysaccharides, history of,
Monosaccharide thiocyanates, 44: 123-139 31:244
Monoses, configuration of, 2153 gel structure of, 24:326
Monosulfide, bis(2-deoxyaltrosid-2yl), 25: 1 39 hydrocolloids, see Hydrocolloids
Monotropein, rubidium salt, crystal structure linseed (flax seed), 24:336
of, 25:90 polysaccharides from, 24:369
Monro model of plant primary cell-wall, mustard-seed, 24:336
42:313 plants, 4:243-29 I
Monuron gas-liquid chromatography of, 28:62
effect on sugarcane, 21:422,426 trifluoroacetic acid in hydrolysis of.
as herbicide, 21:405 28: 16
Morgan-Elson color reaction, 24:8 slippery-elm, 24:371,41:7
Morpholine structure of plant, 35:9
N-acetyl-, solubility of sucrose in, 27: 119 Mucins
N-butyryl-, solubility of sucrose in, 27: 119 backbone and core sequences, 50:3 16-322
N-formyl-, solubility of sucrose in, 27: 1 19 gas-liquid chromatography of, 28:85
N-methyl-, as solvent for sucrose, hydrolysis, by hydrochloric acid,
27:117-118 46:266-267
N-propionyl-, solubility of sucrose in, isolation of carbohydrates from, on
27:119 analytical-scale columns, 46:60
as solvent methanolysis, 46:258
for sucrose, 27: 1 17-1 18 oligosaccharides
for sugars, 27: 107 liquid chromatography separation,
sugar derivatives, 25:403 46:4243
4 4 3,4,5-trimethoxybenzoyl)-,synthesis as sialylated, fractionation, 46:46
tranquilizer, 28:9 structure, 50:3 16-322
Morquio syndrome type B, 'H-NMR 'H-NMR-spectral and mass
spectroscopy spectrometric analysis, 50:322-328
glycoprotein (compound 7), 41:219, structure, 37:3
232-233,235-237 Muconic acid, 2,5-dihydroxy-, polarography of.
glycoprotein (compound 1 l), 41:219, 29: 170
232-233,244246 Mucopeptides, 24:3 14
glycoprotein (compound 15), 41 :2 19, Mucopol ysaccharides
256-259 analysis by gas-liquid chromatography,
glycoprotein (compound 18), 41:219, 28:4344
262-266 biosynthesis of, 26:432439
glycoprotein (compound 19), 41:219,263, deamination and structure of, 31:74
266-268 formation in cell wall by Golgi bodies,
glycoprotein (compound 20), 41:2 19,262, 26:340
267-268 Mucopolysaccharidoses, glycosaminoglycans
Mossbauer spectroscopy, 53:287 in, 25:475477
Mosses, formation of humus from, 46:323-324 Mucoproteins
Motarotation constant, 23: 17 history, 33:8
of sugars, 23:53-56 from Phuseolus vulgaris,35:292
 SUBJECT INDEX
Mucoran, 41: 10 1-1 02
Mucor rouxii, mucoran, 41:lOl-102
Mucous secretions, viscosity, sialic acid effect,
40:218
Mucus glycoproteins, 47:345-347
amino acid composition, 47:349
basic unit, 47:349-352
coiled structure, 47:350-352
containing proline residue, 47:350-35 I
prolyl residue, 47:350
carbohydrate side-chain composition
variability, 47:35 1-3.52
components, terminology, 47:353
composition, 47:347-349
electron microscopy, 47:368-369
gross conformation in solution, 47:370-373
heterogeneity, 47:374-380
Herdan relations, 47:37.5
InJ versus x,47:378-379
interactions with other macromolecules,
47:380
molecular weight distribution. 47: 3 78-3 79
polydispersity and self-association
behavior, 47:377-380
sedimentation coefficient distribution,
47:376-377
terminology, 47:374
thermodynamic non-ideality, 47:3 74-375
importance, 47:345-346
molecular weights, 47:349, 356-367
distribution, 47:378-379
light-scattering, 47:35&358
low-speed sedimentation equilibrium.
47: 359-367
meniscus-depletion technique, 47:365-366
partial specific volume, 47:361
Rayleigh interference optics, 47366
relative techniques, 47:358-359
scanning absorption optics, 47:365-366
thermodynamic non-ideality effects.
47:365
virial coefficient, 47:366
mucin component, 47:348
as polyelectrolytes, 47:373
properties, 47:346
Rayleigh equilibrium interference patterns,
47: 371-3 78
secondary structure, 47:350-35 1
sialylated saccharide-alditols, structures,
45:64
371
tertiary structure
branched models, 47:353-356
linear models, 47:367-370
molecular weights, 47:356-367
star average, 47:361
subunits, 47:3.52-353
T-domains, 47:353
thiol reduction, 47:352-353
Muellitol, 47:6, I5
Mukaiyama condensation methods, glycosyl
fluoride synthesis, 48: 104-107
Multiple internal rotations model, 51: 125
Multirotation. term, 23: 12
Mung bean
cellulose biosynthesis, 41: 108
high-molecular-weight precursors, 41 :138
precursors, 41: 126
cell wall studies on, 42:308-309, 3 1 I ,
320--321, 327, 331
development physiology of, 42:343-344
enzymes from, 32: 12
root of, in biosynthesis of cellulose,
26: 324-3 25
from seedlings, 26:373. 387,391, 397,
406
seedlings, enzyme from, 35:353
sucrose synthetase from, 26:367
uridine 5 -pyrophosphates of o-glucose, D-
galactose, o-xylose, and L-arabinose in,
32:9
Muramic acid, 24:3 14, 48:303
l,h-anhydro-. synthesis of, 34: 124
circular dichroism, 45: 1 12- 1 I3
as donor, 50:8 1,84,90-91
ethanethiolysis of analog of, 32:26
glycosides, synthesis. 50:8 1. 84, 90-91
mycobacteria, 48:308-3 10
N-acetyl-
crystal structure, 25:93, 32:364
ester o f uridine 5-pyrophosphate,
isolation of, and derivatives, 28:328
6-0-(2-acetamido-2-deoxy-~-~-glycosyl)-,
crystallography of, 25:93
N-acetylbenzyl-. crystallography of, 25:93
N-glycolyl-. ester of uridine 5-
pyrophosphate, isolation of, 28:329
synthesis of, 22: 138
Murein, 24:3 14
Murine myeloma, immunoglobulins,
31:313-346
3 72 SUBJECT INDEX
Muscarine
D-(-)-, Erom 2-amino-2-deoxy-~-glucose,
27:208
L-(+)-, from 2-amino-2-deoxy-1.-glucose,
27:207
synthesis of,deamination in, 31:71
Muscarine-related compounds, preparation of,
34: 105
Muscle cells, o-fructose metabolism in, 34:298
Mushroom lectin
carbohydrate-binding specificity, 35: 145
interaction with cellular glycopeptides,
3 5 3 18
with erythrocyte glycopeptide, 35:320
isolation, purification, and structure, 3 5 3 0 8
Mustard
cell-wall studies on, 42281-282
polysaccharide from seed of, 24:374
Mutagenicity
caramel, 47:267-269
melanoidins, 47:269-270
Mutansucrase, 51:141
S. mutuns mutan synthesis, 51:14.7
Mutants, genetic, in cellulose biosynthesis,
41: 143-144
Mutarotase
effect on mutarotation of sugars, 24:3 1,
63-64
mutarotation coefficients and gas-liquid
chromatography in assay of, 28:40
Mutarotation
of u-D-glucose
in cresol and pyridine, 27:104
history of, 23: 12
of 2,5-anhydro-a/dehydo-aldoses, 2 5 2 I3
anomerization and ring change as basis for,
23:13
caramel, 47:249
catalysis by acids and bases, 24: 14
catalytic coefficients ratios for sugars, 24:30
complex and simple, 23: 19
determination of mechanism of reaction by
use of isotope effect, 24:32
of o-fructosylamines, 22:271
of D-glucose, molten and below melting
point, 22497
electronic density and, 24:37
entropy of activation in water-catalyzed,
24:37
equilibria and thermodynamics of, 24:5 1
in gas-liquid chromatography, 28:384 1
of glycoside nitronates, 24: 121
of glycosylamines, 24:47
isotope effect on, 24:28
kinetics of, 23: 16
measurement of, 23:47,44:25
mechanism of, 24:35,38,4042
determination by use of isotope effect,
24:32
of monosaccharides, and mass spectra, 29:50
mutarotase effect on, of sugars, 24:3 1, 63-64
polarography and, 29:139-141
ring contraction and expansion by, 24:46
of sugars
in aqueous solution, mechanism of, 24:35
in N,N-dimethylformamide, 24:6 1
in pyridine, 24:61
in solution, 23: 11-57, 24:13-65
solvents for, 27:120
thermal, ofD-fructose, 22:231, 234
of 5-thio-o-
ribopyranose, 23:215
xylopyranose, 23:208
Mycaminose, 23:273
D-, biosynthesis, 35: 122
synthesis of, 28:297
Mycaminoside
methyl WL-, synthesis, 40:117
methyl DL-,synthesis, 28:297, 40:32
Mycaminosyl-tylonolide, 5-0-4-deoxy-4-
fluorO-p-D-, 48~230-231
Mycaral, L-, synthesis of, 42:103
Mycarose
5-C-methyl-
DL-,synthesis, 40:60
3-epi-o~-,synthesis, 40: 14
D-, synthesis of, 42:79
DL-, synthesis, 40:14-15,20-21,59
~ - @ - D L - , synthesis, 40:20-21, 59-60
L-, 50~158-159
synthesis of, 3582-83, 88,40:114, 129,
41:9,42: 103
natural occurrence of, 42:72, 76
structure of, 42:72
synthesis of, 42:78-79, 115
Mycaroside
methyl 3,4-anhydro-P-, 25: 169
methyl-DL-, synthesis, 40:14-15, 114
Mycinamicins, synthesis, 48: 110
Mycinose, 21:173, 179
 SUBJECT INDEX
Mycobacteria, 51: 170
muramic acid, 48:308-310
polysaccharides, 48:308
Mycobacterium avium
glycolipid antigenicity, 51:229-23 1
glycopeptidolipids, see Glycopeptidol ipids
morphological variations, 51:232
rough mutants, 51:232
Mvcobacterium bovis, containing
phenolphthiocerols, 51:202
M~~cobacteriumfortuitum, trehalose-containing
lipo-oligosaccharides, 51: 195
Mycobacterium gastri, containing
phenolphthiocerols, 51:203
Mycobacterium gordonae, trehalose-containing
lipo-oligosaccharides, 51: 195-1 96
Mycobacterium haemophilum, containing
phenolphthiocerols, 51:203
Mycobacterium kansasii
containing phenolphthiocerols, 51 :202
trehalose-containing lipo-oligosaccharides,
51~188,192-193
Mycobacterium kansasii, glycolipids, f.a.b.-
mass spectrometry, 4 5 5 7
Mvcobacterium leprae
antigenicity, 51:230-23 1
containing phenolphthiocerols, 51 :200-20 I
microscopic properties, 51:233-234
phthiocerol lipids in, 51:234-235
Mycobacterium malmoense, trehalose-
containing lipo-oligosaccharides,
51:193-194
Mvcobacterium marinum. containing
phenolphthiocerols, 51:202-203
Mycobacterium phlei, lipopolysaccharide
degradation by Lossen rearrangement,
31:238
methylation analysis of, 30: 15
Mvcobacterium smegmutis
glycolipids, f.a.b.-mass spectrometry,
45:56-57
trehalase from, 30:25 1
trehalose and glycogen during growth of,
30:255
trehalose hiosynthesis in, 30:242. 244
trehalose 6-phosphate phosphatase from,
30:245
trehalose-containing lipo-oligosaccharides,
51: 197-198
Mycobacterium szulgai, trehalose-contai ning
373
lipo-oligosaccharides, 51: 194
Mycobacterium tuberculosis
antigenicity, 51:23 1
containing phenolphthiocerols, 51:202
oligosaccharides, mass spectrometry of,
29:96
polysaccharides from, 3:3 11-336
Maurice Staceys work, 52:7-8
trehalose biosynthesis in, 30:242
trehalose esters and cord factor in, 30:235
trehalose-containing lipo-oligosaccharides,
51: 196-1 97
Mycodextran, 23:374
acetate, circular dichrolism, 45: I2 1
crystal structure bibliography, 33:394,
35:378
Mycodextranase, 23 :31S.44:265
induction of, 30:262
specificity of, 30:345
Mycogalactan, 23:398
Mycoglycosphingolipids. 24:408
Mycolic acid, trehalose ester, in mycobacteria,
30:235
Mycoplasm pneumoniar, binding specificity,
50:339
Mycoribnin, as inhibitor in trehalose
biosynthesis, 30:242
Mycoside G, gas-liquid chromatography of,
28: 55
Mycosides, methanolysis of. 28: 18
Mycospocidin, inhibition of protein
glycosylation, 40:339-340
Myeloma IgE glycopeptide, structure of human,
37: 180
Myeloma IgM. structure of human, 37: I80
Myeloma proteins
human gG, 44:232
purification by affinity chromatogrphy,
39:44&447
Myristic acid
3-hydroxy-, in lipid A, 26:410
methyl ester, esterification of sucrose with,
33:44
Myronate, potassium, crystal structure
bibliography. 30:452
Myrothecium vernrcaria, o(-L-
arabinofuranosidase of. 42:388
Mytilitol
hexaacetate, proton magnetic resonance
spectroscopy of, 27:24
374 SUBJECT INDEX
Mytilitol (continued)
natural occurrence of, 42:73, 76
structure of, 42:73
synthesis of, 42:78-79, 115
Myxococcusfulvus, lipopolysaccharide, mass
spectrometry of, 29:66
Myxomyceteae, polysaccharides of, 23:368
Myxomycophyta, polysaccharides of, 23:368
N preparation and activity against resistant
Naphthalene
2-P-o-ribofuranosyl-, preparation of, 33: 160
9,lO-trans
cis-2-amino-decahydro-, deamination of,
31:16-17
frans-2-aminodecahydro-, deamination of,
31:15, 17
1-Naphthaleneacetamide, effect on abscission
and ripening, 21:429
1-Naphthaleneacetic acid, effect on abscission
and ripening, 21:429
on cell-wall polysaccharides, 21:38 1
on sugarcane, 21:424
1-Naphthol, complex with V-amylose, crystal
structure bibliography, 33:392
Napthoic acid, esters of 0-(diethylamino-ethyl)
polysaccharides, 29:325
( I-Napthyldiphenylmethyl) group, reductive
cleavage, 39:48
Narbomycin, sugar components desosamine,
28:299
Naringenin, as plant-growth substance, 21:
410
Naringin
dihydrochalcone
structural features, 45:289
sweetness, 45279
taste properties, 4 5 3 11
Nasturtium
cell-wall studies on, 42:287
polysaccharide from seed of, 24:374
Neamine
biological transglycosylation of, 30: 123
3,4-dideoxy-, N-acylation of, 30: I75
minimum inhibitory concentrations of,
30:222
synthesis and activity against resistant
bacteria, 30: 168
minimum inhibitory concentrations of,
30:222
N-acyl derivative, activity against resistant
bacteria, 30:174
neomycin A and, 30: 1 16
1-N- (~-4-amino-2-hydroxybutyryl)-,
minimum inhibitory concentrations of,
30:222
I -N-[(S)-4-amino-2-hydroxybutyryl]-, from
butirosins, antibacterial activity, 30: 132
bacteria, 30: 176
30-methyl-, preparation and antibacterial
activity of, 30: 166
4-O-methyl-, preparation and antibacterial
activity of, 30: 166
from ribostamycin, 30: 130
structure of, 30:188
synthesis of, 30: 1 18, 142
Nebramine, from tobramycin, structure of,
30: 124
Nebramycin factor 6, see Tobramycin
Nebrosamine, from tobramycin, 30: 124
Nebularine
crystal structure bibliography, 32:373
5-phosphate, 22:327
Nectar
flower, gas-liquid chromatography of, 28:43
sugars in, 25304
Nef reaction, 24:69,72, 11 1, 127, 134
synthesis of 2-deoxy sugars by, 21: 150
Negamycin
(+)-, 50:201
synthesis, 40: 18
Neighboring-group reactions, 26:127, 130
complex and simple, 22: 1 1I
effect of halogen on reactivity, 22:207
participation, in sugar reactions, 22: 109-175
in syntheses, 29:3,7
Neiifolin, 21:286
Neisseria meningitidis
capsular polysaccharides, conformations,
41:179
molecular size and immunological
specificity, 41: 182-184
structure, 41:158-164
0-deacetylated capsular polysaccharide,
47: 185
polysaccharide vaccines, 41: 193-195
structure of polysaccharide antigens, 41:200
 SUBJECT INDEX
Neobiosamine B
deamination and structure of, 31:7S
paromobiosamine I and, 30: 1 I8
Neobiosamine C, paromobiosamine II and,
30:118
Neogitostin, 39:302
Neoglucobrassicin, 21 :392
Neoglycoconjugates
antigenicity, 51:229-23 1
glycolipid-based, 51 :203-229
glycopeptidolipid haptens, 51:2 19-220
leprosy-specific, synthesis, 51:204-2 I0
based on 4-aminophenol glycosides,
51:206-207
linker-arm method, 51:205-207
reductive amination, 51:204-205
related to glycopeptidolipids of M. avium
complex, 51:211-227
based on serovar-specific outer regions,
51:211-220
complete oligosaccharide haptens,
51:221-227
synthetic strategy, 51 :2 12
other, synthesis and immunoreactivity,
51:227-229
Neoglycoproteins, 37:225-28 1
applications, as affinity materials,
37:271-279
as antigens, 37:241, 259-267
binding to
liver membranes, 37:273-275
purified binding protein, 37:275-276
as cytochemical markers, 37:279
general, 37:257-259
potential, 37:279-28 1
as substrates
for glycoprotein clearance in iivo.
37:270-273
for lectins, 37:268-269
uptake by cells in vitro, 37:276-277
biological activity, 37:255-257
definition, 37:226
physicochemical properties, 37:254255
preparation, active ester method, 37:241-242
acyl azide method, 37:240-241
amidination, 37:235,246-248
amination, 37:242-245
bifunctional reagents, 37:248-25 1
carbodiimide-facilitated amidation.
37:236-238
37s
desired characteristics of modification
reactions, 37:228-229
diazo coupling, 37:229-234
guanidination, 37:245-246
isothiocyanates, 37:224-225
mixed anhydride method, 37:238-240
summary, 37:252-254
Neobesperidin dihydrochalcone
after-taste. 45:265, 341
relative sweetness, 45:332
structural features, 45:289
sweetness, 45:279
structure relationship, 45:24 1
taste properties, 45:288
third structural feature comprising postulated
glucophore in, 45:234
P-Neohesperidose, taste properties, 45:278-279
Neolactotetraosylceramide
biosynthesis, 40:25 1-252
catabolism, 40:274-276
Neomycins
A, and C, LP, and LP,. stereochemistry of,
30:116
B
allkyl and aralkyl derivatives, preparation
of. 30: 179
3-deoxy-, minimum inhibitory
concentrations of. 30:223
preparation and antibacterial activity of,
30: I72
sterochemistry of, 30: 1 16
biosynthesis, 35: 1 15-1 I8
determination by trimethylsilylation, 28:28
discovery of, 30:112
N-methanesulfonate derivatives, preparation
and activity of, 30: 179
Neosamine, B and C, synthesis of, 30: 1 16
Neosaminide C. methyl 4-deoxy-~1.-,synthesis,
40:47
Neplanocin A, SO: 196
Nervon, 24:398-399
Neuberg, Carl, obituary of, 13: 1-7
Neuraminic acid, 23: 150
5-acetamido-3,5-dideoxy-3-fluoro-,
preparation, 38:238
N-acetyl-u-
(2+3)-P-~-galactopyranosyl-( 1+ 4 ) - ~ -
glucopyranose, 51 :97-99
(2+6)-P-~-galactopyranosyl-( 1+4)-0-
glucopyranose, 51:97-99
376 SUBJECT INDEX
Neuraminic acid (continued)
N-acetyl-P-, 47:34, 158-165
binding to Gd3+,computer modeling,
47: 160-1 6 1
Gd3+effect on I3C-NMR, 47:159-160,
164-165
interaction with CaZ' and Eu3+,47: 160
Mn2+effect on "C-NMR, 47: 162-163,
165
structure, 47: 158
acylated, in gangliosides, 24:413,415
anti-recognition effect, 40:220
deamination of methyl glycoside of, 31:35
derivatives, 24:417
fluorinated, I3C-NMR data for, 46:177
4,9-di-O-acetyl-N-glycolyl-, occurrence,
40: I45
7,9-di-O-acetyl-N-glycolyl-, occurrence,
40: I43
8,9-di-O-acetyl-N-glycolyl-, occurrence,
40: I45
gas-liquid chromatography of, 28:56
history, 40: 132
hydrolysis, 46:254
linkages, structural analysis, by acid
degradation, 38:408409
by methylation, 38:401
liquid chromatography, 46:36-37
mass fragmentography, 38:413415
methoxy-, trihydrate, crystal structure
bibliography, 30:465
methyl, composition in aqueous solution,
42:42,49
methyl P-glycoside, isolation, 40: 132, 148
N-acetyl-, 23:151,24:8,417,419
9-azido-9-deoxy-, synthesis, 40: 178
biosynthesis, 40: 1 7 6 181
composition in aqueous solution,
42:4142
D-, carbon 13 nuclear magnetic resonance
spectroscopy, 41:64
detection, 38:338-340
4,9-di-O-acetyl-, occurrence, 40: 145
7,9-di-O-acetyl-, occurrence, 40: 143-144,
145
8,9-di-O-acetyl-, occurrence, 40: 144-145
enzymic modification, 40: 181-185
ester with cytidine 5'-phosphate, 28:332
3-flUOrO-, 22:199
as enzyme inhibitor, 22:212
history, 33:5-7
isolation, 40: 132
mercaptalation of, 32:26
4-O-acetyl-, occurrence, 40:145
7-O-acetyl-, occurrence, 40: 144
8-O-acetyl-, occurrence, 40: 145
9-O-acetyl-, occurrence, 40: 143-145
4-O-acetyI-9-O-lactyl-, occurrence,
40:145, 160
occurrence, 40:141
4-O-methyl-, synthesis, 40: 146
8-O-methyl-, occurrence, 40: 146
8-O-methyl-, structure and mass spectrum
of, 29:47
peracetylated methyl ester methyl
glycoside, fragmentation and mass
spectrum of, 29:46
reversible cleavage, 40:158,211-214
structure, 38:328-329,40: 132
trimethylsilylation of, 28:28-29
7,8,9-tri-O-acetyl-, occurrence, 40: 143,
145
trisaccharide esters with uridine 5'-
pyrophosphate, 28:33 1
5-N-acetyl-4,7,8,9-tetra-O-acetyl
OL-D-,
nz-bromobenzyl glycoside, crystal
structure bibliography, 34:36 1
N-(benzyloxycarbony1)-, 23: 150
N-(fluoroacety1)-, preparation, 38:252
N-glycolyl-, 24~418,420
biosynthesis, 40:181, 183
ester with cytidine 5'-phosphate, 28:332
isolation, 40:132
mass spectrum of, 29:47
occurrence, 40: 142-143
8-O-methyl-, occurrence, 40: 146
8-O-sulfo-, occurrence, 40: 146
trisaccharide esters with uridine 5'-
pyrophosphates, 28:33 1
4-O-acetyl-N-glycolyI-, occurrence, 40: 145
7-O-acetyl-N-glycolyI-, occurrence, 40: 145
9-O-acetyl-N-glycolyI-, occurrence,
40: 143-1 44
occurrence, 40: 141
oligosaccharides containing, structure
analysis of permethylated, 38:393
in polysaccharides and glycoconjugates,
31:187
and related compounds, 13:237-263
structure of, 29:261
 SUBJECT INDEX
7,8,9-hi-O-acetyl-N-glycolyl-, occurrence,
40:143, 145
Neuraminic acid glycosides, synthesis, 48: 1 14
Neuraminic lactone
N-acetyl-, 24:4 19
N-(benzyloxycarbony1)-, 24:420
Neuraminidases, 24:4 I8,44:208
amino acid sequence, 40: 198
in carbohydrate degradation, 38:413
deficiency, 40:207
degradation of gangliosides, 40:27 1 274
~
effect on glycoproteins, 37:161-163
immobilized, 40: 149,210
inhibitors, 40:209
interaction with glycosidases, 48:35 1-353
molecular weights, 40: 198
occurrence, 40: 195
pathophysiological significance, 40:206-2 1 I
purification, 40: 149-150, 196, 198
receptor-destroying enzyme, 33:5-6
substrate specificities, 40:200-2 10
use of, 25:463
viral, 40:210
Neuronal cells, glycoproteins and glycopeptides
from, isolation and properties of, 35326
Neurospora crassa
polysaccharide, 41:69, 71, 73
trehalase from, 30:25 1
Neutral sugars, hydrolysis of, 46:262- 263
Neutramycin, 21: 173
Neutron irradiation, starch, 51:263-264
Newcastle disease, effect of glycosylation
inhibition, 40:372
Newman projection for phenyl ring, 42: I64
N-Glycoproteins, 43: I36
N-Glycosyl linkage, 43:4, 10
model compounds, 43:lO-11
Nickel, Raney, see Raney nickel
Nickel carbonyl, reduction of
polyhalogenomethyl groups, 28:304
Nicotinamide adenine dinucleotide
for enzymic reduction and labeling with
hydrogen isotope, 27: 132
proton magnetic resonance spectroscopy
of reduced, 27:37,57
and phosphate, in isolation of cytidine
pyrophosphate glycosyl esters, 28:3 I6
in transformations of glycosyl groups,
28:364-369
Nicotinamide mononucleotide,
377
monodeuteriated, proton magnetic
resonance spectroscopy of, 27:38
Nicotinic acid, carbohydrate esters,
ammonolysis of, 31:88-89, 124
Nigeran, 23:374
antitumor activity of, 32:259-260
Barry degradation of, 31:203
circular dichroism, 4 5 8 9
crystallography of, 22:478,33:394, 35:378,
40:384
fungal, 41:69-70
structure of, 30:345
Nigerobiouronic acid, from dextrans, 30:409
Nigerose
acetolysis of, 22:21
p-, octaacetate, preparation of, 34:261
from dextran, 30:378-379,388,393
by acetolysis, 31: 197
in honey, 25:295, 300
liquid chromatography methods for analysis
of, 46:33
Nitrate group
displacement in carbohy-drates by halogen,
22:181
removal of. without desulfonylation, 23:266
Nitrates
ofstarch, 13:331-345
of sugars, 12:117-135
Nitration, of o-fructose, 22:259
Nitric acid
1,4:3,6-dianhydrohexitolesters, 49: 133-
135
in hydrolysis of polysaccharides, 28: 15
Nitriles
a-amino, mutarotation of, 23: 13
acetates, gas-liquid chromatography of,
28:66
acylated
of aldonic acids, 4: 119-1 5 1
sugar, ammonolysis and free sugar
formation, 31534
amino, hydrogenation of, 24:9
ammonolysis of acetylated, mechanism of,
31:110
of acylated aldobionic acid, 31:97
of acylated aldonic acids, 31:82-85
as solvents for sugars, 27: 112
2,2,2-Nitrilotriethanol, as matrix for f.a.b.-
mass spectrometry, 45:26-27
Nitrites, carbohydrate, photolysis, 38: I77
378 SUBJECT lNDEX
Nitroalkanes in branched-chain sugar synthesis,
42: 107- 109
Nitro-alkenic sugars in synthesis of branched-
chain sugars, 42:99-100
Nitroanilides, as protecting groups for
carboxylic acids, 46:202
Nitroanilines
location of third hinding-site in, 45:234-23 5
of structure X-C,H,-Y, taste properties,
45:304-306
sweetness-structure relationship, 45:303-306
third structural feature comprising postulated
glucophore in, 45:234
5-Nitroanilines
2-propoxy-
derivatives, sweetness, 45:303-304
relative sweetness, 45:35 1
2-substituted
binding to sweet-taste receptor, 45:336
sweetness, 45:228-23 I , 233
correlation with Hammett constant and
hydrophobicity, 45:225
structure relationship, 45:303
Nitrobenzyl polymer, a-bromo-2-, 46: 199
2-Nitrobenzylidene derivatives, photochemical
cleavage of, 46: 188
2-Nitrobenzaldehyde, photoinduced oxidation-
reduction of, 46: 181
Nitrobenzene, 2-amino-4-, sweetness, AH, B
system in, 45:221
Nitrobenzene derivatives
2-amino-4-, sweetness, 45:226
4-amino-2-, sweetness, 45:226
Nitrobenzenesulfonate, in displacement
reactions of carbohydrates, 24: 140
3-Nitrobenzoic acid, cyclodextrin inclusion
complexes with, 46:221
4-Nitrobenzoic acid, cyclodextrin inclusion
complexes with, 46:221
p-Nitrobenzoyloxy group, participation in sugar
reactions, 22: 1 18
2-Nitrobenzy1, photochemical cleavage of,
46: 193
2-Nitrobenzyl carbonates, photochemical
cleavage of, 46:19@-191
2-Nitrobenzyl ethers, 46:181-182
photochemical cleavage, 46:181-183, 198
proposed mechanism for, 46: 183
2-Nitrobenzyl glycosides
photochemical cleavage of, 46: 183
proposed mechanism for, 46: I83
2-Nitrobenzyl group. for protection of
carboxylic acids, 46: 198
2-Nitrohenzylidene derivatives
in protection of diols, 46: 188
utilized in syntheses leading to trisaccharides
of biological significance, 46: 189
2-Nitrobenzyloxycarbonyl group,
photochemical cleavage of, 46: 193
2-Nitrobenzyl phosphoric esters, in nucleotide
synthesis, 46:203
Nitro compounds, photolysis, of carbohydrates,
38:160, 165-176
Nitrogen, ring oxygen replacement by,
52:14&141
Nitrogen atom, participation in sugar action,
22: I43
Nitrogen compounds, 53:358
of cyclic monosaccharides, 23: 1 15-232
of D-fructose, 22:262
as solvents for sugars, 27: 1 12-1 23
Nitrogen heterocycles, synthesis from
saccharide derivatives, 25:3 I 1-349,
351-405
Nitrogen nucleophiles, for oxirane aldoses,
25: 125
Nitro group
reaction that proceed with retention of, in
nitro sugars, 24:115
in sugars, reactions which alter or remove,
24: 109
Nitroguanidino group, participation in sugar
reactions, 22: 149
2-Nitropheno1, cyclodextrin inclusion
complexes with, 46:222-224
3-Nitropheno1, cyclodextrin inclusion
complexes with, 46:22 1
4-Nitropheno1, cyclodextrin inclusion
complexes with, 46:221
3-Nitrophenolate ion, cyclodextrin inclusion
complexes with, 46:221
4-Ni trophenolate ion, cyclodextrin inclusion
complexes with, 46:22 I , 223-224
3-Nitrophenyl esters, photosolvolysis of,
46:203
(2-Nitrophenyl)ethylenedioxy acetals, 46: I95
removal of, by strong base, proposed
mechanism for, 46: 196
(2-Nitropheny1)ethylene glycol, 46: 195
(p-Nitrophenyl)hydrazones, liquid
 SUBJECT INDEX
chromatography, pre-column
derivatization procedures, 46:68
3-Nitrophenyloxycarbonyl,46: 193
Nitrophenyl phosphate, 2-(dimethylamino)-4-,
selective phosphorylation of adenosine
with, 33:49
Nitrosyl chloride, reaction with glycals, 24:206
Nitrous acid, deamination of amino sugars by,
25: 181-194
Nitrous oxide, reactions with a-hydroxyalkyl
radicals, 37:21-22
6-Nitroveratryloxycarbonyl group,
photochemical cleavage of, 46: I93
6-Nitroveratryl urethans, photochemical
cleavage of, 46: 193
Nitryl iodide
nitro sugar preparation with, 24:94,99
reaction with unsaturated carbohydrate
derivatives, 28:270, 299
NK-1001 (antibiotic), synthesis of, 30: 160
Nocardic acid, trehalose ester, in mycohacteria,
30:235
Nogalonamide, N-( p-bromobenzy1)-, crystal
structure bibliography, 30:454
Nogalose
D-, synthesis, 42: 120
natural occurrence of, 42:72
structure of, 42:70,7S
synthesis of, 42: 120
Nojirimycin, 23:I 16, 132-133,50:154-155,
51:150
biological activity and structure of.
42: 136-137
composition in aqueous solution, 42:49
proton magnetic resonance spectroscopy of
reduction product of, 27:27
synthesis, 40:96
Nojirimycin glucosidase inhibition,
48:335-336
Nomenclature, 52:44-177; see also
Monosaccharides; Oligosaccharidrs;
Polysaccharides
acetals, ketals and thio analogues,
52: 123-124
aldaric acids, 52:110-112
alditols, 52: 102-103
aldonic acids, 52: 103-106
of aldose oxiranes, 25: 110
aldoses, 52:72-74
amino sugars, 5284-86
379
anhydrides
intermolecular, 52: 12&121
intramolecular, 52: 1 18- 120
carbohydrate, 26:20
of carbohydrate boronates, 35:36
carbohydrates containing additional rings,
52:143-147
bivalent substituent prefixes, 52: 143-145
ring fusion methods, 52:145-146
spiro systems, 52: 1 4 6 147
commissions, 52:49
of conformers of furanoid sugars, 26: I09
of sugars, 26:76-8 1
conventions. 52:52
of cordycepin and cordycepose, 31: 149
cyclic acetals, 52:121-122
cyclic forms, 52:4849
of o-apiose, 31: I37
of deoxy sugars, 21:144, 52:SO-83
of o-galactanases, 32:292
dialdoses. 52:74-75
diketoses, 52:78-79
disaccharides, 52: 148-1 51
enzyme. 33:323-327
of enzymes, 23:306
exo-glycosidases, 40:285
furanose and pyranose, 35:5
for furanose rings, 30:466
glycosides. 52: 132-135
of glycosphingolipids, 24:383,40:237-244
C-glycosyl compounds, 52: 139- 140
N-glycosyl compounds, 52: 137-1 39
of glycosyl esters of nucleoside
pyrophosphates, 28:309
hemiacetals, hemiketals and thio analogues,
52: 122-123
historical development, 52:4849
ketoaldonic acids, 52: 106107
ketoaldoses, 5279-80
ketoses, 52:75-77
of L-arabinanases, 32:279
of L-ascorbic acid, 37:82
of lectins, 35: 145- 146
of nitro sugars, 24:67
N-substitution, 52:117-118
of nucleosides, 24:228
0-substitution, 52: I 12-1 17
of pectinesterases, 33:324
of permethylated glycosides. 29:43, 84
for pneumococci, 33:297
380 SUBJECT INDEX
Nomenclature (continued)
of protein-carbohydrate compounds in urine,
24:435,437
radical ions, 52:131-132
radicals, 52: 129
ring oxygen replacement
by carbon, 52:141-143
by nitrogen or phosphorus, 52: 140-141
selenoglycosides, 52: 136
sulfates, 52:116-117
of tartaric acid, 21:34
thioglycosides, 52: 135-136
thio sugars and chalcogen analogues,
52:86-87
trivial names with systematic equivalents,
52: 172-176
of unsaturated sugars, 24:200
uronic acids, 52:108-110
Nomilin, taste properties, 4 5 3 13
Non-carbohydrate substrate, see Substrate
3-Nonene-2,5-diol, 5-butyl-1 methoxy 1-,
synthesis, 39:141
3-Nonene- I ,2,5-triol, 5-butyl-, synthesis,
39: 142
Non-2-enonate
ethyl 5-acetamido-3,5-dideoxy-~-g~ycero-o-
gulacto-, synthesis by Wittig reaction,
27:274
ethyl 2,3-dideoxy-o-glycero-o-gluco-,
synthesis by Wittig reaction, 27:255
Non-2-enopyranulosonic acid, 5-acetamido-
3,5-dideoxy-o-glycero-~-gulucto-,
occurrence, 40:147, 185
Non-3-enulose, 1,3,4-trideoxy-o-
galucfo-, 5,6,7,8-tetraacetate, synthesis by Nonulosonic acid
Wittig reaction, 27:245
gluco-,5,6,7&tetraacetate, preparation of,
27:245
Non-3-enulosonic acid, 3,4-dideoxy-o-
gulucro-, and methyl and isobutyl esters,
pentaacetates, syntheses by Wittig
reaction, 27:267
gluco-, methyl ester pentaacetate, synthesis
by Wittig reaction, 27:267
Nonglycosylic phosphate, lipid A backbone,
50:223-224
Nonitol, (hydroxymethy1)-branched, natural
occurrence of, 42:76
Non-sugar aglycons, 48:299-300
Nontransition metals, 53:322-326
Nonuloaonic acid, 5,7-diacetamido-3,5,7,9-
tetradeoxy-D-glycero-L-gakzcto-, 47: 198
2-Nonulopyranosidonic acid, m-bromobenzyl
5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-
dideoxy-o-glycero-a-D-gulacto-, crystal
structure bibliography, 34:36 1
Nonulopyranosonic acid
5-acetamido-3-5-dideoxy-P-~-glycero-o-
gulucto, see Sialic acid
5-amino-3,5-dideoxy-~-g~ycero-c~-~-gu~ucfo,
see Neuraminic acid
2-Nonulopyranos-1-onic acid, 5-amino-3,5-
dideoxy-o-glycero-o-gulacto-, see
Neuraminic acid
Nonulosaminic acids, 13:237-263
Nonulose
4,7-anhydro- 1,3-dideoxy-
o-glycero-r-gluco-, synthesis by Wittig
reaction, 27:286-287
o-glycero-L-manno-, synthesis by Wittig
reaction, 27:286-287
5,6:8,9-di-O-isopropylidene-~-glycero-~-
galucto-, synthesis by Wittig
reaction, 27:285
5,6:8,9-di-O-isopropylidene-o-glycero-~-
tulo-, synthesis by Wittig reaction,
27:285
3,7-anhydro-6,8-O-benzylidene-2-deoxy- 1-
C-(p-methoxypheny1)-o-gluco-,
synthesis by Wittig reaction, 27:288
4,g-anhydro- 1,3,9-trideoxy-~-manno-,
synthesis by Wittig reaction, 27:288
o-eiythro-L-galacfo-, gas-liquid
chromatography of, 28:49
5-acetamido-3,5-dideoxy-3-fluoro-o-glycero-
o-gulucto-, preparation, 38:23 8
5-amino-3,5-dideoxy-o-g~ycero-~-gu~ucro-,
see Neuraminic acid
3-deoxy-o-ga~acto-,49:202-204
2-Nonulosonic acid, 3,8,9-trideoxy-9-C-
phosphono-o-munno-, preparation,
38:387
Nonulosono- 1,4-lactone,5-acetamid0-5-deoxy-
o-glycero-o-gulucto-, 2- (diethyl
dithioacetal), preparation of, 32:26
Norleucine
D-, taste properties, 45:315-316
6-diazo-5-oxo-~-,inhibition of protein
glycosylation, 40:344,368
 SUBJECT INDEX
6,[2-formyl-5-(hydroxymethyl)pyrrole-I -yl],
formation of, 46:314
L-, taste properties, 45:3 15-3 16
Normal coordinate analysis, 44: 12, 32-34
computerization, 44:9
Normuscarine, synthesis of, 25:216
P-Noroxetanocin, 50: 196
Nosemu upis, gas-liquid chromatography of
spores of, 28:47
Noviose
composition in aqueous solution, 42:58
L-, biosynthesis, 35:82
natural occurrence of, 42:73
structure of, 42:70
synthesis of, 40:70,42:78-79
Novobiocin, monohydrate, crystal structure,
43:351
N-substitution, nomenclature, 52: 1 17-1 18
N-terminal sequence, proteoglycans,
49:251-253
Nuclear acids, 1:193-245, 11:285-333
Nuclear magnetic resonance spectroscopy,
195-93,21:191, 195
of a,P-unsaturated acids, 27:26 1
of 2-acetamido-
1-N-acetyl-2-deoxy-P-~-,glucosylaniine,
45:98
1-N-(~-aspart-4-oyl)-2-deoxy-P-~-
glucosylamine, 45:98
of acetoxonium salts, 26: 132
of acyloxonium salts, 26: 136
advantages of, 46:73-74
of alkyl ald-3-enulosonates, 27:268
of anhydroalditols, 25:252
of 1,6-anhydrohexopyranoses,34:5 I
anomer determination by, 23:43
applications, 51 :63-64
13C, 51:63-127,53:25,288
dipole-dipole relaxation, 516 - 6 7
experimental methods, 51:71-73
extreme narrowing limit, 51:69
free and diffusive rotational motion,
51~73-74
of labeled glycophoprins, 45: 169- 198
motion narrowing limit, 51:69-70
relaxation mechanisms, 51:7&7 1
relaxation parameters, 51:64
spectral density and, 51:68-70
time-correlation function, 51:64,67-68
of capsular polysaccharide Type 2,33:30 I
381
of carbohydrate boronates, 35:4 I , 70
characterization of anhydrodeoxyalditols by,
23:74, 77, 79
of chromoses, 21 :185
cIs-2,4-dimethyl- 1,3-dioxolane as reference
compound for, 27:209
comparison of relevant parameters of
different nuclei, 46:74
in conformational analysis, 26:55
of acyclic sugars, 26:70
and conformational equlibria of cyclic
acetals, 34: 198-202
conformation of glycofuranosides and, 21:97
of degradation products of polysaccharides,
31:239
of 5-deoxy-5-phosphino-and 5-phosphinyl-i.-
idopyranoses, 42: 165-1 72
of deoxy sugars, 21:202-203
in determination of acetylation of partially
substituted carbohydrate, 33: 19
of deuterated compounds, 27: 147
deuterium location, determination by, 27: 143
of o-g~ucofuranosidurono-6,3-~actones,
33:207-209
1,4:3,6-dianhydrohexitols, 49: 102-1 I0
of dithioacetals, 32:88-92
of fluorinated monosaccharides, 46:74
Fourier-transform, acquisition of the free-
induction decay signal, 27:4849
applications of, 2756-62
digital processing of the free-induction
decay signal, 27:50
distinction of continuous-wave and pulsed
techniques, 27:44
fast Fourier transformation, 27:52-54
noise-stimulated resonance, 27:55
phase correction, 27:54
pulse methods, 27:4549
techniques, 27:43
of glycans, 37:20&205
'H-, 53:288
oligosaccharide physicochemical analysis,
50:3 12-3 14
mucin oligosaccharide chains,
50:322-328
sulfated oligosaccharide chains,
50:330-333
of halogenated sugars, 22: 199,201
of hydrazones and osazones of o-fructose,
22:264
382 SUBJECT INDEX
Nuclear magnetic resonance spectroscopy
(continued)
of ketonucleosides, 42:25&25 I
metal cation-carbohydrate complexes
applications, 47:404 1
metal-sugar complexes, see Metal-sugar
complexes
multiplicity rule, 51: 18
nuclear spin-spin couplings, 51: 17-1 8
origin, 51:18
other nuclei, 4 6 8 0
of polysaccharides, 21:501
ofreducing sugars in solution, 42:16, 18-23,
32,34,6243
resonance condition, 51: 17
of sialic acids, 40: 167
'I9Sn, 53: 19-20
solvents for sugars for, 27:108, 124
spectrometers, 29:25, 27
spectroscopy, conformation determination
by, 24:57
in structural chemistry, 26: I3
and structure of cyclic acetals, 34: 195-198
study of electron-rich positions in sweet
compounds, 45:23 1-232
of sucrose derivatives, 33:275-278
of sugar oxiranes, 25: I7 1
sugars in solution, 49:20-21
of sulfonic esters of carbohydrates,
23:255-256
two-dimensional techniques, 46:74
of unsaturated sugars, 24:265
furanoses, 27:240
phosphonates, 27:297
of vinylthio ethers of sugars, 27:276
Nuclear Overhauser enhancement, 38:26-35,
45:126, 168, 51:16
in combination with nonselective relaxation-
rate measurements, 45: 159
combined with proton spin-lattice relaxation,
45: I 64- 167
single- and double-selective relaxation-rates
with, 4 5 1 60
Nuclear relaxation time, measurement of, 27:59
Nuclear spin-spin coupling, 51: 17-1 8
constants, 51:23-29
finite perturbation theory, 51:26-28
indirect, 51:24-26
Schrodinger equation, 51:23-24
origin, 51: 18
Nucleic acid hydrolases, 27:307
Nucleic acids
characterization of hydrolysis products of,
25:374
conformation of furanoid ring in, 26: 1 1 1
infrared and Raman spectroscopic studies,
44:30
laser-Raman spectroscopy, 44:84-85
nucleosides and nucleotides, crystal
structures of, 25:86-90
polysaccharide derivatives, 29:384-387
separation by cross-linked cycloamyloses,
29:404
structure, 36: 140
Nucleocidin
conformation of, 26: 1 12
structure, 38:196, 198
synthesis of, 28:226,273, 38:237
Nuc leophiles
0-,alcohols and sugars as, 50:32-114; see
d s o 0-Glucosyl trichloroacetimidates,
as donors
0-galactosyl trichloroacetimidates, 50:49,
52-59,84,92-102
trichloroacetimidates of 6-
deoxyhexoses, 50:98, 104-1 10
trichloroacetimidates of mannosamine
derivatives, 50:98, 103
0-mannopyranosyl trichloroacetimidates,
50:58,6M7
reaction with
benzoxonium ions, 39:113, 151-152
oxirane-containing aldoses, 25: 120, 125
with sulfonyloxy groups of alditols,
25264
Nucleophilic agents, oxirane ring cleavage by,
34:l I5
Nucleophilicity, enhanced, P-oxides, 50:29
Nucleophilic reactions, for chain-extension of
carbohydrates, 32:37
Nucleophilic substitutions
in 1,6-anhydrohexopyranoses,34: 85-87,
92
dianhydrohexopyranose preparation by,
34: 107
radical-mediated brominations, 49:79-84
Nucleophlic displacement, 53:148-150
of sulfonates, 39:229-23 1
Nucleoside analogs, synthesis, 40:77-80
Nucleoside antibiotics, see Antibiotics
 SUBJECT INDEX
Nucleoside diphosphates, glycosyl esters, in
polymerization, 41 :125-132
Nucleoside pyrophosphates
glycopyranosyl esters, synthesis of
saccharides from, 26:35 1 4 8 3
glycosyl esters, occurrence of, 26:353
Nucleosides, 21:23, 23:99, 105, 222, 224. .see
also Ribonucleosides
acyclic analogues, preparation of, 32:72-75
acylation of nitro-, 24: 1 I5
acyl migration in acyl derivatives,
33:104105
5-aldehydes, isolation of, 33: 122
anhydro-, 24: 177-188,25:405
anomerization of, 24:47
apiose-containing purine, synthesis,
31: 183-184
arabinosyl, biosynthesis, 35: 123
arsenic-containing, attempted preparation of,
28:253
bacterial, 1 9 2 01-234
3-benzoylpropionyl group as protective
group in, 33:248
book on chemistry of. 27:5
boronates, acetates and benzoates of. 35:53
preparation, 35:38,4548
properties, 35:80
of branched sugars, 42: 13 1-132
bromination by N-bromosuccinimide and
triphenylphosphine, 28:249
C-, P-D-arabinohranosyl, synthesis of,
33:139
structure of, 33: 1 13
synthesis of, 33: 134
of naturally occurring, analogs. and
functionalized C-glycosyl precursors,
33:llI-l88
synthetic analogs, 33: 175-1 88
Wittig reaction in preparation of
precursors for, 33: 1 5 4 158
5-chloro-5-deoxy-,dinucleosides from.
28:287
cobalt-containing, preparation, 35356
column chromatography, boronic acids in,
3563-64
complex formation with boronic acids. 35:49
conformation of furanoid ring in,
26:110-111
crystal structure of, 25:86-90, 30:445466,
31:355-363,369-371,323372-384.
383
34:346, 363 -378,37:408435,
38:485-529
3:5-cyclic phosphates, 22:3 19, 358
cytosine, isolation, 35: 124
deamination in synthesis of, 31:70
2-deoxy-, 24:212
5 -deoxy-4-fluoro-5-iodo-, preparation of,
28:273
2-deoxyhexofuranosyI-, synthesis of, 27:4
deoxyiodo-, preparation of, 28:243
3-deoxy-3-nitro-, hydrogenation of, 24: I 10
derivatives, high-performance liquid
chromatography. 46:28
2,3-dideoxy-, 24:226
errata for 1970-1978,43:375-376
esterification of, 33: 13
with N-(aminoacyl)imidazoles,33:43
fraudulent, 29:4-5
from glycals, 24:217
5 -(glycosyl pyrophosphate) epimerases,
gas-liquid chromatography in
monitoring action of, 28:47
5 -(glycosyl pyrophosphates), 28:307-399
carbodiimides in synthesis of, 28:307-399
chemical reactivity of, 28:356-362
chemical syntheses of. 28:344-356
chromatography of. 28:3 10
degradation of, 28:311-314. 356
enzymic reactions of, 28:362-396
enzymic splitting
of glycosyl linkage, 28:391-397
of pyrophosphate linkage, 28:388
extraction of, 28:3 10
history, 28:308
2-hydroxypyridyl esters of nucleoside 5-
phosphates in synthesis of, 28:353
inversion of hydroxyl group in,
28:369-379
isolation, characterization and structure of
natural. 28:3 10-334
nomenclature, 28:309
preparation of, 28:334-356
transfomiations of glycosyl group,
28:363-368
of glycuronic acids, 36:126-131
halogenation of, 28:247
halogeno sugar, synthesis of, 28:226
5-halo-4-0x0, biological activity, 48:248
hydrolysis of, 22:60
index for 1935-1980,43:405421
384 SUBJECT INDEX
Nucleosides (continued)
isomeric 2-deoxy-C-, 46:28
laser-Raman spectroscopy, 44534
mass spectra of, 21:90
1 -methyl 2-deoxy-, synthesis of, 27:4
2,3-O-benzylidene-, reaction with N-
bromosuccinimide, 39: 103
2 (or 3), 5-diphosphates,22:321
phenylboronates, hydrolysis, 355 1
mass spectrometry, 35:68
5-phosphates from 5 phosphites, 22:341
5 -phosphoroimidazolidates, in synthesis of
glycosyl nucleoside pyrophosphates,
28:346
phosphorolysis of activated, 22:369
5 -phosphoromorpholidates, in synthesis of
glycosyl esters of nucleoside 5-
pyrophosphates, 28:346-35 1
5-phosphorothioate, in synthesis of
pyrophosphates of nucleosides, 28:352
phosphorylating agents for, 22:392-395
phosphorylation of, 22:325
photolysis of o-nitrophenyl ethers,
38: 167-1 68
32P-labelled,synthesis of, 33:49
proton magnetic resonance spectroscopy of,
27:33-39, 81
purine, 17:301-369
purine anhydro-, 24: 185
pyrimidine, 14:283-380.24: 176
containing 2,3-dideoxy sugar, 21: 194
pyrimidine anhydro-, 24: 176-177
5-pyrophosphates
enzymic synthesis of glycosyl esters of,
26:354-366
glycerol and triose esters, 28:334
hexitol and pentitol esters, 28:333
radiation-induced degradation, 37:76
radiolysis and radical-induced scission,
37:55-58
reactions with (bromo(or chloro)-
methy1ene)dimethyliminium bromide(or
chloride), 28:253
regioselective ring cleavage of
tetraisopropyldisiloxane- 1,3-diyl
derivatives, 3 9 5 8
research, 29:2-3
ribo-chlorination or bromination by thionyl
chloride or bromide and
hexamethylphosphoric triamide, 28:250
selective deacylation, 39:3644
selective esterification, 33:53, 59
with acyl azides, 33:45
selective halogenation with N.N-dimethyl
(halomethaniminium) halides, 33:82
with phosphorus-based reagents, 33:
78-80
with tertiary phosphines and carbon
tetrahalides, 33:79
selective metbylations with diazomethane,
33~69-70
selective oxidation of, 33538
selective phosphorylation of, 33:46,4849
selective reactivity of hydroxyl groups in
furanoid, 33:3 1
sulfonylation of, 23:241, 245
sulfur-containing, photolysis, 38: 154-155
synthesis of, 25:218,26:14,31:4,39:153,
46:6
from aldonolactones, 50: 195-201
branched-chain, by Wittig reaction,
27:234235,243
transacetalation of, 33:72
trifluoroacetates, mass spectrometry of,
30:42
unsaturated, 24:226-227
synthesis of, 24:250
Nucleotides, 21:24,22:307419; see also
Mononucleotides; Oligonucleotides;
Polynucleotides
N-alkylation of, 22:382
analogs, antibacterial, 42: 189
apiose-containing sugar, 31: 163
apiosyladenine, deamination of, 31: 153
bacterial, 15:201-234
biosynthesis of sugar, 27:336
book on chemistry of, 27:5
column chromatography, boronic acids in,
3564
complex formation with boronic acids,
35:49
condensation of units, 36: 156-1 67
conversions of, 22:375
crystal structure of, 25236-90,30:445466,
31:355-363,369-371,32:372-384,
34~346,362-378,37:408435,
38:485-529
deamination of, 22:376
2-deoxy-, 24:226
errata for 1970-1978,43:375-376
 SUBJECT INDEX
esterification of, 33: 13
francationation of mono-, dextran derivative
for, 29:326
glycopyranosyl esters of, 18:309-356
halogenation of, 22:377
hydrogenation of, 22:380
index for 1935-1980,43:405421
laser-Raman spectroscopy, 44:84
in liver, effect of o-fructose on, 34:322-324
N-oxidation of, 22379
phenylboronates, mass spectrometry, 35:68
phosphono migration in, 33: 108
phosphorylating agents for synthesis of,
22~392-395
phosphorylation, 49:210-2 13
32P-labeled,22339
precursors in cellulose biosynthesis,
26:323-326
proton magnetic resonance spectroscopy of,
27:33-39
pyrophosphorolysis of sugar, 28:390
radiation-induced degradation, 37:76
radiolysis and radical reactions, 37:47
reaction with hydroxylamine, 22386
selective dephosphonylation, 39:59
sugar
biosynthesis of saccharides from.
26:351483
enzymic conversion of, 32: 10
in interconversion of carbohydrates,
32:8
in Nature, biosynthesis of, 3 2 9
in marine alga, 26:404
sulfonylation of, 22:376
synthesis of, 22324, 27:260
in synthesis of trehalose 6-phosphatq 30:241
synthetic, 22:398416
tritiated, stability and storage of, 27: 139
Nucleotide-sugars, 44:280
phosphorylation, 49:2 13-2 18
Nucleotidyltransferases, 44:280-28 1
Numbering, of carbon atoms in sugars by
Fischer, 21:lO
Nutrition, di-o-fructose dianhydrides and,
52233-234
Nystose, 22230
I3C nuclear magnetic resonance spectra of,
33:277
tetradecaacetate, proton magnetic resonance
spectroscopy of, 27:3 1
385
0
Oats
cell-wall studies on, 42:267, 271,285, 287,
291-292.294,300-301,320,352-
353
hemicellulose-cellulose ratio, 36:253-
255
sugars in hydrolyzates of hemicelluloses,
36~255-251
xylans, 36:234
0-P-o-Glucopyranosyl- (1 -3)-o-
glucopyranose, 43:333
Obituaries
Alfred Gottschalk, 33:l-9
Alva Thompson, 19: 1-6
Bernard Randall Baker, 29:l-10
Carl Neuberg, 13:l-7
Claude Silbert Hudson, 9:xiii-xviii
David James Bell, 30: 1-8
Edmund George Vincent Percival, 10:
xiii-xx
Edmund Langley Hirst, 35: 1-29
Edward John Bourne, 34: 1-22
Emil Hardegger, 38: 1-1 I
Emil Heuser, 15:l-9
Emile Bourquelot, 18: 1-8
Fred Smith, 22:1-10
Geza Zemplen, 14: 1-8
Harold Hibbert, 16:l-11
Hermann Otto Laurenz Fischer, 17:l-14
Hewitt Grenville Fletcher, Jr., 31:l-7
James Colquhoun Irvine, 8:xi-xvii
John Archer Mills, 36: 1-8
John Clinton Sowden, 20:1-10
John Kenyon Netherton Jones, 41: 1-26
Joseph Vincent Karabinos, 36:9-13
Karl Paul Gerhardt Link, 39:l-12
Kurt Heinrich Meyer. 1l:xiii-xviii
Laszlo Vargha, 28: 1-10
Melville Lawrence Wolfrom, 26:146
Phoebus Aaron Theodor Levene, 12: 1-1 2
Richard Kuhn, 24: I
Rudolph Maximilian Goepp, Jr., 3:
xv-xxiii
William Ward Pigman, 37: 1-5
Walter Norman Haworth, 6: 1-9
William Werner Zorbach, 27: 1 4
William Zev Hassid, 32:1-14
Ochiai, H., 46:4
386 SUBJECT INDEX
Ocotea puberula, 46: 13
Ocotein, 46: 13
Octadecane-l,3,4-triol, 2-amino-, see
Phytosphingosine
Octadecanoic acid, methyl ester,
transesterification of carbohydrates with,
33:44
4-Octadecene- 1,3-diol, 2-amino-, see
Sphingosine
3,5-0ctadiyne-2,7-diol, 2,7-dimethyl-, reaction
with sugars, 40:124
Octane
(1 S,2S,3R,4S,5S, 7R)- 1-Acetoxy-2,3,4-tetra-
O-benzoyloxy-7-bromo-6-
oxabicyclo[3.2.1], synthesis, 49:65
(lR, 5R)-6,8-dioxa-3-thiabicyclo[3.2.1]-,
preparation of, 34:105, 148
4,6-Octanedione, 1,l ,1,2,2,3,3,-heptafluoro-7,7-
dimethyl-, lanthanide complex, in proton
magnetic resonance spectroscopy, 29:2 1
1-Octanethiol, odor of, 32:17
Octanucleotide, synthesis, 36: 173
Octasaccharides, 47: 190, 192
of ribonuclease B, 27:325
Octenitol, 48:356-357
Oct-5-eno- 1,4-furanose,3-O-benzoyl-1,2-O- Oct-2-enose, 2,3-dideoxy-1-C-phenyl-o-
cyclohexylidene-5,6,8-trideoxy-a-~-xylo-,
27:250
Oct-5-eno- 1,4-furanos-7-ulose
3-0-benzoyl- 1.2-O-cyclohexylidene-5,6,8-
trideoxy-a-o-xyb, reactions of, 27:250
3-0-benzyl- 1,2-O-cyclohexylidene-5,6,8-
trideoxy-a-o-xyb, synthesis by Wittig
reaction, 27:245
Oct-2-enonamide, 2,3-dideoxy-o-gluco-,4,5.
6,7,8-pentaacetate, synthesis by Wittig
reaction, 27:256
Oct-2-enonate
ethyl 4-acetamido-
3,4-dideoxy-2-O-ethy1-5,6:7,8-di-O-
isopropylidene-o-gluco-, synthesis by Oct-5-enose-7-ulose,6,8-dideoxy-
Wittig reaction. 27:274
2,3,4-trideoxy-~-ghco-,synthesis by
Wittig reaction, 27:255
ethyl 2-bromo-2,3-dideoxy-o-
galacto-, 4,5,6,7,8-pentaccetate, synthesis
by Wittig reaction, 27:257
gluco-, 4,5,6,7&pentaacetate, synthesis by
Wittig reaction, 27:257
ethyl 2,3-dideoxy-
2-C-phenyl-o-g\uco-, 4,5,6,7,8-
pentaacetate, synthesis by Wittig
reaction, 27:256
D-gulacto-, pentaacetate, synthesis by
Wittig reaction, 27:253, 255
synthesis by Wittig reaction, 27:255
4,5,6,8-tetraacetate, synthesis by Wittig
reaction, 27:255
D-gluco-, pentaacetate, synthesis by Wittig
reaction, 27:253
synthesis by Wittig reaction,
27:25+255
methyl 4-acetamido-
6,8-0-benzylidene-2,3,4-trideoxy-o-
gluco-, synthesis by Wittig reaction,
27:255
2,3,4-trideoxy-o-ghco-, synthesis by
Wittig reaction, 27:255
Oct-3-enonate, dimethyl 3-(carboxymethy1)-
2,3,4-trideoxy-5,6:7,8-di-O-
isopropylidene-, synthesis by Wittig
reaction, 27:255-256
Oct-2-enononitrile, 2,3-dideoxy-o-gluco-,4,5,6-
7,8-pentaacetate, synthesis by Wittig
reaction, 27:256
gulucto-, synthesis by Wittig reaction,
27:246
Oct-6-enose
cis(and tran.s)-6,7,8-trideoxy-1,2:3,4-di-0-
isopropylidene-7-nito-a-o-gu~ucto-,
24:112, 127
(@-6,7,8-trideoxy- 1,2:3,4-diisopropylidene-
7-C-nitro-ct-o-gulacto-, irradiation,
38: 174-1 75
6,7,8-trideoxy- 1,2:3,4-di-O-isopropylidene-
a-o-galucto-, synthesis by Wittig
reactions, 27:235
Octenoses, 1-C-aryl uldehydo-, pentaacetates,
syntheses by Wittig reactions, 27:24&247
1,2:3,4-di-O-
isopropylidene-a-o-galacto-, cis-and cis-
trans isomers, 24: 1 12
Oct-3-enulose, 5,7:6,8-di-O-benzylidene- 1,3,4-
trideoxy-o-ribo-, synthesis by Wittig
reaction, 27:245
Oct-3-enulosonic acid, 3,4-dideoxy-
D-urubino-, and tert-butyl ester pentaacetate,
synthesis by Wittig reaction,
27:267-268
 SUBJECT INDEX
L-urubino-, and methyl and isobutyl esters,
pentaacetates, synthesis by Wittig
reaction, 27:267-268
Octitols
6-acetamido-l,5-anhydro-6,8-dideoxy-3,4-0- 3,6-anhydro-2-deoxy-
isopropylidene-
D-ewthro-D-galacro-, 25:249
7-O-methy~-~-eq~thro-~-ga/acto-. 25:
249
1,5-anhydro-
D-eiythro-D-galucto-, 25:249
6,8-dideoxy-N-(4-propyI-~-hygroyI )-D-
eiythro-o-gulucro-, 25249
anhydro-, 25:249,282
conformation of, 25: 105
Octonate, methyl 4-acetamido-2,3,4-tndeoxy-
D-gluco-, preparation of. 27:26 I
Octonic acid
4-acetamido-6,8-0-benzylidene-4-deoxy-~-
threo-L-galaeto-, methyl ester,
preparation of, 27:266
D-threo-L-
gulacto-. preparation of, and 1,4-lactone,
27:266
ido-, preparation of, 27:266
Octopyranose
7-acetamido-
7,8-dideoxy- 1,2:3,4-di-O-isopropyIidene-
L-threo-a-D-gulacto-, hemihydrate,
crystal structure, 43:245-246
6-O-acetyl-7,8-dideoxy- I ,2:3,4-di-0-
isopropylidene-D-erythro-a+-
galucro-, crystal structure, 43:252
6,7,8-trideoxy- 1,2:3,4-di-0-
isopropylidene-D-g~,vcero-r.-grr/ucto-,
crystal structure, 43:347
7-azido-8-deoxy- 1,2:3,4-di-0-
isopropylidene-6-7-dithio-6,7-S
trimethylene-o-erythro-a-D-gulucto-,
crystal structure bibliography, 34:361
8-azido-8-deoxy-l,2:3,4-di-O-
isopropylidene-5,5,6,7-trimethylene-
6,7- dithio-a-L-threo-o-gulucto- crystal
structure bibliography, 32:38 1
6-O-acetyl-7,8-dideoxy-l,2:3,4-di-0-
isopropylidene-7-nitro-,24:99
Octopyranoside, methyl 6-acetamido-6.7,8-
trideoxy-a-DL-g/ycero-DL-
ullo-, synthesis, 40:60
gulacto-, synthesis, 40:60
387
Octoses
6-acetamido-6,8-dideoxy-~-e~ythro-~-
gulacto-. dimethyl dithioacetal, reaction
with hydrochloric acid, 32:60
1-C-( p-methoxyphenyl)-D-gu/ueto-,
synthesis by Wittig reaction, 27:285
4,5:7,8-di-O-isopropylidene-l -C-(p-
methoxypheny1)-D-glycero-D-
gulucto-, synthesis by Wittig
reaction, 27:285
4,5:7,8-di-0-1sopropylidene-l -C-(p-
methoxyphenyl)-D-g!ycero-D-tuk-,
synthesis by Wittig reaction, 27:285
3,7-anhydro-2,8-dideoxy- 1-C-(p-
methoxypheny1)-L-munno-, synthesis by
Wittig reaction, 27:288
deoxy-, melting points and optical rotations
of, 26:288
o-eryrhro-i.-talo-, 47:39
composition in solution, 42:36
dithioacetals, physical constants of, and
peracetates, 32: I 13
DI.-threo-uL-. synthesis, 40:95
o-threo-L-
gulucto-, preparation of, 27:266
talo, composition in solution, 42:36
Y-
composition in aqueous solution,
42~55-56
natural occurrence of, 42:73
synthesis of, 42:126
Octos-6-ulose, (IS)-5,7-anhydro-&deoxy-
1,2:3,4-di-O-isopropylidine- 1 -0-methyl-
u/deh,vdo-D-g~ycero-D-gu/acto-, 1-acetal,
crystal structure bibliography, 37:399
Octulopyranose, 2,7-anhydro-~-glycero-~-~-
manno-. monohydrate, crystal structure
bibliography, 38:438,467
Octulopyranosonic acid. 3-deoxy-~-manno-2-,
48:lll-112
2-Octulopyranosonic acid
2,4,5,7,8-penta-0-acetyl-3-deoxy-~-munno-
deacetylation products, 38:374-375
methyl ester, synthesis, 38:365-367, 375
4,5,7,8-tetra-O-acetyyl-2-chloro-2,3-dideoxy-
o-manno-, methyl ester, synthesis,
38~375-376
Octulopyranosylonic acids, 3-deoxy-D-munno-
2, circular dichroism, 45:107
388 SUBJECT INDEX
Octulose
4,7-anhydro-
1,3-dideoxy-o-ribo-, synthesis by Wittig
reaction, 27:285
1,3-dideoxy-o-xylo-, synthesis by Wittig
reaction, 27:285
5,6,8-tri-O-benzyl- 1,3-dideoxy-o-2-,
synthesis, 48: 116
4,8-anhydro-, 7,9-O-benzylidene- I ,3-
dideoxy-o-gluco-, synthesis by Wittig
reaction, 22288
D-glyCerO-
o-altro-, synthesis, 41:9
D-gUkKtfl-, synthesis, 4 1 9
Or-D-glUC0-2-,sweetness-structure
relationship, 45:253-254
L-galacto-, synthesis, 41:9
r-gluco-, taste properties, 45:254-255
~-gulo-,taste properties, 45:254
L-glycero-, L-galacto-, synthesis, 41:9
Octulose bisphosphates, composition in
aqueous solution, 42:46
2-Octuloses, sweetness-structure relationship,
45:253-254
3-Octuloses, composition in aqueous solution,
42:41
Octulosonic acid, 3-deoxy-o-manno-, 48:297
2-Octulosonic acid
7-(2-aminoethyl)-3-deoxy-manno-,
phosphate, 38:343,345
3-deoxy-
o-manno-
in acidic exopolysaccharides,
38:356-357,361-365
biosynthesis, 38:325
chemistry and biological significance,
38:323-388
composition in aqueous solution, 42:42
in lipopolysaccharides, 38:324
metabolism, enzymes, 38:378-387
inhibitors, 38:387-388
monosaccharide chemistry, 38:373-378
occurrence and linkages in
lipopolysaccharides, 38:334-356
periodate-thiobarbituric acid assay,
38:326-334
phosphate, synthesis, 38:326, 367
phosphate-thiobarbituric acid assay,
38:326-334
polysaccharides containing, carbon- 13%
nuclear magnetic resonance spectra,
389-94
semicarbazide assay, 38:341,343-344
spectroscopic analysis, 38:359-365
structure, 38:357-365
synthesis, by Cornforth reaction,
38:365-369
cyanohydrin, 38:371
by Kuhn reaction, 38:369-371
Wittig synthesis, 38:358,369, 371-373
5-O-rx-~-rhamnopyranosyl-, synthesis,
38:369
5-O-P-o-glucopyranosyl-, synthesis,
38:369
5-O-(P-o-glucopyranosyluronicacid)-,
synthesis, 38:369
5-O-methyl-, synthesis, 38:329, 33 1
5-0-(2-acetamid0-2-deoxy-P-o-
glucopyranosyl)-3-deoxy-, synthesis,
38:369
Octulosonic acid &phosphate, 3-deoxy-o-
manno-2-, synthesis, 49:204,206
Octulosonic acids
3-deoxy-, esters with cytidine 5-phosphate,
28:332
3-deoxy-o-galacto-, synthesis of, 28:77
3-deoxy-o-ghco-, synthesis of,28:77
3-deoxy-o-manno-, 41:159, 164
ester with cytidine triphosphate, 28:333
in polysaccharides and glycoconjugates,
31:187
sodium salt, carbon-13 nuclear magnetic
resonance spectroscopy, 41:64
synthesis and gas-liquid chromatography
of, 28:77
trimethylsilylation of, 28:28
Oct- 1-ynitol, 4,5:7,8-di-O-isopropylidene-o-
glycero-o-talo-, preparation and
cyclization of, 33:130-131
Oct-7-ynopyranose, 7,g-dideoxy- 1,2:3,4-di-O-
isopropylidene-o-glycevo(andL-glycero)-
a-o-galacto-, 24:260
0-(2,6-diamino-2,3,4,6-tetradeoxy-6-C-methyl-
oc-o-eryrhro-hexopyranosyl)-(1- + 4 ) - ~ - 3 -
amino- 1,3,6-trideoxy-l-methoxy-6-
(methylamino)-chiro-inositol,hydrate,
crystal structure, 43:346-347
3-O-(di- and tri-glycosy1)-serine or-threonine
derivatives, properties, 43:200-20 1
Odorotrioside G, 39:302
 SUBJECT lNDEX
Odorous substances, 45223
Ohle, Heinz, 452-9
1,3-O-(hydroxyborylene)-o-mannitol,
monohydrate, 43:37 1
Oleandomycin
desosamine component of, 28:299
sugar component oleandrose, 28:299
Oleandrose, in cardiac glycosides, 28:298
Oleandroside
methyl a-UL-,synthesis, 40:40
methyl DL-,synthesis, 28:298,40:32
Olefins, hydroformylation and
hydro(hydroxymethy1)ation of, 23:6 1
Oleic acid, lithium, potassium, and sodium
salts, as catalysts and solubilizers for
sugars, 21:96
Olgose, monohydrate, crystal structure. 43:268
Oligodeoxyribonucleotides
separation and purification, 36: 193-204
structural integrity of synthetic, 36:204--206
synthesis, 39:64
on polymer supports, 36:207-2 12
protecting groups, 36: 142-143
Ohgo-D-galactosiduronate hydrolases,
nomenclature, 33:327-328
Oligogalactosiduronic acid, f.a.b.-mass
spectrum
effect of acid-dosing, 45:27-28
effect of (pentafluororbenzyl) oxime
derivative, 4 5 3 2
Oligogalacturonic acids, 0-trimethylsily I
derivatives, decomposition rates for, 28:29
Oligogalacturonide hydrolase, nomenclature,
33:327
Oligogalacturonide lyase, nomenclature,
33:327
Oligoglycosiduronic acids, liquid
chromatography, 46:4041
Oligoglycosylalditols, 51: 17 1
homonuclear COSY spectrum, 51:174, 176
'H-NMR spectrum, 51: 174-175
Oligomerization, secondary, polysaccharides,
41: 170
Oligonucleotides
block polymerization, 36:170, 185-1 86
chromatography of, 29:333
phosphate protection groups, 36: 152-1 56
purification, 36: 193-204
synthesis
and protecting groups, 36: I5 1-1 52
389
by selective deacylation, 39:36
Ohgo-( 1+6)-D-glucosidase
activity in utilization of a-u-
glucopyranosides by yeasts,
32: 191-1 99
regulation, 39:388-390
substrate specificity, 39:387
Oligoribonucleotides
condensation catalyzed by RNA ligase,
36:191
separation and purification, 36: 197-204
structural integrity of synthetic, 36:20&206
synthesis, 39:64,66
on polymer supports, 36:212
protecting groups, 36:142-149
by triester method, 36: 186-1 89
Oligosaccharide chains, @linked,
glycoproteins, 50:322, 324
Oligosaccharide precursors, lipid-linked,
biosynthesis pathways, 40:295
Oligosaccharides, 17:121-167,21:27,
53:400405
from Acacia gums, 24:344
acetates, gas-liquid chromatography of,
28:70
acetolysis and anumerization of, 31: 199
acetylated. mass spectrometry of, 29:99-104
N-acetylated or deoxy sugar-containing,
46:29
acidic
animal-derived, large-scale preparative
liquid chromatography, 4 6 5 2
structures proved by methylation and gas-
liquid chromatography, 30:76-78
a-u-mannosidase action on, 28:420
with amino or acetamido groups, I3C-NMR
data for, 42:209-210
analogues, 52:158-159
1.6-anhydr0, preparation of, 34: 158-161
properties and reactions of, 34:161-163,
170
anomeric protons, nonselective spinlatttice
relaxation rates, 45: 149-1 52
f3-amylase action on, 23:337
basic, structures proved by methylation and
gas-liquid chromatography, 30:79
biologically active, carba-, 48:74-86,
279-3 18
alpha amylase inhibitors, 48:X 1-86
validamycins, 48:74-78
390 SUBJECT WDEX
Oligosaccharides (continued)
biosynthesis of, 26:366-376
block synthesis, thioglycosides in,
52: 19 1-198
blood-group, hifluoroacetic acid in
hydrolysis of, 28: 16
branched, 52: 155-1 56
caramel production, 47:222
carbon- 13 nuclear magnetic resonance
signals, identification, 38:22-25
cation complexes, 47: 18-19
cello-, structure of, 26: 16
ceramide, 24:395,400
characterization of, from sucrose, 30:5
chitin-derived, 46:29
chromatography of, 25:9
cleavage of glycosidic linkages, 46:252
I3C-NMRdata for, 42: 193-225
complete haptens, synthesis, 51:221-227
complex
with alkali metal hydroxides, 21:254
with metal salts, 21:221
determining sequence of glycosyl residues
in, 46:58
ionic, liquid chromatography, 46:4549
neutral, liquid chromatography, 46:4 1 4 5
preparative liquid chromatography, 46:60
conformation, 50:335-337
containing 2-acetamido-2-deoxyhexose units,
ultraviolet-absorbances of, 46:65
containing L-rhamnose, 47: 193
crystal structure of, 25:77-80
cyclic, 52: 156-158
liquid chromatography separation,
46:4445
definition of, 21:433, 52:52
degradation by oxidation with chromium
trioxide, 31:229
degree of polymerization, determination by
gas-liquid chromatography, 28:58, 83,
85
derivatives, anomeric C,H bond, carbon-
proton coupling constants, 51:34-35
by endo-o-mannanase degradation of
galacto- and gluco-mannans,
32314316
from enzymic hydrolyzates of o-xylans,
32: 346-3 52
esters with uridine 5-pyrophosphate,28:33 1
with free hemiacetal group, 52:153-154
furanoid, 21:126
gas-liquid chromatography of, 28:67-71
gel chromatography of, 25:32-35
glucosyl trichloroacetimidates, reaction,
50:4142
in glycoenzymes, 27:325
glycoprotein-derived
liquid chromatography, 46:42-43
structural and sequence analysis of, 46:57
gl ycosaminoglycan-derived, liquid
chromatography, pre-column
derivatization procedures, 46:68
from glycosaminoglycans, ultraviolet-
absorbances of, 46:65
guanosine 5-pyrophosphate esters, 28:322
from gums
of galactan group, 24:352
ghatti, 24:354
haptens from glycopeptidolipid antigens,
51:186
high-mannose, preparative liquid
chromatography, 46:60
honey
composition of, 25:295-298
origin of, 25:298-306
hyaluronic acid-derived, liquid
chromatography separation, 46:48
hydrolysis of, 22:53
interaction with asparagus-pea lectin,
35286-288
with concanavalin A, 35:181-186
with lectins, 35: 142
with wheat-germ lectin, 35:219
interglycosidic carbon-peoton coupling
constants, 51:55
ionic, of animal origin, preparative liquid
chromatography, 46:60
of isolychnose series, occurrence, 37:304
structure, 37:305
lipid-linked
in animals, structure, 44:357
in plants, 44:355-356
sources, 44:356
structure, 44:357
laser-Raman spectroscopy, 44:8 1-83
with Le determinants, synthesis, 50:8 1,
8688
linear, structural and sequence analysis of,
46:57
linkage analysis, 5217-18
 SUBJECT INDEX
lipid-linked, assembly and transfer to protein
in vitro, 40:307-312
assembly and transfer to protein in v i w ,
40:299-306
biosynthesis, 40:288-32 I
cell mutants in biosynthesis, 40:3 12-3 14
inhibitors of formation, 40:326-342
liquid chromatography, peak-area analyses,
46:64
of lychnose series, occurrence, 37:306
structure, 37:305
malto-, determination by trimethylsilylation,
28:25
mass spectrometry of, 21:46,93,29:84-105
trimethylsilyl derivatives, 30:39-40
mean, hemiacetal and acetal geometries,
47:72
metabolism of u-galactose-containing,
37:342-372
methanolysis of, 28: 18
methyl a-isomalto, preparation of, 34:262
methylated (fully), gas-liquid
chromatography of, 28: 135
methylation analysis by mass spectrometry,
29:66
methyl glycosides, 47: 199
microbial, preparative liquid
chromatography, 46:60
mucin structure, 50:3 16-322
'H-NMR-spectral and mass-spectrometric
analysis, 50:322-328
N-arylglycosylamine acetates, mass
spectrometry of, 29:99
neuraminic acid-containing, permethylated,
structure analysis, 38:393
neutral
of animal origin, preparative liquid
chromatography, 46:60, 62
structural and sequence analysis of, 46:57
structures proved by methylation and gas-
liquid chromatography, 30:72-75
nitrogen-containing, in human milk, 24:7
N-phenylosotriazole acetates, mass
spectrometry of, 29: 101- 103
occurrence and structure of natural, book,
30:7
of ovarian-cyst blood-group substances,
25:452458
partially fluorinated low-molecular-weight,
48:212
39 I
peptido-, peptide composition of urinary,
24:445
peralkylated, prechromatographic
purification of, 46:20
permethylated, structure analysis,
38:392-394
per(trimethylsily1) ethers, gas-liquid
chromatography of, 28:130-135
1 -phenylflavazole acetates, mass
spectrometry of, 29: I0 1
phosphorylated
fractionation, 46:46
preparative liquid chromatography, 46:60
physiochemical analysis, 50:3 11-3 14
plant-derived
large-scale preparative liquid
chromatography, 46:62
liquid chromatography, 46:41
from polysaccharides by acetolysis, 22:20
preparation of, 34:267,275,47: 180-200
proton magnetic resonance spectroscopy of,
27:30
pyrolysis of, 34:45, 152
qualitative motional description, 51:97-102
quantitative motional description,
51:114117
quinoxaline derivatives. polarography of.
29:157-I 62
raffinose family, biosynthesis pathway.
31:357
in plant kingdom, 37:351-360
the raffinose family of, 9: 149-184
recognition specificity of proteins, 50: 17
reductive-amination, affinity adsorbent
preparation, 39:433434
reductively aminated with aniline, f.a.b.-
mass spectrometry, 45:33
relatives reactivities of hydroxyl groups in,
33:60
selective esterification of, 33:3540
sequences related to Lea and Leb antigens,
50:337,340-341
of sesamose series, occurrence, 37:306
structure. 37:307
sialic acids
from colostrum, gel chromatography of,
25:35
large-scale preparative liquid
chromatography, 46:62
occurrence, 40: 138-140
392 SUBJECT INDEX
Oligosaccharides (continued)
preparative liquid chromatography, 46:60
sialylated, 49:225-226
determinants, 50:337-342
liquid chromatography separation,
46:4546
ultraviolet absorbances of, 46:65
simple
ionic, liquid chromatography separation
of, 46:4041
liquid chromatography, pre-column
derivatization procedures, 46:68
neutral, liquid chromatography analysis,
46:3740
of stachyose series, occurrence, 37:306-309
structure, 37:308
starch-derived, 46:29
from Sterculia urens gums, 24:368
structure of, 35:5
from asparaginylglucosaminuria urine,
37: 198
from fucosidosis urine, 37: 194195,
205
from gangliosidosis urine and tissues,
37: 196
from mannosidosis urine, 37: 182, 190,
205,209
from Sandhoff s disease urine, 37: 197
from sialidosis urine, 37:191-193,205
gangliosides, 24:423
sulfated
preparative liquid chromatography, 46:60
uronic acid-containing, large-scale
preparative liquid chromatography,
46:62
sulfonylation of, 23:241
symbols for defining structures
condensed form, 52:161-162
extended form, 52: 161
short form, 52:162-163
sugar chain representation, 52: 159
symbols, 52: 160
synthesis of, 6:27-81, 21:457,34:159,
36: 136,49:221,51: 15 1-163
acceptor product
formation mechanism, 51:154-157
structures, 51:15 1-1 55
acceptors and acceptor reaction,
51: I5 1-152
applications, 51:162-163
branch linkage synthesis, 51:159-162
combined organic-enzymic approach,
46: 1 8 4 1 8 7
control of dextran and acceptor product
synthesis, 51: 158-1 59
glycosidation methods, 52: 179-182
4-oxopentanoyl group hydrazinolysis,
39:42
on polymer supports, by Koenigs-Knorr
reaction, 34:269
from sucrose and acceptor molecules by
dextransucrases, 30:424-427
thioglycosides as glycosyl acceptors,
52: 197-198
trifluoroacetates, gas-liquid chromatography
of, 28:70, 113
trimethylsilyl ethers
gas-liquid chromatography of, 28:68-70
mass spectrometry of, 29:91-96
underivatized, unreduced, f.a.b.-mass
spectrometry, fragmentation pathways,
4546
unsaturated, 24:253
synthesis of, 29:262
in urine, 24:436,39:330-331
without free hemiacetal groups, 52:151-153
yeast high-mannose, hydrolysis and
acetolysis, monitoring with f.a.b.-mass
spectrometry, 45:49-50
Oligospermia, o-fructose level in, 34:304
Oligostatin, 48:81, 83
Oligosylceramide, from freshwater bivalves,
44:417,419420
Oliose, acetyl-, 21: 184, 186
Olivacine, 46: 13
Olive, development physiology of, 42:341
Olivomose, 21: 184
Olivomycal, L-, synthesis of, 42: 103
Olivomycin, 21:184, 186
Olivomycose, 21:184,50:158-159
DL-, synthesis, 40:20
L-, synthesis of, 40:129,42: 103
natural occurrence of, 42:72
structure of, 42:70
synthesis of, 27:235,242,42:78,94,
114-1 15
Olivose, 21:184
Ombuin, 46: 13
Oncology
sialic acid function, 40:232
 SUBJECT INDEX
sialidase treatment, 40:228
One enzyme-one linkage concept, 44:306-3 11
Onion bulbs, gas-liquid chromatographic
analysis of, 28:68
Onodera, Akifumi, 46:9
Onodera, Fumi, 46:9
Onodera, Koji, 46:9
Onodera, Konoshin
accomplishments, 46:4-5
awards and honors, 462-9
baccalaureate graduation thesis, 46:3
childhood, 46:2
climbing in Himalayas, 46:5
editorial work, 46:8
family, 46: 1-9
fields of research, 46:6
founder of Japanese Society of Carbohydrate
Research, 46:9
interest in mountain climbing, 46:2
investigation of synthetic procedure for
nucleosides, 46:6
Ph.D. thesis, 46:3
scientific research, 46:3-8
study of biochemistry, 46:2-3
as teacher, 46:5
work for Agricultural Chemical Society,
46:8
work for Biochemical Society of Japan, 46:8
work habits, 46:5
work in Laboratory of Biological Chemistry,
46:3
Onodera, Mizuyo, 46:9
Onodera, Yukari, 46:3, 9
Ontogeny, fucolipid role, 39:309
2-( 0-pheny1enedioxy)acetyl group, enzymic
hydrolysis, 39:44
Optically active natural products, enantiomeric
carba-sugars, synthesis, 48:4&4 1
Optical rotation
of I ,6-anhydrohexofuranoses, 34: 154
anomer estimation from, 23:3 1,41
and configuration of deuterated compounds,
27: 146
in conformational analysis, 26:60-64
of deoxy sugars, 26:219-296
Of D-fructose, 22~235
effect of carbohydrate-complex salt
formation on, 21:213
of complexing on, of carbohydrates,
21:228
393
of metal hydroxides on. of carbohydrates,
21:253
of gels, 24:309
of glycofuranosides, 21: 140-141
in glycoside hydrolysis, 22:26
of sucrose, effect of salts on, 21:225
of sugars, 23:53-56
of teichoic acids, 21:344
of I-thioaldofuranosides, 21: 142
Optical rotatory dispersion, 4591, 53:290
of acyclic sugar acetates, 26: 13
of glycosiduronic acid, 36:88
spectrum, of dithioacetals, 32:98
of sugars, 35:5
Orange, development physiology of. 42380
Orange pectinesterase, see Pectinesterases
Orchidectomy, effect on a-D-mannosidase
activity, 28:434, 436
Orcinol reaction, in sugar analysis, 28:223
Orcinol reagent for plant cell-wall residues,
42:215
Orcinol-sulfuric acid reagent, for estimation of
D-fmctose, 22~238
Orconectes limosus. trehalose biosynthesis in,
30:239
Organelles. of yeast cell, 32: 141-142
Organic chemistry, in 19rhcentury, 50:5
Organic compounds, mass spectrometry and
structure of. 21:39
Organolithium compounds, reaction with
aldonolactones, 50: 138-143
dioxolanes. 39: 138
Organomagnesium reagents, reaction with
aldonolactones, 50: 138-143
Organomercurials, research, 2 9 2
Organometallic compounds
for C-glycosylations, 33: 142-145
irradiation, 38: 190-191
Organoselenium
chemistry, 53: 143-145
mediated alkenylations, 53: 18C186
Organotin
analysis, 53: 19-22, 25
nomenclature, 53: 18
preparation, 53: 18-19
reactions, 53:32-33
regioselectivity
factors, 53:33-44
trends, 53:44,60-68
structures, 53:25-32
394 SUBJECT INDEX
Orientation, mechanism of, in plant cell walls,
26~331-335,338
Orosomucoid
a-o-mannosidase in structural studies of
human, 28:445
carbohydrate linkage in, 25:421,444,466
glycopeptides, liquid chromatography
separation, 46:48
isolation of carbohydrates from, on
analytical-scale columns, 46:60
sialylated oligosaccharides, fractionation,
46:46
Orotic acid monohydrate, 43:274
Orotidine 5-phosphate, 22:3 12
ORTEP representation of phosphorus sugars,
42:163, 183
Orthoacetates, of sugars, 21:20
Orthoacetic acid, methyl ester, reaction with
ribonucleosides, 22:340
Orthobenzoic acid, esters of o-fructose
derivatives, 22:248
Orthoesters
of carbohydrates, 1:77-127
derivatives, formation, aldonolactones
reaction with alcohols, 50:149-151
of D-fructofuranose, 22:292
of o-fructose derivatives, 22:248
hydrogenolysis, 39: 127
of cyclic, cyclic acetal synthesis, 39:79
as protecting groups, 36: 144
1,2-Orthoesters, of acylated sugars, glycoside
synthesis from, 34:244,248
Orthoformic acid, ethyl ester, reaction with
ribonucleosides, 22:340
Orthoglyoxylic acid, trithio-, triethyl ester,
formation from dithioacetal, 32:81
Orthosaccharinic acids, and lactones, 22:206
Osage orange
lectin
carbohydrate-binding specificity,
35:268-270
isolation, purification, and properties,
35~267
pigments, structure of, 26: 16
Osazones
chemistry of, 20:139-181
of o-fructose derivatives, 22:263
discovery of, 21:lO
formation mechanism of, hydrogen isotope
effect on, 27: 15 1
phenyl-, in mass spectrometry, 30:43
of sugars, 3:2344
Osladin
structural features, 45:289
taste properties, 45:286-287
Osones, 11:43-96,21:11
Osotriazoles
chemistry of, 18:99-121
conformation of sugar derivatives, 26:
71-72
N-phenyl-, oligosaccharide acetates, mass
spectrometry of, 29: 101-103
Ospolot, 45:5
0-substitution
nomenclature, 52: 1 12-1 13
acyl, 52:112-113
phosphates, 52: 113-1 15
phosphinates, 52: 116
phosphonates, 52: 115-1 16
sugars, composition in aqueous solution,
42:4346
Ouabain, octahydrate, crystal structure,
43:264-265
Ovalbumin, 44:232,239-240
a-D-mannosidase action on, 28:437443
aspartamidoglycans from, composition and
effect of enzymic hydrolysis of,
28:440442
glycopeptides, liquid chromatography
separation, 46:48
hen
I3C-n.mr. spectral reporter regions,
43: 14-1 5
oligopeptides
high-mannose, 43: 11-13
hybrid, 43: 1 1-14
hydrolysis, with trifluoroacetic acid,
46:268
isolation of carbohydrates from, on
analytical-scale columns, 46:60
oligosaccharides, liquid chromatography
separation, 46:4243
sialylated oligosacchairdes, fractionation,
46:46
Ovarian cysts
blood-group
H substance, Smith degradation of,
31:209
substances, 25:426,433,446,452458
glycoproteins, oligosaccharides from, liquid
 SUBJEC'T INDEX
chromatography separation, 46:4243,
60
Ovariectomy, effect on a+-mannosidasc
activity, 28:404, 434
Overhauser effect
'IC-NMR spectra and, 42: 19
in conformational analysis, 26:56
Overmercaptalation, of polysaccharides, 32:29,
32
Ovomucoid
a-D-mannosidase action on, 28:445
carbohydrate linkage in, 25:420
deamination of, 31:236
glycopeptides, liquid chromatography
separation, 46:48
heterogeneity in, 25:446
isolation of carbohydrates from
on analytical-scale columns, 4 6 6 0
on large-scale columns, 46:62
oligosaccharides, liquid chromatography
separation, 46:43
sialylated oligosaccharides, fractionation,
46:46
Ovotransferrin, chicken, glycoprotein
(compound 16), 'H-NMRspectroscopy,
41:219,256,259-261
Ovumucin, activity loss, 33:5
exo-7-Oxabicyclo[2.2.2]hept-5-ene-2-
carboxylic acid, 48:35
7-0xabicycIo[2.2.1]hept-2-ene-exxo-5,6-diol,
5,6,-O-isoprorpylidene-, carbohydrate 1,4-Oxazine, sugar derivatives, 25:403
substrate, 40:75-76
Oxadiazole, 2-(tri-O-acetyl- 1-bromo-cu-o-
arabinopyranosyl)-5-(trifluoromethyl)-
I ,3,4-, synthesis, 49:60
1,3,4-Oxadiazole, 3-amino-5P-DL-
rihofuranosyl-. synthesis, 40:77
Oxadizoles, 5-ary~-2-ethoxy-3-~-gluconyi-2,3- Oxazoline, derivatives, from sugar derivatives,
dihydro-1,3,4-, 50: 155-156
Oxaheterocycles, formation, 47:247-248
Oxalic acid, in hydrolysis of fmctans, 28:20
Oxalyl chloride method for preparation of
ketonucleosides, 42:232,240
Oxane
alkoxy and alkylthio derivatives, exo-
anomeric effect, 47:69-70
derivative, axiakquatorial equilibrium.
47: 59-60
substituted, anomeric equilibrium, 47:54
2-substituted
395
anomeric equilibrium, 47:67-68
axial preferences and Gibbs energy,
47:55-56
bond lengths and angles, 47:98-99
dipolar interactions, 47: 107
non-equivalent lone-pairs, 47: 1 1 1
solvent effects on axial preference,
47:67-68
Oxane ring, conformational properties, 47:53
2-(Oxane-2-yloxy)oxane,conformers, 4 7 9 3
Oxaprostaglandin F,,, 1 1 -deoxy-8-epi-l 1 -,
49: 159
Oxaprostaglandins. 49: I38
Oxathiabicyclo[2.2.2]octane,sugar derivative,
28:290
I ,4-Oxathiane
6-(hydroxymethyl)-2-methoxy-, S-oxide,
isomers. preparation of, 27:222
(2R, 4S,6S)-2- (hydroxymethyl)-6-methoxy-,
S-oxide, crystal structure bibliography,
30:449
(2S,6R)-6-(hydroxymethyl)-2-methoxy-,S-
oxide, crystal structure of, 25:72
Oxazabicyclo[2.2.2]octane, sugar derivative,
28:290
I ,3,2-Oxazaborolane, 2-phenylformation, 35:67
I .2-Oxazine, 3,6-dihydro-cis-6-methoxy-3-
methyl-, substrate for hexonic acids,
40:112
I ,3-Oxazine, sugar derivatives, 25:400402
Oxazinomycin
antiviral and antitumor activity of, 33: 1 I 2
structure of. 33: 1 12- I I3
Oxazole, sugar derivatives, 25:385
Oxazolidinc, sugar derivatives, 25: 150,
375-380
25:356,380-384
I ,2-0xazoIine, carbohydrate derivatives, 31:4
Oxepan, 43:238
Oxepane ring, anhydrohexitols containing,
25:245
Oxetane ring
alditols containing, 25:235, 243
conformation of, 26: 12 1
by isomenzation of oxirane ring, 25: I29
stability of, 25:210
Oxetanes, carbohydrate. preparation of. 28:289
Oxetans, carbohydrate, 24: 172
396 SUBJECT INDEX
Oxidation
anodic, starch in acidic and alkaline
solutions, 51:308-309
of carbohydrate boronates, 3 5 5 7
catalytic, of anhydrohexitols, 25:261
catalytic, of dextrans and length of branches,
30:406410
of o-fructose, 22:284
of glucofuranosidurono-6,3-lactonesand
glucofuranurono-6,3-lactones,
33:229-23 1
of glycol groups in glycofuranosides, 21:
132
halogen, of simple carbohydrates, 3: 129-
148
of halogenated carbohydrates, 22:208
lead tetraacetate, of sugars, 14:941
mechanism of, hydrogen isotope effect on
aldose, 27: 153-1 55
of nucleotides, 22:379
oxidation of cyclic acetals, 34:207
partial, of 1,6-anhydrohexopyranoses,
34:93-96
periodate
of carbohydrates, 11:141
the dialdehydes from, 16:105-158
in characterization of glycogen and
amylopectin, 30:33 1
of dextrans, 30:382-385
of methylated sugars and gas-liquid
chromatography, 30:33, 101
of polysaccharides, enzymic
determination of products, 30:282
degration of polysaccharides by,
31:20&211
and structure determination of
carbohydrate amines, 31: 102-105
and polarography of carbohydrates,
29: 167
of polysaccharides, 29:340
of ring-sulfur atom of 5-thioaldopyranoses,
23:2 12
selective catalytic, of carbohydrates,
33~86-100
employing platinum catalysts, 17: 169-22 1
of sulfonic esters of carbohydrates, 23:258
by transition-metal ions, 37:20
of vinylthio sugar derivatives, 27:283
Oxidation products, 1,4:3,6-dianhydrohexitoIs,
49:155-158
Oxidation-reduction mechanism, of
epimerization, 26:358
Oxidation states, metal ions, 47: 129
P-Oxides, enhanced nucleophilicity, 50:29
Oxidizing agents, for alcohol to carbonyl
oxidation, 31:223
Oxidoreductases, glycoenzymes, 27:309
Oxime ethers, 3-amino-2-hydroxypropyl-
substituted, 49:164
Oximes
carbohydrate, polarography of, 29: 152
effect on f.a.b.-mass spectrometry sensitivity,
4532
gas-liquid chromatography of, 28:49, 70
irradiation of carbohydrate, 38:179, 185
of monosaccharides, gas-liquid
chromatography of trimethylsilyl
derivatives, 28: 110
per(trimethylsily1)ated disaccharide,
gas-liquid chromatography of, 28: 135
sweetness-structure relationship, 45:
296-297
trimethylsilyl ethers of O-methyl, mass
spectra of, 29:77
trimethylsilylation of, 28:30
Oxirane, 1-C-(2,3,4,6-tetra-O-acetyl-P-~-
glucopyranosy1)-lo-, crystal structure
bibliography, 37:400
Oxirane ring
aldoses containing, 25: 109-179
in branched-chain sugars, 25: 167- 169
characterization of, 25: 170-172
cleavage of, 25: 125
reactions involving, 34: 115-1 17
formation in aldoses, 2 5 1 10-120
migration of, 25: 127
reductive cleavage of, 34:141
stability of, 25120,210, 34:131
Oxoformycin B
lower homolog, antileukemic activity of,
33:182-183
structure of, 33: 112-1 13
synthesis of, 33: 134, 172
Oxolane ring
opening of, in alditols, 29257
stability of, 25210
Oxonium ions
in acetalation reaction, 34: 181
acyl-
reactions of. 26:133-135
 SUBJECT INDEX
rearrangement in polyol systems,
26: 135-146
cyclic acyl-, in carbohydrate chemistry,
26: 127-195
mass spectrum of 2,3:4,5-di-O-
isopropylidene-P-o-fructopyranoseand,
26:23 I
Oxonium salts, acyl-, preparation of.
26: 129- 133
4-Oxopentanoyl group, as protecting group,
39:42
Oxopropylthiophene, 3-methyl-2-2-, formation
of, 46:3 18
0 x 0 reaction
application to carbohydrate derivatives,
2359-1 14
with glycals, 23:66,24:210
mechanism of, 23533
stereochemistry of, 23:78
Oxporus populinus, a-L-arabinofUranosidase
of, 42:387
Oxyamlose, chlorite-oxidized, antitumor
activity of, 32:258
Oxycellulose, 23:426,25:6
Oxygen
isotopeI80, effect on anomerization of
sugars, 24:44
lone-pair electrons, 47: 101-102
lone-pair orbitals, back-donation
chloromethoxymethane, 47: 109-1 10
distribution, 47: 109
interactions, 47: 1 1 1-1 12
nucleophilicity, enhancement, 47: 120, I22
radiation and reactions of molecular, with
primary carbohydrate radicals. 37:23
requirement for utilization of glycosides and
galactose, 39:397401
Oxygen atom, participation in sugar reactions,
22:llO
Oxygen nucleophiles, for oxirane aldoses,
25:125
Oxygen ring, formation and cleavage of, in
sugars, 13:9-61
Oxymethylene groups, in polyglycoses, 21 :
450
Oxynervon, 24:398-399
Ozone, oxidative degradation of
polysaccharides by, 31:232
Ozonolysis, of cyclic acetals, 34:207, 39:
8 1-82
397
P
Pachyman, 23 :37 8
antitumor activity of, 32:246,259-260
carboxymethyl ethers, preparation of, 29:
319
fine structure of, 30:369
fungal. 41:73
0-acetyl-. crystal structure bibliography,
35:381,40:390
Pachymaran, antitumor activity of, 32:246-247,
266
and effect of urea on, 32:26 1
Paeniflorin. bromo-ethanolysis product, crystal
structure, 43:351
PA1 human embryonal carcinoma cells.
lactosaminoglycans, f.a.b.-mass
spectrometry, 4 5 5 9
Paints, galactomannans in, 31:31 I , 35:342
Palatinose, 22:230
in honey, 25:297,300
liquid chromatography methods for analysis
of, 46:33
monohydrate, crystal structure bibliography,
31:352
structure of, 32: I93
taste properties, 45:254-255
utilization by yeasts, 32: 194
Palmae, galactomannans from, 31:253-254
Palmitaldehyde. as precursor in biosynthesis of
sphingosines, 24:394
Palmitic acid
in o-galactosylglycerides, 37:326
ester of trehalose 2-sulfate, in
Mycohacterium tuberculosis, 30:236
lithium, potassium, and sodium salts, as
catalysts and solubilizers for sugars,
27:96
methyl ester, transesterification of methyl a-
o-glucopyranoside with, 33:44
Pampas grass, hemicellulose-cellulose ratio,
36:253
Panaxoside A-progenin I acetate, 43:373
Pancreatic ribonucleases, carbohydrate linkage
in, 25:42 1
Pancreatin, hydrolysis of bydroxyalkyl
polysaccharides by, 29:3 19
Pangamic acid, synthesis, 35:54
Pangamolactone, synthesis, 3 5 5 4
PAN gels, cross-linked, 49: 186-1 87
398 SUBJECT INDEX
Panose, 51:151, 153
enzymic action on, 30:277,292, 302
in honey, 25:297,300
liquid chromatography separation, 46:41
preparation of, 34:257
synthesis of, 26: 16
utilization by yeasts, 32: 197
Panstroside, o-fucose-containing, 39:302
Papain, 44:208
Papaya pectinesterase, see Pectinesterases
Paper chromatography
of aldonic acids, 38:3 18
of cyclic acetals, 26:233
in formose research, 29: 175, 206
and mercaptalation reactions, 32:2 1
phenylboronic acid in, 35:58-62
Paper chromatography, of carbohydrates and
related compounds, 9:303-353
Paper electrophoresis
of carbohydrates, 18:6 1-97
metal-sugar complexes, 47:3-5
Paper industry, galactomannans in, 31:311
Paper ionophoresis, sugars, Maurice Stacey's
work, 52: 17
Paper products, plant galactomannans in,
35:342
Purucoccidioides brusiliensis
galactomannan, 41:93
polysaccharide, 41:70, 73
Paraformaldehyde, infrared spectrum of,
29:181
Paraldehyde, reaction with sucrose, 33:255
Paramagnetic species, 47: 130-135
dipolar interaction, 47: 133
electron-spin relaxation, 47: 133-135
Fermi contact shifts, 47: 13 1
hyperfine shifts, 47: 130
pseudo-contact shifts, 47: 130-1 3 1
relaxation agents, 47: 130- 135
scalar coupling, 47: 134
shift agents, 47:130-131
Paramecia, lethality of sonicated starch to,
5 1:306-307
Paramomycin 11, mass spectrometry of, 29:
96
Paramose, 23: 168
Paramylon
biosynthesis of, 26:392
enzymic action on, 30:276
Paraquat, effect on sugarcane, 21:422
Parasorbic acid
DL-, reduction, 40:38
synthesis, 40:21-22
(9-, carbohydrate substrate, 40:119
Paratose, 21:188-189, 23:272
ester of cytidine pyrophosphate, isolation of,
28:3 16
preparation of, 28:300
synthesis of, 33:75,41:10
Paratyphoid B epidemic, Japan, 48:3
Purmeliu caperatu. polysaccharide, 41:76
Paromamine
alkyl and aralkyl derivatives, preparation of,
30:179
derivatives, preparation of, 34:262
formation, 35:113-1 14
inactivation of, 30: 187
isolation and synthesis of, 30: 1 18
structure of inactivated, 30: 188
synthesis of, 30: 140-142
Paromamine 3 '-phosphate
and inactivated paromamine, 30: 188
nuclear magnetic resonance spectrum of,
30: 190
Paromobiosamine, deamination of derivatives
Of, 31:26-28
Paromobiosamine I, neobiosamine B and,
30:118
Paromobiosamine 11, neobiosamine C and,
30:118
Paromomycin, 23: 168
discovery of, 30: 112
o-mannosyl-, isolation of, 30:118
mass spectrometry of, 29:96
stereochemistry of, 30: 1 17
Paromomycin I
alkyl and aralkyl derivatives, preparation of,
30: 179
1-N-acyl derivative, activity against resistant
bacteria, 30:174
Paromose
diethyl dithioacetal, oxidation of, 32:85
synthesis of, 30: 116
Parsley, see Petroselinum crispum
Pasteur, Louis, L-tartaric acid preparation, 50:3
Pasteur effect
in control of glycolysis, 32:168-173
history, 33:4
oxygen inhibition of glycolysis, in
spermatozoa, 34:301
 SUBJECT lNDEX
Pastewella pseudotuberculosis,
lipopolysaccharide, mass spectrometry of,
29:54
Pathogenesis, bacterial, capsular
polysaccharides, role, 41:202-206
Pathogenicity, polysaccharide structure role,
41~206-208
Patrinoside, monohydrate, 43:333
Paucin, monohydrate, crystal structure
bibliography, 38:47&477
Paucirotation, term, 23: 12
Pea, see Pisum .sutivus
Peach
development physiology of, 42:34 I , 347,
370-372,380
gum, structure, 41:X
Peanut lectin, 35:257-262
biological activity, 35:261
carbohydrate-binding specificity,
35:259-261
isolation, 35: 138
purification and properties, 35258
Pear, development physiology of, 4 2 3 4 1-342,
37&372,376,378-379
Pea-tree lectin, composition, purification, and
properties, 35:3 13
Pectase, name for pectinesterase, 33:324
Pectate, 47:32
Pectate lyase, depolymerizing enzymes, 33:
325
Pectic acid, 24:299, 52:330, 352, 414
acetylated, preparation of, 29:330
p-eliminative depolymerization of, 29:245
crystallography of, 22:479480
enzymic degradation by lyase, 33:367
esterification and p-eliminative degradation,
29:247
with propionic anhydride, 29:350
esters, preparation and properties of. 29:
338
oligomers, liquid chromatography, 46:40
structure of, 33:327,41:7
sulfation of, 29:335
Pectic enzymes, see Enzymes
Pectic polysaccharides, 24: 298
chemistry of, 2:235-251
constitution, 35:6
definition, 36:217
enzymes acting on, 5:79-102
gels, biological, 24:326
399
in plant cellwalls, 42:274
biosynthesis, 42321-322.331-332,337
of dicotyledonous plants, 42277-285
fruit ripening and, 42:343,365, 368-378.
373
gel formation, 42:277
interconnections between, 42:304-306
of monocotyledonous plants, 42:285,
287
splitting by p-elimination, 33:323
structure, enzymic analysis. 44: 182-1 86
Pectinase, enzyme from commercial, 29:246
Pectin demethoxylase, name for pectinesterase,
33:324
Pectinesterases
action pattern and specificity, 33:329-337
assay of, 33:343-345
banana, purification of, 33:341
in h i t maturation, 33:381
inhibitors for, 33:336
Michaelis constants for, 33:333
microbial, 33:334-335, 338
pH optima of, 33:335
purification of, 33:342
nomenclature. 33:324
occurrence and formation of, 33:337
orange. purification of, 33:341
plant, 33:33&335
pH optima of, 33:335
purification of, 33:338-343
tomato, molecular weight of, 33:339. 341
purification and characterization of,
33:338-341
Pectinex
endo-o-galacturonanases from, 33:346
pectin lyase from, 33:379
Pectin galacturonase. role in cell-wall changes,
42:369
Pectinic acid, 52:353
Pectin lyase, 44: 183- I84
depolymerizing enzymes, 33:325,379
Pectin methoxylase, name for pectinesterase,
33:324
Pectin methylesterase
association with plant cell wall, 42:337,369,
371-372
in fruit climacteric, 42:364
name for pectinesterase, 33:324
Pectin pectyl-hydrolase, name for
pectinesterase. 33:324
400 SUBJECT INDEX
Pectins, 24:299,301,46:306,326, 52:348,
350-353,53:411412
acid hydrolysis of, correction factors, 46:
254
affinity chromatography adsorbent, 39:4 19
analysis and identification, 44:23
@-eliminatiavedepolymerization of, 29:245
biosynthesis of, 26:399402,32: 1 1
in cell-wall formation, 26:337
circular dichroism, 45: 11 1
dehydration of, 28: I88
galactan in, 42:282-283
galacturonic acid units of, hydrolysis losses,
46:261-262
hydrolysis of methylated, 28:23
in L-ascorbic acid synthesis, 37:147
methanolyzate, structure, 39:5
methylation of, 30: 15, 32: 11
non-fermentable oligosaccharides, liquid
chromatography methods for, 46:52
in plant cell-walls, 26:298, 300
reductic acid from, 28:207
structure of, 33:327
uronic acids, gas-liquid chromatography of,
28:76
Pectin trans-eliminase, from commercial
pectinase, 29:246
Pectolipase, name for pectinesterase, 33:325
@-PelatinA
activation by a-L-arabinofuranosidase,
42:392
structure of, 42:392
Pellicle, acquired, formation of, 30:434
Pelliculuria sasukii, validamycin and
validoxylamine activity against, 48:87
Penicillin
effect on peptidoglycan biosynthesis, 26:43 1
production, Japan, 4 8 : M
Penicillium charlesii, polysaccharides, 41 :95
Penicillium chrysogenum, galactomannan,
41:95
Penicillium citrinium, malonogalactan, 41:87
Penicillium varians, glucogalactan varianose,
41:lOO
Pentadecanoic acid, 3-hydroxy-, gas-liquid
chromatography and mass spectrum of,
30:36
Pentadecathymidylic acid, synthesis, 36: 175
2,4-Pentadienal, 2,5-dihydroxy-, formation of,
and reductic acid from, 28:191-192
2,4-Pentadienone, 3-henzoyloxy-, precursor for
4-deoxy-o~-daunosamie,40: I 1 1
3-Pentadienone, substrate for carbohydrate
synthesis, 40:27
Pentaerythritol
crystal structure bibliography, 31:363
cyclic acyloxonium rearrangements in,
26:142, 144
tetraacetate
crystal structure bibliography, 31:368
rearrangement in liquid hydrogen fluoride,
26:171
tetra(cyanoethy1)-, in gas-liquid
chromatography, 28:45
tetranitrate, crystal structure bibliography,
31:363
trimetbylsilylation, effect of impure solvents
on analysis of, 28:30
Pentanal, 5-hydroxy, as hemiacetal in solution,
42:3 I
1,4-PentanedioI, 4-0-benzyl-1-0-p-tolyl-
sulfonyl-, 22: 144
solvolysis of, 24: 195
1,5-Pentanediol, cyclic phenylboronate,
preparation, 35:35
2,4-Pentanedione
condensation products with o-fructose,
22:288, 305
for enhancing detectability of carbohydrates,
46:67
transition metal chelates in proton nuclear
magnetic resonance spectroscopy, 29:24
1,3,5-Pentanetriol, tripivalate, acyloxonium
rearrangement of, 26: 143
Penta-N.0-acetates, 48:59-60
Penta-N,~-acety~-3-amino-3-deoxy-a-~~-
carba-glucopyranose, 48:61-62
Penta-N,0-acetylamino-deoxy carba-sugars,
48:60,62
Penta-N,O-acetyl-4-amino-4,7-dideoxy-a-o~-
carba-glucopyranose, 48:63
Pentanoic acid, amylase ester, preparation of,
29:330
1-Pentanol, cyclodextrin inclusion complexes
with, 46:222-224
Pentanone, 5-hydroxy-2; acyclic form in
solutions of, 42:30
2-Pentanone 1,5-bisphosphate 1,5-dihydroxy-
hydrate of, 42:32
structure of, 42:32
 SUBJECT lNDEX
Penta-O-acetyl-5-bromo-P-~-glucopyranose, Pent-2-enofuranoside, methyl 5-0-benzoyl-2,3-
synthesis, 49:4549
Pentaric acid, 2,3-di-O-acetyl-4-deoxy-~-
threo-, dimethyl ester, synthesis, 40: I I6
Pentasaccharides
hydrolytic degradation of, 31: 188
methylation of, 30: 11
in plant kingdom, 37:3 11
4-Pentenal, precursor for sugar synthesis,
40:12
2-Penten-I ,5-dial-4-one, synthesis, 40:73
Pent- I -enitol
1,2-dideoxy-4,5-0-isopropylidene-o-e~~~~~/~r~~-,
synthesis, 39: 147
3,4-di-O-acetyl- 1,5-anhydro-2-deoxy-r>-and
r.-evythro-, reaction with lead
tetrafluoride, 25: 195
4-O-acetyl-l,5-anhydro-3-(6-chloro-9-
purinyl)-l,2,3-trideoxy-o-threo-.proton
magnetic resonance spectra, analysis of,
27:82
1-0-acetyl-2,3:4,5-di-U-isopropylident-n-
erythro-, crystal structure bibliography,
34:372
2,3,4-tri-O-acetyl- 1,5-anhydro-o-ei?.thro-.
reaction with hydrogen chloride, 28:266
2,3,4-tri-O-acetyl- 1,5-anhydro-o-threo-,
reaction with hydrogen chloride, 28:266
(Z)- 1-0-acetyl-2,3:4,5-di-O-isopropylidene- Pent-2-enopyranose
D-
erythro-, crystal structure bibliography.
37~434,38:454456
threo-, crystal structure bibliography.
37:434, 38:454
Pent-] -enitol-3-ulose, 1,2-dideoxy-5,6-0-
isopropylidene-D-glycero-. proton
magnetic resonance spectra, analysis of,
27:80
Pent-3-enodialdo- 1,4-furanose, 3-deoxy- 1,243
isopropylidene-a-o-g[ycero-. 24:248
Pent-] -enofuranose, 2,3,5-tri-O-benzoyl-I-
deoxy-o-
eryrhro-, 24:220
threo-, 24:220
Pent-4-enofuranose
5-deoxy- 1,2-0-isopropylidene-3-0-methyl-
P-L-threo-, 24:25 1
3-0-acetyl-5-deoxy- 1,2-0-isopropylidene-P-
L-threo-, 24:250
preparation of, 28:291
40 1
dideoxy-P-o-glycero-. 24:229
bromination in methanol and silver acetate,
28:269
reaction with nitryl iodide, 28:273
Pent-3-enofuranos-5-ulose,3-deoxy-1,2-0-
isopropylidene-5-C-phenyl-a-~-g[ycero-,
and dimer, preparation of, 29:297
9-(Pent-3-enofuranosyluronic acid)adenine,
isopropyl 3-deoxy-P-~-gl,vcero-.
preparation, 36: 128
I -(Pent-3-enofuranosyluronicacid)uracil, 2-0-
acetyl-3-deoxy-P-o-g!ycero-. methyl ester,
preparation, 36: 130
3-Pentenoic acid, trans-2-hydroxy-, precursor
for sugar synthesis, 40:19
4-Pentenoic acid
3-hydroxy-, precursor for sugar synthesis,
40: 19
3jR) hydroxy-, preparation, 40: 114
Penten-5-olides, 50: 190
Pent-2-enonate. ethyl 2,3-dideoxy-
D-glycero-, synthesis by Wittig reaction,
27:254
4,5-O-isopropylidene-~-g~i~cero-, synthesis
by Wittig reaction. 27:253
Pent-2-enono- 1,4-1actone,2,5-di-O-benzyl-o-
gluycero-, 50: 168
3,4-dichloro-2.3,4-trideoxy-P-~-glycero-,
24:246
1,2,4-tri-0-acetyl-3-deoxy-~-g/vcero-,
24:241
Pent-2-enopyranosi de
3,4-dichloro-2,3,4-trideoxy-P-o-g[ycero-
pent-2-enopyranosyl 3,4-dichloro-2,3,4-
trideoxy-P-D-glycero-, 24:245
preparation of, 28:238
methyl 3,4-dichloro-4-deoxy-
a - ~and
- p-o-g/ycero-. proton magnetic
resonance spectra of, analysis of,
27230
o-glycero-, conformation of, 26: 124
methyl 3,4-dichloro-2,3.4-trideoxy-
a-D(and @-o)-gbcero-,24:245
P-D-glvcero-. preparation of, 28:238
methyl 4-0-henzyl-2,3-dideoxy-P-~-
glycero-. preparation of, 28:293
Pent-3-enopyranoside
benzyl2-O-benzyl-3,4-dideoxy-
402 SUBJECT INDEX
Pent-3-enopyranoside (continued)
a-D-glycero-, reaction with nitryl iodide,
28:273,299
4-nitro-a-o-glycero-, preparation of,
28:299
methyl 2-0-benzyl-3,4-dideoxy-, p-L-
glycero-, 24:250
methyl 2-0-benzyl-3,4-dideoxy-, p-L-
glycero-, preparation of, 28:293
Pent-2-enopyranosid-4-ulose, 2,3-dideoxy-~~-,
synthesis, 40:66,72
Pent-2-enopyranosyl bromide, 2,4-di-O-acetyl-
3-deoxy-o-gbcero-, preparation of,
28:266
Pent-2-enopyranosyl chloride, 2,4-di-O-acetyl-
3-deoxy-o-g@cero-, preparation of,
28:266
Pent- 1-enose, 2-deoxy-4,5-0-isopropylidene-
o-eiythro-, diphenyl dithioacetal, preparation
of, 32:57
o-threo-, diphenyl dithioacetal, preparation
of, 29:298
3-0-methyl-o-erythro-, diphenyl
dithioacetal, oxidation and detonation
of, 32534
preparation of, 32:57
3-O-(p-nitrobenzoyl)-o-erythro-, diphenyl
dithioacetal, nuclear magnetic
resonance spectrum and conformation
of, 32:92
preparation of, 32:58
Pent-2-enose
I-C-(p-bromophenyI)-2,3-dideoxy-o-
glycero-, synthesis by Wittig reaction,
27:246
2,3-dideoxy- 1-C-
phenyl-o-gbcero-, synthesis by Wittig
reaction, 27246
(p-methoxypheny1)-D-glycero-, synthesis
by Wittig reaction, 27:246,290
(p-nitrophenyl)-D-gbcero-, synthesis by
Wittig reaction, 27:246
Pent-3-enose, 2,5-anhydro 3,4-dideoxy-
o-glycero-, diisohutyl dithioacetal,
preparation of, 32:52,57
L-glycero-, diisobutyl dithioacetal,
preparation of, 3 2 5 2
Pent-4-enose, 4,5-dideoxy-~-threo-,24:26 1
Pent-2-enoside, methyl 4-0-benzyl-2,3-
dideoxy-P-L-glycero-, 24:232, 250
Pent-3-enoside, methyl 2-0-benzyl-2,3-
dideoxy-P-L-glycero-, 24:232
Pent-4-enoside, methyl 5-deoxy-2,3-0-
isopropylidene-P-o-eryfhro-, 24:25 1
Pent-3-enosid-2-ulose, methyl 4-deoxy-3-0-
methyl-, formation and hydrolysis of,
31:221
Pent-3-enosulose, 3,4-dideoxy-, dehydration of,
28: 172-1 73
I -Penten-3-yn-5-01, 1-ethoxy-, precursor for
sugar synthesis, 40:9
Pent-4-exo-enopyranose, 4-deoxy- 1,2-0-
isopropylidene-p-o-threo-, synthesis,
39: I42
Pentitols
acetals of, 7: 137-207
anhydrides of, 5:191-228
1,4-anhydro-
2-deoxy-~-threo-,infrared spectrum of,
25:252
2-deoxy-~-erythro-,infrared spectrum of,
25:252
preparation of, 31:60-62
1,5-anhydro-, 25:235
anhydro-, 25:23 1-236.272-274
ring opening of, 25:257
I, 1-bis(acylamido)- I-deoxy-, conformations
of, 31:110
I , 1-bis(benzamido)- 1-deoxy-mono-0-
benzoyl-, preparation, 39:3 1
catabolism by yeasts, 32:234
1-C-cyclohexyl-2,3 :4,5-di-O-isopropyl-
idene-, preparation of isomers, 27:218
conformation of, 25: 105
2-deoxy-
m-erythro-, synthesis, 40:109
2-fluoro-, synthesis, 40: 104105
dianhydro-, 25:235
1,2-dideoxy-~-threo-,21: 157
2,3:4,5-di-O-isopropylidene- 1-C-
methyl-, preparation of isomers, 27:218
phenyl-o-gluco-, preparation and
configuration of, 27:218
gas-liquid chromatography of, 28:67
gel chromatography of, 25:3 1
I-amino-1-deoxy-, deamination of, 3 1 : 6 M 2
infrared spectra, 45:294
1-S-ethyl-l-(5-fluorouracy~-~-y~)-l-thio-o-
gluco-, crystal structure bibliography,
38:493
 SUBJECT INDEX
2(S)-4-0-acetyl-3,5-0-benzylidene- I ,2-
dideoxy-2-C-phenyl-o-evythro-, crystal
structure bibliography, 38:472473
synthesis of, 2: 107-1 18
2,3,4,5-tetra-O-acetyl-l-S-ethyl- 1-(5-
fluorouracil- 1-yl)- 1-thio-D-gluco-,
ethanolate, crystal structure
bibliography, 38:499-500
Pentobarhital, cyclodextrin inclusion
complexes with, 46:223-224
Pentodialdo- 1,4-furanose
3-deoxy- 1,2-0-isopropylidene-
P-L-threo-, 24:248
a-o-erythro-, 24:248
0-X)dO-
1,2,-0-isopropylidene-3-deoxy-3-fluoro-
a-, 'H-and I9F-NMR data for, 46: I I2
3-deoxy-3-fluoro- 1,2-0-isopropylidene-a-
, NMR data for, 46: 169
3-0-benzyl- I ,2-O-isopropy~idene-a-a-x,vh-,
reaction with phenylmagnesium
bromide, 27:214
1,2-O-isopropyhdene-a-a-xy/o-, 23:24
~,2-0-isopropylidene-a-o-q~k-, in L-apiose
synthesis, 31:181
1,2-0-isopropylidene-5-uldehydo-a-o-.~~vlo-, Pentofuranoside
and dimer, 25:214
1,2-0-isopropylidene-3-0-methyl-a-o-.rv~o-, 2-deoxy-2-fluoro-, IH- and '"-NMR data
ketenic dithioacetal from, 32:44
Pentodialdose
mercaptalation of, 32:25
2,4-O-benzylidene-o-xyk~-, 1 -(diethy1
dithioacetal), reduction of, 32:55
xylo-, preparation of, 32534
Pentofuranose
D-, peracetylated, carbon-I 3 nuclear
magnetic resonance spectroscopy, 41:49
2-deoxy-
o-evythro-, nucleosides and nucleotides,
crystal structures of, 25:86-90
2,2-difluoro-~-evythvo-.48: 182
2-fluoro-, 'H- and I9F-NMR data for,
46: 109-1 1 1
3-deoxy-
3-fluoro-o-, IH- and I9F-NMR data for,
46:112
threo-, tns(trifluoroacetate), synthesis,
40:83
4-deoxy-, 4-phosphinyl
mass spectrometry of, 42:187-188
403
NMR spectroscopy of. 42:184-187
X-ray crystallography of, 42: 183-1 84
5-deoxy-, 5-fluoro-o-, 'H- and I9F-NMR data
for,46:112-113
derivatives, fluorinated, I3C-NMR data for,
46~168-169
2,3-dideoxy-a, P-aL-g!vcero-, synthesis,
40: 12-1 3
4.5-dideoxy-4 phosphinyl
ORTEP representation of, 42: 184
synthesis and structures of. 42: 179- 18 I
5-0-benzyl-
3-deoxy- 1,2-0-isopropylidene-3-C-
methylene-a-o-erythro-, synthesis by
Wittig reaction, 27:235
2,3-dideoxy-o-glycero-, preparation of,
28:294
2,3,4-trideoxy-
4-C-(phenylphosphinyI)-a~-glycero-.
synthesis, and 1,5-diacetate, 40: 110
4-phosphinyl synthesis and structures of,
42:176-178
Pentofuranose-3 -dose, 5-deoxy- 1.2-0-
isopropylidene-P-L-threo-. reaction with
2-lithio-l,3-dithiane, 32:38
2,3-anhydro-, 25:155-160, 177-179
for, 46: 109-1 1 1
5-deoxy-4-fluoro-, 'H- and "F-NMR data
for, 46: 112-1 13
3-deoxy-3-fluoro-o-, 'H- and I9F-NMR data
for, 46: 1 12
ethyl 3-amino-3-deoxy-~-or-urubino-,
synthesis, 40: 10-1 1
methyl 2.3-anhydro-5-0-benzyyl-
a-o-~vxxo-. synthesis, 40: 1 18
a-o-riho-, synthesis, 40: I I9
P-D-~~xo-,synthesis, 40:119
P-o-ribo-, synthesis, 40: 1 18
methyl 2,5-bis(benzamido)-2,3,5-trideoxy-P-
a-threo-, 23:174
methyl 2-deoxy-
a,P-D-rrythro-, selective phosphorylation
of, 33:46
P -a-ervthro-
preparation of, 29:5
proton magnetic resonance spectroscopy
of. 27:28, 83
P-L-erythro-, 23:276
404 SUBJECT INDEX
Pentofuranoside (continued)
2-(hydroxymethy1)-, formation by
deamination, 31:22
3,4-O-isopropylidene-2-C-methyl-p-~-
erythro-, 23:279
5-0-(methylsulfonyl)o-erythro-,
fluorination, 38:207
5-~-p-tolylsulfonul-3-~-trity~-~-erythro-,
fluorination, 38:207
5-O-p-tolylsulfonyl-~-erythro-,
fluorination, 38:207
5-thio-P-~-erythro-,23:2 14
methyl 3-deoxy-, P-L-qthro-, 23:276
methyl 2,5-dideoxy-a-o-erythro-, 21: 194
methyl 3,5-dideoxy-a-~-erythro-, 21: 194
Pentofuranosulose, methyl 3,4-0-
isopropylidene-P-o-erythro-, reaction with
2-lithio- 13-dithiane, 32:38
L-threo-Pento-l,4-furanos-4-ulose, 4-0-acetyl-
5-acetyl-5-deoxy-5-fluoro-1,2-0-
isopropylidene-3-0-tosyl-P-, 'H- and "F-
NMR data for, 46: 143
Pentofuranos-3-ulose, 5-deoxy- 1,2-0-
isopropylidene-P-L-treo-, irradiation,
38: 123-124
Pentofuranosyl, 1-3-chloro-2,3-dideoxy-5-0-
trityl-6-o-threo-, preparation of, 28:248
Pentofuranosyl chloride, 2-deoxy-o-erythro-,
esters, 21:146
Pentofuranosyl cyanide
P-D-, preparation and reactions of,
33:13 1-142
3-deoxy-2,5, di-O-(p-nitrobenzoyl)-p-o-
eryythro-, preparation of, 33: 142
2-deoxy-3,5-di-O-p-toluoyl-P-o-erythro-,
preparation of, and anomer, 33: 140
Pentofuranosyl fluoride
conformation of derivatives, 26: 11 1
'H- and I9F-NMR data for, 46:106-109
3,5-0-benzoyl-2-bromo-2-deoxy-o-
a-o-arahino-, 'H- and I9F-NMR data for,
46:138
~ - D - x J ~ I -IH-
, and I9F-NMR data for,
46:138
l-(p-o-eryrhro-Pentofuranosyluronic
acid)thymine, 2-deoxy-, preparation,
36: 127
Pentofuranuronate conjugates, enolacetal-
forming p-elimination, 29:273-28 1
Pentoglycans, 53:40 1 4 0 2
Pentonic acid
2-amino-2-deoxy-o-, synthesis, 4 0 12 1
2-amino-2-deoxy-~-,synthesis, 40: 121
3-deoxy-2-C-(hydroxyethyl)-~-erythro-
calcium salt, crystal structure
bibliography, 31:364
strontium salt, crystal structure
bibliography, 31:364
Pentono- 1,4-lactone
2-deoxy-~~-erythro-. synthesis, 40: 19
2,5-dideoxy-o~-threo-,synthesis, 40:20
5-0-acetyl-2-deo,~y-3-S-phenyl-3-thio-o-
threo-, preparation of, and 3-epimer,
32:59
5-0- ( p-bromophenylsulfony1)-2,2'-0-
cyclohexylidene-3-deoxy-2-C-
(hydroxymethy1)-o- erythro-, crystal
structure bibliography, 30:454
5-S-acetyl-2,2'-anhydro-3-deoxy-2-C-
(hydroxymethyl)-5-thio-~-erythro-,
proton magnetic resonance spectroscopy
of, 27:28
Pentononitrile, 2-deoxy-3,5-O-ethylidene-o-
erythro-, preparation of, 28:283
Pentopyranose
D-, peracetylated, carbon- 13 nuclear
magnetic resonance spectroscopy, 41:49
2-deoxy-P-~-erythro-
mutarotation of, 24:59
triacetate and tribenzoate, conformations
in chloroform solution, 26536
2-deoxy-2-fluoro-, 'H- and I9F-NMR data
for, 46:104-105
3-deoxy-3-fluoro-, 'H- and I9F-NMR data
for, 46: 105-106
4-deoxy-4-fluoro-, 'H- and 19F-NMRdata
for, 46: 105-106
derivatives
fluorinated
13C-NMRdata for, 46:167-168
C(or 0)-branched, 'H- and I9F-NMR
data for, 46:141-142
proton spin-lattice relaxation rates, 45: 153
3,4-dideoxy-l,2-di-O-(trifluoroacetyl)-~~-,
synthesis, 40: 109
1-0-acetyl-3-deoxy-
2-C-methyl-5-thio-o~-erythro-,
phenylboronate, synthesis.
40: 103-1 04
4-C-methyl-5-thio-o~-erythro-,
 SUBJECT INDEX
phenylboronate, synthesis,
40: 103-104
1,3,4-tri-O-acetyl-2-deoxy-2,2-difluoro-a-~- methyl 3-deoxy-P-~-erythro-,conformation
erythro-, 48:181-182
1,2,4-tri-O-acetyI-3-deoxy-
2-C-methyl-5-thIo-o~-threo-,synthesis,
40: 103- 104
4-C-methyl-5-thio-o~-threo-, synthesis,
40:103-104
I ,3,4-tri-O-acetyl-2,2-di-chloro-2-deoxy-~- methyl 3,4-O-isopropylidene-P-~-erythro-,
erythro-, preparation of, 28:26 I
Pentopyranoses, 2-deoxy-2-fluoro-o-, 48: I 8 I
Pentopyranoside
2-3-anhydro-, 25:150-154, 171, 176-177
3,4-anhydro-, 25:15&154, 176-177
benzyl2-0-benzyl-3,4-dideoxy-4-nitro-~-t
threo-, 24:94
2-deoxy-2-fluoro-, 'H- and I'F-NMR data
for, 46: 104-1 05
3-deoxy-3-fluoro-, 'H- and "F-NMR data
for, 46:105-106
4-deoxy-4-fluoro-, IH- and I9F-NMR data
for, 46:105-106
ethyl 3-cyano-3,4-dideoxy-a-o~-, threo-.
crystal structure bibliograpy, 34:353
L-erythro-
methyl 4-deoxy-4,4-difluoro-2,3-0-
isopropylidene-P-, 'H- and IYF-NMR
data for, 46: 156
methyl 2-deoxy-2,2-difluoro-3,4-0-
isopropylideneb-P-, IH- and '"F-
NMR data for, 46: 156
methyl 2-amin0-2,3.4-trideoxy-3-fluoro-
threo-
a-L-,'H- and I9F-NMR data for, 46: 128
P-D-, IH- and I9F-NMR data for, 46: 128
methyl 2-bromo-2,3-dideoxy-4-O-methyl-a-
DL-erythro-, synthesis, 40:33
methyl 2-deoxy, carbon- 13 nuclear magnetic
resonance spectroscopy, 41:56
methyl 2-deoxy-
o-erythro-, preparation of, 32:69
2,2-difluoro-3,4-O-isopropylidene-P-~-
erythro-, preparation, 38:226
uL-erythro-, synthesis, 40:54
L-erythro-, conformational equilibria of
anomers, 24:59
3,4-O-isopropylidene-2-C-methyl-o-ribo-, determination by polarography, 29: 167
synthesis by Wittig reaction, 27:293
3,4-O-isopropylidene 2-C-methylene-P-o-
405
erythro-, synthesis by Wittig reaction,
27:292
of, 24:59
methyl 2.3-dideoxy-4-0-methyl-a-o~-
glycero-, synthesis, 40:33
methyl 3,4-di-O-acetyl-2-deoxy-~-fhreo-,
reaction with hydrogen bromide, 28:266
Pentopyranosid-2-ulose
crystal structure bibliography, 37:38 I
tert-butyl3,4-0-isopropylidene-a-~-erythro-,
photolysis, 38: 122-123
Pentopyranosid-3-ulose
a-u-threo-, preparation of, 33:89
- P-o-erythro-, preparation of, 33:89
methyl a-u-and P-n-erythro-, preparation by
oxidation of boronate, 35:57
Pentopyranosid-4-ulose
P-o-threo-and P-L-threo-, preparation of,
33:89
methyl 2,3-dideoxy-( ~S)-DL-, reaction with
P-toluenesulfonylhydrazide,
40: 109-1 10
erythro-Pentopyranos-4-ulosehydrate,
synthesis, 40:62
Pentopyranosyl bromide
3,4-di-O-acetyl-2-deoxy-~-erythro-,
preparation of, 28:265
4-0-acetyl-3-bromo-2,3-dideoxy-~-threo-,
preparation of, 28:264, 266
Pentopyranosyl chloride, 4-0-acetyl-3-chloro-
2,3-dideoxy-u-threo-, preparation of,
28:264
Pentopyranosyl fluoride
3,4-di-O-benzoyl-2-deoxy-o-erythro-
a anomer, 'H- and I'F-NMR data for,
46: 137
P anomer. IH- and I'F-NMR data for,
46:137
'H- and "F-NMR data for, 46:101-103
poly-0-acyl-u-, proton magnetic resonance
spectroscopy of, 27:21
Pentopyranosyl halides, 3,4-di-O-benzoyl-2-
deoxy-, preparation of, 28:265
Pentosans
definition, 36:2 17
formation of, 28: 188
gas-liquid chromatography of, 30:89-90
406 SUBJECT INDEX
Pentose, 48:281
5-acetamido-5-deoxy-, composition in
aqueous solution, 42:50
aldehyde-acetates, preparation of, 32:62
2-amino-2-deoxy; synthesis of, 26: 14
5-amino-5-deoxy-, 23: 119
5-amIno-3,5-dideoxy-o-eyrhrc~-. 23: 130
2,S-anhydro-3-deoxy-o-eyfhro-, reactivity
of, 25:211
5-(benzyloxycarbonyl) amino-, composition
in aqueous solution, 42:50
I-14C,2-deoxy-o-etythro-, 21: 150
catabolism by yeasts, 32:21&219
chromatographic technique for estimation of,
30:7
4-C-(hydroxymethyl)-~-fhreo-,o-apiose
from, 31:176
crystallography of, 25:58
2-d, 2-deoxy-o-etyfhro-, proton magnetic
resonance spectroscopy of, 27: 146
dehydration of, 28: 176, 188,208,46:275
2-deoxy-
o-erythro-, 21:149, 151, 153, 156,25:192
alkaline degradation of, 28:203
composition in solution, 42:22-23, 32,
64
crystallography of, 25:58
crystal structure bibliography, 31:363
dehydration of, 28: 184
Dische test for, 28:224
dithioacetals, hydrolysis of, 32:67
reaction with sulfonyl chloride, 32:48
dithioacetals, selective esterification of,
33:40
gas-liquid chromatography of, 28:4S
mutarotation and gas-liquid
chromatography of, 28:40
5-phosphate, radiolysis, 37:42
phosphorylation of, 33:47
radiation chemistry, 37:33-34
radiation-induced chain reactions in
crystalline, 37:69-7 1
synthesis, 40:120
synthesis of, 28:282
tests for, 28:212
trimethylene dithioacetal, preparation
of, 32:37
or-erythro-, 21: 157
diethyl acetal, synthesis, 40: 12
synthesis, 40:4, 11-12, 18-20,27-28
m-threo-,
diethyl acetal, synthesis, 40: 12
synthesis, 40: 12
D-fhreo-, 21:151, 153
rythro-, liquid chromatography methods
for analysis of, 46:33
L-erythro-, synthesis of, 28:276, 40:114
3,4-O-isopropylidene-~-eyfhro-,
dithioacetals, preparation of, 3 2 5 4
2(S)- and 2(R)- deuteno-o-erythro-,
cytosine derivatives, proton magnetic
resonance spectroscopy of, 27:28
syntheses, 40: 11-13
5-thio-o-erythro-, oxidation, 23:2 14
3-deoxy-
o-erythro-, 21:157, 159, see Cordycepose
oL-threo-, composition in aqueous
solution, 42:64
L-etyfhro-, 21:158
4-deoxy-
eqvhro-, composition in aqueous solution,
42:64
L-eryfhro-, 21: 166
2,3-O-isopropyhdene-o~-eythro-,
synthesis, 40: 109
deoxy-
dithioacetals, physical constants of, and
peracetates, 323105-106
melting points and optical rotations of,
26:281-282
3,5-diacetamido-3,5-dideoxy-, composition
in aqueous solution, 42:50-5 I
dialkyl dithioacetals
oxidation and detonation of, 32:82,84
selective p-toluenesulfonylation of, 33:41
2,4-dideoxy, synthesis, 40:41
2,5-dideoxy-~-eryfhro-,21: 194
3,S-dideoxy-~-eyfhro-,synthesis, 40: 119
2,3-dideoxy-~-g[ycero-,21: 194
difluorinated, 'H- and 19F-NMR data for,
46:lSS
3,4-di-O-benzy1-2-deoxy-r-threo-.
preparation of, 29:261
dithioacetals, physical constants of, and
peracetates, 32: 102-105
esters, 21: 146
in fungal cell walls, 23:413
NMR spectroscopy of, 42: 18
5-0-benzoyl-2-deoxy-D-eyfhro-, ethylene
dithioacetal, preparation of, 32:4S
 SUBJECT INDEX
4-0-benzoyl-3,5-0-benzylidene-2-deoxy-o-
etythro-, diethyl dithioacetal, hydrolysis
of, 3 2 6 8
3,4-O-benzylidene-2-deoxy-o-erytltro-.
ethylene dithioacetal, rearrangement of,
3254
5-0-substituted, 49:26
5-phosphatq 21:158
phosphates, preparation, 49:2 10
proton nuclear magnetic resonance spectra
of, spin decoupling method, 29:29
rearrangement in liquid hydrogen fluoride,
26:176-188
2(S)-d-
2-deoxy-o-erythro-, synthesis of, 27: 131
4,6-0-benzylidene-2-deoxy-o-eryfhro-,
synthesis of, 27: I3 1
2-S-ethyl-2-thio-o-
diethyl dithioacetal, hydrogenolysis by
Raney nickel, 32:76
preparation of, 32:32
syntheses, 405-17
2,3,4,5-tetra-O-acetyl-ukfeh.~do-, in aqueous
solution, 4 2 3 I
trichloroacetimidates, 50: I 1 1
utilization by yeasts and association of
abilities, 32:225-228
Pentose 5-phosphates, aldehydrol fonns of in
aqueous solution, 4 2 3 1
Pentoside, methyl 3-deoxy-~-eryfhro-,2 I : I59
Pentosidulose, methyl 4-0-ethyl-3-O-methyl-~-
0-threo-, degradation of, 31:221
Pentosulose, 3-deoxy-
o-glycero-, reaction with ammonia. 25325
L-threo-, formation from L-ascorbic acid,
28: 192
structures of, and dehydration, 28: 171 I72
- from u-glyceraldehyde. 52:279
Pentos-2-ulose. L-threo-, preparation, 37:87
Pentos-4-u~ose.5-deoxy-o-etythro-, from o-
ribose 5-phosphate radiolysis, 37:43
Pentulofuranose
1,2:3,4-di-O-isopropyIidene-
a-o-etythro-, preparation of, 26:236
P-o-etythro-
hydrolysis of, 26:204
preparation of, 26:236
P-L-, preparation of, 26:236
o-erythro-, configurations of anomers,
26:221
3,4-U-isopropylidene-a-~-ety~hro-,
407
preparation of, 26:236
2,3-O-isopropylidene-~-o-fhreo-, 26:237
2-Pentulofuranose, 1,2:3.4-di-O-
isopropylidene-pa-, selective hydrolysis,
39: 16-1 7
Pentulofuranoside
methyl 1.3,4-tri-O-acetyl-o-etythro-,
configuration of, 26:22 I
methyl 1,3,4-tri-O-benzoyI-o-e~thro-,
configurations of anomers. 26:22 1
Pentulose
5-acetamido-5-deoxy-
o-threo. 23: 188
~-erythro-, 23: 188
1-amino- I .5-anhydro- I -deoxy-o-threo-
hydrate, 23: 120
mass spectrum of, 21:9 I
composition in aqueous solution, 42:3740,
65
1 -deoxy-
o-erylhro-, synthesis, 52:288
o-threo-
biosynthesis
problems. 52:282-284
of pyridoxol, 52:287
chemical and preparative enzymic
syntheses, 52:278-282
isolation from S. hygroscopicus,
52~277-278
as precursor of five-carbon chain of
thiazole in E. coli. 52:275-277
stray thiazolic metabolites with
probably deoxypentulose origin,
52:284-287
synthesis
from diethyl tartrate, 52:28 I
labeled at both ends with deuterium,
52:279-280
with labeled pentulose, 52:281-282
rhreo-, composition in aqueous solution,
42:65
5-deoxy-u-threo-, 21: 175
D-eryfhro-, 26:204
cyclic acetals, properties of, 26:256
preparation of, 26:236
utilization by yeasts. 3 2 2 15
1,5-di-O-benzoyl-3,4-O-isopropylidene-ket~-
o-threo-, preparation of, 26:238
o-rhreo-
408 SUBJECT INDEX

Pentulose (continued) 3-Pentulosonic acid, 2-deoxy-2-fluoro-4,5-0-

cyclic acetals, properties of, 26:257
as plant-growth substance, 21:416
preparation of, 26:237
purification of, and isopropylidene acetal,
26: 198
erythro-2-, liquid chromatography methods
for analysis of, 46:33
isopropylidene acetals, hydrolysis rate for,
26:204
L-erythro-
cyclic acetals, properties of, 26:256
preparation of, 26:236
purification of. and disopropylidene acetal,
26:198
3,4-0-isopropylidene-
o-erythro-, 26:204
I ,5-di-O-trityl-kefo-o-erythro-,preparation
of, 26:237
I(R)-f,o-erythro-, Sphosphate, preparation
of, 27:135
I (S)-t, o-etythro-, 5-phosphatq preparation
of, 27:135
synthesis, 52:281
threo-, composition in aqueous solution,
42:65
2-Pentulose, 42:16,49:26, 34
crystallography of, 25:58
1-deoxy-D-threo-, composition in aqueous
solution, 42:38
0-threo-, preparation from o-xylose, 28:39
L-threo-
preparation, 38:3 14
synthesis of, 28:4
5-S-ethyl-5-thio-o-threo-
preparation of, 33: 100
synthesis, 41:8
sweetness-structure relationship, 45:253
3-Pentulose
cyclic acetals, properties of, 26:274
1,5-di-O-benzoyl-2,4-O-methylene-keto-
eryfhro-, 26:253
r-threo-, 22:243
2,4-O-methylene-keto-erythro-, 26:254
4-Pentulose, 5-deoxy-3-C-(dimethoxymethyl)-
DL-erythro-, dimethyl acetal, synthesis,
4054
Pentulose 1,5-bisphosphate, o-erythro-,
composition in aqueous solutions, 42:32
o-erythro-Pentulose 5-phosphate, 52:289
isopropylidene-DL-,ethyl ester, synthesis,
40: 104
4-Pentulosonic acid, 2,3-di-O-acetyl-5-deoxy-
L-threo-, methyl ester, synthesis, 40:116
5-Pentylbarbituric acid, cyclodexhin inclusion
complexes with, 46:223-224
2-Pentyn-l-al, 5-hydroxy-, substrate for
carbohydrate synthesis, 40:36
Pent- 1-ynitol, I ,2-dideoxy-o-
erythro-, preparation of, and triacetate, 31 :70
threo-, preparation of triacetate, 31:70
2-Pentyn-1-01, 5,5-dimethoxy-, precursor for
sugar synthesis, 40: 12
3-Pentyn-2-01-, 1 , l -ethoxy-5-(tetrahydropyran-
2-yloxy)-, precursor for sugar synthesis,
40:8-9
Peptide chain, elongation
following selective deprotection, 50:294-298
N-glycopeptides, 50:283-287
Peptides
derivatives with uridine 5'-pyrophosphate N-
acetylmuramic acid esters, 28:328
of glycopeptides and peptido-
oligosaccharides of urine, 24:445,447
Peptidogalactomannans
gas-liquid chromatographic analysis of,
28:64
hydrolysis of, trifluoroacetic acid, in, 28: 16
Peptidoglycans, 24:3 14,52: 167-1 68
Bacillus cereus, 44: 198
Bacillus lichenformis, crystal structure
bibliography, 40:399
of bacterial lipopolysaccharides,
biosynthesis, 42:324
biosynthesis of, 26:408,40:339
in bacterial cell-walls, 26:424-432
Micrococcus lysodeikticus, 44: 195, 197
Staphylococcus aureus, 44: 196
synthesis of disaccharide of, 34: 160
Peptidoheteroglycan, 41:96
Peptido-oligosaccharides
peptide composition of urinary, 24:445
in urine (human), 24:436
Peptido-0-phosphonogalactomannan,
biosynthesis, 35354
Peptidopolysaccharides, biosynthesis, in plants,
44: 367-3 73
Peracetylation, with trifluoroacetic anhydride-
acetic acid, 4 3 5 3
 SUBJECT INDEX
Peracetylneuraminic acid ally1 esters, 48: 1 14
Peracylated aldoses
furanose derivatives, 49:49-5 1
pyranose derivatives, 49:4549
radical-mediated brominations, 49:45-5 I
Perbenzoates, liquid chromatography,
precolumn derivatization procedures,
46:68
Perbenzoylated sugars, prechromatographic
purification of, 46:20
Perbismuthate, as cleaving agent for cellulose,
23:6
Perchlorate ion, cyclodextrin inclusion
complexes with, 46:221
Perchloric acid
1,6-anhydrohexopyranose cleavage by, 34:66
cyclodextrin inclusion complexes with,
46:222,224
in hydrolysis of cardiac glycosides, 28: I6
Percival, Edmund George Vincent, obituary of,
l0:xiii-xx
Perillaldehyde oxime
sweetness-structure relationship, 45:296
third structural feature comprising postulated
glucophore in, 45:234
Perillartine, sweetness, AH, B system in,
45:221
Perimycine, 23:155
Periodate
for enhancing detectability of carbohydrates,
46:67
oxidation
of acetals, 34: 192
of aminodeoxy I ,6-
anhydrohexopyranoses, 34: I28
of 1,6-anhydro-P-o-hexopyranoses,
34:104-107
of 1,6-anhydrohexofuranoses,34: I54
and 1,6-anhydrohexopyranose structure,
34:50
of carbohydrate phenylboronates. 3 5 5 7
degradation of polysaccharides by,
31:200-211
nonmodified, dextrinized, and y-irradiated
starch, 51:248
polarography and, of carbohydrates,
29: 167
of polysaccharides, mechanism of, 29:340
in structural analysis of polysaccharides,
35:8
409
and structure determination of
carbohydrate amines, 31: 102-105
Periodate-thiobarbituric acid
assay, 3-deoxy-o-manno-2-octu~ososnic acid,
38~326-334
chromaphores, 38:326, 328, 330,336
Periodic acid. selective oxidation of 1,2-glycols
with, 33:93-95
Periplogenin, 3-P-o-glucopyranosyl-, 21:282
Permeases, glycoside entry into yeast,
39:379-381
Permethylation
completeness detection, 38:390-392
of polysaccharides, 29:3 10
Pernaphthoates, liquid chromatography. pre-
column derivatization procedures, 46:68
Per-0-acetylated di-D-fructose dianhydride
derivatives, "C NMR spectra of the
fructose components, 52:263
Per-0-acetyl dihexulose dianhydrides
I3C NMR spectra, 52:247
'H NMR spectra, 52:250-251
optical rotations and melting points, 52:244
Per-0-acetyl fructose glucose, 'H-NMR
spectra. 52:252
Per-0-acetyl glycosyl di-D-fructose
dianhydrides, 13CNMR spectra of fructose
components, 52:258
Per-0-methyl derivatives, acid hydrolysis,
52:232
Perosamine, 23: 155
Per-0-trimethy Isilylated dihexulose
dianhydrides, partial mass spectra,
52:253
Peroxidase
in fruit climacteric, 42:364
gibberellin suppression of, 42:343
Peroxidation, aldoses, 51: 11-12
Peroxides, organic, radiation-induced reactions
with a-hydroxyalkyl radicals, 37:22
Peroxisomes, of yeast cells, 32: 142
Peroxyl-radical reactions, radiation-induced,
37:23-26
Per-p-bromobenzoates, liquid chromatography,
pre-column derivatization precedures.
46:68
Perseitol, 21: 17
Perseulose, conformational equilibria, 23:32
Persimmon, 42:371
Perturbation energy, second-order, 51 :25-26
410 SUBJECT INDEX
Perturbation theory
chemical reactivity, 47: 122
finite, 51:26-28
Petroselinin, in parsley plant, 31: 140-141
Petroselinum crispum
apiose from, 31:137-138
glycosides from, 31:140-143
glycosides of the plant, 4:57-74
PET technique, labeled 2-deoxy-2-fluoro-o-
glucose, 48: 199-202
PG-I
amino acid composition, 49:248
NH,-terminal amino acid sequences, 49:253
protein core amino acid sequences, 49:255
structure, 49:249
PG-I1
amino acid composition, 49:248
NH,-terminal amino acid sequences, 49:252
protein core amino acid sequences, 49:255
structure, 49:250-25 1
PH
and activity of a-o-mannosidase, 28:412
caramel, 47:2 16-2 17
control and measurement in sugar refining,
52:464-466
effect
on p-eliminative degradation of alginates,
29:251
on formose reaction, 29: 183-1 85
on deamination, 31:65
on stability of metal chelates, 28:422
and stability of a-o-mannosidase, 28:413
Phagocytosis
desialylated erythrocytes, 40:223
macrophages and polymorphs, 41:187
Pharmaceuticals
1,4:3,6-dianhydrohexitolsuse, 49: 161-167
galactomannans in, 31:3 10,3 12
plant galactomannans in, 35:341
sucrose derivatives in, 33:274
Phaseoloside D, isolation and structure, 37:330
Phaseoloside E, isolation and structure, 37:330
Phaseolus aureus, see mung bean
Phaseolus coccineus lectin, carbohydrate-
binding specificity, 35: 145
Phaseolus lunatus
extracts, agglutinating action. 35: 128
lectin
agglutinating activity, 35:243-244, 247
carbohydrate-binding specificity, 35249
composition, 35:247
isolation, 35:138
purification, 35245-246
Phaseolus vulgaris
lectin
carbohydrate-binding specificity, 35: 145,
297-302
composition, 35292
hemagglutinating and mitogenic activity,
35~291-292
interaction with cellular glycopeptides,
35:3 18-320
isolation, 35: 138, 296-297
purification, 35292
structure, 35267
phytohemagglutinin, 35291, 293
Phenacetin, metabolism, and p-D-
glycopyranosiduronic acid conjugate,
36:91
1-Phenethylindoline, 46:3 17
Phenobarbital
cyclodextrin, inclusion complexes with,
46:223-224
effect on glycosylation, 40:345
Phenokarbohydrate derivatives, in higher
plants, 20:371408
Phenolics
from carbohydrates, 46:323
formation of, 46326
glycolipids, purification, 51: 172
Phenols, 53:364-365
4-acetamido-, formation and inactivation,
36:9 1
from 1,6-anhydrohexopyranose trimethyl
ethers in liquid ammonia, 34:77
cyclodextrin inclusion complexes with,
46:222-224
2,4-dinitro-, inhibitor of galactomannan
degradation, 35:361
reaction with glycals, 24:215
as solvents for sugars, 27: 104
Phenol-sulfuric acid, test, in sugar analysis,
28:223
Phenolthiocerols, in phenolic glycolipids,
51:200-203
Phenoxides, reduction of acylalkyl radicals,
37: 19
Phenylacetic acid, 1-ester of p-D-
glycopyranuronic acid, preparation,
36: 106
 SUBJECT INDEX
Phenylalanine
D-, favored conformation, 45:232
L-, cyclodextrin inclusion complexes with,
46:222,224
Phenyl 2-azido-2-deoxy-selenoglycosides,
53:163
Phenylboronates, stability to hydrolysis, 35: Phloridzin, taste properties, 49280
50
Phenylboronic acid
complex formation with carbohydrates,
35:4849
effect in paper chromatography, 35:59-62
reaction with glycosides, 35:32
sulfonylated, in electrophoresis, 35:62
Phenylbutazone, metabolism of, and analog.
36:134
Phenyl 2-deoxy-2-fluoro-~-o-glucopyranoside, fungal, 23:398
48:208
1-Pheny~-(o-g~ucofuran0)-[2,1-6]-imidazolidin- in fruit climacteric, 42:364
2-one,43:333
o-Phenylenediamine, in polarographic
determination of carbohydrates,
29:150-162
Phenylethane, I-amino- I-,Helferichs work on,
45:5
Phenyl glycosides
cleavage, photosensitized by 1,4-
dicyanonaphthalene, 46:184
preparation of, Helferichs work on, 45:4
3-Phenylindoline, 46:3 17
Phenylisocyanates, liquid chromatography, pre-
column derivatization precedures, 46:68
Phenyllithium, reaction with dioxolanes,
39:138
Phenylosotriazoles, sugar derivatives.
conformation of, 26:7 1
Phenyl phosphorohydrazidate, as
phosphorylating agent for nucleostdes,
22:338
Phenylpropanoic acid, 2-(indolin-l-yl)-I-.
46:317
N-Phenylselenophthalimide,53:184
Phenyl selenoribofuranoside, 53:174-177
Phenylselenylation, 53:1 5 4158
Phenylsulfur trifluoride, fluorinating agent, Phosphine dibromide, triphenyl-, selective
38:225
Phenyl tetra-0-acetyl-a-L-idopyranoside,
synthesis, 49:76
Phenyl I-thiohexopyranoside esters, radical-
mediated brominations. 49:64-65
41 1
Phenylurethans. of dithioacetals, preparation of,
32:48
Pheromones, I-6-anhydro-2,3,4-trideoxy-
hexopyranoses in aggregation, of westem-
pine bark-beetle, 34:26
Phizophydium .sphaerothetern, glycogen, 41:69
Phlorizin
catabolism by yeasts, 32:201
effect on trehalase, 30:254
levoglucosan from, 3497
Phormia regina. enzyme from, 30:246
Phosgene, selective chlorination with, in N,N-
dimethylformamide. 33:80
Phoshonogalactans
compositions and yields of, 23:400
Phosphatase
glycoenzymes, 27:308
in honey, 25:303
Phosphate, substituents, lipid A, 50:225-227
4-Phosphate, non-glycosylic, lipid A
substituents, 50:226
Phosphate groups
displacement in carbohydrates by halogen,
22:182
elimination reactions, by radiation, 37:
12-14
lipid A backbone, 50:221-225
protecting groups for, 36:152-156
Phosphate ions, in dextran gel, effect on dental
canes and plaque, 30:439
Phosphates
carbohydrate, mass spectrometry of
boronates of. 35:69
of dithioacetals, preparation of, 32:48
esters, hydrolysis of, 21:328
irradiation of carbohydrate. 38:192-I93
nomenclature, 52:1 13-1 I5
Phosphatides, 24:408
Phosphatidylserine, activator for enzymic
hydrolysis, 40:283
Phosphinates, nomenclature, 52:1 16
bromination with N,N-dimethylformamide
and, 33:78
Phosphinediol group on pyranose ring of
monosaccharides, synthesis of,
42:138-176
412 SUBJECT INDEX
Phosphines
addition to unsaturated carbohydrates,
24:256
bis (5,6-dideoxy-l,2-~-isopropylidene-cy-o-
xylo-hexohranose-6-yl)-, 24:256
with carbon tetrahalides, selective
halogenation with, 33:79
(5,6-dideoxy- 1,2-~-isopropy~idene-ol-o-xylo.
hexohranose-6-yl)-, 24:256
phenyl(5,6-dideoxy- 1.2-0-isopropylidene-
a-~-xylo-hexohranose-6-yl)-, 24:256
biphenyl-
and carbon tetrachloride, reactions with
alcohols and carbohydrates, 28:246
with carbon tetrahalides, selective
halogenations with, 33:79
and N-bromosuccinimide, reactions with
carbohydrates, 28:249
and N-halosuccinimides, selective
halogenations with, 33:77-78
tris(dimethylamin0)-, selective chlorination
with carbon tetrachloride and, 33:79
0-Phosphincoglycosphingolipids,44:4 13
Phosphinothricin, biological activity and
structure of, 42: 189
Phosphite, 1,2-O-cyclohexylidene-cu-o-
glucohranose 3,5,6, crystal structure,
43:228
Phosphodiesterase in plant cell-walls, 42:302
Phosphofructokinase, enzymic activity in liver
metabolism, 34:326
6-Phosphofructokinase
activity in yeasts grown on o-glucose,
32: 166-168
in glycolysis control, 32:169-171
6-Phosphogluconate dehydrogenase in fmit
climacteric, 42:36&365
Phosphoglycolipids, deamination and structure
of, 31:77
Phospholipids, 26:414
Phosphonates
5-deoxy-5-C-methyleneadenosine3-0,5 I -
C-cyclic, monohydrate, crystal
structure, 43:362-363
dipheny ltriphenylphosphorany lidenemethyl,
Wittig reactions with, 27:260,296
nomenclature, 52: 115-1 16
of unsaturated sugars, synthesis by Wittig
reaction, 27:296
Phosphonic acid, 2-aminoethane, biological
activity and occurrence of, 42:188-189
Phosphonium bromide, bromotriphenoxy-, as
reagent for bromination of carbohydrates,
28:240
Phosphonium iodide
iodotriphenoxy-, as reagent for iodination of
alcohols and carbohydrates, 28:240
methyltriphenoxy-
in displacement reactions with deoxy-
halogeno sugars, 28:282
reactions with nucleosides, 28:243
as reagent for iodination of alcohols and
carbohydrates, 28:240
selective iodination with, 33:77
Phosphonium ylides, in Wittig reaction with
carbohydrates, 27:228-239
Phosphonoglunic acid, 43:371
0-Phosphonoglycans, carbon- 13 nuclear
magnetic resonance spectra, 38:82-88
Phosphonoglycosphingolipids
from gastropods, 44:413414
0-,in gastropods, 44:438
0-Phosphonohexopyranans,carbon- 13 nuclear
magnetic resonance spectra, 38:81-88
Phosphonomannans, 26:395,41:8&87
fungal, 23:394,417
0-
carbon-13 nuclear magnetic resonance
spectra, 38:82,86-88
preparation and uses, 36:302
Phosphono migration, in phosphorylation,
33: 108-109
Phosphonyl group on pyranose ring of
monosaccharides, synthesis of,
42: 138-176
Phosphoramidates
of o-fructose derivatives, 22:246
in phosphorylation of nucleosides, 22:337
in synthesis of glycosyl esters of nucleoside
5-pyrophosphates, 28:345-35 1
Phosphorane
(bromoacetylmethy1ene)triphenyl-, synthesis
and reactions of, 27:294
formylmethylenetriphenyl-, preparation of,
27:244
methylene-, derivatives, in Wittig reaction
with carbohydrates, 27:228-239,
33: 153-158
[5-(R)-(3-deoxy-3-fluoro-l,2-0-
isopropylidene-5-0-trityl-cy-o-
 SUBJECT INDEX
xylofuranos-3-yl)-5-hydroxy-2,4-
dioxopyrrolidin-3-ylidene]triphenyl-,
preparation, 38:25 1-252
[5-(,")-(3-deoxy-3-fluoro- 1,-2:5,6-di-0-
isopropylidene-a-u-glucoft1ranos-3-yl)-
5-hydroxy-2,4-dioxopyrrolidin-3-
ylideneltriphenyl-
preparation, 38:250-25 I
X-ray crystallography, 38:28 1
sugar, synthesis of, 27:295
Phosphoric acid
1,4:3,6-dianhydrohexitolsesters, 49: 130-132
as solvent for sugars, 27:94
Phosphoric esters
bacterial polysaccharides, 48:3 13-3 17
of carbohydrates, synthesis of, 31:4
effect on proton nuclear magnetic resonance
spectroscopy, 29:23
of polysaccharides, 29:334
protection of, 46:202-203
Phosphoric triamide, hexamethyl-
photochemical reaction with carbohydrate
esters, 38: 137-142
as solvent
in displacement reactions, 24: 14 I
for sugars, 27: 123
for trimethylsilylation, 28:30
and thionyl bromide or chloride, reaction
with o-rihonucleosides, 28:250
Phosphorochloridic acid
bis (2,2,2-trichloroethyI) ester, selective
phosphorylation of nucleosides with,
33:48
dibenzyl ester
as phosphorylating agent
for 2'-deoxynucleosides, 22:345
for nucleosides, 22:326
for nucleosides, 22:326
selective phosphorylation with, 33:48
diphenyl ester, in selective phosphorylation
of carbohydrates, 33:4647
Phosphorochloridites, in nucleotide formation,
36: 159
Phosphorohydrazidic acid, phenyl ester, as
phosphorylating agent for nucleosides,
22:338
Phosphorolysis, of activated nucleosides,
22:369
Phosphorothioic acid, S-ethyl ester, as
phosphorylating for nucleosides, 22:335
413
Phosphorus
32P-labelednucleotides, 22:339
ring oxygen replacement by, 52: 140-141
starch phosphate content. 51:250, 253
in yeast mannan, 23:391
Phosphorus acid, in nucleotide synthesis,
22:342
Phosphorus compounds
in deoxyhalogeno, sugar synthesis, 28:280
as solvents for sugars, 27:123
Phosphorus halides, replacement of hydroxyl
group in carbohydrates by halogen, 22: 184
Phosphorus-3 1 NMR spectroscopy, 42: 19-20
Phosphorus oxoacid esters, nomenclature,
52:113-1 I6
Phosphorus pentachloride
polycondensation of u-glucose in aqueous,
21:447
reactions with carbohydrate derivatives,
28:239
replacement of hydroxyl group by chlorine,
22: I84
Phosphorus pentachloride-aluminum chloride,
rearrangements of saccharides in, 26: 194
Phosphorus pentafluoride, as catalyst in
polymerization of 1.6-
anhydrohexopyranoses, 34:74
Phosphorus pentaoxide
as catalyst for polycondensation of sugars,
21 :441,452, 454
oxidation and polymerization of sugars with,
46:6
Phosphorus sugars
biological activity of, 42: 188-190
physical properties of, 42: 19 1
synthesis and structure of, 42: 135-191
Phosphorus trichloride
as phosphorylating agent for nucleosides,
22:341-342
polycondensation of D-glucose in aqueous,
21:447
Phosphorylases, 25:8
active sites of, 23:346
amino acids of, 23:345
and amylo-( I-t6)-glucosidase, mechanism
ofaction of, 30:312,328,331
function, 51: 141- 142
in honey, 25:303
kinetics, 23:289, 353
mechanism of action of, 23:356
414 SUBJECT lNDEX
Phosphorylases (continued)
oligo-P-o-mannosyl-( l+4)-, in
galactomannan degradation during
germination of seeds, 35:362,375
preparation and properties of, 30:299-301
properties of, 23:347
purification by chromatography, 23983
by electrophorsis, 23:284
sources of, 23:343
specificity and action of, 23:351
in starch synthesis, 26:384
structure of, 23:344
sucrose, reaction on o-glucose, 3 2 8
in synthesis and breakdown of starch in
plants, 3 2 5
Phosphorylated sugars in aqueous solution,
acyclic forms, 42:20-21
Phosphorylating agents, 22:325
for nucleosides, 22:3?5
for synthesis of nucleotides, 22:392-395
Phosphorylation
of D-fructose by liver, 34:325
enzymic
and inactivation of aminoglycoside
antibiotics, 30: 165
methods, see Enzymic methods
o f sugars, 32:9
of nucleoside boronates, 35:54
of nucleosides, 22:325
selective
of carbohydrates, 33:46-50
of 2-deoxyribonucleosides, 22:343
in transport of monosaccharides into
Saccharomyces cerevisiae, 32: 151
and transport of sugars into yeasts,
3 2 2 31
Phosphoryl chloride
as phosphorylating agent for nucleosides,
22:325,335,341
in selective phosphorylation of
carbohydrates, 33:4648
Phosphotransferase system, PEP-dependent,
34:31&312
Photochemical addition
in branched-chain sugar synthesis,
42: 105-107
method for synthesis of ketonucleosides,
42:236
Photochemistry, of carbohydrates, 18:9-59,
38: 105-193
Photolysis
cyclic acetals, 34:207, 39:86-95
in 6-deoxy-a, a-trehalose synthesis, 28:305
of nitro-olefinic sugar, 24:112
Photosynthesis
radioactive carbon in study of, 32:6
of raffinose family oligosaccharides,
37:35 1-353
sugar conversion in, 32: 1 1
Phrenosin. 24:395, 399
synthesis of, 24:401,403
Phrenosinic acid, 24:396
Phthalazine, 3-(o-gluco-pentitol- 1-yl)-5-
phenyl-l,2,4-trazo1[3,4-a], 50: 156
Phthaloyl group, as protecting group, 29:4
Phthioceranic acid
ester of trehalose 2-sulfate, in
Mycobucterium tuberculosis, 30:236
hydroxy-, ester of trehalose 2-sulfate, in
Mjicobacteriirm tuberculosis, 30:236
Phthiocerol lipids, in M. leprue, 51 :234235
Phycom.vcetes, polysaccharides of, 23:367
Phyllodulcin
proposed AH, B,X systems of, 45:283-285
taste properties. 45:280,282-283, 288
Physarium polycephalum, polysaccharide,
41:88-89
Physical chemistry
of carbohydrates, 15: 1 1-5 1
of starch, 11:335-385
Physical properties
of herbicides, biological activity and, 21:408
of solutions of polysaccharides, 18:357-398
of sulfonic esters of carbohydrates, 23:253
Physical studies, of cyclitols containing four or
five hydroxyl groups, 20: I 1-65
Phytic acid
metabolism in plants, 37:347
in plants, 26:402
Phytoceramides, 24:409
Phytoglucolipids, 24:409
Phytoglycogens
biosynthesis of. 26:383
branching enzyme, 44:256
enzymic degradation of, 30:332
tine structure of, 30:322
Phytoglycolipids, deamination and structure of,
31:7?
Phytoglycosphingolipids, 24:408
Phytohemagglutinin, 35:291, 293
 SUBJECT INDEX
Phytolacca americanum, see Pokeweed
Phytolacca dioica, 46: 13
Phytolacca esculenta lectin, isolation and
properties, 35:310
Phytophthora cinnamoni, polysaccharide.
41:73
Phytophthora infestans, polysaccharide, 41 :69
Phytosphingolipids, 24:382
Phytosphingosines, 24:390
anhydro-, 24:387
p-D-glucosyl-, hydrochloride monohydrate,
crystal structure bibliography,
38:478-479
dehydro-, stereochemistry of, 24:386
derivatives, 24:257
D-glucosyl-, hydrochloride, crystal structure
bibliography, 34:372
N-2-hydroxytetracosanoyl-, 1 -phosphate.
24:409
stereochemistry of, 24:384, 386
synthesis of, 22:138,24:388, 27:237, 258,
262
of C,,-, 24:389
p-antibonding orbitals, CH,, group, 47: 113
Picea engelmann, polysaccharide from bark of,
24:374
Pichia
fermentans, D-ribose transport into, 32: I55
pinus. D-ribose transport into, 32: I55
Pichia hovis, polysaccharide, 41:99
Pichia pastoris, mannan, 41:82
Picoline, from sugars and ammonia, 25:328
Picrocin, DL-, synthesis of, 28:299
Picrocrocin
p-eliminative degradation of, 29:283
structure of, 24:6
Pictet-Andrianoff vacuum process, 47:2 16-2 17
Pigman,William Ward, obituary, 37: 1-5
Pigments, Osage orange, structure of, 26: I6
Pig submaxillary gland, glycoprotein of.
25:433,458
Pillaromycin A, structure, 35:96
Pillarose
natural occurrence of, 42:73
structure of, 35:96,42:71, 81. 125
synthesis of, 42: 125-126
Pinacol, acetoxonium salt from, 26: 132
Pineapple
development physiology of, 42:363, 370,
379
415
stem bromelain glycan, structure, 37: I8 I
Pinitol. as plant-growth substance. 21:416
Piiiner reaction, deoxyhalogeno sugars
preparation by, 28:256
Pinocytosis. in cell wall formation, 26:338
Pinoprenol, structure, 44:346
Pinus. cell wall studies on, 42:268
Pinus elliotti. see Slash pine
Piperazine
derivatives from sugars and ammonia,
25:3 17
2-methyL. solubility o f sucrose in, 27: 1 18
Piperidine
derivatives, from sugar derivatives, 25:394
1 -(3,6,2',3,'4',6'-hexa-O-acetyl-p-
cellobiosy1)-, preparation, 39:30
A-acetyl-, solubility of sucrose in, 27: 1 18
N-formyl-, solubility of sucrose in. 27: 118
as solvent for sugars, 27: 1 17
1-(3,4,6-tri-~-acetyl-~-glucopyranosyl)-,
preparation, 39:30
1 -Piperidinesulfonic acid, as sulfating agent for
dextran, 29:335
3-Piperidino1, (S)-(-)-, absolute configuration
of, 27:209
2-Piperidinone
I-methyl-, as solvent for sugars, 27: 1 18-1 19
as solvent for sugars, 27: 1 19
Piptoparus hetulinus, a-L-arabinofuranosidase
of, 42:387
Piriculariu o ~ z a e
peptidoheteroglycan, 41:96
polysaccharide, 41:75
Pisum sativus
cellulose biosynthesis, 41: 108
precursors, 41 :I26
cell wall studies on, 42:267,282, 300,
327-329,331,350,3555356
development physiology of. 42:343-344,
350,352-353,358-359
enzyme from, in cellulose synthesis, 26:325,
387
lectin, carbohydrate-binding specificity,
35: 199.204
heinagglutinating activity, 35: 197,201
interaction with erythrocyte glycopeptides,
35:32 1
with glycopeptides, 35: 141
isolation, 35: 138, 196
purification, 35: 196
416 SUBJECT INDEX
Pivaloyl chloride, in esterification of
nucleotides, 33: I3
Pivaloyloxy group, reactivity of, in
acyloxonium salt formation, 26: 131
Planteobiose, occurrence, 37:3 10
Planteose
biosynthesis of, 26:373,37:292
derivative, preparation of, 34:264
dihydrate, crystal structure bibliography,
30:455
occurrence, 37:29 1-293
structure, 37:292
Plant fiber, liquid chromatography analysis,
46:52
Plants, see also Cereals; Grasses
a,a-trehalose in, 30:230,234
analysis, monosaccharides and
oligosaccharides in, 30:6
apiose-containing, 31: 139, 145
polysaccharides from, 31:150-152
biochemistry of-a-o-galactosidic linkages,
37~283-372
cellulose biosynthesis in higher, high-
molecular-weight precursors,
41 :138- 142
lipid intermediates involvement, 41: 132,
134-135
cell walls, 42:265-382
acidification hypothesis for, 42:349
Albersheim model of, 42:303-304,
309-314
bacterial, teichoic acids, in, 21:324
of barley and wheat, arabinoxylans,
36:242
biosynthesis of, polymers of, 42:3 15-338
during cell-expansion of fruits,
423345-347
chemical composition, 26:30&302
complex, acidic oligosaccharides from,
fractional liquid chromatography
methods, 46:49
description of, 42:266
development and transformation of,
26:345-349
o-gluco-n-mannans in, 26:403
enzymes bound in, 42:300-302,351
formation of, 26:335-345
fruit ripening and, 42:339-382
cell wall loosening, 42:347-361
hemicellulose in, 26:405,36:257-258
hydrolysis of, trifluoroacetic acid in,
28: I6
hydroxy-L-proline-rich glycoproteins in,
42~298-300
interconnections, 42:307-309
interconnections in, 42:302-3 15
laminar structure of, 26:302-307
liquid chromatography analysis, 46:52
loosening of, 42:347-361
diagram, 42:360
materials, hydrolysis, 46:264
mechanism of orientation in, 26:331-335
microfibril orientation, 41: 123-125
morphology and hiogenesis of,
26:297-349
origin of, 26:335
pectins in, 26:399
plant, effect of plant-growth substances
on, 21:381
polysaccharides of
effect of auxins on, 21:381
f.a.b.-mass spectrometry, 45:66-68
preparation of, 42:273-274
primary, 42:267
structure, 42:269-277,303
protein in, 26:346
role of glycoproteins, in, 44:382-383
sugars, preparative liquid chromatography,
46:60
terminal complexes, 41:121-123
extracts
gas-liquid chromatography of, 28:48,57
uronic acids, gas-liquid chromatography
of, 28:76
glycosides of parsley, 4:57-74
growth substances
effect on carbohydrate systems,
21:377430
on sugarcane, 21:421
flavonoids, 21:409
glycosides and other carbohydrate
derivatives as, 21:408,413
as herbicides, 21:392
gums, 4:243-291,44:375
hemicelluloses from, 36:25&262
isoprenoids
biosynthesis, 44:35 1
metabolism, 44:351
life cycle, lectins in, 35: 148
mucilages of, 4:243-291
 SUBJECT INDEX
oligosaccharides, preparative liquid
chromatography. 46:60
pathology, pectic enzymes in, 33:381 385
physiology
carbohydrate chemistry and, 21:378
pectic enzymes in, 33:381-385
polyprenols, see also Polyprenyl glycosyl
phosphates
occurrence, 44347
structure, 44:346-350
polysaccharides
complex, structural and sequence analysis
of, 46:57
monosaccharide composition of
gas-liquid chromatography analysis,
46:54
liquid chromatography separations,
46:5&55
polyuronides of, 1:329-344
seeds, a-o-mannosidase activity of, 28:404
sialic acid occurrence, 40:134
tissue, cellulose and hemicellulose in,
gas-liquid chromatography of. 28:60
trehalase from, 30:247-248
Plasma-desorption mass spectrometry, acyl
location, 51: 199-200
Plasma extender, 0-(2-hydroxyethyl)-starch as,
29:318
Plasmalemma
biogenesis of microfibrils by, 26:342-345
glycosides
hydrolyzed inside, 39:402404
hydrolyzed outside, 39:353-378,
40 1 4 0 2
passage, 39:349,352
isolation and analysis of, 26:344
in plant cell-wall synthesis, 26:331, 335,
337-338
sugar caniers across, 32: 147, 149
utilization of glycosides hydrolyzed inside,
39:378-397
of yeast cell, 32: 137, 140
Plasma membrane, description of, 42:266
Plasmapexin, sialic acid binding, 40:2 I6
Plasmid, and resistance of staphylococci,
30: 184
Plasmolysis, of cell walls in plants, 26:332
Plasters, plant galactomannans in, 35:342
Plastics, sucrose-based, and polymers,
33:273-274
417
Platelets
activity, effects of heparin, 33:127
membrane. glycoproteins from, 35325
Platelets Factor 4, complexes with heparin,
43:124--125
Platinum, see Catalysts
Platinum catalyst (Adam), in oxidation of
carbohydrate sulfonic esters, 23:258
Platinum ethylenediamine cytidine 5'-
phosphare, dihydrate, crystal structure
bibliography, 38527
Platinum ethylenediamine dichloride, 1 -P-n-
arabinofuranosylcytosine,crystal structure
bibliography, 38:518
Platinum(Il), 2'-Deoxycytidylyl-(3 '+5 ')-2'-
deoxyguanosine-2-hydroxyethanethiolato-
2,2,'2-terpyridine-, hydrate, 43:373
Pleurotus ostreatus, polysaccharide, 41 :73
Plum
cell-wall studies on, 42:3 15
developmcnt physiology of, 42:341, 379
Plymers, starchlike, 23:368
1 -( p-Methylphenyl)-3-rnethyl-4-(o-urubino-
tetritol- 1-yl)imidazolidine-2-thione,
43:371
Pneuntococcus spp.
C-substance. deamination of, 31:78
polysaccharides, 19:303-357,52:6-7
capsular
f.a.b.-mass spectrometry, 45:65
mass spectrometry of, 29:97
gel chromatography of, 25:4344
structure, 41: 171-174
type 2 capsular polysaccharide, degradation
of acetylated, by oxidation with
chromium trioxide. 31:231
type 2 polysaccharide degradation by p-
elimination, 2 18 of sulfone derivative,
31:228
type XA capsular polysaccharide,
deamination and structure of, 31:76
types 1OA and 29, deacetylation4eamination
of capsular substances of, 31:237
type XXlX specific substance, deamination
and structure of, 31:77
type 29 capsular polysaccharide,
deacetylation and partial hydrolysis of,
31:196
type 34 specific polysaccharide, modified
Barry degradation of, 31:203
418 SUBJECT INDEX
Pneumonia
death rate, 41:156
polysaccharide vaccines, 41:191-193
Pneumosamine, N-acetyl-, in Type 5 capsular
polysaccharide, 33:302
Podzol, spectral analysis and identification,
44:24
Pogonopus tubulosus, 46: 13
Point group, 44:12
Poisson distribution, 23:304
Pokeweed
extract, mitogenic activity, 35:309-310
lectin, isolation and properties, 35:309
Polar factors, in selective esterification of
carbohydrates, 33: 13-19
Polarimetry
mutarotation measurement, 23:42,47
of reducing sugars in solution, 42: 17-1 8
Polarography
of aldehydo form of sugars, 42:20
carbohydrate derivatives, 29:108, 149-162
of carbohydrate oxidation and degradation
products, 29:162-171
kinetic currents in, 29:135-149
of monosaccharides, 29:126135
mutarotation and, 29:139-141
and structure of carbohydrates and
derivatives, 29: 142
Pollen
compatibility, 44:381
germination, inhibitors of, 21:410
Pollen tubes, cell-wall extension in, 42:35 1
Polyacrylamide beads, affinity chromatography
adsorbent, 39:407,416417,436
Poly(acrylamide-coallyl2-acetamido-2-deoxy-
D-glucopyranoside) glycopolymers,
51:123
Polyacrylamide gels
in chromatography, 25: 14
fractionation ranges of, 25: 19
immobilization on, 49: 1 8 6 188
Poly[adenosine 5- (o-ribose 5-
pyrophosphate)], 26:48 1
Polyagglutinability, in serology, 35:257
Poly-(a-L-gulopyranuronate), blocks, circular
dichroism, 45: 108
Poly(a-L-guluronic acid), 52:353,355-356,415
Polyamides, I ,4:3,6-dianhydrohexitols,
49: 172-1 73
Polyarabinose, 21:474
Poly( P-D-mannopyranuronic acid), circular
dichroism, 45:108
Poly(P-o-mannuronic acid), 52:353-354,414
Poly(butyl methacrylate), spin-lattice
relaxation-times and nuclear Over-hauser
enhancement values, 38:30
Polycarbonates, 1,4:3,6-dianhydrohexitols,
49: 172-1 73
Poly(deoxyribonucleotides), synthesis,
36~167-180
of double-stranded, 36: 178-1 80
with RNA ligase, 36: 178-1 80
stepwise by diester method, 36: 167-169
by triester method, 36: 173-178
Poly( tl-galactopyranuronic acid), circular
dichroism, 45:109-110
Poly(3,5-dimethylstyrene)sulfonylchloride,
intermediate in nucleotide formation,
36: 157
Polydispersity
defined, 24:337
self-association behavior and. mucus
glycoproteins, 47:377-380
Pol y-( D-mannopyranuronate)
blocks, circular dichroism, 45: 107-108
interference in circular dichroism studies of
CaZ+chelation of alginates, elimination
of, 45: 106
Polyelectrolytes, mucus glycoproteins as,
47:373
Polyethylene glycol
effect on cellulose synthetase complex,
41:145-148, 152
as matrix for f.a.b.-mass spectrometry,
45:26
as solvent for sugars, 27:98
Polyfructosans, see Fructans
Polygalactoglucose, 21 :483
Polygalactose, 21:483
in immunochemistry, 21:506
Polygalacturonases
endo, solubilization of pectic polymers by,
42:304305,372
substrate for, 42:321
enzymes preferring pectate, 33:325
in fruit climacteric, 42:364
on plant cell-wall, 42:337, 351
Poly(ga1acturonic acid)
biosynthesis of, 42:321
lyases, mode of action, analysis of, 46:54
 SUBJECT INDEX
Polygdlacturonide digalacturonohydrolasc,
33:327
Polygalitol, 25:237-238
Polyglucose, 21:462463,465,467,469.47 I,
48 1
fractionation of. 21:505
glycosidic linkages in, 21:448
in immunochemistry, 21504
Polyglucan, dextranglucosidase degradation of,
30:396
Polyglycoses, 21:433
from aldopyranosyl fluorides, 21 :460
nuclear magnetic resonance spectroscopy of,
21:501
preparation of, 21:491
sulfates, as heparin substitutes, 21:508
X-ray diffraction of, 21:501
Polyglycosiduronic acids, crystal structure
bibliography, 33:403
Polyhydric compounds
acetates, gas-liquid chromatography of,
28:153-155
gas-liquid chromatography of, 28:90-98
per(trimethylsilyl) ethers, gas-liquid
chromatography of, 28: 15 I-! 52
trifluoroacetyl derivatives, gas-liquid
chromatography of, 28:l 14
2-Polyhydroxyalkylimidazoles,50: 1 52
Polyhydroxy compounds, cation complexes,
47:11
Polyhydroxypyrrolidines, glucosidasc
inhibition, 48:344-347
Polyisoprenyl phosphates as possible
polysaccharide intermediates, 42:327-
330
Poly-( L-gulopyranuronate acid), blocks.
circular dichroism, 45: 107-1 OX
Poly(r-proline), mutarotation of, 23: I2
Polymaltose, 21:463,475
in immunochemistry, 21:506
Polymannose, 21:466,483
Polymerases, specificity toward structure of
monosaccharide substrates, in bio-
synthesis of bacterial polysaccharidcs,
44:338-339
Polymer complexes, 53:413
Polymerization, see also Copolymerization;
Degree of polymerization
of acetals, 34:208
addition, 21:477
419
of anhydroaldoses, mechanism. 39: 173-
176
of I ,6-anhydrohexopyranoses. 34:69-74
ofanhydro sugars, 39:158-160, 173-212
block, of oligonucleotides, 36: 170
caramel, 47:245
catalysis by boric acid. 21:466
by hydrogen chloride, 21:462
by ion-exchange resins, 21:464
catalysts for, of sugars, 21:447, 452
condensation. of carbohydrates, 21 :434
of cyclic acetals, 39: 152
degree of, of cellulose on heating, 23:430,
435
effect of pressure on, tl:467
epoxide, 21:491
of glycofuranosides, 21 :138
graft co-, of polysaccharides, 29:358-360
mechanism, factors affecting, 41:145-150
glycosyl esters of nucleoside diphosphates,
41: 125-1 32
polysaccharide chain growth, 41: 135
in methyl sulfoxide, 21:449,453
of mononucleotides, 36: 169-1 70, 184
in solid state, 21:461
sugars, hydrogen fluoride, 47:202
thermal, 21:476
Polymers
furanose. 21:138
molecular-weight detemiination by gel
chromatography. 25: 14,22
networks structures from, 24:270
orientational measurements in, 44:27
X-ray diffraction studies on, 22427
Polymethylgalacturonases, enzymes degrading
substrates, 33:325
Polymorphism
in chitin, 2 4 5 0 , 4 5 5
immune action, 41: I87
Polynucleotides, see also Nucleotides
chromatography of, 29:333
crystallography of, 22:479
structural integrity of synthetic, 3 6 : 2 0 4
206
synthesis of, 33:70,36:135-213
by block condensations, 36: 171-173
on polymer supports, 36:207-2 13
protecting groups, 36: 139-1 56
uses, in molecular-biological problems,
36:138
420 SUBJECT INDEX
Polyols
complex formation with cations of Group I1
and with borate ions, laser-Raman
spectroscopy, 44:83-84
cis-diols-containing, 53:7 1,95-100, 103
trans-diols-containing, 53:44, 6 1-68
electrophoretic and thin-layer mobilities,
47:35-36
electrophoretic behavior, 47:4
threo-threo configuration, 47: 145
tridentate complexes, 47: 10-1 1
Polyoxin C, 23: 1 16
Polyoxins, biosynthesis, 35: 125-126
Polyoxyethylene isosorbide, 49: 136
Polyphosphoric acid, in selective
phosphorylation of carbohydrates, 33:47
Polyphosphoric acid esters, in glycoside
synthesis, 21:448
Polypodium vulgare L., 45:286
Polyporus annosus, see Fomes annosus
Polyporus circinatus, glycogen, 41 :69
Polyporus fomenturius, fucomannnogalactan,
41:lOO
Polyporus igniarus, fucomannogalactan,
41:lOO
Polyporus ovinus, fucomannogalactan, 41: 100
Polyporus pinicolu, fucoxylomannan, 41:98
Polyporus squamosu.~.heteropolysaccharide,
41:lOO
Polyporus tumulosis, xylomannan, 41:96
Polyprenyl diphosphate trisaccharides, enzymes
of biosynthesis, specificity toward
structure of monosaccharide residues of
substrates, 44:336-337
Polyprenyl glycosyl diphosphates, 44:285-286
Polyprenyl glycosyl monophosphates,
44:284-285
Polyprenyl glycosyl phosphates
characterization, 44:344-345
as intermediates in synthesis of complex
glycans, 44:343
solubility properties, 44:344
Polyrhamnose, 21:474
Poly(ribonuc1eotides)
protection and deprotection of hydroxyl
groups, 36: 141
synthesis, by diester method, 36: 180-1 84
with RNA ligase, 36:189-193
by stepwise block condensation,
36:185-186
by triester method, 36: 186-1 89
Polyn'bose, glycosidic linkages in, 21:448
Polysaccharases, extraction from germinating
seeds. 32:306
Polysaccharide antigens, see Antigens
Polysaccharide-degrading enzymes, mode of
action, liquid chromatography analysis,
46:53-54
Polysaccharide gum, 53:411412
Polysaccharide hydrolases
ethylene effects on, 42:363
in fruit ripening, 42:365
role in cell-wall extension, 42:35 1
Polysaccharide hydrolyzates, isolation of, on
large-scale columns, 46:62
Polysaccharide-protein conjugates,
immunogenicity, 41: 197-200
Polysaccharides, 21:27,47: 167-1 68,
51:133-164, 5 2 ~ 3 1 1 4 3 9
acetals, preparation of, 29:339
acetates, determination of acetyl content in,
29:330
acetolysis of, 22:20
hydrolysis of, 22:26, 53, 85
structure of, 22:8
sulfated, crystallography of, 22:481
unit-cell parameters for, 22:422423
X-ray structure of, 22:421482
adducts with alkali metal hydroxides, 21:254
affinity-chromatography matrices as
derivatives of, 29:388-399
aldehydo, preparation of, 28:286
6-aldehydo, preparation of, 29:337
alduronic acids in, 47: 177
algal, gas-liquid chromatography of, 28:59,
30:93-94
alkaline degradation of, 13:289-329
alkaline thermochemical degradation, 4 2 3 15
alkyl ethers, preparation and
physicochemical properties of,
29~310-315
amination of, 29:342
amino, 24:321
crystal structure bibliography, 35:38 1-385
sulfates, 24:291
aminoalkyl and alkylaminoalkyl ethers,
29:322-325
2-amino-2-deoxy-~-ga~actose-containing,
23:402
amino sugar derivatives, 52:166
 SUBJECT INDEX
amylaceous,routine characterizationof,
30:326-332
analysis of, 28:188
anhydrides, preparation of, 29:343
from animal and seaweed tissues, 24:293
from Annona muricata L., 24:374
anomeric protons, nonselective spinlattice
relaxation rates, 45:149-152
antibiotic derivatives, 29:387
antigenicity and immunogenicityof, 31:3 14
apiose-containing,31: 15C152
associated with wood cellulose, 10:283-
333
bacterial, 2:203-233,ll: 15,271-340
antitumor, 32:236-243
antitumor activity of, 32:267,270
effect on blood supply in antitumor
activity, 32:264
capsular, lipid intermediates in, 26:430
crystal structure bibliography,
3633&332,40:395-399
determinationof 0-acyl groups by mass
spectrometry, 29:67
interaction with galactomannans,31:301
L-fucose, 39:301
from beech, 24:376-377
biogenesis of, 26298
by Golgi bodies of matrix, 26:339
biosynthesis of, lipid intermediates in,
28:390
blood SOUP, 4:37-55
branched, immunodominance, 41: 177-178
branching, determination of degree of,
21:496
from bull seminal-plasma, antitumor activity
of, 32:257
capsular
conformation and serological
specificityl78-12
definition, 41:185
as human vaccines, 41:155-208
immune response to bacterial infection,
41: 186-191
and immunity, 41:191-202
immunologicalspecificity determinants,
41~175-178
location and immune response,
41: 183-186
molecular mimicry, 41:208
molecular size, 41:182-183
42 I
role in bacterial virulence, 41:202-206
role in complement, 41:187-189
role in pathogenicity, 41:206-208
structural heterogeneity,41: 174-175
structures, 41: 15&174
gas-liquid chromatographyof, 30:92-93
Klebsiella K-type 9 and K-type 47, mass
spectrometry of, 29:90
mass spectrometry of, 29:55,66
from Pneumococcus Type 11, mass
spectrometry of, 2 9 9 7
of microorganisms,26:408
Type 1 capsular, purification and structure
of, 33:298
Type 2 capsular, structure of, 33:298-301
Type 4 capsular, structure of, 33:301-302
Type 5 capsular, structure of, 33:302
Type 6 capsular, structure of, 33:303
Type 7 capsular, purification and structure
Of, 33:303-305
Type 9N capsular, structure of, 33:306
Type 10A capsular, structure of,
33:306-309
Type 11A capsular, structure of,
33~309-310
Type 12 capsular, purification and
structure of, 33:3 10
Type 13 capsular, structure of,
33~311-312
Type 14 capsular, structure and
immunologicalproperties of,
33:3 12-3 13
Type 18A capsular, structure and
serological properties of, 33:3 13
Type 19 capsular, purification and
structure of, 33:313-314
Type 23 capsular, structure of, 33:314
Type 29 capsular, structure of, 33:315
Type 31 capsular, structure of, 33:316
Type 33B capsular, structure of,
33:3 16-3 18
Type 34 capsular, structure of,
33:31&320
Type 37 capsular, structure of, 33:320
caramel production, 47:222
carbamates, preparation of, 29:344
carbanilates, preparation of, 29:344
carbonates, preparation of, 29344
carbon-13 nuclear magnetic resonance
signals, identification, 38:22-25
422 SUBJECT INDEX
Polysaccharides (continuedj
carbon- 13 nuclear magnetic resonance
spectroscopy, 38: 13-104
carboxylakyl ethers, 29:3 19-322
carboxymethylated, determination of, 29:320
cation complexes, 47: 18-19
cell-wall, effect of indole-3-acetic acid and
of I-naphthaleneacetic acid on, 21:381
characterization of, 21:473
chemical repeating units, 52:321, 324-325
3-chloro-2-hydroxypropylated,29:325
circular dichroism, 45:78,85-92
classification of, 24:376
from Combreturn leonense gum, 24:375,377
complex
with alkali-metal and alkaline-earth-metal
salts, 21:221,224
determining sequence ofglycosyl residues
in, 46:58
on surface, 47:43
composed of more than one kind of residue,
52: 166-167
configuration, of anomeric linkages, 21:496
conformation, analysis, 33:388,35:8
containing uronic acids, solvolysis, 47: 181
of corm sacs of Wutsonia pyrumidutu,
24:371
covalent secondary derivatives, uses for,
29:398400
cross-linked, heterogeneous, 29:357
homogeneous, 29:353-357
crystal structure, 33:387404,35:377-385,
36~315-332,40:381-399,52:321-323
deacylation and methanolysis of aliphatic
carboxylic esters, 29:332
definition, 5 2 3 2 1-323
degradation, 31: 185-240,48:96
acidic, 31: 187-200
by @-elimination,31:212-229
by deamination, 31:232-237
with hydrazine, 31: 195
by hydrolysis, 31: 187-196
by oxidation with chromium trioxide,
31:229-232
pathways for, 29:23 1-232
by periodate oxidation, 31:200-2 11
preceded by oxidation, 31:220-226
of sulfone derivatives, 31:226-229
by Weermann and Lossen rearrangements,
31~237-238
3-deoxy-D-munno-octulosylonic acid-
containing, carbon- 13 nuclear magnetic
resonance spectra, 38:9 1-94
derivatives
anomeric C,H bond, carbon-proton
coupling constants, 51:34-35
chemically reactive, 29:305405
classification, 29:308
scope, 29:306-308
determination by enzymic hydrolysis to
monosaccharides, 30:280-28 I
deuteration, 38: 19-20, 22
o-fucopyranosides, 39:302
o-galactose-containing, 37:332-339
dialdehyde derivatives, preparation of,
29:339
diphenylborinates, carbon-1 3 nuclear
magnetic resonance spectra, 38: 103
from D-mannitol, 32:5
D-xylose-containing, carbon- 13 nuclear
magnetic resonance spectra, 38:95
dye derivatives, 29:350-353
enzymes depolymerizing
endo action pattern, 44:147-148
exo action pattern, 44:147-148
enzyme (water-insoluble) derivatives,
29:361-375
enzymic degradation of, 23:299,34:8
enzymic synthesis of, 26:324,34:8
enzymolyses and proton magnetic resonance
spectroscopy, 27:41
esters, 29:329-338
ethers, 29:309-329
f.a.b.-mass spectrometry, fragmentation
pathways, 45:43
Fourier-transform infrared spectroscopy,
44:63
fractionation and isolation of structurally
homogeneous, 24:334-337
fractionation of, 21:493
fragmentation by mercaptolysis, 26: 13
fungal, 23:3674[7
antitumor activity of, 32:243-248
exocellular, neutral sugar, 36:278-279
gas-liquid chromatography of, 28:44,
30~93-94
structural chemistry, 41:67-103
furanose-containing, carbon-I 3 nuclear
magnetic resonance spectra, 38:68-72
galactan group, 24:341
 SUBJECT INDEX
galactomannan-related, structure of.
31:267-269
galacturonorhamnan group, 24:36 1
gel chromatography of, 25:3549
gellan family, 52:383-393, 4 2 8 4 3 1
helical parameters and conformation
angles, 52:385
welan, 52:389, 391-393,432434
gelling, interaction with galactornannans,
31:284
gels and networks, structures, conformation
and mechanism in formation of.
24:267-332
glucuronomannan group, 24:354
glycoproteins, glycopeptides and
peptidoglycans, 52: 167-168
glycosidic linkages, 21:498
cleavages of, 46:251-272
graft copolymers, 29:358-360
of gram-negative bacteria, 15:27 1-340
halogen derivatives, 29:348
having P-o-xylan backbone, enzymic
analysis, 44: 158-164
having (1+4)-P-~-glucan backbone,
enzymic analysis of, 44: 150-1 58
having (1+4)-P-~-mannan backbone.
enzymic analysis of, 443164182
helix diffraction theory, 52:320
hetero-, 23:403,411
hexopyranuronate residues in natural. 29:23 I
high-temperature transformation of,
46:295-307
historical background, 51: 133, 135
homogeniety of, 21:494
homopolysaccharides, 52: 1 63
in honey, 25:306
hydrocolloidal, 13:265-287
hydrolysis of, 28: 1 4 2 3
products of methylated, 23:412
hydroxyalkyl ethers, 29:3 15-3 19
imidocarbonates, preparation of, 29:345
incorporation of labeled monosaccharides
into, 27: I79
interactions
with castor-bean lectin, 35:274
with concanavalin A, 35: 166- 169, 1 79
with lectins, 35: 140
with lentil lectins, 35: 194
with myeloma immunoglobulins,
35:3 17
423
iodine, 53:277
with seed galactomannans, 31:241-3 12
in interstellar space. 44:3 1
iodoacetates, 29:338
isolation of, 21:492,53:209-212
Klebsiella, see Klebsiellu spp.
laser-Raman spectroscopy, 44:75, 8 1-83
lichen
antitumor activity if, 32:248-249
structural chemistry, 41:67-103
linkage analysis, 52: 17-18
linkage designation, 52: 164
lipid intermediates in plant, 26:430
liquid ammonia effect on, 27:91
mannose-conraining, carbon- I3 nuclear
megnetic resonance spectra, 38:60-68
of marine algae, 32:4-5
mass spectra of, 21:46
mercaptolysis and structure determination,
32:29
metabolism of o-galactose-containing,
37342-372
methods in structural chemistry of, 15:53-89
methylation of, 25:6,29:3 10-3 15, 36:239,
264
mass spectrometry and, 29:62-7 1
purification by gel chromatography, 30: 16
from mice tissue, antitumor activity of,
32:257
microbial, 32229
cell wall. glucan component structure,
30~361-366
exocellular, 36:265-3 13
acidic, 36:272, 274-275
acidic sugar-containing. of commercial
importance, 36:292-302
amino sugar, 36:272, 280
biosynthesis, 36:286-289
fermentation methods, 36:289-29 1
genotype improvement, 36:286
genotype maintenance. 36:273
isolation and purification, 36:29 1
modilication and release, 36:289
neutral, of commercial importance.
36:303-3 13
neutral sugar, 36:272, 2 7 6 2 1 1
selection of microbes, 36:273
sources and types, 36:270-272
stimulants to usage, 36:268-272
Maurice Stacey's work, 52:6-8
424 SUBJECT INDEX
Polysaccharides (continued)
molecular-weight determinations of, 25:28
mono-and di-saccharides enzymically
released from, structural and sequence
analysis of, 46:57
more-branched, 52:39340 1
E. coli M41 capsular, 52:396-398,
434437
galactomannans, 52:395-396
helical parameters and conformation
angles, 52:394
R. trifolii capsular, 52:398401,437439
xanthan, 52:395
morphology of plant cell-wall, 26:302
from mountain-pine pollen, 24:363
muco-, chemistry of, 2:161-201
from mustard(white) seed, 24:374
of Mycobacterium tuberculosis, 3:3 1 1-336
newly discovered, nomenclature,
52: 1 6 4 165
nonbiological derivatives, circular dichroism,
45~75,119-124
noncovalent complexes of, 29:398402
noncytotoxic antitumor, 32:235-275
nucleic acid derivatives, 29:384-387
orientation, infrared dichroism study,
44:26-27
oxidation with dinitrogen tetraoxide, 29:346
p-aminobenzyl ethers, in insolubilization of
enzymes and preparation of
immunoadsorbents, 29:327
partially methylated, preparation of, 31:223
permethylated, f.a.b.-mass spectrometry,
45:37
permethylation of,29:3 10
phosphoric esters, 29:334
physical properties of solutions of,
18~357-398
from Picea engelmann (spruce) bark, 24:
374
plant
antitumor activity of, 32:253-257, 274
effect on cell volume and vacuolization
in antitumor activity, 32:265
cell walls
acidic, 42:266
alterations outside plasma membrane,
42:337-338
biosynthesis of, 42:315-338
cellulose, 42:29&297
o-glucans, 42:293-294
hemicelluloses, 42:268-269, 274275,
2 87-292
interconnections among, 42:303-309
pectic polysaccharides, 42:277-287
purification of, 42:274
types of, 42:274277
metabolism, 37:366-372
structure, 35: 10
from plant cell walls, 44:358-359
pneumococcal, 19:303-357,33:295-322
biosynthesis of, 33:296
gel chromatography of,25:4344
purification of, 33:29&297
preparation, 52:213-214
properties of, ofLipomyces spp., 23:415
protein-, 24:292
proton nuclear magnetic resonance
spectroscopy of,27:3943,29:12,26
pyrolysis of, 34:3845
pyruvic acid assay in, by enzymic method,
30:284
qualitative motional description, 51:102-104
quantitation of I3C-signal intensities,
389-37
quantitative motional description,
51:117- 124
bistable (two-state) jump model, 51:120
Dejean-Laupretre-Monnerie model,
51:121
difhsion in cone model, 51:119-120
Hall-Weber-Helfand model, 51: 122
Jones-Stockmayer model, 51:118-119
log(c2) model, 51:117-118
quinoxaline derivatives, polarography of,
29: 157-1 62
from red-spruce compression wood, 24:374
reductive-cleavage, 46:27 1
relative reactivities of hydroxyl groups in,
33:60-64
residue configuration designation, 52: 163
(1+3)-linked, 52:356-364,364383
galactoglucan, 52:362-364
helical parameters and conformation
angles, 52:357
( 1-3)-a-o-glucan, 52: 36 1-362,4 16
(1+3)-P-D-Xyh, 52~361
structure, 52:417418
(1+4)-linked, 52:326-356,364383
agarose, 52:368-370,420
 SUBJECT INDEX
alginic acid, 52:353-356
amylose, 52:340-349,407412
carrageenans, 52:36&368,418419
cellulose, 52:326, 329-332,405
chitin, 52:333-334,405
chondroitin sulfate, 52:378-382,424426
dermatan 4-sulfate, 52:382-383
helical parameters and conformation
angles, 52:327-328, 364-366
hyaluronan, 52:370-378,42 I
keratan 6-sulfate, 52:383-384
mannan, 52:334-338,406
pectin, 52:348, 35G353,4134.14
from Succharomyces cerecisiue, structure of,
323
sasa, antitumor activity of, 32:268
of seaweeds, 8:3 15-3.50
secondary oligomerization, 47: 170
from seed boxes of Watsoniu versveldii.
24:371
selective catalytic oxidation of, 33:88
selective esterification of, 33:3540
serogroup, carbon- 13 nuclear magnetic
resonance spectra, 38:81-88,96
serological cross-reaction, 41 :20 1-203
from Serratiu murcescens, antitumor activity
Of, 32~236-239
shape and size of molecules of, 7:289-332,
11:3 85-393
sialic acids
carbon- 13 nuclear magnetic resonance
spectra, 38:89-9 I , 95
occurrence, 40: 138-139
soil, chromatography of, 25:43
from soy-bean, 24:362
starchlike, 23:368
stereochemistry of, 33:389
stereoregular, synthesis, 39: 158, 199
structural analysis of, 21:494,33:389
enzymic methods of, 30:257-370
by gas-liquid chromatography, 28:47
structure, 35:5, 7,41:4, 7, 10, 51:135-138
and conformation of gel-forming, 24:270
determination of, 29:339-340,
31~185-I86
enzymes in analysis of, 21:502
immunochemistry in study of. 21504
substituted residues, 52: 167
sugar-cane bagasse, antitumor activity of,
32:254,268
425
sulfated
carbon- 13 nuclear magnetic resonance
spectra, 38:72-81
crystal structure bibliography, 33:404
sulfates, desulfation of, 29:336
sulfonic esters, 29:337
sulfonylation of, 23:24 I
sulfuric esters, preparation of, 29:335-337
from sycamore, 24:374
synthatic linear, 23:304
synthesis of, 21:431-512,34:250
by bacteria, 51:135-138
in growing plant cell, 26:339
mechanisms, 51:139-151
de n o w , two-site insertion mechanism,
51: 144-149
enzyme covalent intermediate
formation, 51:141
glucan synthesis inhibition, 51: 150-
151
primer-dependent, from nonreductng
end, 51:141-144
substrates and glucansucrase activity,
51 :139--141
in plants
functional aspects, 44:383
lipid intermediates in, 44:384-385
from tamarind seed, 24:373
thiosemicarbazide derivatives of periodate-
oxidized, antitumor activity of, 32:258
tirmethylsilylation of, 28:3 1, 29:329
tritiated, preparation and position of tritium,
27: I88
from Tropeoleum mujus (nasturtium) seeds,
24:374
uronic acid derivatives, 52: 165
acid hydrolysis of, 31: 193
@-eliminationand degradation of,
31:2 14-220
used as thickeners, analysis and
identification, 44:23
uses of synthetic, 21:507
xanthates, preparation and uses of, 29:346
x-ray diffraction analysis, 52:314325
computer model building, 52:3 18-320
data presentation, 52:320-32.5
Linked-Atom Least-Squares analysis,
52:319
oriented fiber, 52:316-317
powder pattern, 52:3 15
426 SUBJECT INDEX
Polysaccharides (continued)
types of diffracting specimens,
52:3 14-3 17
xylan group, 24:371
xyloglucan group, 24:372
yeast
antitumor, 32:249-252
antitumor activity of, 32:267
cell-walls, 32:138-140, 229
Polysaccharide side-chains, structural and
sequence analysis of, 4 6 5 7
Polysaccharide synthase
localization in cell, 42:331
in plant cell-wall biosynthesis, 42:3 16
Poly(sialo) glycoproteins, f.a.h.-mass
spectrometry, 45:65
Polysialylgangliosides, formation, 40:2 17
P olysphondylium pallidum
cellulosic cell-wall, 41: 108
lectin, isolation and properties, 35:309
Polystyrene, gels, in chromatography, 25: 15
Polystyrene resins, in acetal synthesis, 39:79
Polysucrose, gel chromatography of, 25:42
Polytran, see Scleroglucan
Polyurethanes
1,4:3,6-dianhydrohexitols,49: 172-173
foams, anhydrohexitols for, 25:267
Polyuronic acids, hydrolysis of, 46:263
Polyuronides of plants, 1:329-344
Polyvinyl alcohol, trimethylsilylation of,
28:3 1
Polyxylose, 21:463,474
Poppy, opium, gas-liquid chromatographic
analysis of, 28:49
Populin, gel chromatography of, 2 5 5 0
Porasil, 25: 15
Porcine thyroglobulin glycopeptide, structure,
37: 177
Poria cocos. polysaccharide, 41:73
Poria vaporaria, a-L-arabinofuranosidase of,
42:387
Porphyran, 24:278
structure, enzymic analysis, 44: 189-190
Porphyra perforata, see Algae, red
Portuguese man-of-war toxin, red cell receptor,
45: 170
P osidonia
apiose-containing polysaccharides from,
31:150
galacturonan of, 42:281
Potassium acetate, complex with sucrose,
21:223
Potassium P-o-glucuronate dihydrate, crystal
structure bibliography, 31:364
Potassium bromide, complex
with amylose, crystal structure bibliography,
33:392
with sucrose, 21:215
Potassium chloride, complex with sucrose,
21:223
Potassium chondroitin 4-sulfate, 52:379-381,
424
Potassium o-glucarate, crystal structure
bibliography, 38:422423
Potassium o-gluconate, crystal structure
bibliography, 31:364
Potassium o-gluconate monohydrate
crystal structure bibliography, 30:448
(form A), crystal structure bibliography,
32:356
(form B), crystal structure bibliography,
32:357
Potassium ferrate, oxidation of methyl CX-D-
aldohexopyranosides with, 33: 100
Potassium fluoride, fluorination agent, 38:220
Potassium gellan, 52:38&389,428429
Potassium hyaluronate
crystal structure bibliography, 33:402
3-fold helix, 52:377
4-fold helix, 52:374-375
Potassium iodide, complex with sucrose,
21:215,223
Potassium ion, effect on reducing sugars in
solution, 42:33-34
Potassium myronate, crystal structure
bibliography, 30:452
Potassium native gellan, 52:389-391,43043 1
Potassium permanganate, cyclic acetal
oxidation, 39:82
Potassium selenocyanate, 53: 148-159
Potassium rert-butoxide, in methylations,
38:392
Potassium thiocyanate, reaction with D-
fructose, 22:279
Potato, see Soianum tuberosum
Potential barrier, 51:78
Potential-function calculations, anomeric and
exo-anomenc effects, 47: 103-106
Praseodymium complex, in conformational
analysis of acetals, 34: 198
 SUBJECT INDEX
Precipitation, enzyme purification by specific,
23:284
Precipitin, 53:222
reaction, theory of, 31:320-321
Pregnanediol, conjugate with P-0-gluco-
pyranosiduronic acid, preparation, 36:93
Prelog-Djerassi lactone, synthesis of, 42: 1 12
Prelogs rule, for configurations, 27: 193,
199-201
Preparation, of P-glucuronidase, 14:38 1 4 2 8
Pressure, effect on hydrolysis of pyranosides,
22:34
Pringsheim, H., 4 5 9
Procion dyes, for cellulosic materials, 29:35 I
Procollagen, conversion into collagen,
40:364-366
Proflavine 2-deoxycytidylyl-(3+S)-
gunosine, hydrate, crystal, structure,
43 :329-3 3 0
Proflavine cytidylyl-(3 +5 )-guanosine
8.5 H,O, crystal structure, 43:33&332
methanolate, pentadecahydrate, crystal
structure, 43:300
sulfate, hydrate, crystal structure,
43: 306-3 07
Prolectin, isolation, 35: 149, 229
Pro1ine
4-hydroxy-~-
in glycoprotein linkages, 2541 8
in plant cell-wall, 26:346
hydroxy-L-, in urine compounds, 24:44S
Prolyl residue, 47:350
Pronase in plant cell-wall purification, 42:273
Propane
1,2-bis(benzoyloxy)-3-chloro-,acetoxonium
salt from, 26:130
1,2-diacetoxy-3-chloro-, acetoxonium salt
from, 26: 130
2,3-(2R)-epoxy-l-(2,3,4,6-tetreacetyl-~-~-
glucopyranosy1)-, crystal structure
bibliography, 38:468
1,3-Propanediamine,N,W-dimethyl-,
complex with cellulose, crystal structure
bibliography, 40:388
1,2-Propanediol
3-acetoxy-, reaction with 2-acetoxy-2-
methylbutanoyl chloride, 33:84
3-chloro-, reaction with 2-acetoxy-2-
methylbutanoyl chloride, 33:84
radiolysis and free-radical chemistiy, 37:27
427
1,3-Propanedithiol, in dithioacetal preparation,
32: 19
Propanoic acid, cyclodextrin inclusion
complexes with, 46:221
Propanol
2,2-dimethyl- 1-, cyclodextrin inclusion
complexes with, 46:222-224
2-methyl-2-, cyclodextrin inclusion
complexes with, 46:222,224
Propanol, 3-methoxy-, solubility of sucrose in,
27537, 89
I -Propano1
complex with sodiocellulose, crystal
structure bibliography, 33:395
2-(dimethylamino)-, enantiomers and
benzilic and glycolic acid esters, effect
on nervous systems, 27:210
2-Propanol
cyclodextrin inclusion complexes with,
46:222,224
1-(dimethylamino)-,enantiomers and
benzilic and glycolic esters, effect on
nervous system, 27:210
photochemical reaction with 3,4,6-tri-O-
acetyl-o-glucal, 38: 119-120
Propanone
1,3-dihydroxy-2-, taste-structure relationship,
45:252-253
I -hydroxy-2-. 4 6 ~ 3 12
formation, 46:293
reaction with, 45: I , 3
dicarbonyl compounds, 45: 13
2-Propanone
I -D-arabinofuranosyl-, preparation of,
33: 154-1 55
1-o-glucofuranosyl-, preparation of,
33: 156155
1,3-dihydroxy-
electroroeduction of, 29: 133-1 34
ester of uridine 5-pyrophosphate.
isolation of, 28:334
polarographic determination of,
29:l SO-I51
1,3-dimethoxy-, electroreduction of,
29: 133
1-D-ribofuranosyl-,Preparation of,
33: 154-155
2-Propanone phosphate, 1,3-dihydroxy-2-
hydrate and keto form of, 42:32
structure of, 42:32
42 8 SUBJECT INDEX
2-Propanone-3-r, 1,3-dihydroxy-, 1 -phosphate,
configuration of, 27: 141
Propanoyl halides, 2-acetoxy-2-methyl-,
reactions with diols, 33:83-85
Propanoylthiophene, 2-methyl-3-, formation of,
46:3 18
Propenal, see Acrolein
Propene, 2-acetoxy-, in acetal synthesis,
39:76
1-Propene
1-(2,3,5-tr-O-acety~-D-arabinofuranosy~)-,
preparation of, 33: 144
I-(2,3,5-tri-O-acetyl-~-xylohranosyl)-,
preparation of, 33:144
I-Propenyl group, as protecting group, 3 9 5 0
Properdin, effect of antitumor polysaccharides
on level of, 32:271
Propiolic acid, 3-ribofuranosyl-, preparation of,
33: I45
Propionaldehyde, 3-hydroxy-, see
Hydracrylaldehyde
Propionic acid
amylose ester, preparation of, 29:330
3-benzoyl-, esters, reaction with hydrazine
hydrate-acetic acid-pyridine, 33:248
Carbohydrate esters, ammonolysis of, 31238
2,2-dichloro-
effect on sugarcane, 21:426
as plant-growth substance, 21:402
3-hydroxy-, see Hydracrylic acid
2-(o-chlorophenoxy)-, effect on sugarcane,
21:424
2-(2,4,5-trichlorophenoxy)-
effect on sugarcane, 21:425
as herbicide, 21:392
Propionic-2-d acid, in determination of
hydrogen configuration in sugars, 27: 143
Propionitrile, 2,2'-azobis(2-methyl-), in
reduction of chlorodeoxy sugars, 28:303
Propionyloxy group, reactivity of, in
acyloxonium salt formation, 26: 131
2-Propanone
1,3-dihydroxy-, from D-fructose irradiation,
22:243
I -hydroxy-, in D-fructose degradation,
22:242
Proportionality constant, 51: 17
Propyl alcohol, solubility of sucrose in, 27:89,
98
Propylation, of lipopolysaccharide, 30: 15
Propylene, 3-chloro-, copolymerization with
sucrose, 33:274
Propylene glycol, as solvent for sucrose, 27:98
Propyl sulfoxide, as solvent for sugars, 27: 108
Prostaglandin endoperoxide synthase, high-
mannose carbohydrate chains, f.a.b.-mass
spectrometry, 4 9 6 3
Prostaglandin Fla, synthesis of, 42: 112
Protamine, heparin binding, 43: 1 17
Proteases, 23:287
effect on cellulose synthetase complex,
41:145
glycoenzymes, 27:308
Protecting groups
for amino groups, 36:150-152
cyclic acetals, 39:72, 155
light-sensitive, 46: I80
modifier, 46: 180
for phosphate groups, 36:152-156
photochemical removal of, 46: 179-180
photosensitive, application to biological
models, 46:203-204
for polynucleotide syntheses, 36: 139-1 56
selective removal, 39: 13-70
for sugar hydroxyl groups, 36: 142-149
Protein activators, enzymic hydrolysis of
glycosphingolipids, 40:28 1-286
Proteinxarbohydrate linkages, 2 5 4 1 7 4 3 9
in glycoenzymes, 27:3 18-323
Protein glycosylation, see Glycosylation
Protein-polysaccharides, 24:292
Proteins
biosynthesis of, 26:382
carbohydrate-binding, of plants and animals,
see Lectins
carbohydrate compounds, in urine human,
24:435452
chromatography (gel) of globular, 25: 18
crystallography of, 2 5 9 3
egg white, carbohydrate linkages in, 25:420,
445
in glycoenzymes, 27:3 14-3 18
glycopeptide binding, 50:298-299
molecular-weight determination by gel
chromatography, 25:23
muco-, chemistry of, 2: 161-201
oligosaccharide recognition, specificity,
50: 17
peptide-chain conformation and
glycosylation, 37: 183-184
 SUBJECT INDEX
in plant cell wall, 26:346
salivary, dextran complexes, in dental
plaque, 30:439
separation of, polysaccharide derivatives for,
29:326
serum, carbohydrate linkages in, 25420
synthesis in respiratory climacteric of fruits,
42~365-366
Protein-starch complexes
characteristics, 53:405
native, 53:405406
synthetic, 53:406411
Proteodermatan sulfate, hydrolysis, with
trifluoroacetic acid, 46:268
Proteoglycan aggregate, structure, enzymic
analysis, 44:21&217
Proteoglycan-hyaluronate complex, Fourier-
transform infrared spectroscopy, 44:6 I
Proteoglycans, 43:45, 136,49:239-259
amino acid sequence analysis, 49:254-
255
biological roles, 49:257-259
biosynthesis, 40:364366
explant culture, 49:257
primary culture, 49:254,256-257
carbohydrate-protein linkage regions,
49:242-243
carbon-13 nuclear magnetic resonance
spectra, 38:36, 78-80
isolation and fractionation, 49:243-244
Mr values, 49:248-249
N-terminal sequence, 49:25 1-253
structure of, 33:8,37: 170
Proteolysis, glycoprotein, glycosylation effect,
40:356-359
Proteopolysaccharides, in urine (human),
24:436440
Proteum micrubiiis. 0-specific
polysaccharides, 47: 181-1 82
Profeus vulgaris, lipopolysaccharide from,
antitumor activity of, 32:241-242
Protocatechualdehyde, di-0-acyl derivatives.
hydrolysis of, 28:2
Protofibrils, 26:316, 319
Protoglucal
di-0-acetyl-, formation and degradation of,
28:204
formation of, 28:204
Proton chemical shifts
additivity rules, 41:365-371
429
coupling constants and line widths,
41:212-213
and coupling constants for compounds 1 and
2, 41:221
structural-reporter groups, 41:304305,3 17.
330,332,370
of compounds 3 and 4,41:226,346
of compound 5,41:230,351
of compounds 6,7, and 10-12,
41:232-233
of compounds 8,9, and 13,41:239
of compounds 14, 15, and 16,41:256
of compounds 17-20,41:263
of compounds 21-30,41:272-273
of compounds 31-34,41:286-287
of compounds 35-38.41 :292-293
ofcompounds 3941,41:300
ofcompounds 4245,41:310-311
ofcompounds 4&51,41:314315
of compounds 52 and 53,41:327
of compound 54,41:331
of compound 55,41:334
of compounds 55-60,41:337
ofcompounds 61-63,41:346
of compounds 63 and 68-72,41:360-361
of compounds 64-67,41:351
fucose groups, 41:305-332
of mannose residues, 41:249-305
Proton-coupling constants, isohexides, 49: 105
Proton-donating groups, at active site, 48:378
Proton-flip experiment, 51:21
Proton magnetic resonance spectroscopy
of amino 1.6-anhydrohexopyranoses,34: 127
analysis, assignment of transitions in, 27:77
computerized iterative, 27:73-77
criteria for good, 27:80
experimental errors and variation of
parameters in, 27:77-80
limitations of first-order, 27:66-71
manual, 27:71-73
non-equivalence of nuclei in, 27:62-66
of 1,6-anhydrohexofuranoses,34: 153
of 1,6-anhydrohexopyranoses,34:56-61
of carbohydrates, 27:7-83
configuration of o-evythro-pentulose
denvatives and, 26:221
in conformational analysis, 26:56
conformation of cyclic acetals, 26:222
of dextrans, 30:380-382
and diastereotopism, 27:63
430 SUBJECT INDEX
Proton magnetic resonance spectroscopy
(coniinued)
enantiotopic nuclei, 27:64
of glycopyranosiduronic acids, 36:86-88
instrumentation, automatic control and
data acquisition, 27:17
field-frequency stabilization, 27:14-1 6
magnets and probes, 27:ll-I3
signal-averaging techniques, 27:16
spectrometer consoles, 27:13
superconducting solenoids, 27:18-21
magnetic nonequivalence, 27:64
of methyl 2,3,4-tri-O-acetyl-l-O-acyl-o-
glucopyranuronates, 36:1 10-1 11
of monosaccharides, 27:21-30
structure of cyclic acetals and, 26:226
virtual coupling in, 27:68-71
Proton nuclear magnetic resonance
spectroscopy
aldopyranans, 39:198
carbohydrates, 41:27-28
deuteration, effect on, 29:15
esterification effect on, 29:14
Fourier-transform, partially relaxed, 29:37
of hexoses and pentoses, spin-decoupling
method, 29:29
hidden-resonance problem in, 29:1 1-40
high-resolution, literature data, 41:214-218
structural analysis of carbohydrate chains
related to glycoproteins, 41:210-
374
structural-reporter groups, 41:211-213
hydroxyalkylation determination by,
29:316
intemuclear double-resoance (IN-DOR),
29:29-37
maltose and derivatives, 39:249-253
of methylated polysaccharides, 29:313
paramagnetic shift-reagents in, 29:16-25
solvents, effect on, 29:13
spectrometers, 41:373
and high-field magnets for, 29:25
spin-decoupling and spin-tickling,
29:27-29,31
spin-pumping mechanism, 29:32
Proton shielding, by chelation of Ca*+,47:129
Proton spin-lattice relaxation rate, 45:125-168
analysis of data, 45142-145
applicability to molecules with flexible
conformations, 45:166-168
as basis for configurational assignments,
45:153
carbon-l3,45:137
combinations of nonselective and/or single-
selective relaxation-rates, 45:164-167
cross-correlation effects, 45:130-131, 143
cross-relaxation effects, 45130-131,138,
143
density-matrix theory, 45:138
deuterium, 45x137
deuterium substitution, 45:158,164,166
effect on rate of receptor proton,
45~157-158
dipolar interactions, dynamic range
limitation, 45:165-166
dipole-dipole interaction, 45:128
dipole-dipole mechanism, simplified
version of, 45:127
double-selective inversion experiments,
45:141-1 42
double-selective relaxation rates,
45134135,159
exo-anomeric effect, 45:162
experimental methods for, 45:138-142
failure to provide information on spatial
arrangement of protons, 45153-154
for homonuclear spin-system, 45:128
initial relaxation-rate, 45:143
definition, 45:131
intemuclear distances, calculation,
45:137-138
interpretation of, 45:126-127
interproton distances, 45:163
calculation, 45:127
determination, 45:137-138
error introduced into, 45:147
quantitative interpretation in terms of
molecular conformation, 45:I68
and relative efficiency of relaxation
pathways between protons,
45:164-165
inversion-recovery experiments
requirements for static-field homogeneity,
45:I46
systematic error in, 45:145
inversion recovery (1 8O0-f-90"-AT-PD),
pulse sequence, 45138-141
limitations, 45:163-165
magnetization-recovery curve,
45:130-131
 SUBJECT INDEX 43 1

measurements, 45: 138-147 sequence, 45: 139-140

methods, comparison of relative merits of,
45: 165-166
for multispin system, 45: 128-129
nonselective relaxation experiments,
45: 163
nonselective relaxation rates, 45: 128.
131-133
extraction of p,j values from, 45: 157-
158
statistical analyses, 45: 168
stereochemical implications, 45: 147-
159
painvise additivity of relaxation
contributions, 45: 127-128
problems
from intermolecular dipolar contributions,
45: 146
from paramagnetic relaxation due to
dissolved oxygen, 45: 146
progressive-saturation[90-(t-900)NT]
pulse sequence, 45: 140
random errors, 45: 147
relative relaxation-efficiency between two
protons, as function of interproton
distance, 45: 153-1 54
rL,and si,
definition, 45: 129-130
evaluation, 45: 136-137
and molecular motion, 45: I37
separation, 45: 13&135
saturation-recovery (9O0-r-9O0-AT-PD), I
sequence, 45: 140
selective pulse experiments, systematic
errors in, 45:145-146
selective relaxation rates, 45: 163
stereochemical implications, 45: 159- 163
single-selective relaxation rates.
45133-134, 159, 163
stereochemical implications of,
45: 147- 163
in strongly coupled spin-systems, 45: I38
systematic errors, 45: 145-147
tailored excitation experiments, 45: I42
theory, 45:128-138
general formulation, 49128-130
three distinct proton-proton relaxation
pathways in six-membered ring in
4C, conformation, 45: 150
three-pulse (1 80-t-900-AT-PD-90")NT
triple-selective relaxation rates, 45: 135,
I63
Protopectin, conversion into pectin and pectate
in plant maturation, 33:381, 383
Protoplasts
cellulose biosynthesis, 41: 109
from yeast cell-walls, 32:140
(5)-Protoquercitol,taste properties, 45:29 1
Prototheca zopfii
cellulose biosynthesis, 41: 127
high-molecular-weight precursors,
41 :137- 138
lipid intermediates involvement.
41:133-134
cellulosic cell wall, 41: 108
cell wall polysaccharide biosynthesis in,
42~325-326,330,332,336
diagram, 42:328
Protoyuccoside C
occurrence, 37:328
structure, 37:329
Protoyuccoside E
occurrence, 37:328
structure, 37:329
Protozoa, sialic acid occurrence, 40: 136
Protuberic acid, structure, enzymic analysis,
44:247-248
Pseudo-a-oL-galactose, 45292
Pseudoaldobiouronic acids, mass spectra of,
29:85
Pseudoaldotriouronic acids, from xylans,
36:238
Pseudo-P-DL-glucose, 45292
Pseudocellobiouronic acid, hydrolysis of,
46:299
rate constants and activation energies for,
22:68
Pseudocidamine, racemic, 46: 13
Pseudo-contact shifts, 47:13&13 I
Pseudocorydine, 46: 13
Pseudocytidine, synthesis of, and (Y anomer,
33: 179
Pseudohalogens, reactions with unsaturated
sugars, 28:270
Pseudomonas aeniginosa
extracellular polysaccharide, 47: 189
kanamycin-neomycin phosphate transferase
in, 30: 199-204
lipid A, 50:244245
432 SUBJECT INDEX
Pseudomonas aeruginosa (continued)
methylated oligosaccharide fragment,
47: 179-180
0-specific polysaccharides, 47: 175, 177,
182-183, 196, 198
Pseudomonas aurantiaca 3 1,O-specific
polysaccharide, 47: 188
Pseudomonasfluorescens 36 1,O-specific
polysaccharide, 47: 1 8 6 1 8 7
Pseudomonas stutzeri amylase, preparation and
activity of, 30:301
Pseudonigeran
carbon-13 signals, 38:23
circular dichroism, 45:89
fungal, 41:69-70
structure, enzymic analysis, 44:265
Pseudo-oligosaccharides, 48:348
spirodioxanyl, 52:220-221
Pseudosubstrates, 48:348-349
o-glycals, 48:349-357
glycosyl fluorides, 48:357-359
Pseudo-sugars, see Carba-sugars
Pseudouridine
-a-,43~312
monohydrate, crystal structure
bibliography, 30:458
proton magnetic resonance spectroscopy
of, 27:34
5 '-(a-o-glucopyranosyl pyrophosphate),
enzymic preparation of, 28:338
6-aza-, see 6-Azapseudouridine
p-, proton magnetic resonance
spectroscopy of, 27:34
discovery of, 33: 1 1 1
structureof,33:112-113
synthesis of, 33:164-167
synthetic analogs, 33: 175-1 80
Pseudouridylic acid, 22:323
Psichosine, 24:394, 396
N-2-hydroxytetracosanoyl-,3-sulfate,
24:405,407
N-tetracosanoyl-, 3-sulfate, 24:405
Psicofuranine, 21: 174, 24:252
biosynthesis, 35123
Psicofuranose, 1,2:3,4-di-O-isopropylidene-
P-D-, 26:220,250-251
L-, 26~249
Psicopyranose
3,4-anhydo- 1,2-O-isopropyhdene-p-~-,
26:246
p-D-,conformation of, 25: 103
1,2:4,5-di-O-cyclohexylidene-~-~-, 26:25 1
1,2:4,5-di-O-isopropylidene-
p-D-,26:250
3-O-p-tolylsulfonyl-, fluorination, 38:
222
3-0-acetyl- 1,2:4,5-di-O-isopropylidene-P-
D-, 26:276
1,2-0-isopropylidene-p-~-, 26:203,25 1
Psicose, 7:99-136,23:280,25:60
cyclic acetals, 26:249-25 1
D-
alkaline degradation of, 46:292
in aqueous solution
composition, 42:29,37,41,44,62,65
NMR spectroscopy, 42: 19
cyclic acetals
gas-liquid chromatography of, 26:235
properties of, 26:272
retention times of per(trimethylsily1)
ethers and other derivatives, 26:235
in methanol, 42:62
purification of, and disopropylidene
acetals, 26: 198
synthesis, 41:8
1-deoxy
composition in aqueous solution, 42:65
furanose stability in solution, 42:29
keto-o-, pentaacetate, reaction with
ethanethiol, 32:33
L-
cyclic acetals, properties of, 26:272
purification of, and disopropylidene
acetals, 26:198
lack of crystalline form of, 42: 16
liquid chromatography methods for
analysis of, 46:33
nucleosides of, 42:227
6-0-benzoyl- 1-deoxy-o-, diethyl
dithioacetal, demercaptalation of,
32357
5-@methyl-~-,composition in aqueous
solution, 42:46
6-O-methyl-o-, composition in aqueous
solution, 42:46
preparation, 36: 11
Psicose 6-phosphate, D-, composition in
aqueous solution, 42:46
Psicoside, methyl a-DL-, synthesis, 40:71
Psychosine, biosynthesis, 26:449,40:247
 SUBJECT lNDEX
[Pt(diethylenetriamine)(guanosine)]di-
(perchlorate), crystal structure, 43:294
Pteridine, derivatives, preparation from
Amadori compounds, 22:278
Pterins, sugar, 25:399
Pullulan, 51:103
biosynthesis, 44:367
carbon- 13 nuclear magnetic resonance
spectra, 38:4&48, 101
circular dichroism, 45:89
definition, 30:336
fine structure of, 30:332-338
fungal, 23:372, 382,41:72
carbon-I3 nuclear magnetic resonance
spectrum, 41:71
gel chromatography of, 25:42
isopullulanase action on, 30:302
from plant cell-walls, 44:359
properties, production, and uses.
36:3 1&3 12
structure, enzymic analysis, 44:256-257
trimethylsilylation of, 28:3 1
tri-0-benzoyl-, proton magnetic resonance
spectroscopy of, 27:40
Pullulanase, 23:360,373,44:148, 253-254.
256
action pattern of, 30:272
and @-amylase,in characterization of
amylaceous polysaccharides, 30:328,
33 1
heat stability of, 30:279
in hydrolysis of starch, 36:33
induction of, 30:262
preparation and properties of, 30:293-296
and pullulan structure, 30:333-338
purification by chromatography, 23:283
specificity of, 30:268
Pulmonary glycoprotein, 44:232
Pulse and chase experiments, 51:145
Pummerer rearrangement, 40: 101-104
Purine
2-acetamido-6-chloro-, reaction with tri-0-
acetyl-o-glucal, 24:2 18
9-[3-amino-3-deoxy-5-0-(methylsulfonyl)-
P-~-ribofuranosyl]-6-(dimethylamIno)-,
cyclization of, 24: 187
6-amino-9-(2-deoxy-3-S-ethyl-3-thio-P-~-
threo-pentofuranosy1)-, 24: 166
9-P-~-ribofuranosyl-
crystal structure bibliography, 32:373-374 Purine nucleotides, biosynthesis of, 22:374
433
5-phosphate, 22:327
6-(benzylamino)-9-~-~-nbofuranosyl-,
crystal structure bibliography, 37:
426
9-b~tyl-[6-~S]mercapto-,metabolism to
I-thio-I-glucosiduronic acid, 36: 103
6-chloro-Y-
P-I-ribofuranosyl-, crystal structure
bibliography, 34:365
(2,3-dideoxyglyc-2-enopyranosyl)-,
conformations of. 26: 124
(3.4-di-0-acetyl-2- deoxy P-o-epthro-
pentopyranosy1)-, crystal structure
bibliography, 30:466
conjugates with l-thio-u-
glucopyranuronaniides, preparation,
36:98
o-arabinosyl-6-thio-, preparation of, 29:6
9-[3-deoxy-3-( p-niethoxypheny1-i.-
alanylamino)-P-o-ri bofuranosyll-6-
(dimethylamino)-, dihydrochloride
pentahydrate, crystal structure
bibliography, 30:464
D-glucuronic acid conjugates, synthesis,
36: 129
9-(2,3-dideoxy-P-o-g!ycero-
pentofuranosy1)-. 21: 194
6-(dimethylamino)-9-~-~-ribofuranosyl-,
5-phosphate. 22:33 I
o-ribofuranosyl-6-thio-, crystal structure
bibliography, 31:370
9-ethyl-[6-3sS]mercapto-,metabolism to 1
thio-D-glucosiduronic acid, 36: 103
6-methy1-9-P-o-ribofuranosyl-, crystal
structure bibliography, 34:368
6-(methylthio)-P-~-ribofuranosyl-.
monohydrate, crystal structure
bibliography, 37:42 1
9-(2-0-acetyl-3-chloro-5 -0-pivaloyl-P-o-
xylofuranosyl)-6-(pivalamido)-,
preparation of, 28:279
9-(4-0-acetyl-2.3-dideoxy-a-~-and-P-~-
gl.~crro-pent-2-enopyranosyl)-6-
chloro-, proton magnetic resonance
spectra, analysis of, 27:82
Purine nucleosides
apiose-containing, synthesis of, 31: 183-184
5-phosphate, radiolysis and radical
reactions, 37:47
434 SUBJECT INDEX
Purines
N-glycosyl derivatives, 21:23
nucleosides of, 17:301-369
Puromycin, 22: 128
dihydrochloride pentahydrate, crystal
structure bibliography, 30:464
research, 29:2-3
Puromycin aminonucleoside, antitumor activity
of, 29:4
Purpurosamines
B, synthesis, 40:4748
C, derivative, preparation, 44: 128
gentamicin C components, 30: 126-127
Purpurosaminide, C
methyl diacetyl-DL-, synthesis, 40:35
methyl diacetyl-DL-epi-,synthesis, 40:35
Pustulan
antitumor activity of, 32:248-249, 261
carbon-13 nuclear magnetic resonance
spectra, 38:49]
circular dichroism, 45:85-87, 89
crystal structure bibliography, 40:391
properties and antitumor activity of, 32:263
relative reactivities of hydroxyl groups in,
33:57, 64
structure, enzymic analysis, 44:275
Pyramine
biosynthesis, 52:305-306
5-amino- 1-(p-D-ribofuranosyl)imidazole
pathway, 52:301-302,305
eukaryote-prokaryote dichotomy,
52~305-306
histidine pyridoxol pathway, 52:305
degradation, 52:274
mass-spectrometric fragmentation,
52:274-275
synthesis
irnidazole ring expansion, 52:293 -294
in yeasts, 52:303-306
participation of o-glucose, 52:303-304
participation of L-histidine and
pyridoxol, 52:303-304
man
3-a-bromotetrahydro-2o,4p-dimethoxy-,
preparation of, 28:274
2-alkoxy-5,6-dihydro-2H-pyran,
hydrohalogenation and
hydroxyhalogenation of, 28:276
2-alkoxytetrahydro-
derivatives, dipole moments and
conformational analysis of, 26:66
photolysis, 39:95
3~-bromotetrahydro-2a,4-a-dimethoxy-,
preparation of, 28:274
4~-chloro-3-a-(ethyIthio)tetrahydro-2~-
methoxy-, preparation of, 28:275
2-chlorotetrahydro-, conformation of, 26:66
2,3-diacetoxytetrahydro-,mass spectra of
cis- and trans-, 21:62
tetrahydro-
interconversion of conformers, 26:91
2-methoxy-, hydrolysis of, and derivatives,
22:64
microwave spectroscopy of, 26:55
2-(nitromethyl)-, 24: 105
Pyran-2,6-dimethanol, tetrahydro-, 23:62
Pyran-2-methano1, tetrahydro-, 23:62
Pyran-3-methano1, tetrahydro-, 23:62
Pyranoid enolones, in branched-chain sugar
synthesis, 42:102-103
Pyranoid enones in synthesis of branched-chain
sugar synthesis, 42:10&102
Pyranoid rings, conformation of, 34: 199-200
Pyranoids
conformation of, 25:102, 104
saccharides, energy relations, 47: 1 17
stability of enolacetal, 29:291-298
sugars, see Sugars
Pyranone, 2-hydroxy-6-(hydroxyethyl)-
3(2H,6Hj-, 46~323
Pyran-2-one
(4s. 6S)-4-dimethyl-tert-butylsilyloxy-6-
[(dimethyl-tert-butylsilyloxy)rnethyl]-
tetrahydro-2H-, 50:190
tetrahydro-, as solvent for acylation of
cellulose, 27:106
Pyran-4-one, 3-hydroxy-2-methyl-4H-,
46:320-321
Pyranose
aldo-, anomeric equilibria of, 42:25,37
D-aldohexo-, orientations of hydroxyl groups
for, 45:75
anhydro-3-deoxy-3-fluoro-P-~-ido-, 2,4-di-
O-acetyl-1,6-, 'H- and I9F-NMR data
for, 46: 1 14
p-, 5 1 ~ 9 6 9 7
carba-, 48:22
circular dichroism, 45235
o-o-aldo-
hexo-, 45:74
 SUBJECT INDEX 43s

pento-, 4 5 7 4 of activation for hydrolysis of, 22:X I

derivatives, radical-mediated brominations, 4(or 6)-deoxy-4(or 6)-fluorohexo-, I3C-NMR
49:4549 data for. 46:163-165
formation from reducing sugars in solution, 2(or 3)-deoxy-2(or 3)-fluorohexo-,"C-NMR
42:16-68 data for, 46:161-163
stability, 42:24-27 propyl and 2-propy1, hydrolysis rates for,
temperature effects, 42:32-33 22:73
2,3-hexodiulo-2,6- 5-thio, hydrolysis and methanolysis of,
1,2:4,5-di-O-cyclohexylidene-P-o- 22:37
erythro-, reduction of, 26:25 I Pyranosid-4-ulose, 51:2 17-2 18
1,2:4,5-di-O-isopropylidene-P-~-e@1r.o-, Pyranosyl fluorides, 3,4,6-tri-O-acetyl-2-deoxy-
26:250 2-[ I8F]fluoro-a-~-g~uco- and p-o-munno-,
thin-layer chromatography of, 26:234 48:190-192
mean, hemiacetal and acetal geometries. Pyranosyl transfer, with glycosidases,
47:72 49: 232-23 3
methylated, effect on stability of, 42:25 Pyranuronates, with enolacetal linkage,
monosaccharides, hydrogen bonding, preparation of, 29:285-29 I
44: 15-16 Pyrazine
2(or 3)-deoxy-2(or 3)-fl~orohexo-.~T-NMR alkylated, formation of, 46:315
data for, 46: I6 1-1 63 2,5-bis( D-arabino-tetritol-1-yl)-, preparation
4(or 6)-deoxy-4(or 6)-fluorohexo-,"C-NMR of, 31:91
data for, 46:161-165 2,5-bis( ~-xylitol-1-yl)-, preparation of,
polarimetry of, 42:17 31:89, 124
shift-changes, 47:7-8 5-( 1-deoxy-D-erythro-tetritol-1-yl)-2-(0-
Pyranose rings arabino-tetritol- 1-yl)-, preparation of,
4 C , ( ~conformation,
) 455'4-75 31:91
chair conformations, 4 5 7 4 6 4 1-deoxy-o-erythro-tetritol- 1 -yl)-2-( D-
conformers, 51:6-7 arubino-tetritol- 1-yl)-, preparation of,
fragmentation of, 21 :47 31:88
mass spectrum of, 21:61 6-( 1-deoxy-o-glycerol- 1-yl)-2-(o-threo-
monosaccharides with phosphorus in, glycerol-I-yl)-, preparation of, 31:89
42: I 38- 176 6-( 1-deoxy-L-threo-tetritol-1-yl)-2-( L-
stability of, 21:136 xylitol-I-yl)-, preparation of, 31:89,
Pyranosides 124
a. e, a sequence, 47:41 derivatives
aryl, rate constants and activation energies formation in ammoniation of molasses,
for hydrolysis of, 22:82 25:349
deoxy, rates of hydrolysis of, 22:55 from sugars and ammonia, 2 5 3 16-3 18,
effect of configuration of carbon atoms on 328,335
hydrolysis of, 22:52 formation, pathways of, 46:3 17
history, 23:3 2-methyl-, solubility of sucrose in, 27: 118
hydrolysis of, 22:27 solubility of sucrose in, 27: 1 18
effect of anomeric configuration on, as solvent for sugars, 27:96
22:4344 3,6-Pyrazinedione, 1,2-dihydro-, see Maleic
rate constants and kinetic parameters of, hydrazide
22:4849 Pyrazine ring, in fructosazine, 22:280
isomerization to furanosides, 22:4 Pyrazofurin A, ~ ~ - 2 - e p isynthesis,
-, 40:78
methyl deoxy-, carbon-I3 nuclear magnetic Pyrazol[4,3-d]pyrimidine, 7-amino-3-P-D-
resonance spectroscopy, 4156-57 ribofuranosyl-, monohydrate, crystal
o-and p-nitrophenyl, rate constants and heats structure bibliography, 31:357
436 SUBJECT INDEX

Pyrazole structure of, 33: 113

4-p-~-ribofuranosyl-,derivatives,
33: 183-184
3-(carboxamido)-4-p-~~-ribofuranosyl-,
synthesis, 40:77
3(5)-(1-deoxy- 1,2:4,5-di-O-isopropyIidene-
D-manno-pentitol- 1-
y1)-, isomerization,39:27-28
derivatives, from sugar hydrazones, 25:366
3-(~-eryfhro-1,2,3-trihydroxypropyl)-,
23:163
3-(2,3-O-isopropylidene-p-~-
erythrofuranosyl)-4,5-
di(methoxycarbony1)-1-
(p-nitropheny1)-, crystal structure
bibliography, 37:43 1
3-phenyl-4-a-~-and-P-D-nbofuranosyl-,
preparation of, 33: 184
3-( 1,2,3-trihydroxy-~-erythro-propyl)-,
26241
5-Pyrazolecarboxamide, 4-p-~-ribofuranosyl-,
preparation of,33: 184
3,5-Pyzoledicarboxamide, 4-p-0-
ribofuranosyl-, preparation of, 33:184
Pyrazoline, derivatives, from sugar derivatives,
25:364
Pyrazolo [4,3-6]-5,7(4H,6H)-pyrimidinedione
3-a-0- and-p-D-arabinofuranosyl-,
preparation of, 33:183
3-p-~-ribofuranosyl-,see Oxoformycin B
3-(2,3-O-isopropylidene-p-~-
erythrofuranosy1)-, antileukemic activity
Of, 33:182-183
Pyrazolo [4,3-d]-7(6H)-pyrimidinone
3-p-~-ribofuranosy~-, see Fotmycin B
3-(2,3,-U-isopropylidene-~-~-ribofuranosyl),
preparation of, 33:173
Pyrazolo [3,4-d]pyrimidine
4-amin0-2-P-marabinofuranosyl-,
preparation of,33: 186
4-amino-2-(2-deoxy-p-~-eryfhro-
pentofuranosy1)-, preparation of,
33: 186
F'yrazolo [4,3-4 pyrimidine
7-amino-3-p-~-ribofuranosy1-, see Fonnycin
7-(methylthio)-3-~-~-ribofuranosyl-,
preparation of, 33: 180
Pyrazomycin
analogs, synthesis of,33:183, 184
antiviral activity of, 33: 1 11, 113
synthesis of, 33: 174
Pyrazomycin B
antiviral activity of,33: 112
structure of,33: 113
synthesis of,33: I74
Pyridazine, 3-methyl-, 23:162
4,5-Pyridazinediol, 1,4,5,6-terahydro-6-
methyl-, 23:162
3-Pyridazinone,4,5-dihydro-6-phenyl-,
preparation of, 33:248
6-Pyridazinone,4-hydroxy-1-p-D-
ribofuranosyl-, crystal structure
bibliography, 38:529
Pyridine, 53:373-374
cyclodextrin inclusion complexes with,
46:222,224
derivatives
carbohydrate substrates, 4 0 9 6 1 0 1
from sugar and ammonia, 25:3 17,
328-329
mglucitol compound, crystal structure
bibliography, 30450
effect on mutarotation of carbohydrates,
28:39
mutarotation of sugars in, 24:61
as solvent
for mutarotation of D-glucose, 27:104
for sugars, 27:117-118
in sulfonylation of carbohydrates, 23:236
for trimethylsilylation,28:29
sugar composition in, 42:22,60-6 1,68
2,5-Pyridinedicarboxylic acid,
cyclodhexaamyloseester, 29:403
2-Pyridinemethanol
~-~Y&oxY-, 23:143
5-hydroxy-, 23~132
Pyridinium bromide
3,6,2',3,'4',6'-hexa-O-acetylmatosyI-,
preparation, 3932
4-methyl-N-(tetra-O-acetyl-a-~-
glucopyranosy1)-, conformation of,
26: 107
N-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-
dinitroanilino)-~-~-glucopyranosyl]-,
preparation of,34:269
3,6,3',4,'6'-penta-O-acetyllactosyl-,
preparation, 39:32
3,3 ',4'-tri-O-acetyllactosyl-, preparation,
39:32
 SUBJECT INDEX
Pyridinium chloride
N-benzyl-3-hydroxy-, 23: 140
N-benzyl-5-hydroxy-2-(hydroxymethyl)-,
23:141
Pyridinol
2-methyl-3-, formation of, 46:3 12-3 I3
6-methyl-3-, 46:3 12
2-Pyridinol
as bifunctional catalyst of mutarotation,
24:27
esters of nucleoside 5-phosphates, i n
synthesis of pyrophosphates, 28:353
3-Pyridinol, 23: 120
2-Pyridinone
4-hydroxy-1 -(3-D-ribOfUranOSyl-,crystal
structure bibliography, 31:356
as solvent for mutarotation of o-glucose,
27: I05
Pyridin-2-yl I-thio-(3-D-glucopyranoside,
monohydrate, crystal structure,
43:225-226
Pyridizinium compounds, preparation, 37: 143
Pyridone, 1-((3-u-GIucopyranosyluronicacid)-
2(1H)-
synthesis, and (3-D-glucosiduronase action,
36: 125-126
2,3,4-tri-O-acetyI-4-methoxy-, preparation,
36: I29
4-Pyridone), 2,2-anhydro-(1-P-o-arcrhino-
furanosyl-2-hydroxy-, crystal structure
bibliography, 38:439440,488
Pyridoxol, biosynthesis, 1-deoxy-D-threo-
pentulose in, 52:287
2-Pyridyl thioglycoside, 51:2 17-21 8
Pyrimidines
(3-D-arabinOfuranOSyl-,synthesis of, 29:7
cleavage of bond with thiazole, 52:27 1-272
D-g~UCUrOniCacid conjugates, synthesis,
36: 129
precursors, biosynthesis of thiamine
diphosphate, 52:269-27 1
Pyrimidines, nucleosides of, 14:283-380
Pyrimidinium chloride), 2,2-anbydro-( 1 +-D-
arabinofuranosyl-2,4-diamino-5-fluoro-,
crystal structure bibliography, 38: 527
Pyrimidinone, 4-amino- 1-(il-amino-4-deoxy-P.
u-glucopyranosyluronic acid)-2( I m-,
monohydrate, crystal structure, 43:320
Pyrimido [5,4-4 pyrimidine, 6-amino- 10- ((3-
o-ribopyranosy1amino)-, crystal structure
437
bibliography, 34:369
Pyrocatechol. 46:290
Pyrocellulose, 23:426
Pyrodextrins, 22:483
manufacture, 47:3 18
methylation analysis, 47:308-3 10
structure of, 26: 16
Pyrogallol, 46:290
Pyrolysis, 46:273-274
CX-D-glUcOSe, 4 7 ~ 3 0 4 3 0 5
ofcellulose, 22:511,23:419474.456
rate of, 23:444445
of hexoses. 1,6-anhydrohexofuranoses
prepared by, 34:151-153
of hexuronic acids, 28: 188
isothermal. of cellulose. 23:457
of levoglucosan, 23:460462,34:69
mechanism of, of starch and cellulose,
34:4345
of monosaccharides, 34:4546
of oligosaccharides, 34:45, 152
of polysaccharides, 34:3845
of starch, 22:483, 47:335-344
flash, 22504
physical changes in solid, 22:486
structural changes in solid, 22:489
volatile decomposition products, 22:498
sugars, 47:270-278
Pyrolyzate, composition, 47:272-273
2-Pyrone, 3-acylamido-, 50:165-166
a-Pyrones, (3-elimination, 50: 165.- 166
y-Pyrone,3,5-dihydroxy-2-methyl-, 22:284
P yrophosphates
nucleosides, biosynthesis of saccharides from
glycopyranosyl esters, 26:35 1 4 8 3
tetra-p-nitrophenyl, as phosphorylating
agent, 22:328
Pyrophosphorolysis, of sugar nucleotides,
28:390
Pyrophosphorylases
in biosynthesis of sugar nucleotides, 32:9
sugar nucleotide, 28:335
Pyrophosphoryl chloride, selective
phosphorylation with, 33:49
Pyrroles
and derivatives from sugar derivatives,
25~361-364
Garcia Gonzalez, work on, 45: 13-14
Pyrrolidine
derivatives, from amino aldoses, 29357-361
438 SUBJECT INDEX

Pyrrolidine (continued) 3-0-P-~-rhamnopyranosyl-,as plant-growth

N-acetyl-, solubility of sucrose in, 27: 1 18 substance, 21:410
N-formyl-, solubility of sucrose in, 27: I 18 3-(6-O-P-~-rhamnopyranosyI-o-
2-Pyrrolidinone g1ucopyranosyl)-, as plant-growth
N-methyl-, as solvent substance, 21:410
in displacement reactions, 24: 141 derivatives, as plant-growth substances,
for methylation of carbohydrates, 30: 1 1 21:410
for trimethylsilylation, 28:30 Quercetrin, as plant-growth substance, 21:410
3-(R)-acetamido-spiuo-3,-4-R-(3-deoxy- Quercitols
1,2:5,6-diisopropylidene-aribo- (+)-proto-and (-)-vibo-, rearrangement in
hexofuranose-3-y1)-, crystal structure acetic acid-sulfuric acid, 26: 189
bibliography, 38:468469 proton magnetic resonance spectroscopy of,
3-(S)-acetamido-spiro-3,4-R-(3-deoxy- 27:24-25
1,2:5,6-di-O-isopropylidene-c~-o-ribo- sweetness-structure relationship, 45:24 1
hexoduranos-3-yl)-, crystal structure Queuosine 5-phospahte, hydrate, 43:335
bibliography, 38:469470 Quinic acid
Pyrroline, derivatives, from sugars, 25:361 methyl ester, selective esterification of,
3-Pyrroline-2,5-dione, 3-P-o-ribofuranosyI-, 33:40
crystal structure bibliography, 30:457 rearrangement
3-Pyrrolin-2-one, l-acetyl-3-benzamido-4- in acetic acid-sulfuric acid, 26: 191
(2,3,4,6-tetra-0-acetyl-P-~- of reduction product in liquid hydrogen
glucopyranosy1oxy)-, crystal structure fluoride, 26: 173
bibliography, 38:48048 1 structure of, 42:77
Pyrrolo[2,3-d]pyrimidine, 4-amino-7-P-o- synthesis of, 42: 129
ribofuranosyl-, see Tubercidin Quinicol
Pyruvaldehyde, 46:32 1 2,5-anhydro-, 29208
formation, 46:293 5-O-p-tolylsulfonyl-epi-, solvolysis of,
from oL-glyceraldehyde, 28: 174 25208
polarography of, 29:150-152, 164 Quinine
reaction with ammonia, 25:347 L-gulonate, preparation, 38:299
Pyruvate acetal, 51:212 taste properties, 45:313
Pyruvate kinase, enzymic activity in liver Quinine HCI, taste properties, 4 5 3 1 I
metabolism, 34:326 Quinocyclines A and B, biosynthesis, 35:91-96
Pyruvic acid 0-Quinovopyranosyl trichloroacetimidates,
assay of, in agar and other polysaccharides, 50:105, 110
by enzymic method, 30:284 Quinovose
cyclic acetals, 48:304-306 CI-D-, taste properties, 45:242
mechanism of formation of, 28:200 r>-, sweetness-structure relationship, 45:24 I
polarography of, 29: 147 Quinovosides, 50: 105
Quinoxaline
carbohydrate derivatives, polarography of,
Q 29: 154-1 62
2-(~-arabino-tetraacetoxyhuty~)-, 25:396,
Q enzyme, 23:363 398
purification by chromatography, 23:283 conformation of sugar chain in, 26:71
Quebrachitol preparation and polarography of, 29: 157
as plant growth substance, 21:416 2-(~-arabino-tetritoI-l-yl)-, 45: 14
rearrangement in acetic acid-sulfuric acid, derivatives, from sugar derivatives, 25:373,
26:191 396-399
Quercetin 2,3-dimethyl-, polarography of, 29: 154-1 56
 SUBJECT INDEX
2-(2-furYl)-, 4 5 ~ 1 4
IH-pyrazolo[3,4-b], 1-phenyl-,
monosaccharide derivatives, 37:233
2-(3-hydroxy-2-furyl)-, 45: 14
2-methyl-, in polarographic determination of
pyruvaldehyde, 29: 152
polyhydroxyalkyl-, conformation of, 26:72
2-QuinoxalinecarboxaIdehyde,polarography
of, 29:157
R 49:4142
(2R, 4R)-DioxolanedicarbaIdehyde, from I ,6-
anhydro-P-o-hexopyranoses,34: I04
Rabbit-ear effect, acetal segment of 2-
methoxyoxane, 47: 107-1 08
Racemic amino carba-sugars, synthesis
2-amino-2-deoxycarba-hexosesand relatives,
48~59-63
carba-glycosylamines, 48: 52-59
Racemic carba-sugars, synthesis
from Diels-Alder adduct of furan and acrylic
acid, 48:29-36
McCasland's three carba-sugars, 48:26-27
from my-inositol, 48:28-29
Racemization, occurring during glycosylation
or peptide coupling, '3C-n.m.r
spectroscopy for testing, 43:37-39
Radiation
chemistry of carbohydrates, 16: 13-5X
of L-sorbose, conversion into r-ascorbic acid,
37:107-108
of L-tagatose, conversion into L-ascorbic
acid, 37: 107-1 08
techniques, for free-radical reaction study,
37:7-77
Radical intermediate stabilization, radical-
mediated brominations, 49:68-7 1
Radical-mediated brominations, 49:37-9 I
I ,6-anhydrohexopyranose derivatives,
49:51-54
I ,5-anhydropentofuranose derivatives.
49:54
carbon radical stabilization factors, 49:70-7 1
elimination reactions, 49:85-91
C-glycosylbenzene and C-
glycosylheterocycle esters, 49:59-60
glycosyl cyanide esters, 49:57-59
glycosyl halide esters, 4 9 : 6 M 1
439
glyculose and glycosulose derivatives,
49:54-57
hexopyranoside esters, 49:62-64
hexuronic acid derivatives, 49:4245
hydroxyl group protection, 49:42
introduction at C-5,49:39
miscellaneous compounds, 49:65
peracylated aldoses, 49:45-5 I
phenyl 1-thiohexopyranoside esters,
49:64-65
reaction conditions and suitable compounds,
regiochemistry, 49:67-7 1
hydrogen atom abstraction, 49:67-68
radical intermediate stabilization,
49:68-71
stereochemistry, 49:7 1-75
hydrogen atom abstraction, 49:71-72
products, 49:73-75
radical intermediate conformation,
49:72-73
substitution reactions, 49:75-85
nucleophilic substitutions, 49:79-84
radical reactions leading to, 49:84-85
substitution by hydrogen, 49:75-79
Radical-radical reactions, of carbohydrate
radicals by radiation, 37: 17-1 8
Radical reactions, leading to substitutions,
radical-mediated brominations, 49:84-85
Radical-scavenger reactions, of carbohydrate
radicals, by radiation, 37: 18-23
Radiochemical stability, of hydrogen-isotope
labeled compounds, 27: 138
y-Radiolysis, of solvent water, 37:7-9
Radish, cell wall studies on, 42:301
Raffinose, 21:30, 51:152
biosynthesis of, 26:372-374,37:354-359
catabolism by yeasts, 32:183,233
I3C nuclear magnetic resonance spectra of,
33:277
crystal structure of, 25:77
derivatives, preparation of, 34:264
effect on sucrose manufacture, 37:299-300
f.a.b.-mass spectrometry, 4 5 2 0
family of oligosaccharides, 9: 149-1 84
in honey, 25:290,295
hydrogen bonding in, 25: 100
nonselective spin-lattice relaxation rates,
45: 149
occurrence, 37:294-300
440 SUBJECT INDEX
Raffinose (continued)
0-D-hctofuranosyl-, isolation and structure,
37:3 11
of oligosaccharides, biosynthesis pathway,
37:357
in plant kingdom, 37:351-360
pentahydrate, crystal structure bibliography,
30:455
photosynthesis, 37:35 1-353
pyrolysis of, 34: 152
solubility in liquid ammonia, 27:91
in methanol, 27:97
effect of calcium chloride on, 27:95
spin-lattice relaxation of I3C nuclei in. 27:60
structure, 35:5,37:295,39:359
sweetness, effect of infrared hydroxyl
absorption bands and hydrogen-bonding
strength, 45217
utilization by yeasts, 32:205-208,
39~375-378
and associations of abilities, 32:223
Raman effect, physical principles of, 44:67-70
Raman spectroscopy, 4453, 16-22,67-68,70,
53:28&287
advantages of, 44:70,8 1
band assignments, 44:3&39
of carbohydrates, 44:8
complementarity to infrared spectroscopy,
44:69
depolarization ratio, 44:68
electro-optical parameters, 44:35-36
noncomputer results, in analysis and
identification of food carbohydrates and
biological samples, 44:22-24
polarization directions of beams in, 44:68-69
of water, 44:70
Ramazol dyes, for polysaccharides, 29:353
Rana cutesbianu lectin, isolation and
properties, 35:3 15
Raney nickel
reductive cleavage of carbon-sulfur bonds,
3275-79
reductive desulfurization by, 5: 1-28
Ranuncoside monohydrate, crystal structure
bibliography, 31:350
Ranunculin, synthesis, 50: 183
Rape seed
cell wall studies on, 42:278, 282-284, 287
mass spectrometry of polysaccharides from,
29:66
Rare-sugar nucleosides, preparation of,
42:245-246,257
Rata constants, in polargraphy, 29: 137-143
Raucaffricine, slmcture, 37:330-33 1
Rayleigh scattering, 44:67-68
mucus glycoproteins, 47:359-360
Rayleigh-Schrodinger sum-over-states theory,
51:27
(R)-3-(2-deoxy-P-~-erythro-pentofuranosyl)-
3,6,7,8-tetrahydroimidazo[4,5-6]-1,3-
diazepin-%ol,43:373
Reactions
of amino sugars with beta-dicarbonyl
compounds, 20:303-355
of cellulose, 19:219-246
energypaths, 47:116-118
the formazan, in carbohydrate research,
13: 105-167
free-radical reactions, see Free-radicals,
reactions
the Maillard, 14:63-134
mechanisms
of chemical, hydrogen isotope effect on,
27:151
of mutarotation of sugars in aqueous
solution, 24:35
media
acids (organic) as, 27:102
alcohols as, 27:99
of monosaccharides with beta-ketonic esters
and related substances, 11:97-143
Reactivity
conformation effect on, 26:5 1
of cyclic acetals of aldoses and aldosides,
39:7 1-1 56
relative, of hydroxyl groups in
carbohydrates, 8: l 4 4 , 3 3 : 1 1-109
replacement-oxidation correlations.
33:9 1-92
and structure correlations of D-
glucofuranosidurono-6,3-lactones,
33~205-210
of sulfonyloxy groups, 24: 139
Reactone dyes, for polysaccharides, 29:352
Rearrangement
acetal migration, 34:205
of acetals, 26:220
during acetolysis, 22: 19
of acyloxonium ions in monosaccharides,
26: I46168
 SUBJECT INDEX
in polyol systems, 26: 135-146
of alkoxyalkyl radicals by radiation,
37:1415
allylic, 24:249
of glycals, 24:213
of 2-hydroxyglycals, 24:221
Amadoh, 10:169-205,22:267,269
benzilic acid, in alkaline degradation, 28:205
in dehydration of sugars, 28: 171
in lactic acid formation, 28: 197
in saccharinic acid formation, 28: 194
branched-chain sugar synthesis by,
42:109-113
of cyclitols with acetic acid-sulfuric acid,
26: 188-1 9 1
in deamination reactions, 31:ll-13
Heyns, 22:268
Lobry de Bruyn-Alberda van Ekenstein,
28:161, 163, 168
monosaccharide esters in liquid hydrogen
fluoride, 26:176-188
peroxide-induced, of acetals to esters, 39: I50
of polyol esters in liquid hydrogen fluoride,
26:169-176
of saccharides with Lewis acids, 26: 192-1 95
Wagner-Meerwein, 24: 193
Rebaudoside A, taste properties, 45:285-286
Receptor
o-galactose-specific, 40:220
sialic acids as components, 40:22%232
Recognition systems
in animals cells, 44:378-379
in plants, 44:378-382
Red blood cell, role of glycophorin A i ti.
45:17&171
Red kidney bean, see Phaseolus vulgirris
Reducing sugars, 46:214
alkaline degradation, reaction model,
52:453454
in aqueous solution, 42: 15-68
acyclic-form determination, 42:20-22
composition variation with temperature,
42:32-33
compound separation, 42: 16
inorganic compound effects on, 42:33
NMR spectroscopy, 42: 16, 18-20
polarimetry, 42: 17-1 8
stability of various forms in, 42:2434
enolization, in acid solution, 52:457
mutarotation and isomerization, 52:450
44 I
in nonaqueous solvents, 42:60-62,68
in solution, 49: 19-35
aldohexoses and aldopentoses, 49:25-26,
33
aldotetroses and related sugars, 49:26, 34
amino sugars, 49:29-30, 34
branched-chain sugars, 49:30-3 1
furanose content in organic solvents,
49:3 1-32
gas-liquid chromatography, 49:2 1-22
heptuloses, 49:28
hexuloses and pentuloses, 49:27-28
HPLC, 49:22
NMR spectroscopy, 49:2&21
partially @substituted sugars, 49:28-29
relative stability
uldehyde and keto forms, 49:2425
composition variation with temperature,
49:25
furanose form, 49:23-24
hydrated carbonyl forms, 49:25
pyranose form, 49:22-23
in solvents other than water. 49:3 1-32,
35
sugars having fused rings, 49:3 1
thio sugars, 49:30
Reductic acid
from D-xylose and other pentoses, 28: 176
effect on color formation, under sulfate-
pulping conditions, 46:325
formation of, 28:191,46:288
from hexuronic acids by decarboxylation,
28: 186
preparation and properties of, 28:207-212
as product after acid exposure of o-xylose,
46:276
Reductic-'T acid, preparation of, 28:210
Reduction
of alkoxycarbonyl function, 29:286
of a-0x0 esters of carbohydrate derivatives,
27:201
asymmetric, with complexes of lithium
aluminum hydride, 27: 195-199, 216
biochemical, at the expense of sugars,
4~75-117
of chlorodeoxy sugars, 28:302-303
of o-fructose, 22:283
enzymic, and labeling with hydrogen
isotopes, 27: 132
of hexuronic acid residues, 24:341
442 SUBJECT INDEX
Reduction (continued)
by hydride reagents and labeling of sugars
with hydrogen isotopes, 27: 129-132
by hydrogen in deuterium oxide, 27: 132
of nucleotides, 22:380
by phenoxides, of acylalkyl radicals, 37: 19
of sugar sulfonates by lithium aluminum
hydride, 23:269
by transition-metal ions, of acylalkyl
radicals, 37:19-20
of w-deoxy-o-halo sugars, 22:206
Reductones, 47:249-250
formation of, 28:207
polarography of, 29: 170
Redundant coordinates, 44:34
Reformatsky-type reactions, aldonolactone
carbonyl group, 50:136-138
Refractive index
mutarotation measurement by, 2 3 5 0
and specific rotation of methyl D-
galactosides, 30:4
Regiochemistry, radical-mediated
brominations, 49:67-7 1
Regioselectivity
factors, 53:3344
hydrogenolysis, 39: 123-124
trends, 53:44, 6 0 4 8
Reichstein, T., 46: 13
Relaxation reagents, 47: 131-135
nonspecific, 47: 13 1-132
specific, 47: 132
Relaxation time, molecular-weight dependence,
51533
R-enzyme, 23:363
Repellents, beetle, 24:7
Replacement reactions, mechanisms of, in
carbohydrate chemistry, 9: 1-57
Reproduction, a-o-mannosidase effect on,
28:436
Repulsion, by nonbonded atoms in
conformational changes, 25: 104
Resins
catalysis of polymerization by ion-exchange,
21:464
ion-exchange
as catalysts in glycofuranoside formation,
21:104
cellulose derivative as, 29:326
in hydrolysis of glycoproteins, 28: 17.22
levoglucosan derivatives, 34:76
melamine, anhydrohexitols for, 25:67
from periodate-oxidized starch, 29:358
sucrose copolymers in, 33:274
Resolution, of racemic carbohydrates and
substrates, 40: 113-1 I7
Resonance energy hypothesis, of sweetness,
45:2 18
Resonance Raman effect, 44:84
Resorcinol, as reagent for estimation of D-,
fructose, 22:237
Respiration
in plants, effect of auxins on, 21:387
respiratory climacteric in fruits, 42:361-368
Restricted internal diffusion model, 51: 127
Retention times
factors affecting, 30:47
of furanosides and pyranosides, 28:54
in gas-liquid chromatography, 28:45,69,
30:31
of 0-trimethylsilyl derivatives, 28:82
stereoisomeric structure and, 28:33
Retinoic acid, 1-ester with D-glycuronic acid,
36: 105
Reverse anomeric effect, 26: 108,4759
definition, 4752-53
Reversion, of saccharides, 21:442
R factor, and resistance of Gram-negative
organisms, 30: 184
Rhamnal, L-, methoxymercuration of, 24:210
Rhamnan, methylated, gas-liquid
chromatography and periodate degradation
of, 30:33
Rhamnazin, synthesis of, 24:6
Rhamnetin, synthesis of, 24:6
Rhamnitol
acetylation of, 28:35
1,5-anhydro-~-,25:237
1,2:3,4-di-O-isopropylidene-~-, selective
hydrolysis, 39:22
2,3-di-0-methyl-, acetate, gas-liquid
chromatography of, 30:31
4-0-P-~-galactopyranosyl-~-, crystal
structure bibliography, 38:452
Rhamnofuranose
1,5-di-O-acetyl-~-,preparation, 39:55
2,3-O-isopropylidene-
L-, nuclear magnetic resonance spectra of,
34:201
5-O-p-tolylsulfonyl-~-,displacement
reactions of, 24: 171
 SUBJECT INDEX
Rhamnofuranoside
ethyl a-L-and p-L-,21: 112
preparation form dithioacetal, 32:68
methyl a-L-,formation from dithioacetal,
32:68
methyl 2,5-di-O-methyl-3-0-
(methylsul fonyl)-a+, displacement
reaction of, 24: 165
methyl 2,3-0-isopropylidene-
a-L-, synthesis, 39:166
p-L-, synthesis, 39: 167
Rhamnofuranosylamine, N-acetyl a-L-,
configuration of, 31:109
Rhamnogalacturan
I, in plant cell walls
changes in, 42:368,370,373-375, 377,
381
interconnections, 42:305, 309
purification, 42276
structure, 42278-279
11, in plant cell-walls, 42:287
changes in, 42:369-370,377.38 I
interconnections, 42305,309
purification, 42:276
structure, 42:280-281
Rhamnogalacturonan, 44: 182-1 83
I1
f.a.b.-mass spectrometry, 45:67-68
heptasaccharide isolated from, sequence
of, 4567-68
oligosaccharides, liquid chromatography
fractionation, 46:49
Rhamnomannan, 41:89-91
carbon- 13 nuclear magnetic resonance
spectra, 38:61-68
carbon-13 signals, 38:23
gas-liquid chromatographic analysis of,
28:50
Rhamnononitrile, tetra-0-acetyl-L-, reaction
with ammonia, 31:82
Rhamnopyranose
a-D-, ester of guanosine, 5-pyrophosphate,
enzymic preparation of, 28:32 I , 344
p-L-
ester of thymidine 5-pyrophosphate,
isolation of, 28:323
ester of uridine 5-pyrophosphate, bio-
synthesis of, 28:326
1,2:1,2-dianhydride, O - ( ~ - D -
galactopyranosyluronic acid)-,
443
gas-liquid chromatography and
structure of, 30:26
144)-
3,6-di-0-methyl-~-o-glucopyranosyl-(
2,3-di-O-methyl-~-,51 :204
2,3-0-isopropylidene-4-U-methyl-~-1.-,
47:30
:I
1,2:3,5-bis(ethylboronate), selective
cleavage, 3 9 5 5
peracetate, ammonolysis of, 31:87
tetra-0-acetyl a,p-t-, ammonolysis of,
31:123
1.2,3,4-tetra-0-benzoyl-~-, ammonolysis of,
31536
Rhamnopyranoside
4-O-benzoyl-3-O-methyl-a-i.-, 51:209
benzyl exo-2,3-0-benzylidene-4-0-(2,-3,4,6-
tetra-~-benzy~-a-D-ga~actopyrdnosy~)-
a-L-.synthesis, 39: I33
benzyl4-0-allyl-2,3-0-benzylidene-~-, exo,
hydrogenolysis regioselectivity, 39: I32
benzyl 2,3-0-benzylidene-~-,endo- and exo-,
hydrogenolysis regioselectivity, 39: I32
benzyl4-0-benzyl-2,3-0-benylidene-~-,
endo- and exo-, hydrogenolysis
regioselectivity, 39: 132
ethyl 2,3-di-O-acetyI-4-0-benzyl-1 -thio-a-
L-, 51~226-227
8-methoxycarbonyloctyl2,3-di-O-methyl-a-
L-, 51~208
methyl a-L-,reaction with sulfuryl chloride,
33:74
methyl 6-chloro-6-deoxy-a-~-,
tri(chlorosulfate), preparation of, 33:74
methyl 4-0-benzoyl-2,3-isopropylidene-a-
L-, reaction with dibromomethyl methyl
ether, 39: 120
methyl 2,3-0-benzylidene-
a-L-
reaction with butyllithium, 39: 142-
143
synthesis, 39:78
5-O-acetyl-a-~-,reaction with N-
bromosuccinimide, 39: 107
methyl 2,3-0-isopropylidene-a-~-, reaction
with methyltriphenoxyphosphonium
iodide, 28:242,282
methyl 4-0-methyl-2,3-di-O-
(trifluoroacety1)-a-L-, selective
alcoholysis, 39:29
444 SUBJECT INDEX
Rhamnopyranosyl, 3,6-di-O-methyl-a-o-
glucopyranosyl-( 1+4)-2,3-di-O-methyl-
a-L-rhamnopyranosyl-(1+2)-3-0-methyl-
a-
L-, 51:200-201
,%amnopyranosylamine, N-benzoyl-L-
oxidation and configuration of, 103
preparation of, 31:86
Rhamnopyranosyl chloride, 2,3-0-
isopropylidene-4-0-methyl-a-~-, reaction
with base, 39:147
0-(a-L-Rhamnopyranosy1)-(1-t2)-6-deoxy-a-
L-talopyranose, 51: 179
0-Rhamnopyranosyl trichloroacetimidates,
50:105, 108-109
Rhamnose
(Y-L-
hydrate, solubility in ethanol, 27:98
taste properties, 45:242
p-L-,taste properties, 45:242
configuration of, 21 :17
D-
occurrence in Nature, 21: 172
polarography of, 29:126
synthesis of, 21:177, 289
determination of enantiomeric form, 46:66
O-(3,6-di-O-rnethyl-P-o-glucopyranosyl)-
(1+4)-0-(2,3-di-0-methyl-a-~-
rhamnopyranosyl-( 1+2)-3-0-methyl-
L-, 51:204205
in fungal cell walls, 23:413
L-, 48:283, 51:226
derivatives, cyclic acetals, table, 34:240
dibenzyl dithioacetal, reaction with
mercury(I1) chloride in methanol,
32:68
dimethyl acetal, formation from
dithioacetal, 32:68
dithioacetals, selective methylation of,
33:66
reaction with sulfuryl chloride, 33:76
and ethylamine, reaction between, 46:3 13
gas-liquid chromatography of, 28:46-17
gel chromatography of, 2 5 3 2
infrared spectrum of, 23:39
Maurice Stacey's work, 52: 13
1,2-(methyl orthoacetate), 21:20
nonselective spin-lattice relaxation rates,
45: 148
occurrence in Nature, 21:171
in plant cell-wall hydrolyzates, liquid
chromatography analysis, 46:55
proton spin-lattice relaxation rates, 45: 150
solubility in methanol, 27:97
synthesis of, 27:4
sweetness-structure relationship, 45:24 1
utilization by yeasts, 32:224
liquid chromatography
methods for analysis of, 46:33
separation, 4 6 5 3
methyl ethers of, 7:l-36, 10:257-272
2-0-(a-o-galactopyranosyluronic acid)-L-,
24:361, 364, 366,316
0-(P-o-glucopyranosyluronic acid)-( l+3)-
0-(a-o-galactopyranosyluronicacid)-
(1+2)-~-, 24~366
0-(galactopyranosyluronic acid)-( 1+2)-0-
rhamnopyranosyl-( 1-+4)-0-(galacto-
pyranosyluronic acid)-( 142)-, 24:364
2,3-0-isopropylidene-r-, composition in
aqueous solution, 42:59
oligosaccharides containing, I3C-NMR data
for, 42:205-207
i!-O-methy]-~-,composjtion in aqueous
solution, 42:45
3-0-methyl-~-,24:359
from Klebsiellu 0-group 10
lipopolysaccharide, 29:67
from Rhodopseudomonas capsulata
lipopolysaccharide, 29:67
in pectic polysaccharides, 42:277-278
relation to galactose, 21: 16
synthesis of, 23:261,274
Rhamnose antibodies, 53:229-230
L-Rhamnose nucleosides, 'H-NMR spectra of,
42951
Rhamnose synthon, 4-0-methyl-~-,51:222
D-Rhamnose synthon, 51:223
L-Rhamnose thioglycoside, 51:22 1-222
Rhamnosides, SO: 105
methyl a - ~ -selective
, periodate oxidation of,
33:95
methyl 2,3-0-isopropylidene-4-0-
(methylsulfony1)-a+-, displacement
reactions of, 24:153, 190
a-L-Rhamnosyl linkage, 47: 192-193
Rhamnosyl trichloroacetimidate, 51:223-224
Rharnnusfrungulu. frangulin B from, 31: 147
Rhamonpyranose, a-L-,monohydrate, crystal
structure bibliography, 38:430
 SUBJECT INDEX
Rheology, 53:292
Rhinocludiellu, polysaccharide, 36:30 1
Rhinocladiellu elicitor, polysaccharide, 41 :88
Rhinocludiellu munsonii, polysaccharide,
41:102
Rhizobia
acidic polysaccharides, f.a.b.-mass
spectrometry, 45:66
p-(1+2)-glucans, f.a.b.-mass spectrometry,
45:68
Rhizobium japonicum 3IIb 83, extracellular
polysaccharide, 47: 189-1 90
Rhizohium leguminosarum, extracellular
polysaccharides, 47: 190-1 92
Rhizobium meliloti, mass spectrometry of
polysaccharide from, 29:68
Rhizobium trifolii
capsular polysaccharide, 52:39840 I
extracellular polysaccharides, 47: 190. 192
Rhodinose, 21:195, 50:158
Rhodinoside, methyl p-D-,preparation of,
28:294
Rhodobucter capsulutus, lipid A, 50:232-234
Rhodobacter sphaeroides, lipid A, 50:232-234
Rhodomycin, 21 :195
Rhodopseudomonas cupsuluta.
lipopolysaccharide, mass spectrometry of,
29:67
Rhodopseudomonas viridis, lipopolysaccharide,
mass spectrometry of, 29:66
Rhodotorulu,flava, a-L-arabinofuranosidase
from, 42:387-388,390-392
Rhodotorula glutinis
K-24, hcomannnogalactan, 41:101
mannan, 41:78
monosaccharide transport into, 32: 155-157
Rhodymenan, D-xylan from Rhodymenia
palmutu, 32:348
Ribitol
2-arnino-2-deoxy-~-,deamination of, 31:63
1,4-anhydro-
D-, 25~233
sweetness-structure relationship, 45:257
tribenzoate, isomerization of, 25:258
DL-, 25:208,23 1
gas-liquid chromatography of, 28:57
L-, 25: 198
1,5-anhydro-, D-, laser-Raman spectroscopy,
44:83
2,5-anhydro-
445
1-deoxy-I,]-difluoro-o-, 22:196, 201,
24:205,25:196, 235
synthesis, 38: 196
I-deoxy-l,l-difluoro-~-, 25: 196
1,I-difluoro-, synthesis, 38:233
2-0-~-D-glucopyranosyl-D(and I-)-,
degradation of, 21:356
conformation of, 25: 104
crystal structure of, 25:59,31:364
D-
catabolism by yeasts, 32:226
derivatives, synthesis, 41:s
2-deoxy-2-fluoro-, 22: 199,20 I
2-deoxy-2-fluoro-o~-,synthesis, 38:238,
40: 105
5-deoxy-2,3-0-isopropylidene-~-, 23:274
1-deoxy-2-0-methyl-1-nitro+-, 24: I30
1,5-dideoxy-, phenylboronate, structure,
35:43
1,5-di-0-benzoyl-2,4-0-
benzylidene-, esterification and hydrogen-
bonding, 33: 16
methylene-, esterification and hydrogen-
bonding, 33: I6
2,4:3,5-di-O-benzylidene- 1-deoxy- 1-
(2,5-dioxo-N-phenyl-3-pyrrolylidene)-~-,
synthesis by Wittig reaction, 27:256
(2,5-dioxo-3-pyrrolylidene)-~-, synthesis
by Wittig reaction, 27:256
infrared spectrum, 45:294
L-, ester of cytidine 5'-pyrophosphate.
biosynthesis and isolation of, 28:333
liquid chromatography methods for analysis
of, 46:33
4-~-(2-amino-2-deoxy-~-g~uco-pyranosy~)-
D-, deamination and structure of, 31:76
5-0-benzoyl-4-C-(benzoyloxymethyI)-
1,2:3,4-di-O-isopropylidene-~-,
selective hydrolysis, 39:23
2,4-0-benzylidene- 1-deoxy- 1-(2,5-dioxo-3-
pyrrolyhdene)-o-, synthesis by Wittig
reaction, 27:256
I-phosphate, solvolysis of, 25:208
radiolysis and free-radical chemistry, 37:27
selective oxidation with mercuric acetate,
33:99
sweetness-structure relationship, 45: 295
2,3,4-tri-O-benzyl- 1,5,-di-O-p-tolylsulfonyl-,
solvolysis of, 24:196
Ribitol dehydrogenase, production of, 30:263
446 SUBJECT INDEX

Ribitol phosphate, bacterial polysaccharides, data

(methoxymethyl)-~~-,'~C-NMR
48:316 for, 46: 169
Riboflavin, analongs, research, 29:2 'H-
1 -O-acetyl-5-O-(methoxymethyl)-~1-,
Riboflavine and I9F-NMR data for, 46: I I I
complex with 5'-bromo-5'-deoxyadenosine, I -O-acetyl-2,3,5-tri-O-benzoyl-4-deoxy-4-
trihydrate, crystal structure fluoro-p-,13C-NMRdata for, 46: 172
bibliography, 30:459 phosphorus derivatives of, physical
hydrobromide monohydrate, crystal structure properties, 42: 191
of, 25:92,31:368 3-deoxy-
photochemistry, 38: 149 I ,2:5,6-di-O-isopropylidene-3-C-methyl-
selective phosphorylation of, 33:50 D-, synthesis of, 27:282
synthesis of, 24:5 1,2-O-isopropylidene-3-thiocyanato-~1-~-,
Riboflavine 5 '-(alkyl phosphate), preparation, 44: I45
39:60 5-deoxy-
Riboflavine hydrobromide monohydrate, 3-C-( 1,3-dithian-2-yl)-1,2-0-
conformation of, 26:69 isopropylidene-P-L-, preparation of,
ol-o-Ribofurano[1,2-~-2-oxazolidinone,crystal 32:38
structure bibliography, 37:376 3-C-(hydroxymethyl)- 1,2-0-
Ribofuranose isopropylidene-a-DL-, synthesis,
4-acetamido- 40:82
5-di-O-acetyl-2,3-di-O-benzoyl-4-deoxy- 1,2-O-isopropylidene-3-O-p-tolylsulfonyl-
D-, 23: I86 CI-D-, displacement reactions of,
l-O-acetyl-4-deoxy-2,3,5-tri-O-p- 24: 152
nitrobenzoyl-p-D-, 23: I92 1,5-di-O-acetyl-3-C-(R)-
1,2,3,5-tetra-O-acetyI-4-deoxy-~-, 23: 184, (ethoxycarbonyl)methyl-5(R), 1 '(R)-N-
186 formylepimin0-2,3-O-isopropylidene-p-
2,3,5-tri-O-acetyl-4-deoxy-~-, 23: 185 D-, crystal structure bibliography,
5-acetamido-5-deoxy-~-,23: 172 37:434
a-D-,glycosides and N-glycosyl derivatives, 3,5-di-O-benzoyl- 1,2-0-
preparation of, 31:4 (diphenylmethy1idene)-a-w, reaction
1,Sanhydro- with 2.4-
P-D-,synthesis, 39: 165 bis(trimethylsilyl)oxypyrimidine and
2,3-O-benzylidene-p-o- stannic chloride, 39: 153
polymerization, 39:206 1,5-di-O-trityl-o-, selective cleavage, 39:47
synthesis, 39: 165 L-, derivatives, synthesis, 50: 132
2,3-O-isopropylidene-o-, formation of, methyl 2,3-di-O-benzoyl-5-deoxy-~-,
34: 184 22: 120
p-D- methyl mono-O-benzoyl-5-deoxy-o-, 22: 120
1,5:2,3-bis(phenylboronate).preparation 1-O-acetyl-2,3,5-tri-O-benzoyl-
and structure, 35:44 p-D-,reactions with aromatic compounds,
1,5:2,3-di- 33: 159-160
[(diethylamido)thionophosphate], with terminal alkenes, 33:162
crystal structure, 43:23&235 p-L-, 22:121
conformation of, 34:201 5-0-benzyl-
D- 3-deoxy-3-C-(hydroxymethyl)-1,2-0-
5-deoxy-5-fluoro-, 'H- and I9F-NMR data isopropylidene-a-D-, preparation of,
for, 46: 1 12 27:243
nucleosides and nucleotides, crystal 1,2-O-isopropylidene-3-C-methyl-~1-~-,
structures of, 25:86-90 preparation of, 27:243
1 -0-acety-2-deoxy-2-fluoro-5-0- 2,3-O-benzylidene-P-~-,
 SUBJECT INDEX
diastereoisomers, 34: 196
preparation of, 34: 184
1,2-O-isopropylidene-
a-D-
formation of, 34: 184
selective esterification of, 33:35
3,5-di-O-p-tolylsulfonyl-a-o-,
displacement reactions of, 24: 15 I
2,3-0-isopropylidene-
D-
conformation of, 34:201
preparation of, 34: 1 8 4 185, 188
reaction with (ethoxycarbonyl-
methy1ene)triphenylphosphorane.
33:155
selective oxidation with silver
carbonate-on-Celite, 33:97
synthesis, 39:75
DL-, synthesis, 40:69
5-O-(p-bromophenylsulfonyl)-3-deoxy-3-C-
(R)-(ethoxycarbonylformamido )-
methyl- I ,2-O-isopropylidene-a-o-.
crystal structure, 43:348
I ,2,3,5-tetra-O-acetyl-p-~-,crystal structure
bibliography, 31:353,37:392
tetra-0-acetyl- p-D-
reaction with methanethiol, 32:35
rearrangement in hydrogen fluoride,
26:181
tetra-0-acetyl-4-thio-
D-, 23:220
L-, 23:220
tetra-0-benzoyl-p-o-, rearrangement in
hydrogen fluoride, 26: 181
4-thio-p-~-,and tetrakis(p-nitrobenzoate),
23:22 I
1,3,5-tn-O-benzoyl-o-o-
preparation of, 31:4
proton magnetic resonance spectra. virtual
coupling in, 27:69
rearrangement in hydrogen fluoride,
26:181
2,3,5-tn-O-benzoyl-o-, reaction with
(ethoxycarbon ylmethylene)
triphenylphosphorane, 33: 156
2,3,5-tri-O-benzyl-~-,reaction with
(ethoxycarbonylmethylene)
triphenylphosphorane, 33: 157
1,3(2),5-tri-O-trityl-
D-, selective cleavage, 39:47
447
2(3)-0-acetyl-o-, selective cleavage,
39:4748
Ribofuranoside, 53: 174
alkyl I-thio-a+-, preparation from
dithioacetals, 32:66
benzyl P-D-, 21:125
selective phosphorylation of, 33:46
p-chlorophenyl p a - , 21: 12 1
ethyl 2,3-anhydro-5-(tetrahydropyran-2-yl)-
D-, 25: 120
ethyl 1-thio-a-o-. 21:I 15-1 16
isopropyl I-thio-a-o-, 21: I15
methyl 4-acetamido-4-deoxy-p-~-,23: 185
methyl a+, 21:122
conformation of, 21:98
preparation of, 34:281
methyl 5-(adenin-l-yl)-5-deoxy-2.3-0-
isopropyhdene-p-o-, 23: 141
methyl 2-amino-2,3-N, O-benzylidyne-2,5-
dideoxy-5-C-
pentadecyhdene-P-o-. 24:257
tridecylidene-p-o-, 24:257
methyl 2,3-anhydro-
a-D-,conformation of, 21:99
p-D-, 23: 108
conformation of, 21:99
p-L-.23~277
methyl 5-azido-5-deoxy-2,3-di-O-p-
tolylsulfonyl-p-o-, 24: 145
methyl P-D-, 21:121,23:280
conformation of, 21:98
preparation of, 34:278
methyl 5-deoxy-
2.3-O-isopropylidene-5-[(purin-6-
yl)amino]-p-o-, 23: 141
5-[9-(tetrahydropyran-2-yl)purin-6-
yl]amino-2,3-di-O-p-tolylsulfonyl-~-
D-, 23:141
methyl 5-0-acetyl-2,3-anhydro-p-~-, 0x0
reaction with, 23: 108
methyl 5-0-benzoyl-2,3-0-
isopropylidene-p-o-, reaction with
dibromomethyl methyl ether. 39: I20
methylene-p-o-, preparation of, 34: 191
methyl 5-O-benzyl-P-~-,preparation of,
28:294
methyl 2,3-O-benzylidene-
p-D-, irradiation, 39:88
5-O-methyl-P-o-, reaction with N-
bromosuccinimide, 28:277,39:101
448 SUBJECT INDEX
Ribofuranoside (continued)
reaction with
5-O-(methylsulfonyl)-P-~-,
N-bromosuccinimide, 26: 164
methyl 2,3-0-isopropylidene-
P-D-,23:214
5-O-(methylsulfonyl), fluorination, 38:207
5-O-(methylsulfonyl)-o-,displacement
reactions of, 24: 142
reaction with
diethyl sodiomalonate, 33: 149
with mercuric cyanide, 33: 132
with 1,2,5-trimethoxybenzene and zinc
oxide, 33:159
methanol or with 1,2,3,4-tetra-O-
acetyl-P-o-glucopyranose, 34:280
methyl 5-0-trityl-P-~-,24:230
methyl 4-thio-
D-, 23:22 1
L-, 23:222
methyl I-thio-P-D-, formation of, 32:35
methyl 2,3,5-tri-~-p-tolylsulfonyI-P-o-,
displacement reactions of, 24: 165
phenyl (3-D-, preparation of, 34:278
Ribofuranosiduronic acid, methyl 2,3,-0-
isopropyiidene-P-D-, preparation, 36:68
Ribofuranosyl acetate, 8-oxabicyclo[3.2. I ]
octa-2,6-diene, 2,3,4,4-tetrachlori-, methyl
2-2,3-0-isopropylidene-p-, synthesis
from, 33:163
Ribofuranosylamine, 4-a-Carba-P-o-, 48:23
P-o-Ribofuranosyl azide, 2,3-0 isopropylidene-
5-0-phosphone-, 22:374
Ribofuranosyl benzimidazole, 5,6-dimethyl- 1-
a+-, crystal structure, 43:293
Ribofuranosyl bromide
3,5-di-O-benzoyl-
a-D-, reaction with methanol or with
1,2,3,4-tetra-O- acetyl-P-o-
glucopyranose, 34:280
2-0-nitro-P-o-, reaction with methanol or
with 1,2,3,4-tetra-0- acetyl-P-o-
glucopyranose, 34:280
2-0-(p-nitro-benzoyl)-P-~-,reaction with
methanol or with 1,2,3,4-tetra-0-
acetyl-P-o-glucopyranose, 34:280
2-0-acetyl-3,5-di-0-benzoyl-P-~-, reaction
with methanol or with 1,2,3,4-tetra-O-
acetyl-P-o-glucopyranose, 34:280
tri-0-benzoyh-, preparation of, 31:4
2,3,5-tri-O-benzyl-
p-D-,reaction with mercuric cyanide,
33: 138
D-, methanolysis of, 34:281
Ribofuranosyl chloride
2,3-O-isopropylidene-5-0-trityf-P-~-,
reaction with diethyl sodiomalonate,
33: 152
5-O-(methoxycarbonyl)-~-,2,3-carbonate,
methanolysis of, 34:281
2,3,5-tri-O-benzyl-P-o-, reaction with
2,6-dibenzyloxypyridin-3-ylcadmium,
33:178
with diethyl sodiomalonate, 33: 149
diethyl sodiomalonate, 33: 150
Ribofuranosyl cyanide
5-0-benzoyl-
P-D-,preparation, 39:39
2,3-O-isopropylidene-P-~, preparation and
reductive hydrolysis of, 33: 135, 137
2,3,5-tri-O-benzoyl-, P-n-
preparation of, 33: 132
reaction with 2-amino-2-cyanoacetic acid
derivatives, 33: 185
reductive hydrolysis of, 33: 134
selective debenzoylation, 39:39
N-P-o-Ribofuranosylcyanu~cacid, proton
magnetic resonance spectroscopy of,
27:35
Ribofuranosyl fluoride
2,5- and 3,5-di-O-benzoyl-P-o-, 26:177
D-
2,3-acetoxonium-5-0-acetyl-P-, I3C-NMR
data for, 46: 169
2-0-acetyl-3,5-di-0-benzoyl-P-, ' H- and
I9F-NMR data for, 46: 108
3-0-acetyl-2,5-di-0-benzoyl-P-, 'H- and
I9F-NMR data for, 46:108
5-0-acetyl-2,3-di-O-benzoyl-P-, 'H- and
I9F-NMR data for, 46:108
synthesis, 48: 101
2,3,5-tri-U-acetyl-, 'H- and "F-NMR data
for, 46: I07
2,3,5-tri-O-benzoyI-
"C-NMR data for, 46: 169
IH- and "F-NMR data for, 46:108
3,5-di-O-benzoyI-a-o-, 26: 177
2,3,5-tri-O-benzyl-P-o-, synthesis, 48:99
tri-0-benzoyl-
a-D-, proton magnetic resonance
spectroscopy of, 27:82
 SUBJECT INDEX
P-D-, 26: 177
proton magnetic resonance spectroscopy
of, 27232
Ribofuranosyl halide, 3,5-di-O-benzoyl-~-,
preparation of, 31:4
Ribofuranosylimidazo-[2,1-d]purine, 7-ethyl-3-
P-D-, chloride, monohydrate, crystal
structure, 43:365
Ribofuranosyl isothiocyanate, 2,3,4-tr-O-
benzoyl-P-o-, 44: 142
I3C NMR, 44:141
infrared spectrum, 44:141
P-o-Ribofuranosyl phosphate, preparation of,
33:47
Ribofuranosyl-2-thiothymine, 1 -P-D-.
synthesis, 44:98
9-( P-D-Ribofuranosyluronic acid)adenine,
preparation, 36: I27
I -(P-D-Ribofuranosyluronic acid)uracil
Sarnino-, preparation, 36: 126
methyl ester, preparation, 36: 130
5-nitro-, preparation, 36: 126
preparation, 36: 127
Ribonic acids, analytical high-performance
liquid chromatography, 46:34
Ribonolactone
P-elimination, 50: 189
D-
O-benzylidene derivatives, physical
constants for reassigned structures,
50: 1 2 6 1 2 7
syntheses from, 50:192-195
Ribono-1 ,4-lactone
5-deoxy-o~-,synthesis, 40: 19
nucleophilic additions, 38:317
2,3-O-isopropylidene-5-O-(tetrahydropyran-
2-y1)-0-, reaction with 2-lithio-2-
methyl- 1,3-dithiane, 32:39
sulfonylation of, 23:245
Ribonolactam, 5-amino-2,3-benzylidene-5-
deoxy-D-, 23: 164
Ribonucleases, 25:446, 44:232
amino acids of, 27:315,3 I 7
B 36:150-152
a-D-mannosidase as structural reagent for,
28:444
glycopetides, liquid chromatography
separation, 46:48
structural analysis, 43: 15-1 7
carbohydrates of, 27:307,325-326, 340
449
conformational structure of, 27:327
deoxy, amino acids of, 27:3 15-3 I6
as glycoenzyme, 27:308
horse pancreatic, glycoproteins (compounds
44 and 45), H-NMRspectroscopy,
41:306-307,309-312.316
purification by chromatography, 27:3 10
Ribonucleic acid ligase, bacteriophage T4-
induced, Escherichia coli. 46: 182
Ribonucleic acids
chromatography of, 29:333
deoxy-, structure, 36: 140
D-g~ucosyl2-deoxy-.26:475
structure, 36:140
synthesis and separation of, O-(2-
diethylaminoethy1)cellulose in, 29:
325
Ribonucleosides
acetals, 22340
2- and 3-phosphate,phosphono migration
in, 33:108
2:3-cyclic phosphates, 22:3 12, 355
D-, acetalation by enol ethers, 34: 188
2-deoxy-
3-and 5-phosphate, 22:343-344
3:5 -cyclic phosphates, 22360
monophosphates, 22309
3 -O-acyl-2-0-(4-methoxytetrahydropyran-
4-yl)-, preparation, 39:38
2 ,3-O-(dibutylstanny1ene)-, as activating
group in esterifications and alkylations,
33:70
2(or 3). 5-diphosphates, 22366
2-phosphate, 22312,348
3-phosphate, 22:312,348
5-phosphates, 22:309,325
reaction with isobutyl diphenylborinate,
35:39
selective esterification of, 33:3 1-32
selective phosphoIylation of, 33:49
Ribonucleotide reductase, and hydrogen-
isotope action on sugars. 27: 156
Ribonucleotides, protecting groups,
Ribo-oligonucleotides, synthesis of, 46: 18 1
Ribopyranose
5-acetmido-5-deoxy-o-, 23: 172-1 73
a - D - , 45:74
confonnation in solution, 26:85
conformation of, 26:67
450 SUBJECT INDEX
hbopyranose (continued)
bromo-2,3-
1,6-anhydro-4-O-benzy1-3-
dideoxy-pa-, preparation of, 34: I32
p-D-,47: 13
conformation in solution, 26535
derivatives, conformational equilibria,
47:62
g.1.c. of aqueous solutions of, 42:23
tetraacetate
conformational equilibria, 26:89-92
conformations of, 24:57
proton magnetic resonance spectroscopy
of, 27:22
5-[(benzyloxycarbonyl)amino]-5-deoxy-
a-D-, 23:191-192
p-D-, 23:191-192
D-
2-deoxy-2-fluoro-
a,@-,'H- and "F-NMR data for, 46:
104
1,3,4-hi-O-acetyl-, IH- and I'F-NMR
data for, 46: 104
1,3,4-tri-O-acetyl-2-deoxy-2-fluoro-
a anomer, I3C-NMR data for, 46: I67
p anomer, I3C-NMR data for, 46: 168
5-deoxy-5-phosphinyl-~-, synthesis and
structure of, 42: 145
1,2:3,4-di-O-isopropylidene-
(Y-D-,
formation of, 34: 184
hydrolysis of, 34:204
5-thio-a-~-,selective hydrolysis, 39: I7
1-O-acetyl-3-benzamido-2,4-di-O-benzoyl-3- methyl 2,3-anhydro-
deoxy-3-C-(ethoxycarbonyl)-p-~-, and
nucleoside, conformations of, 26: 109
3-O-benzoyl-l,2,4-O-benzylidyne-a-o-
conformation of, 26530
proton magnetic resonance spectra,
iterative analysis of, 27:78
3,4-O-isopropylidene-o-
preparation of, 34: 185, 188
synthesis, 39:75
1,2,3,4-tetra-O-acetyl-a-o-, crystal structure
bibliography, 38:7,452453
tetra-0-acetyl-P-D-
reaction with methanethiol, 32:35
rearrangement in hydrogen fluoride,
26:177, 181
1,2,3,4-tetra-O-acetyl-5-[(benzyloxy-
carbony~)amino]-5-deoxy-a-~- and p-
D-, conformation of, 26:89
tetra-O-acetyl-5-deoxy-5-C-
(ethylphosphiny1)-D-,physical
properties of, 42: 19 1
tetra-0-benzoyl-
a+-, conformation in chloroform solution,
26536
p-o-
conformation in chloroform solution,
26:86
rearrangement in hydrogen fluoride,
26:177, 181
I -thio-p-o-, tetraacetate, proton magnetic
spectroscopy of, 27:68
5-thio-o-, derivatives, 24: 146
mutarotation of, 24:49
Ribopyranoside
benzyl p-D-,catalytic oxidation of, 33:88
3' deoxy-, minimum inhibitory
concentrations of, 30:22 1
3',4'-dideoxy-, minimum inhibitory
concentrations of, 30:22 I
phosphorylation of, 30: 195
synthesis and activity against resistant
bacteria, 30: 171
ethyl 3,4-anhydro-p-~-,25: 154
methyl 4-acetamido-
4-deoxy-m-~-,22:133,23:184
4-deoxy-p-o-, 23: 184
methyl 4-amino-4-deoxy-2,3-0-
isopropylidene-P-L-, dearnination of,
31:42
a - ~and++-,
- conformations of, 26: 125
p-D-, 25: 152
methyl p-D-, 22: 125,23:280
catalytic oxidation of, 33:89
crystal structure bibliography, 32:357.
38:428
reaction with sulfuryl chloride, 33:75
methyl p-DL-,synthesis, 40:68
methyl 2-C-
(aminomethyl)-, deamination, 31:53
( 1,3-dithian-2-yl)-3,4-O-isopropylidene-p-
D-, chemical shift values for, 32:41
methyl 2-deoxy-3,4-O-isopropylidene-2-
(salicylideneamino)P-o-, 24: 152
methyl 3,4-dichloro-3,4-dideoxy-f3-~-, 2-
chlorosulfate, preparation of, 28:237,
33:75
 SUBJECT INDEX
methyl 1,5-dithio-
(Y-D-
hemihydrate, crystal structure
bibliography, 30:465
tetartohydrate, crystal structure
bibliography, 32:358
p-D-,crystal structure bibliography,
32:358
preparation of, 32:35
methyl 5-0-benzoyl-2,3-0-benzylidene-~-
D-, reaction with tetraethylammonium
p-toluenesulfonate, 39: 152
with triphenylmethyl fluoroborate, 39: 108.
152
methyl 3,4-O-isopropylidene-2-(2-methyl- I,Ribopyranosyl fluoride
3-dithian-2-(2-0-methyl- 1,3-dithian-2-
y1)- p-D-, chemical-shift values for,
32:41
methyl 3,4-0-(R)-benzylidene-P-~-,
isomerization, 39:26
methyl 4-S-acetyl-2,3-0-isopropylidene-4-
thio-p-o-, 24:192
methyl S-acetyl-2,3-0-isopropylidene-4-thio-
p-D-, 23:221
methyl 4Sbenzoyl-
2,3-O-isopropylidene-4-thio-P-t-, 23:220
4-thio-p-~,23:220
methyl l-thio-
OL-D-, crystal structure bibliography,
30:465,31:348
p-D-, preparation of, 32:35
methyl 5-thio-
(Y-D-, crystal structure bibliography,
31:349
p-D- crystal structure bibliography, 31:349
methyl tri-O-methyl-p-D-, mass spectrum of,
21:60
methyl 2,3,4-tri-0-acetyl-5-amino-5-deoxy-
5-N-(methoxycarbonyl)-, synthesis,
40: 100
3-N- (carboxymethy1)-, preparation of,
30:131
3,4,5-trideoxy-,synthesis and antibacterial
activity, 30:171
trifluoromethyl2,3,4-tri-0-acetyl-2-deoxy-2-
fluoro-p-o-, preparation, 38:233
Ribopyranosylamine, N-(p-bromopheny1)-a-o-
2,4-benzeneboeronate, conformation of,
26:116
2,4-dibenzeneboronate, crystal structure
45 1
bibliography, 31:368
2,4-phenylboronate, preparation and
structure, 35:46
Ribopyranosyl bromide
tri-0-acetyl-p-o-, conformation of, 26:87
tri-0-benzoyl-o-, preparation of, 3 1 : 3 4
Ribopyranosyl chloride, 3,4-dichloro-3,4-
dideoxy-~-o-,2-chlorosu~fate, preparation
of, 28:238
Ribopyranosyl cyanide
tri-0-benzoyl-, proton magnetic resonance
spectroscopy of conformers of, 27:23
2,3,4-tri-0-benzoyl-p-o-, proton magnetic
resonance spectroscopy of, 27:68
D-
3,4-di-O-acetyl-2-deoxy-2-bromo-, IH-
and l9F-NMR data for, 46: 136
3,4-di-O-acetyl-2-deoxy-2-fluoro-a-, IH-
and 19F-NMRdata for, 46: 155
2,3,4-tri-O-acetyl-, IH- and I9F-NMR data
for, 46: 102
2,3,4-tri-O-acety1-2-fluoro-p->H- and
I9F-NMR data for, 46:143
2,3,4-tri-O-benzoyl-, H- and I9F-NMR
data for, 46: I02
3,4-di-O-acetyl-2-fluoro-p-o-, preparation,
38:233
2,4-di-O-benzoyl-P-o-, 26: 177
3,4-di-O-benzoyl-p-o-, 26: 177
2,4-di-O-henzoyl-P-~-,26: 176
per-~-acetyl-2-deoxy-2-fluoro-~-o-,
synthesis, 38:204
tri-0-acetyl-P-o-, 26:177
2,3,4-tri-0-acetyl-2-fluoro-~-~-, preparation,
38:233
Ribopyranosylpurine, 6-methoxy-9-p-o-,
hemihydrate, crystal structure, 43:325
Riborunanose
cis-2,3-diamino-2,3-dideoxy-~-, preparation
of, 29:8
2,3,5-tri-O-methyI-o-, polargraphy of,
29: 142
Ribose
2-acetamid0-2-deocy-o-, preparation from
dithioacetal, 32535
4-acetamido-4-deoxy-~-,23: 184
5-acetamido-5-deoxy-o-, 23: 171
1-0-acetyl-2,3,4-tri-O-benzoyI-4-fluoro-p-
D-, synthesis, 49:80-81
452 SUBJECT INDEX
Ribose (continued)
a-D-, 2,4-phenylboronate, preparation and
structure, 3 9 4 4
2-amino-
2-deoxy-~-,22:134
2-deoxy-~-,deamination of, 31:26
3-amino-, 3-deoxy-o-, 22: 128
synthesis, 29:3
5-amino-, 5-deoxy-D-, 23:13 1
2,5-anhydro-~-
dialkyl dithioacetal, 25: 198
diisobutyl dithioacetal, 24: 175
hydrolysis of, 32:64
2,5-anhydro-3,4-di-O-p-to~yku~fonyI-o-,
diisobutyl dithioacetal, preparation of,
32:5 1
reaction with sodium iodide-N,N-
dimethylformamide-zinc dust, 32:52
5-(benzyloxycarbonyl)amino-5-deoxy-~-,
composition in aqueous solution, 42:50
chemistry of, 6:135-174
2-C-(hydroxymethyl)-o-
composition
in aqueous solution, 42:54
in dimethyl sulfoxide, 42:68
isolation of, 31: 136
composition
in aqueous solution, 42:26, 64, 134
in nonaqueous solvents, 42:68
D-. 21:17
acetonation of, 34: 184-1 85
benzylidenation of, 34: 184
derivatives of cyclic acetals, Table,
34:216215
diphenyl dithioacetal, crystal structure
bibliography, 34:372
aldehydo form, detection, 42:20
catabolism by yeasts, 32:226
crystalline form, 42: 18
crystallography of, 2 5 5 8
1,2:3,4-diacetal, selective hydrolysis,
39:16
dialkyl dithioacetal
alkyl 1-thio-a-o-ribofuranosidesfrom,
32:66
reaction with p-toluenesulfonyl
chloride, 25:198
diethyl dithioacetal, 43:371
conformation of, 26:72
irradiation, 39:94
diisobutyl dithioacetal, reaction with p-
toluenesulfonyl chloride, 32:5 1
dimethyi dithioacetal, preparation of,
32:23,35
diphenyl dithioacetal, 43:372
conformation of, 26:72
preparation of, 32:22
dithioacetals
reaction with sulfonyl chlorides in
pyridine, 32:48
selective esterification of, 33:4041
5-phosphate, preparation of, 33:47
enantiomeric carba-sugars, synthesis,
48:44
ester of thymidine 5'-pyrophosphate,
occurrence of, 28:322
Fourier-transform infrared spectroscopy,
44:65-66
gel chromatography of, 2 5 3 1-32
halogen derivatives, 22:215
liquid chromatography of, 42:24
mercaptalation of, 32:22
nonselective spin-lattice relaxation rates,
45: 148
(p-bromophenyl) hydrazone, crystal
structure bibliography, 31:367
derivatives, preparation of, 31:3
(p-bromophenyl) hydrazone
crystal structure of, 25:92
hydrogen bonding in, 2 5 9 8
5-phosphate, ally1 radical formation by
radiation, 37: 14
oxidation by transition-metal ions,
37:20
radiation chemistry, 37:33-34
radiolysis, 37:4246
radiolysis in D , , 37:20
polarography of, 29: 127, 141
preparation by electroreduction of D-
ribono-l,4-lactone, 29: 125
proton spin-lattice relaxation rates, 45:
152
pure and commercial, infrared spectra,
44~65-66
stability constants, 47:29
synthesis from L-glutamic acid, 28:294
transport into Rhodotorula glutinis, and
Pichia fermentans, 32:155
I ,3,4-tri-O-benzoyl-P-, 'H- and 19F-NMR
data for, 46: 104
 SUBJECT INDEX
2-deoxy-
D-, synthesis of, 28:8
2-fluoro-, derivatives, 22: 190
2-fluoro-~-,preparation, 38:240
5-deoxy-
3-C-(dimethoxymethyl)-o~-, dimethyl
acetal, synthesis, 40:64
D-, 21:176-177, 179
5-fluoro-o-, 22: 179
preparation, 38:207
2,4:3,5-di-O-benzylidene-
aldehydo-o-,Wittig reaction with, 27:23 I
D-, ethylene dithioacetal, selective
hydrolysis, 39:22
di-0-benzylidene-o-, preparation of, 34: I 84
2,3:4,5-di-O-isopropylidene-~-,
diphenyl dithioacetal, fragmentation and
mass spectrometry of, 32:96
dithioacetals, preparation of, 32:53
DL-,synthesis, 40:8-10,73
L-
derivatives of cyclic acetals, table,
34:2 14-21 5
synthesis of, 22: 12 1
mutarotation of, 23:23
5-O-benzoyl-2,4-O-benzylidene-~-, dipropyl
dithioacetal, reaction withp-
toluenesulfonyl chloride, 32:5 I
3-0-(2,6-diamin0-2,6-dideoxy-P-~-
idopyranosy1)-o-, deamination of
derivatives of, 31:26-28,75
4,5-ChopropylIdene-o-, dithioacetals,
preparation of, 32:53
5-S-methyl-5-thio-o-, dimethyl dithioacetal
formation of, 32:35
2,3,4,5-tetra-O-acetyl-o-,
diethyl dithioacetal, ultraviolet photolysis
of, 32:78
diisobutyl dithioacetal, nuclear magnetic
resonance spectrum and conformation
of, 32:91
4-thio-o-, composition in aqueous solution,
42:53
5-thio-~-,23:214
composition in aqueous solution, 42:53
1,3,4-tri-O-benzoyl-2-deoxy-2-fluoro-o-,
proton magnetic resonance spectra,
analysis of, 27230
2,3,5-tri-O-benzyl-4-O-p-tolylsulfonyl-o-,
dimethyl acetal, displacement by
453
alkoxyl group, 24: 194
Ribose 5-phosphate, composition in aqueous
solution, 42:46
Ribose-t, D-, detection and distribution in rat
tissue, autoradiography in, 27: 181
Ribose-3-t, D-, preparation of, 27: 137
Riboside
methyl p-D-,selective periodate oxidation of,
33:95
methyl 2,3-di-O-acetyl-4-S-benzoyl-4-thio-
p-D-,acetolysis of, 22:20
Ribostamycin
discovery of, 30: 112
isolation, structure, and synthesis of,
30:130-131
minimum inhibitory concentrations of,
30:22 1
N-acylation of, 30: 175
phosphorylation of, 30: 195
synthesis of, 30: 112, 162
Ribostamycin 3-phosphate, by
phosphorylation, 30: 195
Ribostamycin 5-phosphate, 3,4-dideoxy-,by
phosphorylation, 30: 195
Ribosyluronic acid uracil, 5-nitro-1- p - ~ - ,
monohydrate, crystal structure,
43:274-275
Ribitol
1 ,banhydro-
D-, from 1,4-anhydro-~-xylitol, 26: 175
tri-0-benzoyl-o-, rearrangement in
hydrogen fluoride, 26: 174
conformation of, 26:69
Ribovarin, see Virazole
Ribulose
D-
cyclic acetals, properties of, 26:256
preparation of, 26:236
L-, cyclic acetals, properties of, 26:256
Riburonic acid, 3-C-(hydroxymethyl)-o-
natural occurrence of, 42:76
structure of, 42:77
synthesis of, 42:8 1
Rice
cell wall studies on, 42:271,287,294, 300
starch, dextrinization, 47:289
Rich
carbohydrate-binding specificity, 39274
immunization, 35: 129
isolation, 35:270
454 SUBJECT lNDEX
Ricin (continued)
purification, 35: 138,271
toxicity, 35:271
Ricinus communis lectin, see Castor-bean
lectin; Ricin
Rickamicin, see Sisomicin
Rifamycin, synthesis of, 42:96
Ring change, mutarotation and, 23: 13
Ring contractions
and expansion by mutarotation, 24:46
in fluorinations, 38:200
during sulfonate displacement, 24: 188
Ring expansion, in glycosyl fluoride synthesis,
38:201
Ring fusion methods, 52:145-146
h g s
furanoid, stability of, 21:135
opening of, in anhydroalditols, 2 5 2 5 6
pyranoid, stability of, 21: 136
shape, notation, cyclic monosaccharides,
52:69
size
cyclic monosaccharides, 52:59
effect of conformation on, in sugar
reactions, 22: 17 1
on hydrolysis of glycosides, 2 2 4 2
structure
determination of, of sugars in solution,
23:41
factors affecting, 23:23
gas-liquid chromatography and, 28:50
of sugars, 23:3
Ripening, 21:429
of fruit, cell wall role in, 42315, 339-382
Ristocetin, effect on peptidoglycan
biosynthesis, 26:430
Robinia pseudoaccacia lectin, robin, interaction
with erythrocyte glycopeptide, 35320
isolation and properties, 3 5 3 1 1
Rodenticide, warfarin, discovery, 39: 1
Roots, of grasses, polysaccharides, 36:245
Rose, cell wall studies on, 42:281,283, 288
Ross test, for sugar oxiranges, 25: 170
Rotation, hindered, of acetyl group in
monosaccharides, 23:193, 197
Rotational platinum-shadowing, mucus
glycoproteins, 47:367
Rous sarcoma virus, 44:232-238
(2R,3S)-2-isobutylthrearic acid
natural occurrence of, 42:73,76
structure of, 42:71
synthesis of, 42:127-128
Rubidium P-D-glucuronate dihydrate, crystal
structure bibliography, 31:364
Rubranitrose
D-, synthesis of, 42: 123
L-, synthesis of, 42: 123
natural occurrence of, 42:73
structure of, 42:70,78
synthesis of, 42123
Ruff degradation, of higher sugars to deoxy
sugars, 21:153, 177
Rumen, microbial hemicellulase system,
32:34&346
Ruthenium tetraoxide
method for ketonucleoside synthesis, 42:232
for oxidation
of alcohol to carbonyl compound, 31:223
of carbohydrate sulfonic esters, 23:258
of isolated hydroxyl groups, 34:97, 100
oxidative degradation of polysaccharides by,
31:232
Rutin
as plant-growth substance, 21:410
sodium mono-0-(propylsulfony1)-, 23:239
Rutinose, taste properties, 452278-279
Rydon reagents
for halogenation of carbohydrates, 28:240
reactions with nucleosides, 28:243
Ryegrass
a-,a-trehalose from ergot of, 30:232
arabinogalactan, 36:244
cell wall studies on, 42:271,291,293-294,
300,315
endosperm cells of perennial, 36:261
hemicellulose-cellulose ratio, 36:253
hemicellulose-lignin complex from
perennial, 36:260
hemicelluloses, 36:258-262
leaf mesophyll cells, 36:259-262
xylans, 36:235
5
Saccharides
biologically active, 48:205-222
metabolism, 48:206
biosynthesis, from glycopyranosyl esters,
18:309-356, 26:35 1-483
 SUBJECT INDEX
caramel from, in presence of additives,
47:223
complex formation with cations of Group I1
and with borate ions, laser-Raman
spectroscopy. 44:83-84
conformational energy, 47:88
course of decomposition, 47:33&337
cyclic-hemiacetal formation by, Helferichs
work on, 45:3
force-field, 47: 105
y-irradiation, 47:276
from glycoproteins, liquid chromatography
separation, 46:56-57
monomeric, high-temperature transformation
of, 46:275-295
acidic conditions, 46:275-280
basic conditions, 46:281-284
nitrogen heterocycles from, 25:35 1 4 0 5
reactivity
hydrolysis, 47: 119-120
stereoelectronic effect, 47: 1 19
solid-state structures, 47:70
synthesis, 44:341, 50:2 1-22
from acetylated glucosyl
trichloroacetimidates, 50:41,4344
from mannosyl trichloroacetimidates,
50:58,6245
thermal treatment above melting points,
47:226
treatment with mineral acids or alkali,
47:226
Saccharification, of wood, 4:153-188
Saccharin
after-taste, 45:265, 341
and sucrose, comparison of, 45:34 I
sweetness, 45:205,226,23 1
AH, B system in, 45:22 1
early explanations of, 45:202-206
structure relationship, 45:297-303
thio analog, bitterness, 45:3 10
third structural feature comprising postulated
glucophore in, 45:234
three-dimensional x-ray analysis of, 45:30 I
Saccharinic acid nucleosides, preparation of,
42:248
Saccharinic acids, 12:35-79, 25:341
analysis of, 31:213
in D-fructose degradation, 22:239
formation of, 28:163, 193-194,46:281-282,
29 1
455
four-carbon, 13: 169-1 88
gas-liquid chromatography of, 28:7 1, 73,
75
per(trimethylsily1) derivatives, gas-liquid
chromatography of, 28:141-142
preparation of, 28: 198
Saccharonivces hailii. o-fructose fermentation
by, 32: I53
Succharoni.yce.s hisporus. in honey
fermentation, 32: 129
Succharom.vces carlshergensis.
phosphonomannan. 41:86
Saccharomyces cerevisiae
cell wall shwture of, 32: 138
polysaccharide from, structure of, 32:5
sugar removal from citrus molasses by,
32:128
transport of glycosides into, 32: 158-1 59
of monosaccharides into, 32: 148
chitin, 41: 103
phosphonomannnan, 41:86-87
polysaccharide, 41:73,77-80
sugar utilization, 39:348
Saccharom.vce.s,fermentati. polysaccharide,
41:74
Saccharomvces,fragilis, polysaccharide. 41 :74
Snccharomyces phuseolosporus,
polysaccharide, 41:99
Succharomyces rouxii
degradation of acetylated by oxidation with
chromium trioxide, 31 :230
in honey fermentation, 32: 129
mass spectrometry of, 29:63-65
polysaccharide, 41 :77
Succharomvcrs uvarum, sugar removal from
vitamin C concentrate by, 32: 128
transport of glycosides into, 32: 158-159
Sachse-Mohr theory, of conformation of
sugars, 2 6 5 0
Saeman hydrolysis, 46:263-264
Saffron, picrocrocin in, 24:6
Sagarose, 25: 14,23
Sake, ethyl a-o-glucoside in, and gas-liquid
chromatography, 28:54-55
Salicin
aerobic respiration by yeasts on, 32: 144
catabolism by yeasts. 32:20 I
gel chromatography of, 25:47
levoglucosan from, 34:27
structure. 39:358
456 SUBJECT INDEX
Salicin (continued)
utilization by yeasts and associations of
abilities, 32:222
Salicyclic acid-cytidine complex, crystal
structure, 43:357
Salicylaldehyde, alkali metal chelates, 21:265
Salicylic acid
3,5-dinitro-, as reagent in o-fructose
estimation, 22:239
1-ester with-o-ghcuronic acid, 36: 104-1 05
as herbicide, 21:408
as plant-growth substance, 21:409
Salireposide, gel chromatography of, 2 5 5 0
Saliva, analysis by gas-liquid chromatography,
28:44,81
Salivary glycoproteins, hydrolysis, with
trifluoroacetic acid, 46:268
Salmonella spp.
lipopolysaccharides
degradation by Lossen reaction, 31:211
mass spectrometry of, 29:53
periodate oxidation of, 31:211
oligosaccharides related to those of
I3C-NMR data for, 42:220-222
glycosides of, I3C-NMR data for,
42:222-223
Salmonella kentucky lipopolysaccharide,
degradation of acetylated, by oxidation
with chromium trioxide, 31:230
Salmonella newport lipopolysaccharide,
degradation of acetylated, by oxidation
with chromium trioxide, 31:231
Salmonella strasbourg lipopolysaccharide,
degradation of acetylated by oxidation
with chromium trioxide, 31:230
Salmonella typhimurium
lipid A, 50:217
LT2 lipopolysaccharide, degradation of
methylated, 31:225
monophosphoryl lipid A, f.a.b.-mass
spectrometry, 4557-58
395 MS lipopolysaccharide, hydrolysis and
structure of, 31:188
Salts, 53:316-322
catalytic effect on mutarotation of sugars,
24:28
effect on sugar solubility, 27:95
Sambunigrin, 21:23
Sandhoff s disease
glycoprotein (compound 6), 'H-NMR
spectroscopy, 41:2 19,23 1-234
glycoprotein (compound 14), 'H-NMR
spectroscopy, 41 :2 19,254-257
oligosaccharides from urine, structure,
37: 197
Saponins
hydrolysis of steroidal, 28:15
steroidal, gas-liquid chromatography of,
28:46
Saponoside D
isolation, 37:330
structure, 37:33 1
Sapophoric groups, 45:202-203,218
Sarcoma 180 tumor cells, cancer antigens from,
antitumor activity of, 32:257
Sarkaran, a pullulan, 30:337
Saurine, 46: 13
Sauroxine, 46: 13
Scalar coupling, 47:134
Scarlet runner-bean lectin, carbohydrate-
binding specificity, 35: 145
Schardinger dextrins, see Cyclodextrins
Schiff bases
derived from D-glycosyl thiosemicarbazide
and L-arabinosyl thiosemicarbazide,
synthesis, 44: 106-107
in neoglycoprotein preparation, 37:242-
245
Schima liukiuensis, 46:3
Schistocerca gregaria, a,-a-trehalose
biosynthesis in, 30:238
Schizophyllan, antitumor activity of,
32:246-247
Schizophyllum commune, polysaccharide, 41 :70
Schizosaccharomyces polysaccharide, 41 :69
Schizosaccharomyces ociosporus.
galactomannan, 41:92
Schizosuccharomyces pombe
galactomannan, 41:92
polysaccharide, 41:74
Schmidt-Rutz reaction, 24:69, 127, 129
Schrodinger equation, in magnetic field,
51:23-24
Scleroglucan
antitumor activity of, 32:246-247, 259-260
preparation, properties, and uses,
36~305-307
Sclerotan, structure of, 30:366
Sclerotina fructigena, a-L-arabinofuranosidase
from, 42:387
 SUBJECT INDEX
Sclerotina libertiana, cY-L-arabinofuranosidase
from, 42387
Sclerotinan, antitumor activity of, 32:246
Sclerotina sclertiorum, a - ~ -
arabinofuranosidase of, 42:388
Sclerotinia. gum, 36:305
Sclerotium, scleroglucan, 36:305-307
Scopolia juponicu, a-L-arabinofuranosidase
from, 42387,389,391
SDS,see Sodium dodecylsulfate
Sea urchins
sialoglycolipids, see Sialoglycolipids
sulfolipids, see Sulfolipids
Seaweed, polysaccharides from. 8:3 15-350,
24:293
Secondary-ion mass spectrometry, 4924-25
Sedimentation
coefficients
of a-amylases, 23:309
of P-amylases, 23:333
of phosphorylases, 23:348
enzyme molecular-weight determination by,
23:287
of glycoenzymes, 27:312
Sedoheptulosan
acetylation of, 33:24
catalytic oxidation of, 33:87
conformation of, 25: 101, 103
crystallography of, and monohydrate, 25:63
cyclic acetals, 26:252
structure by proton magnetic resonance
spectroscopy, 26:227
monohydrate, crystal structure bibliography,
31:366
taste properties, 45254-255
1,3,5-tri-O-acetyl-, preparation of, 33:24
Seluginella kraussinana, selaginose from,
30:237
Selaginose, from Selaginella kraussinana,
30:237
Selenium, 53: 144-145
in hemiacetal rings of monosaccharides,
23:206
Selenodisaccharides, 53: 177-1 80
2-Se-phenyl-2-, 53: 154- I57
1-Selenoglucopyranoside, o (and p)-nitrophenyl
P-D-hydrolysis of, 22:37
Selenoglycosides, see also spec$c sugars
chemistry, 53: 143-145
cyclization-mediated reactions, 53: I 8 6 1 88
457
0-glycosidation with, 53: 170
glycosylation by, 53: 167-1 70
as glycosyl donors, 52: 199, 53: 170-177
nomenclature, 52: 136
nucleophilic displacement, 53:148-150
opening, 53: 150-154
phenylselenylation, 53: 154-1 58, 161--167
preparation, 53: 145-148
tethered approach connection, 53:300-30 1
Selenoglycosyl azides, 2-Se-phenyl-2-,
53: 162- I63
Selenolactonization, 53: 19 1-1 92
Seleno sugars, 1: 144-145, 22:205, 23:232
Self-association behavior, polydispersity and,
mucus glycoproteins, 47:377-380
Self-consistent field wavefunction, 51 :27-28
Self-consistent perturbation theory, 51 :27
SELRESOLV, 51:22
Semen
a-D-mannosidase, in, 28:403
bull seminal plasma, plasma, polysaccharide
from, antitumor activity of, 32:257
D-fruCtoSe in, 34:304-305
Semicarbazide, in polarographic determination
of carbohydrates, 29: 152
Senescence of plants, cell-wall changes in,
4 2 3 15
Sensory system function, 45325-326
Sephadex, 24:268,3 13,25: 14
applications of, 29:354
in chromatography of urine protein-
carbohydrate compounds, 24:440,
444
fractionation ranges of, 25: 18
0-(2-aminoethyl)-, preparation of, 29:323
Sephadex A-50, 0-(2-diethylaniinoethyl)-, in
ion-exchange chromatography, 24:335,
338
Sephadex imidocarbonates. preparation of,
29:345
Sepharose, 25:14
fractionation ranges of, 25: 18
mechanism of activation, 49: 181-1 82
Septanoid sugars, conformation of, 26: 1 13
Septanoses. 23:228
derivatives, proton spin-lattice relaxation
rates, 45: 153
from reducing sugars in solution, 42: 16, 29
Sequoyitol, as plant-growth substance, 21:
416
458 SUBJECT INDEX
LSerinatocopper (11)
bis-0- (p-D- xylopyranosy1)-, crystal
structure bibliography, 30:465
di-0-p-o-xylopyranosyl-, crystal structure
bibliography, 31:359
Serine
L-
a-and p-o-glycosyl derivatives, 13C-NMR
chemical-shift data, 43:22
carbohydrate chains linked to, in
gl ycoproteins, 26:458
in cell wall glycoproteins, 42:298-299
I3C-NMR spectral data, 43:22,25-26
configurational correlation with D-
glyceraldehyde, 27:207
configuration of, 26:13
derivatives, glycosylation, 43: 156-1 72
in glycoprotein from sheep and ox, 33:7
in glycoprotein linkages, 25:418,425
L-ascorbic acid, crystal structure, 43:211
mass spectra of acetylated 0-glycosyl
derivatives, 29:105
3-0-~-glycosyl,43: 156-1 75
0-glycosyl derivatives, synthetic,
43:135-201
as precursor in biosynthesis of
sphingosines, 24:394
0-(2-acetamid0-2-deoxy-a-~-
galactopyranosy1)-r-, glycoprotein
linkage, 25:426
0-P-D-xylopyranosyl-L-
copper(I1) complex, crystal structure
bibliography, 34:356
crystal structure bibliography, 34:355
glycoprotein linkage, 25:434
0-glycosyl derivatives, 43:27-28
Serology
Dolichos bcjlorus lectin in, 35:226
Helispomutia lectin in, 35:226, 239,241
lectins in, 35: 129
lipid A, 50:258-260
polyagglutinability in, 35:257
Ules europeus seed extract in, 35:224,289
Serotonin, sialic acid binding, 40:2 16-2 17
Serotransfemn
conformation, 37:206-212
glycoprotein (compound 3 1 and 32) from
rabbit, 'H-NMR spectroscopy, 41:270,
283-287
glycoprotein (compound 33) from human,
'H-NMR spectroscopy, 41:270,283-
288
structure, 41:170
Serotransferrin glycan, primary structure,
37:20 1-203
Serrutiu murcescens, polysaccharides
and antitumor activity, 32:236-239
gas-liquid chromatography, 28:59
Sesamose
occurrence, 37:303
oligosaccharides, occurrence, 37:306
structure, 37:307
structure, 37:302-303
S-glycosyl linkage, 43:4
Shafizadeh, Fred, 44: 14
career accomplishments, 44:5
development of thermal analysis methods,
44:4
education, 44: 1
investigation of cellulose, 44: 1-2
study of synthesis of biologically significant
amino sugars, 44:2
teaching ability, 44:5-6
at University of Montana Wood Chemistry
Laboratory, 4 4 : 3 4 , 6
work for Weyerhauser, 44:2-3
work on morphology and biogenesis of
cellulose and plant cell walls, 44:4-5
Shallenberger A.H., B hypothesis, 45200-201,
213-223,231,246,257-261,264,271,
283-285,292,297-299,303-307,322,
34 1
Shape, of some polysaccharide molecules,
7:289-332, 11:385-393
Shear's polysaccharide, antitumor activity of,
32:236,264
Sheep
rumen, carbohydrates, 35: 1 1
submaxillary gland, glycoproteins, 25:446
Shift reagents, 47: 13C13 1
relaxation times, 47: 130
Shigellu flesneri
lipopolysaccharides, 53:254
oligosaccharides related to, I3C-NMR data
for, 42:223-224
Shigellu sonnei, 0-specific polysaccharide,
47: 176
Shikimic acid
rue-, methyl ester, 26: 172
structure of, 42:77-78
 SUBJECT INDEX
synthesis of, 42:129
Shortening composition, anhydroglucitols for,
25268
Shorygina reaction, 34:78
Showdomycin, 25243
2,5-anhydro-5-deoxy-3,4-dihydro-2,3-0-
isopropylidene- 14-methyl-,
hydrobromide, crystal structure
bibliography, 31:368
antitumor and antibacterial activity of,
33:112
crystal structure of, 25:84,30:457
o~-2-deoxy-,synthesis, 40:78
~ ~ - 2 - e p isynthesis,
-, 40:78
inhibition of protein glycosylation,
40:343-344
structure of, 33:112-113
synthesis of, 27:256, 33: 159, 167- I69,40:80
Sialic acid, 13:237-263,40:131-234
abbreviations, 40: 134-135
analysis, 40:152-176
circular dichroism, 40: 170
colorimetric methods, 40:153-160
gas-liquid chromatography, 40: 164- 165
histochemical, 40: 171-176
lectins and antibodies, 40: 175-1 76
mass spectrometry, 40: 165-1 67
nuclear magnetic resonance spectroscopy,
40: 167-1 70
periodate oxidation, 40: 157, 160- I62
spin-labelling, 40: 170-1 7 1
thin-layer chromatography, 40: 162- I64
x-ray crystallography, 40: 170
biological significance, 40:214-234
biosynthesis, 40: 176-1 88
cation binding, 40:2 16
determinant group in polysaccharide
immunology, 41: 175-1 76, 178, 182
dihydrate, crystal structure bibliography,
31:350
enzymic release from glycosidic linkages.
40: 195-2 1 1
3-fluOrO-, 22:199,212
function, anti-recognition effect, 40:220-229
due to negative charge, 40:2 15-2 1 8
effect on macromolecular structure,
40:218-220
of gangliosides, 24:4 I7
glycoenzyme constituent, 27:302,307, 321
glycoprotein carbohydrate chains, H-NMR
459
spcctroscopy, 41 :269-305
in glycoproteins, 25:413,463
high-performance liquid chromatography,
46:3 I
history, 33:&6, 40: 132
hydrolysis, 46:254,270
immunogenicity, 40: 176
isolation, acid hydrolysis of glycosidic
bonds, 40: 147-148
enzymic hydrolysis of glycosidic bonds,
40:149-150
in keratan sulfate, 25:440
linkages, stability of, 31:199
liquid chromatography, pre-column
derivatization procedures, 46:68
metabolism, 40: 183, 207
methanolysis, 46:254
methyl ester monohydrate, crystal structure
bibliography, 31:351
naturally occurring, 49: 195-196,200-203
nucleotide esters, enzymic synthesis,
40:186-188
occurrence, 40: 134147
oligosaccharides, from colostrum, gel
chromatography of, 2 5 3 5
polysaccharides containing, carbon- I3
nuclear magnetic resonance spectra,
38:89-91, 95
purification, chromatography on cellulose,
40: I5 1-1 52
ion-exchange chromatography,
40:150-151
receptor components, 40:229-232
reversible cleavage, 40:158,211-214
substitution patterns, H-NMR analysis,
50:331-332
synthesis of, 27:275
tumor antigen masking, 40:227-229
ultraviolet-absorbances of, 46:65
in urine (human), 24:438439,441
Sialidases, 24:418, 44:208
amino acid sequence, 40: 198
in carbohydrate degradation, 38:4 I3
deficiency, 40:207
degradation of gangliosides, 40:271-274
effect on glycoproteins, 37: 161-163
immobilized, 40: l49,2 10
inhibitors, 40:209
interaction with glycosidases, 48:35 1-353
molecular weights, 40: 198
460 SUBJECT INDEX
Sialidases (continued)
occurrence, 40: 195
pathophysiological significance, 40:206-
21 1
purification, 40:149-150, 196, 198
receptor-destroying enzyme, 3 3 : 5 4
substrate specificities, 40:200-2 I0
use of, 25463
viral, 40:210
Sialidosis, 40:207
glycoprotein (compound 2 l), IH-NMR
spectroscopy, 41:269-274
glycoprotein (compound 22), 'H-NMR
spectroscopy, 41 :270-272,274-275
glycoprotein (compound 29), 'H-NMR
spectroscopy, 41:270,273,279, 282
glycoprotein (compound 30), IH-NMR
S P ~ C ~ ~ O S C O41~270,273,279-281,
P~,
283
glycoprotein (compound 38), 'H-NMR
spectroscopy, 41:270,292,298
glycoprotein (compound 39), 'H-NMR
spectroscopy, 41:270,298-300
glycoprotein (compound 40), 'H-NMR
spectroscopy, 41:270,298, 300-302
glycoprotein (compound 4 l), from sialidosis,
IH-NMR spectroscopy, 41:270,300,
302-305
glycoprotein (compound 23 and 24), 'H-
NMR spectroscopy, 41:270-272,
275-276
glycoprotein (compound 27 and 28), 'H-
NMR spectroscopy, 41:270,273,277,
280
glycoprotein (compound 36 and 37),
'H-NMR spectroscopy, 41:270,
292-298
structure of oligosaccharides from urine,
37:191-193,205
Sialoglycoconjugates, calcium binding of bone
tissue, 40:217
Sialoglycolipids, 44:388
from Asteroidea. 44:430434
carbohydrate chain structure, mass
spectrometry, 44:403
containing sulfated sialic acid, 44:424,
426427
distribution, 44:437
distribution, in marine invertebrates,
44:426437
of echinoderms
biological role of, 44:435436
structure, 44:437
and evolutionary position of animals,
44:436437
occurrence, 44:392
of sea urchins, 44:423-128,437438
in vertebrates, 44:437
Sialoglycopeptide, from tumor cells, 35:327
Sialoglycoprotein, properties of, of erythrocyte
membrane, 35:318-3 19
Sialoglycosaminoglycans,gel chromatography
of, 2 5 4 4
Sialoglycosphingolipids, mass spectrometry of,
29:96
Sialosides, synthesis, 49:231
Sialosylgalactosylceramide, biosynthesis,
40:253
Sialosyllactosylceramide
biosynthesis, 40:254
sialidase action, 40:273
Sialosylneolactosylceramide, biosynthesis,
40:253
Sialosyltransferase, 40:253-255
activity, 40:192-194
ganglioside, 40: 192
occurrence, 40: 188
purification, 40: 189
specificity, 40:190-191
Sialyl aldolase, synthesis with, 49: 194-204
N-acetylmannosamine derivatives, 49: 195,
197-199
naturally occurring sialic acids,
49: 195-196,200-203
N-acetylneuraminic acid, 49: 194-194
3-deoxy-o-g~ycero-~-ga~ucto-nonu~osonic
acid, 49:202-204
Sialylation, with transferases, 49:223, 225-
23 1
heptasaccharide synthesis, 49:228-229
immobilized sialyltransferases, 49:225,
227-228
sialoside synthesis, 49:230-23 1
soluble transferases, 49:225-226
tetrasaccharide-glycosidesynthesis,
49:228
trisaccharide synthesis, 49:229
Sialyllactose methanolysis, 46:258
Sibiromycin, degradation product of, synthesis,
42: 122
 SUBJECT INDEX
Sibirosamine
4-epimer of, synthesis, 42:98
natural occurrence of, 42:73
structure of, 42:70, 121
synthesis of, 42: 12 1
Sickle conformation, 26:72
Silane
chlorotricyclohexyl-, selective etherifications
with, 33:53
chlorotriisopropyl-, selective etherification
with, 33:53
chlorotrimethyl-
purification of, 28:30
trimethylsilylation of sugars with, 28:23
fluorotrimethyl-, effect on chromatography.
28:33
teut-butylchlorodimethyl-, selective
etherification with, 33:53
Silica beads, porous, in chromatography, 25: 15
Silica gel-glutaraldehyde, immobilization on,
49:188-189
Silicon compounds
per (trimethylsilyl) ethers of sugars in
mutarotation studies, 24:60
trimethylsilyl ethers
of D-fructose and its derivatives, 22258
of oligosaccharides, mass spectra and,
21:93
Silicone polyester (ECNSS-M), organa. in
gas-liquid chromatography, 28: 60
Silkmoths, a,a-trehalose 6-phosphate
biosynthesis by, 30:238,244
Silver benzoate, reaction with dithioacetals,
3260
Silver carbonate-on-celite, selective oxidation
with, 33:97
Silver fluoride, reaction with 6-bromo-or 6-
iodo-6-deoxyaldohexopyranoses,33:263
Silver ion, trivalent, as cleaving agent for
cellulose, 23:6
Silver methanesulfonate, sulfonylation of
carbohydrates by, 23:239
Silver salts, in Koenigs-Knorr reaction, 34:246,
275
Silver trifluoroacetate, reaction with iodine on
unsaturated sugars, 28:272
Silyl ethers, 1,4:3,6-dianhydrohexitoIs,
49: 145-146
Simazine, as herbicide, 21:407
Simmons-Smith reagent, 28:305
46 I
Simple sugars. liquid chromatography, pre-
column derivatization procedures. 46:68
Sinapyl alcohol polymer in lignin, 42:269
Sindbis virus S-4 glycan, structure, 37: 175
Sinigrin
crystal structure of, 25:71, 38:440
monohydrate, potassium salt, crystal
structure bibliography, 30:452
Sisal, cell-wall studies on, 42:268, 280
Sisomicin
dihydro-, preparation and structure of,
30: 129-130
discovery of, 30:112
isolation and structure of, 30: 128- 130
mass spectrometry of, 29: 105
penta-N-(benzyloxycarhony1)-,garamine
from, 30: 129
structure of, 29:286
Sissotrin, from biochanin-A, 31: 147
Sitosterol, conjugate with methyl 2,3,4-tri-O-
acetyh-o-gaiactopyranosiduronate, 36:93
Size, of some polysaccharide molecules,
7:289-332,11:385-393
Skatole, as reagent for D-fructose estimation,
22:238
Skewed log distribution, 51:79, 117-1 18,
125-1 26
Slash pine, hemicellulose fraction of, 46:306
Slime mold
glycoprotein, oligosaccharides, liquid
chromatography separation, 46:4243
high-mannose oligosaccharide, f.a.b.-mass
spectrometry, 45:63
polysaccharide, 41:88
(1+4)-P-~-glucan biosynthesis, 41: 108, 128
trehalase in, 30:253
trehalose biosynthesis in, 30:239-241
Sludge, definition, 36:229
Smell, and sensory system, 45:325
Smith, Fred, obituary, 22:l-10
Smith degradation, 22:7,24:349
ofAcacia gums, 24:345, 347
of capsular polysaccharide type 2,33:301
of carbohydrates, 3 5 9
in cellulose structure study, 26:326
by chemical modification of polysaccharides,
31:192
methylation structural analysis, 38:407408
modified, of capsular polysaccharides,
31:239
462 SUBJECT INDEX
Smith degradation (continued)
of plant cell-wall polysaccharides, 42:277,
28 I-282,284
of polysaccharides, 24:340,342,28:98-101,
31~203-210
of xylans, 36:235,242
Snail
galactan
Barry degradation of, 31:203
degradation by Weermann reaction,
31:211
Smith degradation of, 31:209
L-arabinanases from, 32:283
lectin
carbohydrate-binding specificity, 35:242
composition, 35:240
hemagglutinating activity, 35:239
isolation, 35: 138
purification and properties, 35:240
Snow tussock, hemicellulose-cellulose ratio,
36:253
Sodiocellulose, crystal structure bibliography
of, and regeneration complexes,
33:394-395
Sodiocellulose 11, crystal structure
bibliography, 35:379
Sodium aluminate, 53:325
Sodium amalgam, aldonolactone reduction,
50:157
Sodium amide, sucrate production by, in N,N-
dimethylformamide or methyl sulfoxide,
27:93
Sodium L-ascorbate, crystal structure, 31:364,
37:83-84
Sodium a i d e , reaction with deoxy halosucrose,
33:26&268
Sodium borohydride, effect on ketonucleoside
stability, 42:248
Sodium borohydride-d, deuteration of sugars
with, 27:129
Sodium borohydride-t, tritiation of sugars by,
27: I29
Sodium bromide, complex with sucrose,
structure of, 21:236
Sodium carbonate, complex with sucrose,
21:213
Sodium carboxylates, effect on proton nuclear
magnetic resonance spectroscopy, 29:23
Sodium chloride, 53:322-323
system with o-glucose, 21:211
Sodium chondroitin 4-sulfate, 52:379, 381
Sodium cytidine 2,3-cyclic phosphate,
dihydrate, crystal structure, 43:357-358
Sodium D-glucuronate, circular dichroism,
45: 104- 105
Sodium diammineplatinum(I1) inosine 5-
monophosphate, crystal structure,
43:308-309
Sodium diphenylborinates
boronates from, 35:3941
carbohydrate, preparation, 35:70
Sodium diphenylborinates, polysaccharide,
carbon-I3 nuclear magnetic resonance
spectra, 38: 103
Sodium o-isoascorbate, monohydrate, crystal
structure bibliography, 38:42042 1
Sodium dodecylsulfate, 53:375-376
Sodium ethoxide, complex with o-glucose,
21:258
Sodium P-D-glucopyranuronate, monohydrate,
crystal structure, 43:338
Sodium 1.-gulonate, preparation, 38:299
Sodium heparinate, see Heparin
Sodium hyaluronate
circular dichroism, 45:113-114
crystal structure bibliography, 33:402,
35:383-385
3-fold helix, 52:375-376
4-fold helix, 52:372-374
Fourier-transform infrared spectroscopy,
44:61
structure, 52:421
Sodium hydride
in methylations, 30:53
and methyl sulfoxide in methylation of
carbohydrates, 30: 12-13
sucrate production by, in N,N-
dimethylformamide or methyl
sulfoxide, 27:93
Sodium hydrogensulfite, 1,6-anhydro-
hexopyranose cleavage by, 34:69
Sodium iodide
complex with sucrose, 21:215
systems with sucrose, 21:211
Sodium ion, effect on reducing sugars in
solution, 42:33
Sodium isosorbide 5-nitratq 49: 134-135
Sodium metaperiodate, selective oxidation of
1,2-glycols with, 33:93-95
Sodium methoxide
 SUBJECT INDEX
complex with o-glucose, 21:258
reaction with sugar sulfonates, 23:279
sucrate production by, in N,N-
dimethylformamide or methyl
sulfoxide, 27:93
Sodium pectate, 52:350,352-353
structure, 52:4 1 3 4 1 4
Sodium perchlorate, cyclodextrin inclusion
complexes with, 46:222,224
Sodium poly-(L-gulopyranuronate), chelation of
Ca2+to, circular dichroism, 45: 105-1 06
Sodium saccharin, relative sweetness, 45332
Sodium salicylate, 53:3 19
Sodium strontium-a-o-,galactopyran- uronate
hexahydrate, crystal structure
bibliography, 34:348
Sodium taurodeoxycholate, activator for
enzymic hydrolysis of glycosphingolipids,
40:281-285
Sodium thiosulfate-phenolphthalein test, for
sugar oxiranges, 25170
Sodium thymidylyL(5 +3 )-thymidylate-( 5 ), Solatriose, 24:7
dodecahydrate, crystal structure
bibliography, 37:43 1 4 3 2
Sodium (trimethylenediamine)bis(inosine 5-
phosphato)platinum(II)inosine 5 -
phosphate, hydrate, 43:374
Sofa conformation, 26: 122
Soil
carbohydrates in, 16:335-355
organic matter, spectral analysis and
identification, 44:24
polysaccharides, chromatography of, 25:43
Solanesol, 44:349
structure, 44:346
Solanidine, 24:7
Solanine, 24:7
Solanum gluucophyllum, 46: 14
Solanurn tuberosum
cell-wall studies on, 42:308
D-glucose from, 2 5 7
extracts
o-mannitol determination in, by gas-liquid
chromatography, 28:57
gas-liquid chromatography of, 28:43
lectin
amino acids, 35:211
carbohydrate-binding specificity, 3 5 2 I2
hemagglutinating activity, 3 5 2 10
isolation. 3 5 1 3 8
463
purification, 35210
starch
alkali number as function of milling
duration, 51:256
compressibility, 51:255
dextrinization, 47:289,291-292
dextrins from. 47:3 17-3 18
solubility, 47:291,293
disruption in electrolyzer, 51:308-309
gelatinization, 51:25&25 1
enthalpy, native and freeze-dried,
51:297
temperatures, 51:296
properties, after high-energy electron
irradiation, 51 :265-266
Staudinger index and viscosity, 51:257
thermal analysis, 51:248-249
thermolyzed or UV-irradiated, spins.
51:295-296
water-soluble dextrins as function of water
content, 51:27 I
Solubility
caramel, 47:217
determination of, of sugars, 27:90
mutarotation constant and, 23: 18
mutarotation measurement by, 23:5 I
of quinoxaline carbohydrate derivatives,
29: IS8
solvation and, of sugars, 27:86-90
of sugars, 23: 19
test, for enzyme purity, 23:28S
Solutions, of polysaccharides, physical
properties of, 18:357-398
Solvation
of carbohydrate-metal salt complexes,
21:226
effect on ring structure and conformation,
23:33
energy, 47:89-90, 1 IS
solubility and, of sugars. 27:86-90
Solvent effects, 53:270-272
Solvent exchange
base-catalyzed, in labeling sugars with
hydrogen isotopes, 27: 133
enzyme-catalyzed, in labeling sugars with
hydrogen isotopes, 27: 134
hydride and proton exchange related to
enediol or oxido-reduction mechanisms,
27:156-162
464 SUBJECT INDEX
Solvent exchange (continued)
of hydrogen isotopes, mechanism of, 27: 153
localization of proton movement,
27: 162-1 7 1
on oxidation in deuterium oxide of hydrazino
group, labeling of sugars with hydrogen
isotopes by, 27:135
platinum-catalyzed in deuterium oxide,
27:137
Solvents
acids (organic) as, for sugars, 27: 102
aliphatic amines as, for sugars, 27:112
aprotic, for sugars, 27:105-123
for carbon-I 3 nuclear magnetic resonance
spectroscopy, 41:29-30
for chromatography of glycosyl esters of
nucleoside pyrophosphates, 28:3 1I
for displacement reactions, 28:229
of carbohydrate sulfonic esters, 24: 140
effect
on ammonolysis of carbohydrate acyl
esters, 31:99-102
on deamination of amines, 31:16
on decomposition of nitrosoamides of
carbohydrates, 31:68
on conformation, 26:86, 95, 104
on formation of anomeric cyanides,
33:141
on glycosidation reactions, 34:277
on mutarotation
of monosaccharides, 28:39
of sugars, 24:15,60,62
on proton chemical shifts, 29: 13
in reduction with lithium aluminum
hydride, 23:269
heterocyclic, for sugars, 27: 1 17
inorganic, for sugars, 27:90-96
nonaqueous
for carbohydrates, 27:85-125
reducing sugar composition in, 4236042,
68
organic, for proton magnetic resonance
spectroscopy of polysaccharides, 27:40
for sugars, 27:96-123
protic, for sugars, 27:96-105
for sulfonylation of carbohydrates, 23:236
for trimethylsilylation, 28:29
water, access to active site, 48:38&381
Solvolysis
chitin, 47:171-172
of glycosyl halides, 22:38
hydrogen fluoride in methanol, 47: 195
mechanism of, 31:4
and of deamination, 31: 1 1
of sulfonates of sugars, 25:203-209
techniques, 47: 173-1 74
Solvophobic theory, 47:89
Somatostatin, glycosylated, 50:299
Sophora japonica lectin
agglutinating activity, 35250-254
carbohydrate-binding specificity, 3 5 2 5 1
isolation, 35:138
purification, 35:250
Sophorose
@-eliminationand degradation of, 31:212
benzylidene derivatives, reactions with N-
bromosuccinimide, 26: 164
interaction with concanavalin A, 35: 184-186
liquid chromatography methods for analysis
of, 46:33
mass spectrometry of, 29:99
monohydrate, crystal structure bibliography,
38:45045 1
pyrolysis of, 34:45
structure, 35:186
Sophorosyldihydrochalcones,p-D-,45280
Sorbic acid, precursor for sugar synthesis,
40:24-26
Sorbitol, see Glucitol, D-
Sorbofuranose
4,6-anhydro-2,3-O-isopropylidene-a-~-,
24: 172
1-deoxy-2,3 :4,6-di-O-isopropylidene- 1-,
phthalimido-a-L-, crystal structure
bibliography, 37:405
1-deoxy-2,3:4,6-di-O-isopropylidene- 1-,
thiocyanato-a-L-, 44: 145
2,3:4,6-di-methylene-a-~-, 26:248
1,3:4,6-di-O-benzylidene-, p-L-,26:2 10
2,3 :4,6-di-O-benzylidene-, a-L-, 26:2 10,
248
2,3 :4,6-di-O-(2-butylidene)-, a-L-,26:248
2,3 :4,6-di-O-cyclohexylidene-, a-L-, 26:249
1,3:4,6-di-O-ethylidene-, p-L-, 26:209,247
2,3 :4,6-di-O-ethylidene-, a-L-,26:209,247
1,2:4,6-di-O-isopropylidene-
01-L-, 26:206-207
conformation of, 26: 12 1
mass spectrum of, 26:233
p-L-,26:208
 SlJBJECT INDEX
1,3:4,6-di-O-isopropylidene-, P-L-, 26:208,
246
2,3:4,6-di-0-isopropylidene-
a-D-,26:246
01-L-, 26~245
conformation of, 26:223
effect of temperature on preparation of,
26:201-202
electro-oxidation of, 29: 122, 124
mass spectra of, 29:77
mass spectrum of, 26:232
preparation of, 26:206
2-0-acetyl-l,3:4,6-di-O-isopropylidcne-~-~-, 1,2-O-isopropylidene-a-t-,
conformation of, 26:222
1-0-(2-ethoxy-2-propyI)-2,3:4,6-di-O-
isopropylidene-a-L-, 26:206
1,2-0- isopropylidene-a+-, 26:208
2,343- isopropylidene-a-L-, 26:245
effect of temperature on preparation of,
26:20 I
mechanism of preparation of, 26:206
1,4,6-tri-0-acetyl-2,3-0-isopropylidene-a-~-, ethyl 4,5-di-O-acetyl- 1,3-O-isopropylidene-
conformation of, 26:223
Sorbofuranoside
4-chloro-4-deoxy-a-~-galactopyranosyl
1,4,6-trichIoro- 1,4,6-tndeoxy-P-i1-,
sweetness, 45269
methyl 4,6-di-O-acetyl-l,3-0-
isopropylidene-P-L-, confonnation of,
26:222
methyl 4,6-0-isopropylidene-a-~-,
conformation of, 26:223
Sorbopyranose
a-D-,conformation in solution, 26:86
a-I.-
conformation in solution, 26:86
sweetness-structure relationship,
45:250-252
taste properties, 45:242
6-amino-6-deoxy-~-,23: 145
D-
4-deo~y-4-fluoro-a-,'~C-NMR data for,
46:173
4-deoxy-4-fluoro- 1,2-0-isopropylidene-
p-, 'H- and I9F-NMR data for,
46: 144
4-deoxy-4-fluoro-a-o-, 48: 183
5-deoxy-5-fluoro-a-~-,preparation, 38:2 I 8
1,2:3,4-di-0-isopropylidene-P-~-,26:2 I3
26:2 13
1,2:4,5-di-0-isopropylidene-P-t.-,
465
a - ~ -crystal
, structure, 43:2 17
L-
S-deoxy-5-fl~oro-a-,'~C-NMR data for.
46: 173
selective oxidation of. 33:86
taste properties, 45254
3-0-acetyl- 1,2:4,5-di-O-isopropylidene-P-~-,
conformation of, 26:225
5-0-acetyl- 1.2:3,4-di-O-isopropylidene-p-~-,
conformation of, 26:225
1,2-O-ethylidene-a-~-,26:209.247
I ,3-0-ethylidene-u-~-,26:209, 247
26:246
acetonation of, 26:205
1,2-O-isopropyIidene-4-O-methyl-~-~-,
263246
1,2-O-isopropylidene-4-0-niethyl-P-~-,
conformation equilibrium, 36:5
3.4.5-tri-0-acetyl- 1,2,-0-isopropylidene-a-
L-, conformation of, 26:224
Sorbopyranoside
a-L-.conformation of, 26:224
methyl 4-amino-4-deoxy-a-~-,24:97
methyl 4-deoxy-4-nitro-a-~-,24:97
methyl I ,3-0-benzylidene-4,5-di-O-
(methylsulfony1)-a+-, displacement
reactions of, 24: 16 I
Sorbosazine, preparation of, 31: 125
Sorbose, 7:99-136
2,3: 4,6-di-O-isopropylidene-t.-, electro-
oxidation of, 29: 122
6-acetamido-6-deoxy-~-,composition in
aqueous solution, 4 2 5 0
a-D-
conformation of, 23:30
minus a-D-xylose, difference-circular
dichroism spectra, 45:8 1
a - ~ -crystallography
, of, 25:61,31:365
6-arnino-6-deoxy-r-, composition in aqueous
solution, 42:49
1-chloro- I -deoxy-L-, preparation of, 28:247
composition in aqueous solution, 42:32,
37-38.41.65
D-
cyclic acetals, properties of. 26:263-271
polarography of, 29: 126
6-deoxy.. composition in aqueous solution,
42:38,65
4-deoxy-4-fluoro-a-~-preparation, 38:2 I8
466 SUBJECT INDEX
Sorbose (continued)
1-deoxy-L-, composition in aqueous solution,
42:65
1,4:3,6-dianhydro-~-,25261
2,3 :4,6-di-O-isopropylidene-~-, reaction with
triphenylphosphine-carbon
tetrachloride, 28:247
1,6-di-O-trityI-o-, diethyl dithioacetal,
preparation of, 32:46
DL-, 21~12-13
crystallography of, 25:61
L-
absorptive rate by human jejunum, 34:289
acetalation of, mechanism of, 26:205-218
ammonolyis of, 31:90
conformation of, 26:213
conversion into L-ascorbic acid,
37~105-112
oxidation, chemical, 37: 106-1 10
fermentative, 37: 108-109, 1 11-1 12
synthesis from D-glucitol, 37:91-92,
1I4
cyclic acetals, 26: 198,245-249
properties of, 26:263-271
thin-layer chromategraphy of, 26:233
dihexulose dianhydrides from,
52: 2 18-220
from ~~-2,3-dihydroxypropanal,
49: 193-1 94
effect of alkali tetraborate on rotation of,
23:36
electro-oxidation of, 29: 123
infrared spectrum of, 23:39
L-galactosaccharinic acids, from, 28: 195
from L-idose rearrangement, 28:5
oxidation of, 22:4
pentaacetate, Wittig reaction with, 27:247
proton magnetic resonance spectra and
structure of acetalation products,
26:226
reaction with acetone, 26:201
selective oxidation with silver carbonate-
on-celite, 33:97
solubility in methanol, effect of calcium
chloride on, 27:95
transport into yeast cells, 32:148
utilization by Saccharomyces
cerevisiae, 32: 148
utilization by yeast, 32:230
trimethylsilylation of, 28:24
liquid chromatography methods for analysis
of, 46:33
1-O-benzoyl-3,5:4,6-di-O-ethylidene-~-,
26:247
1,3-O-benzylidene-r-, proton magnetic
resonance spectroscopy and
tautomerization of, 26:226
1,3,4,5,6-penta-O-acetyl-keto-
D-, reaction with ethanethiol, 32:34
L-
ammonolysis of, 31:89
photolysis, cyclobutanol formation,
38:128
preparation, 36: 11
6-S-ethyl-6-thio-~-,preparation of, 33: 100
3,4,5,6-tetra-O-benzoyl-keto-~-, preparation,
37: 1 14
Sorbose 6-phosphate, composition in aqueous
solution, 42:46
Sorboside, methyl (Y-DL-, synthesis, 40:71
Sorburonic acid, L-, dehydration of, 28: 189
Sordelli, A,, 46: 1 1
Somidipine, 49: 163
Sorption, 53:304-307,3 12-313
Sowden, John Clinton, obituary of, 20: 1-1 0
Soybean
agglutinin, glycoprotein (compound 72), 'H-
NMR spectroscopy, 41:366
cell wall studies on, 42:278,280-281,
283-284,327,358-359
ethyl a-o-galactoside in, 37:320
extracts, ethyl a-D-gaiactoside in, and
gas-liquid chromatography, 2 8 5 4
lectin
amino acids, 35:234
biological activity, 35238
biophysical characteristics, 35:233-234
carbohydrate-binding specificity,
35236238
hemagglutinating activity, 35:23 1
interaction with cellular structures, 35:3 17
isolation, 3 5 1 3 8
purification, 35:232-233
toxicity, 35232
lectin glycan, structure, 37: 175
polysaccharides of, 24:362
Spadicol, 44:349
structure, 44:346
Spear grass, hemicellulose-cellulose ratio,
36:253
 SUBJECT INDEX 467

Specificity, of enzymes, in the domain of Sphingolipidosis, 40:265-266, 268

carbohydrates, 949-78 Sphingolipids, biosynthesis of, 26:442450
Specific rotation Sphingosines, 24:382
products of dextrinization, 47:301 biosynthesis of, 24:394
and refractive index of methyl D- derivatives trichloroacetimidate
galactosides, 30:4 glycosylation with, 50:58-59
Spectinomycin D-galactosyl-, 24:394,396
biosynthesis and structure, 35: 1 18-1 2 I dihydro-, 24:382,384-385,390-393
dihydro- synthesis by Wittig reaction, 27:238
formation, 35: 119, 121 gas-liquid chromatography of, 28:56
preparation and antibacterial activity, N, (2-hydroxytetracosanoyl)-, 24:396
30:181 N-acyl-, linkage with oligosaccharidemoiety,
discovery of, 30: 112 24:42 1
N,N-bis (trifluoroacety1)-, and 9- natural and synthetic, 24:39&393
trifluoroacetate, antibacterial activity of, N-stearoyl-, o-glucosides and lactoside,
30:181-182 24:42 I
structure of, 30:136 3-0-benzoyl-N-octadecanoyl- 1-0-(2,4,6-tri-
Spectroscopy, see also specific o p e O-acetyl-/3-~-galactopyranosyl)-~~-
I3C NMR, 53:25 dihydro-, 24:408
of o-fructose and derivatives, 22:236 O-~-galactosyl-N-(2-hydroxytetracosanoyl)-,
electron resonance, 53:287-288 sulfate, 24:403
of gels, 24:309 palmitoyl-, D-galactosides, 24:421
infrared, 53:286 stereochemical aspects of, 24:384
and carbohydrate chemistry, 19:2349 structure. 40:236-237
in conformational analysis, 26:54 synthesis and structure of, 27:238,241
of sugar oxiranes, 25: 170 Spinach
of lectins, 35: 134 chloroplasts, thiamine synthesis, 52:277
microwave, in conformational analysis, gibberellin effects on cell cultures of, 42:343
2655 Spindle-tree lectin, carbohydrate-binding
Mossbauer, 53:287 specificity, 35:145
nuclear magnetic resonance, in Spin-lattice relaxation time, 38: 15, 26, 28-35,
conformational analysis, 26:55 45: 128
Raman, 53:286-287 Spin-spin relaxation times, measurements,
Il9Sn NMR, 53:19-20 51:72
spectra Spiramycin, sugar component mycaminose,
infrared, of carbohydrates, 12: 13-33 28:297
mass, of monosaccharides with acetmido Spire[( 1-acetyl-2-(methyl4,6-0-benzylidene-
in ring, 23:201 2,3-dideoxy-a-D-arubino-hexopyranosid-
spectrometers, nuclear magnetic resonance, 3-yl)aziridine], crystal structure,
29:25,21 43:247-248
UV, 53:284285 Spirodioxanyl pseudo-oligosaccharides,
visible, 53:28&285 52:220-22 1
Spergualin, 48: 10 Spiro systems, nomenclature, 52: 146147
Spermatozoa Spleen, gangliosides, of, 24:432
o-fructose metabolism in, 34:298-305 Sponge
regulation of, 34:302 glycolipid content, see Glycolipids
fmctolysis by, 34:300-302 lectin, isolation and properties, 3 5 3 15-3 16
Sphuerophorus globosus, polysaccharide, 41 :76 Spongoadenosine, synthesis of, 31:4
Sphinganine, 24:382,384-385,390-393 Spongothymidine, 24: 180
4-o-hydroxy; 24:384 Spongouridine, 24: 180
468 SUBJECT INDEX
Spore germination, a,-a-trehalose as energy
source in, 30:255
Sporobolomyces roseus, glucogalactans, 41 :
100
Sporobolomyces singularis, in glycosyl
transfer, 32:128,209
Sporothrix schenchli
amylose, 41:68
galactomannan, 41:93
polysaccharide, 4 1:73
rhamnomannans, 41:90
Spruce, polysaccharides from, 24:374
Spurlin analysis
of methylation of D-glucose, 33:54,56
of relative activities of hydroxyl groups,
33:61, 64, 67
Squeegee, definition, 36:229
Srivastava method, of methylation of
carbohydrates, 30: 1 1, 15
SS-56-C, antibiotic, discovery of, I 12 isolation
and structure of, 30: 134
Stability
of aldose oxiranges, 25: 120
of carbohydrate-metal salt complexes,
21:227
of cyclic acetals, 26:202
of furanoid and pyranoid derivatives, 21: 135,
29:291-298
of sulfonic esters of carbohyderates, 23:257
Stabilizers, 0-(carboxyrnethyl) cellulose as, for
milk proteins, 29:32 1
Stacey, Maurice, 52: 1-19
amino sugar work, 52: 15
analytical chemistry, 52: 18
authoring papers, 52:4
awards, 52:6, 19
childhood, 52: 1-2
community roles, 52:3-4
desosamine work, 52: 14-15
dextran work, 52:8-9
DNA studies, 52:11-12
effects of y-radiation on saccharides studies,
52:17
fluorine chemistry, 52: 18-19
gram-staining reaction studies, 52: 12
horticultural interests, 52:2
influence of colleagues, 52:4
Mason professor of chemistry, 52:3
polysaccharide structure work, 52: 17- I8
promotion of collaborations between
universities and industryigovemment,
52:4
sporting prowess, 52:4
typhoid fever vaccine work, 52:6
University of Birmingham, 52:2-3
vitamin C research, 5 2 : 5 4
Stachyose
biosynthesis, 26:374,37:285,288, 356358
in fenugreek seeds, 35:352
carbon- 13 nuclear magnetic resonance
spectrum, 38:3 1
catabolism by yeasts, 32: 183
I3C nuclear magnetic resonance spectra of,
33:217
in endosperm during germination, 35:357
hydrate, crystal structure bibliography,
34:372
nonselective spin-lattice relaxation rates,
45: 149
occurrence, 37:303-304
of oligosaccharides, occurrence, 37:306309
structure, 37:308
photosynthesis, 37:35 1-353
spin-lattice relaxation of )C nuclei in, 27:60
structure, 37:303
Stannic chloride, in anhydridization of hexoses,
34:46
Stannous chloride dihydrate, as catalyst for
diazomethane methylations, 33:70
Staphylococci, kanamycin-neomycin phosphate
transferase in, 30:204
Staphylococcus aureus
Copenhagen, teichoic acid from, 21:360
H, teichoic acid from, 21:359
teichoic acid from, 21:342
Staphylococcus lactis. teichoic acid from,
21:342,347,350
Starch, 46:295, see also Corn starch
a-amylase action on, mechanism of, 23:328
absorption curves, ultrasound effects, 51:306
acetals, preparation of, 29:339
acetate, in food industry, 29:330
acetobrominolysis of, 22:23
acid hydrolysis of, 46:296
action of water on, 47:303
adipate, in food industry, 29:330
affinity chromatography adsorbent, 39:419
alginate complexes, 53:411412
alkali-lability, 47:293,295
amino derivatives of, 26: I6
 SUBJECT INDEX 469

amylose and amylopection in, detemiination y-radiation effect, 47:225

of, 32:6 guest complexes
analysis by gas-liquid chromatography, alcohols, 53:360-361, 363-364
28:47 aldehydes, 53:365-366
beta-amylolysis value, 47:298-299 amines, 53:373-374
biosynthesis of, 26:382-386,30:320 ammonium salts, 53:322-326
canna, structure of, 32:5 Arrhenius acids, 53:313-314
carboxymethyl ethers, preparation of, 29:3 19 bases, 53:313-314
cellulose complexes, 53:412413 carboxyamides, 53:374
changes in solid during pyrolysis carboxylic acids, 53:367-372
physical, 22:486 carboxylic esters, 53:372-373
structural, 22:489 dyes with, 53:376-385
composition, 36:16 ethers, 53:365
hydrolysis, acid catalyst system, 36:20-30 formation, 53:348-349
acid-catalyzed, 36:42 haloalkanes, 53:357
economic considerations, 36:34 hydrocarbons, 53:352-353
enzyme-catalyzed, 36:3 1-43 ketones, 53:366-367
physical characteristics, 36: 18 metal hydroxides, 53:3 14-315
sweeteners, 36: 15-56 monosaccharides with, 53:400415
containing fatty acids, 47:303-304 nitrogen-based compounds, 53:357,358
cross-linked, preparation and use of, nontransi tion metals, 53:322-3 26
29~353-355 oligosaccharides with, 53:400405
decomposition, 47:279-28 1 phenols, 53:364-365
degradation to D-glucose with glucoamylase, preparation. 53:350-352
30:28 1 salts, 53:316-322
degree of dextrinization, 47:286-287 sorption, 53:312-313
6-deoxy-6-iodo-, preparation of, 29:348 structures, 53:263-264, 346-348
depolymerization, 47:280 sulfates, 53:375-376
derivatives, 53:411412 sulfur-containing, 53:359-360
dextrin complexes, 53:411412 vitamins, 53:374-375
dextrins from, structure of, 22:490 hydrogen fluoride as solvent for, 27:93
differential thermal analysis, 22:487, 489, hydrolysis of, 22:85
47~299-300 iodine complex
effect of auxins on, 21:386 alcohol effects, 53:283
end-group assays, 3 5 8 applications, 53:296-298
in endosperm and cotyledon during chemical properties, 53:293-294,296
germination, 35:356-361 electrolyte effects, 53:272
enzymes for degradation and synthesis of, formation, 53:278-284
23~281-366 history, 53:264-266
enzymes in structural analysis of, organic compound effects, 53:272-274
30~302-332 physical properties. 53:284292
enzymic conversion into D-glucose and u- preparation, 53:266-268
glucose-D-fructose mixture, 34:286 protein effects, 53:272-274
enzymic degradation of. 3:25 1-3 10. solvent effects, 53:270-272
17:407430,25:9,30:285-302.33:4 starch origins, 53:268-270
enzymic synthesis of, 17:371407, 25:Y, state, 53:268-270
34:6 structure, 53~274-278
ferricyanide number, 47:294,296 iron complex, 53:326--327
flondean, 2 5 9 laser-Raman spectroscopy, 44:83
fractionation of, 1:247-277, 16:299-333 lipid complexes
470 SUBJECT INDEX
Starch (continued)
characteristics, 53:385-386
digestibility, 53:399400
functional properties, 53:396-399
native, 53:386-387
preparation, 53:387-388, 390-392
properties, 53:392-393,395
structure, 53:392-393
mercaptolysis of partially methylated, 32:47
methylation analysis of rice, 30:5
modification, 51:243-3 10
depolymerization, 5 1:244
electrical phenomena, 51:307-3 10
freezing, 51:296-298
infrared radiation, 51:298
irradiated
applications, 51:292
biological studies, 51:291-292
irradiation
with high-energy electrons, 51:263,
265-267
with neutrons, 51:263-264
ultrasonic, 51:245-246,302-303,
305-307
visible and ultraviolet light, 51:292-
296
with x-rays, 51:263-265
mechanical, 51:254262
alkali number and milling duration,
51:256
compression effect, 51:254-255
conductivity and compression, 51:261
dielectric constant, pressure and
humidity effects, 51:261-262
DTA and DTG curves, compression
effect, 51:258-259
gelation temperature under high
pressure, 51:257-258
organoleptic changes, 51:256
powder diffractogram and compression,
51:260
shaking and compression effect on
spins, 51:254
microwave radiation, 51:299-304
nonconventional, 51 :244248
solvent effects, 51:248-253
desiccation effects, 51:248, 25G25 1
mashing, 51:25 1-252
microscopic observation in normal and
polarized light, 51:250,252
sorption-desorption hysteresis,
5 1:248-249
thermal analysis, 51:248-249
water, 51:250
molecular-weight determination, and starch-
iodine reaction, 29:400
nitrates of, 13:331-345
0-(carbamoylethy1)-, preparation of, 29:328
0-(2-hydroxyethyl)-
degree of substitution in, 29:3 17
hydrolysis of, 29:3 I8
as plasma extender, 29:3 18
pyrolysis of, 22:504
0-vinyl-, preparation of, 29:326
oxidation, 37: 1 18
periodate-oxidized, derivative in
insolubilization, 29:34 1
phosphates
phosphorus content, 51:250,253
preparation of, 29:334
physical chemistry of, 11:335-385
polarography and reactivity of, 29: 159
polymer complexes, 53:413
polymerization in hydrogen fluoride, 21:446
polysaccharide complexes, 53:4114 12
preparation and properties of esters of,
1~219-307
protein complexes
characteristics, 53:405
native, 53:405406
synthetic, 53:40&411
pyrolysis of, 34:3845, 152,47:335-344
course of decomposition, 47:336-337
effect of inorganic salts, 47:340
fragmentation, 47:338-339
gaseous and liquid fractions, 47:336,339
kinetics, 47:340
mechanism of, 34:4345
origin of starch and, 47:336
pressure and temperature, 47:336
products, 47:336, 338
volatile decomposition, products from,
22:498,502-503,505-506,508
volatile products, 47:336, 339
radiation-induced degradation, 37:75
rate of dextrinization, 47:286,288
relative reactivities of hydroxyl groups in,
33:64
screw model of, 46:215
sodium glycolate, 25:8
 SUBJECT INDEX
solubility in methyl sulfoxide, 27: 108-109
structure of, 26:16,35:10
from sweet corn, structure of, 3 2 5
synthesis, 2 5 8
synthetase, 23:364, 26:384
kinetics, 23:289
syrups, analysis by gas-liquid
chromatography, 28:58
thermal degradation of, 22:483-5 15
thermal stability of, 22:498
transformation, see Dextrins
water complexes
analysis, 53:310-312
binding capacity, 53:320-32 I
problems, 53:298-300
sorption, 53:304-307
starch origins, 53:307-3 10
water in, 53:300-304
xanthates, preparation and use of, 29:346
Starch-iodine reaction, and complex formation,
29:398
Starch Round Table, 39:9
Starfish, glycolipids, see Glycolipids
Staudinger equation, viscosity-molecular
weight, 29:319, 321
Stearic acid, methyl ester, transesterification of
carbohydrates with, 33:44
Stereocaulonjaponicum, polysaccharide, 41 :76
Stereochemistry
and ammonolysis of disaccharides, 31:96
of p-eliminative degradation of alginic acid,
29:251
of heparin, 29:243, 25 1
synthetic models for, 29:255-27 I
biochemistry and, 21:34
of branched-chain sugars, 32:40
conformation and, 26:75
of cyclic acetals, 34: 198-202
of cyclic derivatives of carbohydrates,
10: l-53,36:4
and cyclization of dithioacetal sulfonates,
3249
cytostatic activity and, of carbohydrates,
28:7
of deamination of carbohydrate amines.
31~10,12-17
and displacement of sulfonyloxy groups in
dithioacetals, 3 2 5 1
of dithioacetals, 32:20-23, 90,98-100
effect on enzymic reactions of glycosyl
47 1
esters of nucleoside pyrophosphates,
28:364
on hydrolysis of glycosyl esters of
nucleoside 5 '-pyrophosphates,
28:358
effect on hydrolysis of glycosides, 2242,
52
enzymes in determination of, 27: 141
formulas, writing of, in a plane, 3: 1-22
of hydnde exchange, 27: 159
of hydrogen transfer, 27: 170
and mass spectrometry, 21:79,92,30:39
of nucleoside synthesis, 29:4
of oxirane derivatives of aldoses, 25: 122
of 0x0 reaction, 23:78
of phytosphingosines and sphingosines,
24:384
of polysaccharides, analysis of, 33:389
radical-mediated brominations, 49:7 1-75
of sugars, 3 9 5
of Wittig normal and abnormal products,
27:290-292
Stereoisomers, mass spectra of, 21:59
Stereoselective synthesis, of asymmetric
sulfoxides, 27:222
Stereoselectivity
of ammonia addition to a, p-unsaturated
acids, 27:264
carbohydrates in asymmetric syntheses,
27~192-204,214
in deoxynitroalditol formation, 24: 106
in hydrogenation, hydroboration, and
mercuration-demercuration of
unsaturated sugars, 27:241-244
hydrogenolysis, 39: 124135
Stereospecificity, fluorination of carbohydrates,
38:259,266
Steric effects, in sulfonylation of carbohydrates,
23~237
Steric factors
effect on conformational equilibria, 26:95,
106, 124
in selective esterification of carbohydrates,
33: 13-1 9
Steric hindrance
in ammonolysis of disaccharides, 31:93, 95
effect
on displacement reactions, 24: 152
on gel chromatography, 2 5 3 1
on reactivities of hydroxyl groups, 33:28
472 SUBJECT INDEX
Steric hindrance (continued)
on trimethylsilylation or
dimethylsilylation, 28:32
Steric strain, effect on selective periodate
oxidation of cyclic glycols, 33:94
Steroidal saponins, hydrolysis of, 28: 15
Steroids
in biosynthesis of polysaccharides, 26:439
conjugates with o-glucuronic acid, synthesis,
36~92-96
fluorinations, 38:2 19, 230
of glycosiduronic acids, preparation,
36:77-78
0-trimethylsilyl and hifluoroacetates, 28:3 1
selective acylation with ethoxycarbonyl
chloride, 33:20
trimethylsilylation of, 28:26, 28
Sterol o-ghcosides, biosynthesis of, 26:454
Steryl glucosides, trimethylsilylation of, 28:28
Stevia rehaudiana Bertoni. 45:285
Stevioside
1,6-anhydride formation from, 34:33
structure of, 31:4,45:289
taste properties, 45:285-286
Stoichiometry
of carbohydrate-alkali metal alcoholate
formation, 21:259
of carbohydrate-alkali metal hydroxide
complexes, 21:248
of carbohydrate-alkaline-earth metal
complexes, 21:25 1
of carbohydrate-metal salt complexes,
21:222
Stokes-Einstein-Debye equation, 51:74
Stokes lines, 44:68
Stoppani, A.O.M., 46:13
Storage glycoproteins, in plants, functional
aspects, 44:383
Strawberry, development physiology of,
42:341-342,346-347,363,313-375,
378-379,381
Strehloside, 39:302
Strecker degradation, 46:311-312,315,317
Streptamine
biosynthesis, 35: I 17
deamination of peracetate, 31:36
2-deoxy-
in gentamicin and sisomycin, 29: 105
N-acylation of, 30: 175
configuration of, 30: 1 18
synthesis of, 30: 116
deoxy-
biosynthesis, 35:104, 117
trifluoroacetate, gas-liquid
chromatography of, 28537
1,3-di-N-acetyl-
1,3-di-N-methyl-5-0-methyl-2-deoxy-,
from gentamkin C, 30: 127
from sisomicin derivative, 30: 130
from tohramycin, 30: 124
2,4-di-O-acetyl-l,3-di-N-methyl-5-0-
methyl-2-deoxy-, preparation of,
30: 124
5-0-methyl-2-deoxy-, from kanamycin
derivative, 30: 122
6-O-methyl-2-deoxy-, configuration of,
30:117
from ribostamycin derivative, 30: 13I
di-N-acetyltetra-0-acetyl-, 24: 101
1,3-di-N-(benzyloxycarbonyl)-2-deoxy-,
isopropylidene derivative, preparation
of, 30: 143
1,3-di-N-methyl-
2-deoxy-, preparation of, 30: 124
4,5-di-O-methyl-3-deoxy-,
stereochemistry of, 30: 123
4,6-di-O-a-o-, glucopyranosyl-2-deoxy-,
synthesis of, 30: 162
4,6-di-O-( 6-amino-6-deoxy-a-o-
glucopyranosyl)-2-deoxy-, synthesis
and antibacterial activity, 30:160
N-methyl-5-O-P-~-talopyranosyl-2-deoxy-,
from destomycin A, 30: 133
4-0-(a-~-glucopyranosy~)-2-deoxy-,
synthesis of, 30:146-147
5-0-(a-o-g~ucopyranosyl)-2-deoxy-,
synthesis of, 30: 149
6-0-(a-o-glucopyranosyl)-2-deoxy-,
synthesis of, 30:145, 147
4-0-( 4-amino-4-deoxy-a-o-
glucopyranosyl)-2-deoxy-,synthesis of,
30:147-148
4 - 0 4 6-amino-6-deoxy-a-o-
glucopyranosyl)-2-deoxy-, synthesis of,
30:142, 145
5 - 0 4 2-arnino-2-deoxy-a-~-
glucopyranosyl)-2-deoxy-, synthesis of,
30: 148-1 49
6-0-( 2-amino-2-deoxy-a-o-
glucopyranosyl)-2-deoxy-,preparation
 SUBJECT INDEX
and activity of, 141, mino)-,
dihydrochloride pentahydrate, crystal
structure bibliography, 30:464
6-0-(3-amino-3-deoxy-a-~-glucopyranosyl)-
2-deoxy-, synthesis of, 142-144,30:158
6-0-(4-amino-4-deoxy-a-~-glucopyranosyl)-
2-deoxy-, synthesis of, 30: 148
6-0- (3,6-diamino-3,6-dideoxy-a-~-
glucopyranosyl)-2-deoxy-,preparation
and activity of, 30: 142
4-O-glycosyl-2-deoxy-, preparation of,
30: 129
preparation, selective deacetylation. 39:34
synthesis of, 33:91
Streptidine
biosynthesis, 35102-107, 109
configuration of, 26:14,30: 114
L-, biosynthesis of, 27: 177
6-phosphate, biosynthesis, 35: 103- 106,
109
in streptomycin group of antibiotics. 30:
113
synthesis of, 26: 14,30: 1 14
Streptobiosaminide, benzyl a - ~ -preparation
, arabinofuranosidase from, 4 2 3 8 6 3 9 1
of, 30: 154
Streptococcus spp.
dextran synthesis by, 30:373-375
S.faecalis, 3-O-a-~-glucopyranosyl-a, p-
trehalose, from, 30:237, 53:212-2 13
S.mutans, 51: 137-138,53:20+20.5
in cariogenic plaques, 30:436
mutan synthesis by mutansucrase. 51: 147
S. sanguis, in cariogenic plaques, 30:436
teichoic acid from group D, 21:344
Group B
capsular polysaccharides, conformations,
41:181
immunological response, 41: 177
structure, 41:167-170
capsular polysaccharide vaccine.
41 :196-1 97
Streptococcus pneumoniae
capsular polysaccharides, 47: 176-1 77
conformations, 41: 180
structure, 41:170-147
polysaccharide vaccines, 41:191-193
type 9, capsular polysaccharide, Smith
degradation product, f.a.b.-mass
spectrometry, 4 5 6 6
Streptolin, hydrolysis of, 34: 122
473
Streptolydigin, 21: 196
Streptomutin A, production and structure,
35: I06
Streptomyces spp.
branched-chain sugars from antibiotics from,
42:76
o-glucose isomerase source, 36:47
Streptomyces curacoi, 46: I4
Streptomyces,frudiae,antibiotics from, mass
spectrometry of, 29:96
Streptomyces griseochromogenes
ketonucleoside intermediate from, 42262
Streptomvces h-vgroscopicus
1-deoxy-D-threo-pentulose isolation.
52:277-278
trehalase in, 30:229,253
trehalose 6-phosphate in, 30:241
Streptomyces 2755 lectin, isolation,
purification, and composition, 35:307
Streptomyces massasporeus. a - ~ -
arabinofuranosidase from. 42:387-388,
390-391
Streptomyces purpurascens, a-L-
Streptomycetes, a,-a-trehalose in, 30:234,242
Streptomycin
a-and p-salts, 30: 115
biosynthesis and structure, 35: 102-1 10
chemistry of, 3:337-384
crystal structure, 25:80,43:349-350
derivatives, preparation and antibacterial
activity of, 30: 178
dihydro-
biosynthesis, 35: 102
3-phosphate, structure of, 30:219
synthesis of, 30: 1 12, 153-1 56
synthesis of, and derivative, 34:28 1-282
dihydrodeoxy-, preparation and activity of,
30: I 78
discovery of, 30:111-112
fermentation of, 30: 1 16
hydroxy-, discovery of, 30: 1 12
inactivated, structure of, 30:2 16
mannosido-, discovery of, 30: 1 12
mannosidohydroxy-. preparation of, 30: I 16
mercaptolysis
in preparation of, 31: 190
and structure determination, 3 2 2 9
N-demethyl-, discovery of, 30:112
preparation of, 30:116
474 SUBJECT INDEX
Streptomycin (continued)
NN-(dialkoxyphenylthio) carbamoyl-
dideamidinodihydro-, preparation and
activity of, 30:178
6-phosphate, biosynthesis, 35: 109
production, Japan, 48:6
structure determination of, 26: 14
structure of, 30: 1 14
synthesis of, 30: 153-156
undecabenzoyl-, antiviral activity of, 30: 178
2-Streptomycin-imidaolidine,1,3-dibenzyl-,
preparation and activity of, 30: 178
Streptomycin oxime sesquiselenate
tetrahydrate, crystal structure of, 2 5 8 0
Streptomycin phosphate transferase, origins and
purification of, 30:218-219
Streptomycylamine, dideguanyl-, preparation
of, 30:178
Streptopmycin adenylyl transferase, origin of,
30:215-218
Streptose
a, P-m-dihydro-, synthesis, 40:82
3-deoxy-, synthesis, 40:83
dihydro-
composition in aqueous solution, 42:55
L-, biosynthesis, 35:98-102
natural occurrence of, 42:72
structure of, 42:70
synthesis of, 42:78-79
3-dihydro-, synthesis, 40:82
DL-
synthesis, 42:113
tetramethyl acetal, synthesis, 40:64
hydroxy
natural occurrence of, 42:72
structure of, 42:70
identification of, 32:78
L-, hiosynthesis, 35:98-102
natural occurrence of, 42:72
preparation of, 32:38
in streptomycin group of antibiotics, 30:113
structure of, 26:14,42:70
synthesis of, 30: 1 14,42:78-79,8 1
Streptothricin, hydrolysis of, 34: 122
Sheptoviridin, effect on protein glycosylation,
40:339,341
Stromatinia, gum, 36:305
Strontium 3-deoxy-2-C-(hydroxymethyl)-o-
evthro-pentonate, crystal structure
bibliography, 31:364
Strontium ion, effect on reducing sugars in
solution, 42:33
Strontium L-arabinonate pentahydrate, crystal
structure bibliography, 31:363
Strontium 4-0-(4-deoxy-P-~-threo-hex-4-
enopyranosyluronic acid)-a-o-
galactopyranuronate, hydrate, crystal
structure bibliography, 37:386
Strontium oxide, complex with sucrose, 21:
213
Strophanthidin
a- and P-D-rhamnosides, synthesis of, 27:4
3-0-(Cr-D-lyXOSyl)-,21~286
3-a-~-mannopyranosyI-,21:292
3-a-o-rhamnopyranosy~-,21:296
3-fl-D-XylOpyranOSyl-, 21 :28 1
3-a-~-arabinopyranosyl-,21:281,285
3-P-o-glucopyranosyl-, 21:281,288,312
~-~-D-ghKOSyl-~-~-D-g~UCOSy~-~-
cymarosyl-, 21:293
3-P-o-rhamnopyranosy1-, 21:296,3 13
3-0-( 6-deoxy-a-~-mannopyranosyl)-, see
Convallatoxin
3-(6-deoxy-P-~-gulosyl)-, 21 :286
description, 21:274
3-(2,6-dideoxy-P-o-ribo-hexopyranosy1)-,
21:308
3 - 0 - ( a - ~ - m a ~ o s y l )preparation
-, and
cardiotonic activity of, 27:4
Strophanthidin glycosides
cardiotonic activities of, 21:3 14
properties of, 21:313,319
Strophanthidol
19-O-a-~-rhamnopyranosyl-, 21:294
3-P-o-glucopyranosyl-, 21:288
3,19-di-0-( a-L-rhamnopyranosy1)-, 2 1:294
K-Strophanthin-h, 21 :293
K-Strophanthoside, 21:292,51: 101
structure, 38:33
Strospeside, 39:302
Structural chemistry, of the hemicellulose,
14:429468
Structural sequences, in polymers, 38: 14
Structure, see also spec@ substances
and antitumor activity, of polysaccharides,
32:258-262
crystallography and, of carbohydrates,
25:53-56
of cyclic acetals, mass spectrometry and,
34: 192-1 94
 SUBJECT INDEX
nuclear magnetic resonance spectroscopy
and, 34:195-198
deamination in determination of, 3 1:7 1-79
determination of. of carbohydrate aniides,
31: 102-1 10
enediol, polarography and detection of.
29:168-171
of glycoproteins, 25:407-408
of herbicides, biological activity and, 21 :408
mass spectormetry in analysis of natural
carbohydrates, 29:41-105
molecular,
of cellulose, 19:2 19-246
of dextran, 15:341-369
of glycogen, 12:261-298
of sucrose, 4:l-35
and polarography of carbohydrates and
derivatives, 29: 142
of polysaccharides, enzymic methods of
analysis of, 30:257-370
and reactivity correlations, of D-
glucofuranosidurono-6,3-lactones,
33~205-210
Strychnine, ~-gulonate,preparation, 38:299
Styracitol, 25237
Styrene
copolymerization
with 1,6-anhydro-2,3,4-tri-O-methyl-P-~-Sucrates, preparation of, 2792. 1 I0
glucopyranose, 34:74
with 6,l ',6'-tn-O-(p-
vinylbenzoyl)sucrose, 33:274
polymers, gels, in chromatography, 25: I5
Submaxillary mucin, 44:240
Substituents
determination by mass spectrometry, 21 :44
effect on conformation, 26:86
on conformational population, 26:95. 106
effect on mass spectra, 2 1 5 4
effect on mercaptalation of sugars, 32:27-36
migration of, in carbohydrates, 33: 100- 109
neighboring-group participation in sugar
reaction, 22: 109-175
N-Substituted aldosylamine
conversion, into I -amino- 1-deoxy-2-kctose3
46:308-309
formation of, 46:308
Substitution reactions, radical-mediated
brominations, 49:75-85
Substrate, non-carbohydrate, sugar synthesis,
40: 1-129
475
Succinic dehydrogenase in fruit climacteric,
42:365
Succinimide
N-bromo-
in acetal preparation, 34: I9 I
cyclic acetal bromination, 39:96-107
oxidation of 4.6-0-benzylideneglycosides
by, 22: 198
reaction with
benzylidene acetals, 26: 163-1 68
cyclic acetals, 34:206
0-benzylidene sugars, 28:268,27&
278
with triphenylphosphine
reactions with carbohydrates, 28:249
selective bromination with, 33:78
N-chloro-
chlorination of carbohydrates with, 28:250
reaction with cyclic acetals, 39: I 18
N-iodo-
iodination of carbohydrates by, 28:250
reaction with hydrazino carbohydrates,
28:279
Succinoglucan, gas-liquid chromatography of,
28:47,93
Succinoglycan depolymerase, 44:225-226
Sucrase, inhibition by acarbose, 48:88
Sucrose, see also Sugar
acetates, benzoates, and 3-
benzoylpropionates, physical properties
of. 33:284
preparation of, 33:245-250
acid hydrolysis, 52:455456
in water and in deuterium oxide, 24:29
a-D-galactosides, 37:289-3 1 1
aminolysis of, 27:99
ammonolysis of, in liquid ammonia, 27:93
6- and 6'-bromodeoxyhepta-0-
(methylsulfony1)-, preparation of,
33:258
6- and 6'-O-trityl-. preparation of,
33:238-239
3',6'-anhydro-. synthesis of, 33:253
anhydro derivatives, physical properties of,
33:286
preparation of, 33:253-255
aqueous
laser-Raman spectroscopy, 44:73-74,
7680
476 SUBJECT INDEX
Sucrose (continued)
solute-solvent interactions, vibrational
spectroscopic studies, 44:86
aqueous syrups, pH, 47:239
azidodeoxy, preparation of, 33:266-268
binding to taste papillae, 45:329-330
inactivation by heating in boiling water,
45:330-33 1
biological properties of derivatives of,
33:274
biosynthesis of, 26:366-368,32:7-8
calcium complexes, laser-Raman
spectroscopy, 44534
caramelization, 47:2 19-220
caramels, 52:222-223
carbonates, preparation of, 33:252
catabolism by yeasts, 32:183,233
C-C and C - 0 bond-lengths in, 44: 15
c h e m i s e of, 33:235-294
6-chloro-6-deoxy-, preparation of, 33:77,
26 1
chlorodeoxy-0-p-tolylsulfonyl-,
hexabenzoate, preparation of, 28:256
chlorosulfates
physical properties of, 33:285-286
preparation of, 33:250-253
cleavage by dextransucrase, 51: 146-147
13C nuclear magnetic resonance spectra of,
33:277
complexes with alkali metals, 21:223
with sodium bromide, structure of,
21:236
with sodium carbonate, 21:213
with sodium iodide, 21 :2 15
conformation of, 26:llO
copolymerization with 3-chloropropylene
oxide, 33:274
cryoprotective effect, 4 4 8 9
crystalline adducts, 47:2
crystal structure of, 25:76,31:352
cyclic acetals, physical properties of, 33:287
preparation of, 33:255-256
decomposition, 47:239
degradation, 52:44 1 2 6 6
alkaline, 52:44&449
chloride salts effect, 52:461
effects on manufacture, 52:458466
color from degradation products, 52:462
control and measurements of pH,
52~454466
inversion rates and sucrose loss,
52:460464
statistical process control, 52:463
and dental caries, 30:433
and dental plaque, 30:435
deoxy derivatives, physical properties of,
33:289
preparation of, 33:264-266
4-deoxy-4-fluoro-galacto-, 48:2 15
deoxyhalo derivatives, relative sweetness,
45266-268
derivatives, 0-methylated, large scale
preparative liquid chromatography,
46:62
determination of hydration numbers, 44:87
dextran from, structure of, 32:5
D-fruCtOSe from, 22~232
6,6-diamino-6,6-dideoxy-, preparation of,
33:269
1 ,4:3,6-dianhydro-,synthesis of, 33:253
3,6:3,6-dianhydro-,synthesis of, 33:253
6,6-diazido-6,6-dideoxy-
2,3,4,1,3,4- hexa-0-(methylsulfony1)-,
preparation of, 33:267
hydrogenation of, 33:269
6,6-diazido- 2,3,4,1,3,4-hexa-0-benzoyl-
6,6-dideoxy-, preparation of, 33:267
6,6-dibromo-6,6-dideoxy-2,3,4,1,3,4-
hexa-0-(methylsuifony1)-, preparation
Of, 33~258-259
6,6-dichloro-6,6-dideoxy-
2,1:3,4-di-O-isopropyIidene-, preparation
of, 33:256
hexabenzoate, preparation of, 28:256
preparation of, 33:77,261-262
6,6-dideoxy-, 23:274
6,6-diiodo-2,3,4,1,3,4-hexa-O-
(methylsulfony1)-, preparation of,
33:257
1,2,3,4,3,4-hexa-O-(rnethylsulfonyl)-
6,6-di(thiocyanat0)-,synthesis,
44:138
hexa-O-(rnethylsulfonyl)-6,6-
di(thiocyanat0)-, physical properties
of, 33:294
2,1:4,6-di-O-isopropylidene-
preparation of, 33:255
tetracetate, ammonolysis, 39:33
1,6-di-O-methyl-, taste properties, 45262
4,6-di-O-methyl-, taste properties, 45262
 SUBJECT INDEX
6,6-di-O-methyl-, taste properties, 45:262
1,6-di-O-p-tolylsulfonyl-, 23:243
reaction with benzoyl chloride in pyridine.
28:256
6,6-di-O-p-tolylsulfonyl-, 23:243
I ,6-di-O-trityl-
nuclear magnetic resonance spectra of,
33:276
preparation of, 33:242
6,l -di-0-trityl-, preparation of, 33:242
6,6-di-O-trityl-, preparation of, 33:24&242
effect on metabolism of ethanol, 34:3 18
effects of alkali tetraborates on rotation of,
23:36
in endosperm and cotyledon during
germination, 35:357
enzymic synthesis of, 5:2948
esterification with methyl tetradecanoate,
33:44
esters, herbicidal properties of, 21:4 I6
in food, liquid chromatography separation,
4652
galacto-
deoxyhalo derivatives, relative sweetness,
45:266-268
sweetness-structure relationship, 45:263
gas-liquid chromatographic analysis of,
28:68
halides, physical properties of, 33:288
preparation of, 33:257-263
2,3,4,1,3,4,6-hepta-O-acetyl-
6-amino-6-deoxy-, synthesis of, 33:269
6-chloro-6-deoxy-, nuclear magnetic
resonance spectra of, 33:277
6-deoxy-, preparation of, 33:265
6-deoxy-6-iodo-, reaction with silver
fluoride, 33:263
Koenigs-Knorr reaction with, 34:264
6-O-trityl-, synthesis of, 33:239
2.3,4,1,3,4-hepta-O-acetyl-, 6-deoxy-6-
iodo-
deiodination of, 33:265
reaction with silver fluoride, 33:264
2,3,4,6,1,3,4-hepta-O-acetyyl-
6-deoxy-, preparation of, 33:265-266
Koenigs-Knorr reaction with, 34:264
methylation of, 33:243
6-O-methyl-, preparation of, 33:243
preparation of, 33:247
2,3,4,6,1,3,4,6-hepta-0-acetyl-, 4-0- Sucrose (continued)
477
methyl-, preparation of, 33:243
2,3,4,6,1,3,6-hepta-O-acetyl-
4-0-(trideuterioacetyyl)-, fragmentation
pattern and mass spectrum of,
33:280
preparation of, 33:247
2,3,6,1,3,4,6-hepta-O-acetyl-
methylation of, 33:243
nuclear magnetic resonance spectra and
structure of, 33:276
4-0-(trideuterioacetyl)-, fragmentation
pattern and mass spectrum of. 33:280
oxidation of, 33:271
preparation of, 33:247
2,3,4,1,3,4,6-hepta-O-benzoyl-, oxidation
of, 33:271
2,3,1,3,4,6-hexa-O-acetyI-
4,6,-0-isopropylidene-, preparation of,
33:255
6-chloro-6-deoxy-, preparation of, 33:263
4,6-O-benzylidene-, preparation of,
33:255
tritylation and acetylation of, 33:239-240
2,3,4,1,3,4-hexa-O-acetyl-
6-chloro-6-deoxy-6-0-p-tolylsulfonyl-,
preparation of, 33:257
6,6-diazido-6,6-dideoxy-, hydrogenation
of, 33:269-270
6,6-dibromo-6,6-dideoxy-, reaction with
silver fluoride, 33:264
6,6-dichloro-6,6-dideoxy-
I3C nuclear magnetic resonance spectra
of, 33:277
preparation of, 33:257-258
6,6-di-O-p-tolylsulfonyl-, sulfonate
displacement in, 33:257
6,6-di-O-trityI-
detritylation and acyl migration in.
33: 106
detritylation of, 33:246
2,3,4,3,4,6-hexa-O-acetyl-, 6,l -di-0-
trityl-, preparation of, 33:242
2,3,4,6,3,4-hexa-O-acetyl-
16-di-O-methyl-
mass spectrum and fragmentation
pattern for, 33:280
preparation of, 33:244
1,6-di-O-trityI-, preparation of, 33:243
methylation of, 33:244
478 SUBJECT INDEX
2,3,6,1,3,4-hexa-O-acetyl-, preparation of,
33:247
2,4,1,3,4,6-hexa-0-acetyl-, 3,6-anhydro-,
preparation of, 33:253
3,4,6,3,4,6-hexa-O-acetyl-
2, I -di-O-methyl-, preparation of, 33:244
1-di-0-trityl-, preparation and de-
esterification of, 33:240
2,l -(diphenylsily1)-
preparation of, 33:256
reaction with acetic acid, 33:240
methylation of, 33:244
preparation and tritylation of, 33:240
hexa-O-acetyI-6,6-dideoxy-, 6,6 -di-
(thiocyanat0)-, physical properties of,
33:294
2,3,4, I ,3,4-hexa-O-benzoyl-
6,6-bis(chlorosulfate),reaction with
pyridinium chloride, 33:259
reaction with sodium azide, 33:260
6,6-dichloro-6,6-dideoxy-, preparation
of, 33:259
6,6-dideoxy-, preparation of, 33:265
6,6-dideoxy-6,6-diiodo-
hydrogenation of, 33:265
reaction with silver fluoride, 28:292,
33:264
6,6-di-0-(3-benzoylpropionyl)-,
preparation of, 33:248
6,6-di-O-p-tolylsulfonyl-
preparation of, 33:241
reaction with sodium azide, 33:267
6,6-di-0-( terr-butyldimethylsilyl)-,
selective cleavage, 39:67
6,6-di-O-trityl-, detritylation of, 33: 106,
246-247
preparation of, 33:241,247
reaction with sulfuryl chloride, and 6,6-
bis(chlorosu1fate) preparation, 33:25 1
hexa-O-benzoy1-6,6-dideoxy-, 6,6-di-
(thiocyanat0)-, physical properties of,
33:294
as high-energy glycosyl donor,
polysaccharide and oligosaccharides
syntheses, 51: 139-140
history, 21:29,34:286
in honey, 25:291,295
hydrolysis of, 21:131, 22:31,34
effect of concentration of rate of, 22:41
in human intestine, 34:287-288
rates, 52:460-462
inhibitory action on pectinesterase, 33:337
liquefaction, 46:294
mercaptalation of, 32:28
metallation of, in liquid ammonia, 27:93
methylation of, 33:243-245
methyl ethers, physical properties of,
33:283
preparation of, 33:243-245
microbial oxidation of, 33:271
mono(dodecanoate), preparation of,
33:272-273
natural forms, 21:29
in nectars, 25304
nitrogen-containing derivatives, physical
properties of, 33:290
preparation of, 33:266-270
nonselective spin-lattice relaxation rates,
45: 149
nuclear magnetic resonance spectra and
structure of, 33:275
nucleotide esters from, 42:338
occurrence in plants, 37:289-290
octaacetate, proton magnetic resonance
spectra of, 27:30-3 1
octa-0-acetyl-
nuclear magnetic resonance spectra of,
33:275-276
preparation of, 33:248
selective deacylation, 39:28
selective de-esterification of, 33:247
octa-0-benzoyl-, selective deacylation, 39:32
octa-0-benzyl-
physical properties of, 33:294
preparation of, 34:259
octa-0-(ethoxycarbony1)-,preparation of,
33:252
octa-0-methyl-, preparation of, 33:245
octa-0-(methylsulfony1)-, reaction with
sodium azide, 33:267
with sodium bromide, 33:258-259
4,6-0-isopropylidene-, preparation of,
33:255
oligosaccharides
from acceptor molecules and, by
dextransucrases, 30:424-427
containing residues of, )C-NMR data for,
42:202-203
4-O-methyl-
preparation of, 33:244
 SUBJECT INDEX
taste properties, 45:262
6-0-methyl-
preparation of, 33:244
taste properties, 45:262
optical rotation of. effect of salts on, 21:225
in solution of metal salts, 21:229-230
1 -0-trityl-
nuclear magnetic resonance spectra of.
33:276
preparation of, 33:240
6-O-trityl-, nuclear magnetic resonance
spectra of, 33:276
1 ,2,3,4,3,4-penta-O-acetyI-, 1,6,1.6-tri-
0-p-tolylsufonyl-, 23:242
2,3,4,3,4-penta-O-acetyI-
methylation and deacetylation of. 33:245
synthesis of, 33:245-246
6,1,6-tri-O-p-tolylsuIfonyl-
deacetylation of, 33:249
synthesis of, 33:254
2,3,6,3,4-penta-O-acetyI-
6-chloro-6-deoxy-4, I -di-0-fonnyl-,
preparation of, 33:262
methylation and deacetylation of, 33:244
preparation of, 33:239, 246, 267
4, I ,6-tri-O-p-tolylsulfonyl-, alkaline
alcoholysis of, 33:254
penta-0-acetyltri-0-p-to1ylsulfonyl-,
displacement reaction of, 24: 147
2,3,4,3,4-penta-O-benzoyI-
6,6-dichloro-6,6-dideoxy-
1-(chlorosulfate), preparation and
reactions of, 33:260
preparation of, 33:252, 263
6,6-dichloro-6,6-dideoxy- I -O-formyl-,
formyl group removal from. 33:263
preparation of, 33:246
reaction with sulfuryl chloride and 6,1,6-
tris(chlorosu1fate) preparation,
33:251
synthesis of, 33:246
6,i ,6-tri-0-(3-benzoyIpropionyl)-,
preparation of, 33:248
6, I ,6-tri-O-trityI-, detritylation of.
33:106, 249, 267
and acyl migration in, 33:239, 246
methylation, and acyl migration in,
33:106
6,1,6-tris(chlorosulfate), reaction with
pyridinium chloride or with sodium
479
azide. 33:260
per-0-(trimethylsilyl)
derivative, gas-liquid chromatography of,
28: 130-1 3 1
ether and per(trifluor0acetate). gas-liquid
chromatography and retention times
of, 28:70
phenols from. 46:295
6-phosphate, synthesis of, 33:271
polarography of, 29:126
p-toluenesulfonylation of, 33:36
pyrolysis of, 34:45
quantitatively motional description, 51:115
radiolysis and radical-induced scission,
37:52
raffinosc effect on manufacture, 37:299-300
reaction with
acetyl bromide or acetyl chloride, 2 2 2 3
acrolein, effect of zinc chloride on,
27:95
with fatty acid ester, salts of palmitic
and oleic acids as catalysts and
solubilizers in, 27:96
paraldehyde, 33:255
with sulfuryl chloride, 33:76, 25 1-252,
26 1
sulfuryl chloride, 28:239
reducing properties, 47:218,220
relative reactivities of hydroxyl groups in,
33:60
selective benzylation of, 33:60
selective chlorination with methanesulfonyl
chloride-N, N-dimethylformamide
complex, 33:261-263
selective etherification with
chlorotricyclohexylsilane, 33:53
selective oxidation with lead tetra acetate,
33396
selective p-toluenesulfonylation. 33:248
selective tritylation of, 33:52, 238-243
solubility in acetone, 27: 107
in acetone, effect of zinc chloride on,
27~95
in alcohols, 27:89
in alkoxy alcohols, 27:99
in anhydrous hydrogen fluoride, 27:93
in ethanol, 27:98
in ethyl and methyl carbamates, 27: 1 13
in heterocylic solvents, 27: 1 17-1 19
in liquid ammonia, 27:91
480 SUBJECT MDEX
Sucrose (continued)
in methanol, 27:97
effect of calcium chloride on, 27:95
in methyl sulfoxide and in propyl
sulfoxide, 27: 108
in polyhydric alcohols, 27:98
in sulfolanes, 27: 1 1 1
in thiocyanates, 27:95
solvents for, 27:85, 87
spin-lattice relaxation of I3C nuclei in, 27:59
structure-making effect on water, 44:86
structure of, 21:128,35:5,39:356,51:93
and configuration of, 4:l-35
properties relationships, vibrational
spectroscopic study, 44:88
and synthesis of, 33:236-238
and utilization by yeasts, 32191-195
as substrate for dextransucrases, 30:423
as substrate inhibitor, 51: 150-1 5 1
sulfates, and sulfites, preparation of,
33:250-253,252
sulfonates, physical properties of,
33:285-286
sulfonylation of, 23:242
sweetness, 45214,231,233,238
effect of infrared hydrogen-bonding
strength, 45217
structure relationship, 45263
time-intensity relationships for, 45:346
synthesis of, 25: 165,26:323
adenosine 5 -pyrophosphate CY-D-
glucopyranosyl ester in, 28:395
system with barium oxide, 21:213
with sodium iodide, 21:211
with strontium oxide, 21:213
tetrachlorotetra-0-mesyI-guluclo-derivative,
proton spin-lattice relaxation,
45: 154-1 57
3,3 ,4,6-tetra-O-acetyl-
2,1:4,6-di-O-isopropylidene
deacetalation of, 33:245
nuclear magnetic resonance spectra of,
33:276
preparation of, 33:255-256
6,l -di-0-trityl-, preparation of, 33:242
synthesis of, 33:245
3,4,3,4-tetra-O-acetyl-
2,1:6,6-di-O-(diphenylsilyl)-
deacetalation of, 33:245
preparation of, 33:256
synthesis of, 33:245
2,6,1,6-tetra-O-p-tolylsulfonyl-
deacetylation of, 33:250
tetra-0-acetyl-2,l :4,6-di-O-isopropylidene-,
selective hydrolysis, 39: 17-1 8
2,6,1,6-tetra-O-p-tolylsulfonyl-, preparation
of, 33:250
thermal activation, 523222
thermal degradation, 47:220, 245-246
transesterification of, 33:272
6,1,6-triamino-6,I ,6-trideoxy-,
preparation of, 33:270
2,1:3,6:3,6-trianhydro-, preparation of,
33:253
3,6: 1 ,4:3,6-trianhydro-,preparation of,
33:36,254
6,1,6-triazido-2,3,4,3 ,4-penta-O-benzoyl-
6,1,6-trideoxy-, hydrogenation of,
33:270
6,1,6-triazido-6,1,6-trideoxy-
hydrogenation of, 33:270
structure and synthesis of, 33:267-268,
270
4,1,6-trichloro-4,1,6-trideoxy-, gulucto-,
45:333
relative sweetness, 4 5 2 6 6 2 6 8
4,6,1 ,6-trichloro-6.1,6-trideoxy-, relative
sweetness, 45:332
6,1,6-trichloro-6,1,6-trideoxy-
preparation of, 33:262
relative sweetness, 45332
trimethylsilyl ether, gas-liquid
chromatography of, 28:58
2,3,6-tri-O-acetyl-4,1,6-tn-O-
(methylsulfonyl)-, preparation and
reaction with sodium azide, 33:267, 269
tri-0-(ethoxycarbony1)-, preparation of,
33:252
4,6: 1,3:4,6-tri-O-ethylidene-
2,3-O-(oxidodiethylidene)-, from
paraldehyde and sucrose, 33:255
from paraldehyde and sucrose, 33:255
4,1,6-tri-O-methyl-, synthesis of,
33:244245
6,1,6-tri-O-methyl-, synthesis of, 33:245
6,1,6-tri-O-p-tolylsuIfonyl-, 23:242
identification of, 33:36
preparation of, 33:248-250
structure of, 33:253
6,1,6-tri-O-(p-vinylbenzoyl)-,
 SUBJECT INDEX
copolymerization with styrene and
methyl methacrylate, 33:274
6,1,6-tri-U-trityl-, preparation of, 33:239,
24 1
6,I ,6-tris(acetamido)-
2,3,4,3,4-penta-O-acetyI-6,1,6-
trideoxy-, preparation and structure
of, 33:270
6,1,6-trideoxy-, preparation of, 33:270
trityl ethers, physical properties of, 33:282
preparation of, 33:238-243
unsaturated derivatives, physical properties
of, 33:289
preparation of, 33:263-264
utilization by yeasts, 32: 146, 194-1 99
and associations of abilities, 32:223
delayed, 39:374
utilization of, 4:293-336
water loss, 47:218-219
Sucrose octaacetate, proton nuclear magnetic
resonance spectrum, 29:36
Sucrose 6-phosphate synthetase, 26:368
Sucrose sodium bromide dihydrate, crystal
structure bibliography, 31:367
Sucrose synthetase, 26:367, 385
nucleotide ester synthesis by, 4 2 3 16
Sugar
aconitic acid as by-product in manufacture
of, 6:23 1-249
conformational analysis, see Carbon-proton
coupling constants
industrial development, 36: 19-20
paper ionophoresis, Maurice Staceys works.
52:17
pre-industrial history, 36: 18
production flowchart
beet, 52:442,444
cane, 52:443444
Sugar acetates, bitterness, 45:3 18
Sugar acids, fluorinated
2-NMR data for, 46: 170
H- and 19F-NMR data for, 46: I16
Sugar alcohols,
higher-carbon, configurations of, 1: 1-36
and their derivatives, metabolism of,
1: 175-1 92
Sugar analogs, inhibition, of lipid-linked
oligosaccharide formation, 40:326-338
of protein glycosylation, 40:33&338
Sugar analyses
481
anthrone test, 28:220-222
carbazole test. 28:222
dehydration reactions in concentrated acid
solution, 28:2 18-222
orcinol test in, 28:223
phenol-sulfuric acid reaction, 28:223
Sugar anomers, separation of, 46:70
Sugar beets
history. 34:286. 36: 19
juices, dextran removal from, by fungal
endodextranase, 30:395
molasses, D-fructose from, 22:232
Sugar cane
bagasse, polysaccharide, antitumor activity
of. 32:254, 268
cell wall studies on, 42:271, 294, 300
effect of plant-growth substances on, 21:421
eyespot disease, 37:321
history, 36: 18
juice
composition of, 8:291-3 14
dextran removal from, fungal
endodextranase, 30:395
gas-liquid chromatography of, 28:48
molasses, 3:113-128
composition of, 8:291-214, 26:15
Sugar chains. representation in
oligosaccharides, 52: 159
Sugar colorants, spectral analysis and
identification, 44:23-24
Sugar derivatives, having mixed substituents,
circular dichroism, 45: 11 1-1 19
Sugar industry
dextrans in, 30:442444
polarography in, 29: 128
products, color and turbidity of, 9:247-284
refining, granular adsorbents for, 6:205-230
Sugar isothiocyanates, 44:93
conversion
into substituted thioureides, 44: 105
into thioureido derivatives, 44: 100
into thioureido intermediates, 44:97
as intermediates in synthesis of nucleoside
analogs, 44:97-123
reaction with
amines, 44:97-113
amino acids, 44: 113-1 17
ammonia, 44:97-113
carboxylic acids, 44: 113-1 17
diamines, 44: 1 19- 121
482 SUBJECT INDEX
Sugar isothiocyanates (continued)
diazomethane, 44:121-122
enamines, 44:117-119
hydrazides, 44:99-100
hydrazines, 44:99
synthesis, method, 44:93-97
Sugar methyl ethers, bitterness, 45318
Sugar nucleotides, 44:341
biosynthesis of, 42:3 15-3 16
conformations of, 46:7
history, 28:307-308
Sugar oxiranes, use in synthesis of branched-
chain sugars, 42:95-97
Sugar phosphates, 49:207-210,212
enzymes for phosphorylation, 49208
ATP regeneration, 49:208-210
pentose phosphate preparation, 49:210
liquid chromatography separation of, 46:36
preparation of, 32:8
radiolysis, 37:4241
Sugars, 37:32-42, see also Amino sugars;
Anhydro sugars; Deoxy sugars; Reducing
sugars; speczjk sugar
acetates, acid-catalyzed anomerization of,
24:43
acetylated, acid anomerization in deuterium
oxide and in water, 24:29
acetylenic derivatives, synthesis of, 31:71
acetylenic precursors, 40:34
action of lead tetraacetate on, 14:9-61
acyclic
conformational analysis of, 26:68-73
Grignard reaction with, 27:217
intermediates during Wohl degradation,
26:9
in solution, 23:38
aldehydo and keto, Wittig reactions with,
27229-239
alkali action on reducing, 26: 14
alkenic precursors, 40:430
amino, 21:17,24:9,25:6
aspects of the chemistry of, 14:213-281
aziridine sugars from, 25:353
deamination of, 25: 182,31:9-79
derived from antibiotic substances,
18:259-308
gas-liquid chromatography of, 28:56,78,85
methanolysis in determination of, 28: 18
trifluoroacetates, gas-liquid
chromatography of, 28:87
trifluoroacetic acid in determinationof,
28: 16
trifluoroacetyl derivatives,gas-liquid
chromatography of, 28: 114
trimethylsilylation of, 28:24,27, 29
trimethylsilyl derivatives, gas-liquid
chromatography of, 28: 143-146
intermediate for synthesis of, 25382
mass spectrometryof, 21:67,93,3039-40
methylation of, 30:22
methyl ethers of, 13:189-214
oxirane sugar derivatives from, 25: 118
preparation of, 24: 109,33:232-234
properties of, 15: 159-200
reactions with beta-&carbony1
compounds, 20:303-355
rearrangement of, 26:161
synthesis of, 26: 14,29:3
2-amino, see Sugars,2-amino-2-deoxy
5-amin0, synthesis,40:99-101
aminodeoxy, 2 5 6
dithioacetals, physical constants of, and
peracetates, 32:118-121
mercaptalation of, 32:27
formation in reaction of sugars and
ammonia, 25:333
preparation of, 33:269-270
synthesis of, 24: 147
2-amino-2-deoxy-,7:247-288
1,2-cis-glycosides,preparation of, 34:268
dehydration of, 28182
hydrolysis of, 22:61
3-amino-3-deoxy, preparation of, 22: 131
3-amino-2,3-dideoxy,synthesis of,
27~262-263
amino-substituted, circular dichroism,
45:99-100
anhydro, 22:4,25:6
acetates and methyl ethers, gas-liquid
chromatography of, 28: 148
degradation mechanism of 2,5-,
28: 165-166
formation of l,6-, in hydrolysis of
polysaccharides, 28:20
gas-liquid chromatographyof, 28:87-89
per(trimethylsily1) ethers, gas-liquid
chromatography of, 28: 147-148
preparation of 2,5-, 28:287
boronates, properties, 35:79
paper chromatography of,
 SUBJECT INDEX
phenylboronic acid in, 35:60
chemistry of, 2:37-77
cleavage of, 22187-188, 191
dithioacetals, physical constants of and
peracetates, 32: 121-122
formation, 22:202
by mutarotation, 24:46
mass psectrometry of, 29:74
from sugar sulfonates, 23:279
thio, 22:156
2,3-anhydro, 0x0 reaction with, 23: 105
2,5-anhydro
properties of, 25220-229
related compounds and, 25:181-228
utilization of, 25:215-218
3,6-anhydro
derivatives, interatomic oxygen-oxygen
distances, 45:273
mercaptalation of, 3 2 2 8
anhydroepoxy, 0x0 reaction with, 23: 102
anions, catalytic activity of, 24:24
aqueous, infrared spectra, 44: 18
azides, aziridine sugars from, 25:354
azidodeoxy, dithioacetals, physical constants
of, 32: 122
aziridine derivatives, 25352
p anomers, binding to sweet-receptors,
45:248
benylidene acetals, reactions with N -
bromosuccinimide, 28:276-278
3-benzoylpropionyl group as protective
group in, 33:248
benzyl ethers of, 12:137-156
biochemical reductions at the expense of.
4~75-117
biogenesis of, 26:298
biosynthesis of, of antibiotic substances,
35:81-126
boronates, see Boronates
branched-chain, 22:286, 23:60, 93-94. 99,
279,24:137,48:287-288
amino, 29:8
preparation of, 32:39
antibiotic components, 3582-1 02
cyclic acetals in preparation of, 34:209
synthesis of, 34:97, 100, 158
history, 31:136
of natural occurrence, 11:263-283
oxiranes of, 25: 167
preparation of, 3 2 3 8
483
stereochemistry of, 32:40
synthesis of, 33:94,40:13-17,80-84
type A, synthesis of, 31: 179
bromodeoxy, displacement reactions,
28:283
6-bromo-6-deoxy, 22: 198
I ,3-butadienyl ethers, cycloaddition,
40: 123-128
C-acetyl-branched, 35:92,94-95
C-alkylated and C-arylated unsaturated,
physical properties of, 27:239-24 1
with carbon-phosphorus bond, preparation
of, 28:285
of the cardiac glycosides, 17:65-120
in ' C , conformation, taste properties, 45269
in ' C , conformation, taste properties, 45:269
C-glycosylated alkenes, preparation and
properties of, 27:233-244
chemical-ionization mass spectra of,
29~81-84
chlorodeoxy
preparation of, 28:231-239,255,278
reduction of, 28:302-303
synthesis, 33:73,41:9
circular dichroism spectrum, 4 5 7 5
C-methyl-branched, biosynthesis, 35:97
colors, 47:214
column chromatography, boronic acids in,
35:64
configuration of branched-chain, 27:2 15
conformational analysis of, and derivatives,
26~49-125
constitution and ring structure of, 2 5 4
containing fused-ring systems, conformation
of. 26: 1 14
cyclic analogs with imino group, 48:335-341
cyclobutene derivative, 27:299
D-
relative sweetness, 45:258
superpositioned over same receptor site,
45:236
degradation and dehydration of, 28: 163
deoxy
carbon- 13 nuclear magnetic resonance
spectroscopy, 41:55
mercaptalation of, 3 2 2 7
synthesis of, 32:75
preparation, 36: 10
from amino sugars, 31:60
properties of, 26:279-296
484 SUBJECT INDEX
Sugars (continued)
rate constants and equilibrium constants in
polarography of, 29: 143
synthesis of, 23:267,269,27 1,274,
21:274,281,33:264-266
2-deoxy-, 8:45-105
2-halo, 22:193,206
periodate-thiobarbitc acid assay,
38:326
4-deoxy-, synthesis, 40:41-48
deoxy-, preparation, 38: 157
deoxyfluoro, 22:192,198
deoxyhalo, 25: 194
oxirane aldoses from, 25: 118
preparation, 25: 126
by nucleophilic displacement of
sulfonates, 33:257
deoxyhalogeno
3,6-anhydro-ring
displacement reactions of, 28:281-290
elimination reactions, 28:290
formation, 28:287
from glycals, 28261
from hydrazino carbohydrates, 28:279
neighboring-group reactions of, 28:290
preparation, by reaction with
phosphorus-containingreagents,
28:239-250
preparation by direct replacement of
hydroxyl group, 28:230-260
preparation by displacement reactions,
28227-230
preparation by reaction with
(halogenomethy1ene)dimethyliminiu
m halides, 28:25@-251
preparation of, 28:257,263
reductive dehalogenation of,
28:299-304
synthesis and chemisby of, 28225-306
synthetic utility of, 28:281-306
dithioacetals, physical constants of,
32: 122-123
deoxyiodo
carbohydrate oxetanes, preparation of,
28:289
preparation of, 28:243
reactions of, 28:282
synthesis of, 28:280
irradiation, 38: 186189
deoxynitrounsaturated, 28:299
derivatives, synthesis, aldonolactonesacetals
use, 50:130-132
determination
of enantiomeric form, 46:66
of hydration numbers, 44:87
diamino, 48:292
preparation of, 33:232-234
cis-2,3-diamino-2,3-dideoxy, synthesis of,
29:s
3,6-dideoxy, preparation by hydrolysis,
2814,19
with difluoromethylene group, synthesis,
48: 183
di-p-bromobenzoate derivatives, circular
dichroism, 45: 123-124
dithioacetals, 26:13,32:15-123
mass spectra of, 29:71-73
electrophoresisof, sulfonylated
phenylboronic acids in, 3562
enantiomeric carba-sugars from, 48:41-49
enediol acyclic, formation in dehydration
reactions, 28:167-171
energies of activation for mutarotation of,
24:55
enol, thioenol, and enamino groupings as
precursors of carbonyl sugars,
21:270-283
enolacetal furanoid and pyranoid, stability of,
29:291
epimino, 23:278,25:352-356
epithio, 22:156, 192
epoxide, deoxy sugars from, 21:152,159
epoxy, 23:234
epoxyanhydro, 0x0 reaction with, 23: 102
exchange of hydrogen and oxygen atoms
with solvents, 23:37
fermentation, 50:8-10
filtration, 53:402
formyl- or hydroxymethyl-branched,3 5 9 8
freeze-dried, Fourier-transform infrared
spectroscopy, 44:6345
furanoid
conformations of, 26: 109-1 12
crystalline, conformation of, 26: 110
with fused rings, conformation of,
26: 12-122
gas-liquid chromatography of, boronic acids
in, 35:65
halogenated
0x0 reaction with, 23:109
 SUBJECT MDEX
reactions of, 22:201
separation and identification of, 22: 199,
201
hamomorphous, 23:28
heterocyclic derivatives, 44:9 I
higher-carbon, 17:15-63
configurations of, 1: 1-36
of honey, 25:285-309
hydrazones of, 3:2344
in hydrolyzates of hemicelluloses from oat
plants, 36:255-257
infrared spectra of, 23:39, 41
at low temperatures, 44:28
ionic forms, 23:41
ionizing radiation of, 26: 15
isothermal determination of, gas-liquid
chromatography and, 28:8 1
L-
relative sweetness, 45:258
sweetness-structure relationship,
45:258-259
labeled
at anomeric center by aldonolactones,
50: 161-1 62
with isotopes of hydrogen, 27: 127-190
liquid chromatography of separation,
pyranose forms during, 42:23
location of third binding-site in, 45:234-235
in mesophyll cells of ryegrass and their
hydrolyzates, 36:260
metallation of, in liquid ammonia, 27:Y2
methylated, 48: 300-302
acetates and hifluoroacetates, gas-liquid
chromatography of, 30:86
gas-liquid chromatography of.
30:9-110
miscellaneous ethers, gas-liquid
chromatography of, 30: 102
model studies on, 30:54-55
periodate oxidation and gas-liquid
chromatography of, 30:33, 101
trimethylsily ehters, gas-liquid
chromatography of, 30:83-85
partially, identification by mass
spectrometry, 29:46
rate constants and equiliburium constants
in polarography of, 29: 143
methylation of, 24:7, 30:4
history, 23: 1
methyl ethers, sweetness-structure
485
relationship, 45:261-265
methyl glycosides of the common,
12:157-187
monoamino, 48:290-292
mutarotation
catalysis by mutarotase, 24:63-64
catalytic coefficients, ratios for, 24:30
in constants and optical rotations of,
23:53-56
in N,N-dimethylformamide, 24:61
in pyridine. 24:61
rates of, determination, 46:71
in solution, 23:ll-57, 24:13-65
neighboring-group participation in reactions
of, 22:109--175
nitrates of, 12: 1 17-135
nitro, 24:67- I37
acetalation of, 24:116
acylation of, 24: 1 I5
historical, 24:68
hydrogenation of, 24:109
hydrolysis and methanolysis of, 24: 1 18
nomenclature of, 24:67
nucleophilic additions and elimination-
additions, 24: 130
reaction with amines, 24: 136
with reactive methylene compounds,
24: 137
nitrogen-containing, preparation of,
33: 266-270
nitrogen heterocycles from, 2535 1 4 0 5
0-methyl oximes, per(trimethylsily1) ethers,
mass spectra of, 29:77
as 0-nucleophiles, see Nucleophiles, 0-
osazones of, 3:2344
oxygen ring in, formation and cleavage of,
13~9-61
paper chromatography of, phenylboronic
acid in. 3 5 5 9 , 61
phenyl glycosides of the cotnmon,
12:157-187
polarimetry of, 42: 17-18
polycondensation in methyl sulfoxide,
21:449,453
polymerization, hydrogen fluoride, 47:202
pyranoid
conformation, 26:74
in solution. 26:84-98
crystalline, conformation of, 26:8 1-84
pyranose anomer, separation, 46:70-7 1
486 SUBJECT INDEX
Sugars (continued)
pyrolysis, 47:270-278
composition of evolved gases, 47:272,274
composition of gases, 47:27 1-272
furan derivatives, 47:276,278
total gas evolution, 47:272-273
water formation, 47:274
radiocarbon-labelled, synthesis of, 32:8
reaction with
alkali, 25~341,345
with aqueous ammonia, 25:3 11-349
amino acids, 42223
reducing
composition in solution, 42: 1 5 4 8
fission in alkaline solution, 25:345
methods for studying in solutions,
42: 17-24
oxidation with lead tetra-acetate, 33:96
relative configurations, proof by Fischer,
50:2
removal from cell walls, 47:201
residues, glycosidic linkage lability,
42194195
reversion, 47:245
ring structure of, 23:3
seleno, 1:144-145,22:205,23:232
separation
by gel chromatography, 2936
on ion-exchange columns, 47:38
septanoid, conformation of, 26: 113
simple, structure, and sweetness, 45:238-259
solubility, 23: 19
determination of, 27:90
stock, before caramelization, 47:240-24 1
structure of, 3 5 5
anomeric center in, 44: 14
and sweetness, 49238-3 10
substituted and derived, composition in
aqueous solution, 42:42-60
sulfates, 20:183-218,2510
sulfonic esters
displacement of, 25: 198-22
solvolysis of, 25203-209
sweetness, 45230
contraction coefficient, 45206
differences in, hypothesis about, 45:220
effect of infrared hydroxyl absorption
bands and hydrogen-bonding
strength, 4S:2 1 6 217
and hydrogen bonding, 45:214217
synthesis
from non-carbohydrate substrates,
4O:l-129
and separation, 36:5
trifluoroaceticacid in, 34:8
taste, importance of configuration in, 49207
and their derivatives, column
chromatography of, 10:55-94
related to altrose, 1:37-76
thermodynamic constants for mutarotation
of, 24:56
thio, 1:129-144,22:204,23:206
developments in the chemistry of,
18:123-199
dithioacetals, physical constants of, 32: 123
mutarotation of, 24:49
synthesis, 40: 101-104
transesterification, 49:235-236
transformation
in alkaline medium, 47:253
from cyclic to acyclic, 47:246
transport
anhydroalditols in, 25269
into yeast cells, 32:147-159,230
tritiated, for assay of enzyme activity, 27: 180
stability of, 27:139
unsaturated, 20:67-137,24: 199-266
chemical properties of, 27:249
physical properties of, 27:248
Wittig reaction in synthesis of,
27:227-239,244248
conformations of, 26: 122
formation of, 22:202
halogen addition to, 22:193, 195
nuclear magnetic resonance of, 24:265
oxirane sugar derivatives from, 25: 119,
167
rearrangement in hydrogen fluoride,
26: 187
synthesis of, 21: 194,33:263-264
utilization by yeasts, 32:125-134, 145-147,
39:347-404
generalizations and speculations,
32~221-222
o-deoxy-, 22:206
o-halo, reduction of, 22:206
Wittig reaction with free and partially
protected, 27:284292
Sugar-sphingosine conjugates, see
Glycosphingolipids
 SUBJECT INDEX
Sugar starvation, effect on glycosylation,
40:346
Sugar thiocynates, 44:92-93
synthesis
method, 44:123-139
by sN2nucleophilic displacement
reactions of sulfonyloxy groups in
hexopyranoses by thiocynate ion,
44:123-135
of sulfonyloxy groups in pentofuranoses
by thiocyanate ion, 44:135-139
Suicide inactivators, 48:364
Sulfation, of polysaccharides, 29:335
Sulfadimethoxine,D-glucuronic acid conjugate,
36:124-125
Sulfamates
hetero-, sweetness-structure relationship,
45:302
sweetness-stnrcture relationship,
45:297-303
Sulfamethomidine,o-glucuronic acid
conjugate, 36:125
Sulfamic acid, tetrahydro-2H-thiopyran-4-,
45299
Sulfate derivatives, circular dichroism,
45:92-94
Sulfate groups, determination of N-, in
polysaccharides, 29:343
Sulfates, 53:375-376
nomenclature, 52:116-117
of simple sugars, 20:183-218
Sulfate transferases, in mucopolysaccharide
biosynthesis, 26:437
Sulfatides, 24:383,395,403,40:237
synthesis of, 24:407
Sulfating agents, for sugars and glycosides,
33:50
Sulfation
of glycoproteins, 25:47&472
in mucopolysaccharidebiosynthesis, 26:437
Sulfhydryl groups, 23:117
in P-amylases, 23:334
ketonucleoside reaction with, 42:264
in phosphorylases, 23:347
Sulfides, carbohydrate, photolysis, 38:152
Sulfite pulping, color-stopping reaction in,
46:324-325
Sulfites, cyclic, of dithioacetals, preparation of,
32:48
Sulfoglycosphingolipids,24:383,395,403,
487
40237
synthesis of, 24:407
Sulfoisoxazole, o-glucuronic acid conjugate,
3 6124-125
Sulfolanes, solubility of sucrose in, 27:87, 11 1
Sulfolipids,44:387
in Mycobacterium tuberculosis, 30:236
plant, 2572
of sea urchins, 44:428
Sulfonamides
glucuronic acid conjugates following, 36:124
Helferichs work on, 495
Sulfonamido group, participation in sugar
reactions, 22:151
Sulfonate group
displacement in carbohydrates by halogen,
22:178
intramolecular displacement of, 33:125-131
Sulfonates, 53:3 75-376
carbohydrate, photolysis, 38:153-157,
162-163
nucleophilic-displacementreactions,
39~229-231
Sulfones
as antituberculosisagents, 29:2
carbohydrate, photolysis, 38:153-157,161
polysaccharide, degradation of, 31:226-229
of 5-thioaldopyranoses,23:212
Sulfonic acids, 53:359-360
1,4:3,6-dianhydrohexitolsesters, 49:125-130
Sulfonic anhydrides, sulfonylationof
carbohydrates by, 23:238
Sulfonic esters
of bridged-ring systems of carbohydrates,
displacementreactions of, 24:153
of Carbohydrates, 8~107-215,23:233-280,
24:139-197
physical properties and chemical stability
of, 23:253,257
of dithioacetals, formation and reactions of,
32:48-52
reaction with lithium aluminum hydride
and hydrogenolysisof sulfonyloxy
groups, 32:52
stereochemistry and displacement of
sulfonyloxy groups, 32:51
infrared spectroscopy of, 44:30
nucleophilic displacement of, 34235,107,
125
of polysaccharides, 29:337
488 SUBJECT INDEX
Sulfonic esters (continued)
of sugars
displacement of, 25: 198-202
solvolysis of, 25:203-209
Sulfonylation
of carbohydrates, 28:255
selective, 23:240, 244
by sulfonyl halides, 23:236
of nucleotides, 22:376
of pentose dithioacetals, 24: 175
Sulfonyl halides, in sulfonylation of sugars,
23:236
Sulfonyloxy group
displacement, 24:139
in aldoses, 25:llO-117
by fluorine, 48:130-131
of primary by fluorination, 38:204-212
of secondary by fluorination,
3 8 ~ 18-225
2 as sulfating agent for polysaccharides,
reaction with nucleophiles, 25:264
Sulfothiazole, D-glucuronic acid conjugate,
36: 124-125
Sulfotransferases, in glycoprotein biosynthesis,
25472
Sulfoxides
carbohydrate, photolysis, 38: 153-157
stereoselective synthesis of asymmetric,
27:222
of 5-thioalsopyranoses, 23:212
Sulfur, in hemiacetal rings of monosaccharides,
23:206
Sulfur compounds
of cyclic monosaccharides, 23: I 15-232
Of D-flUCtOSe, 22:281, 304
Sulfur dioxide, liquid, as solvent for sugars,
27:94
Sulfuric acid
hydrolysis
of glycoconjugates, 46:266
of polysaccharides, 28: 15
monosaccharide recoveries after,
46~259-260
pH of aqueous solutions of, 46:252
polymerization of o-glucose in, 21 :446
Sulfuric acid-acetic acid, rearrangements of
cyclitols in, 26:188-191
Sulfuric esters, of polysaccharides, 29:335-337
Sulfur monochloride
reaction with methyl a-o-glucopyranoside,
28:256,33:82
replacement of hydroxyl group in
carbohydrates by chlorine, 22: 183
Sulfur nucleophiles. for oxirane aldoses,
25:125, 139
Sulfur trioxide-N,N-dimethylformamide,
reaction with sucrose, 33:252
Sulfur trioxide-pyridine, selective sulfation
with, 3 3 5 0
Sulfuryl chloride
in chlorodeoxy sugars preparation, 28:300
maltose derivative reactions, 39:23 1-233
reaction with carbohydrates, 28:230-239,
33:250,259,41:9
with sucrose, 33:251-252,261
replacement of hydroxyl group in
carbohydrates by chlorine, 22: 183
selective chlorination of carbohydrates with,
33:72-77
29:335
Sultams, Helferichs work on, 4 5 5
Sunflower seeds, cell-wall studies on, 42:280
Sunn-hemp lectin, isolation, purification, and
properties, 35:306
Suosan, sweetness, 45:304
Surface-active compounds, Amadori
compounds, 22:279
Surface activity
of anhydroalditols, 25:255
of C-alkylated hexitols, 27:241
Surface-coating agents, sucrose unsaturated
fatty acid esters and ally1 ethers as, 33:273
Surfactants
anhydroalditols, 25:270
anhydrohexitols, 25:267
long-chain fatty acid esters as, 33:271
Suzuki, Bunsuke, 46:2-3
Svedberg equation, 47:357
Swainsonine, a-o-mannosidase inhibition,
48:342,344
Sweet clover disease, cattle, 39:2,5-6
Sweeteners
industrial development, 36: 19
nonsugar, sweetness-structure relationship,
45:295
nutritive, definition, 36: 15
from starch, 36:15-56
structure, 45:3 17-3 18
Sweetness, 45:200, see also Bitterness
AH, B concept, 45:200-201,213-223.231,
 SUBJECT INDEX
246,257-261,264,271,283-285,292,
297-299,303-307,322,341
AH, B system, 45:2 17-21 8
in various compounds, 45:221
AH, B units, 45:238
3- and 4-hydroxyl-groups role in,
45:243-245
and anomeric configuration, 45:207
biochemistry of, 45:325-349
chemoreception, possible courses of events
in, 45:346-349
comparisons, between two compounds,
45:341
degree of, methods of determining,
45:344-345
depression by bitterness, 45:239-240
of D-fructose, 22:23 I
early theories of, 45202-206
fundamental structural requirements for,
45~207-237
hydrophobic bonding concept, 45:223-23 I
3-hydroxyl groups role in, 45:260-261
4-hydroxyl groups role in, 45:260
6-hydroxyl groups role in, 45:261
initial mechanism of, 45:350
intensity, 45:350
different in sensory perception if, at
different concentrations, 45350-35 1
intensity versus time curves, 45:344
and lipoid solubility, 45:223
measurement, methodology, 45:349-35 I
perception, 45:201
plateau of maximum intensity, concentration
dependence of, 45:342-343
quality of, 45:339-349
queue hypothesis of, 45345-349
receptor, initial stimulation, 45:222
receptors participating in, 45:237
role of structure in, 45:200
saporous groups involved in, 45:227
and sensory system, 49325-326
side-tastes with, 45:340
stereochemistry, 45201-3 10
steric features in, 45:213
and structure of sugars, 45238-3 10
strucutural parameters for, schematic
representation, 45:3 15-3 17
and temperature, 45:221-222,250, 342
time-intensity relationship in, 45:34&345
tripartite concept, 45231-237
489
Sweet-sensitive protein, 45:328
Sweet-taste inhibitors, 45:336-339
Sweet-taste modifiers, 45:339
initial reaction with taste receptor
membranes, 45:338
Sweet-taste receptor, model, 45:335-336
Sweet-tasting compounds
AH,B,X glucophore of, 45:233
y-sites, 45:233-234
third structural feature comprising postulated
glucophore in, 45:233-234
Sycamore
cell wall studies on, 42:271, 275, 277-278,
280,282-285,288,298-305,336-337,
358,368-369,394
polysaccharides from, 24:374
Symmetrical diols, 53:44
Symmetry operations, 44: 12
Syneresis, 24:303
of agars gels, 24:277
of galactomannans, 31:242
Svnsepalum dulcijcum. 45:290
Synthesis
biochemical, of monosaccharides,
11:185-262
carbohydrate use in asymmetric, and
configuration proof. 27: 191-225
chemical. of D-glucuronic acid, 8:23 1-249
deamination of amines in, 3 1:70
of dextran, 15:34 1-369
dithioacetals ion, 32: 16
enzymic,
of glycogen and starch, 17:371407
of sucrose and other disaccharides.
52948
stereoselective, of asymmetric sulfoxides,
27:222
Synthetase
cellulose, 26:390
glucan, 26:383
starch, 26:384
sugar, 26:385
T
Tagatofbranose
I ,2:3,4-di-O-isopropylidene-o-,
26:25 I
2,3-O-isopropylidene-P-~-.and triacetate.
26:276
490 SUBJECT INDEX
Tagatopyranose
4-acetamido-4-deoxy-P-~-,tetraacetate,
24:97
OI-D- and P-D-, conformation in solution,
26:86
D-, 4-deoxy-4-fluoro- 1,2-0-isopropylidene-
P-,C-NMR data for, 46:173
1,2:4,5-di-O-isopropylidene-~-~-, 26:276
Tagatopyranoside, methyl 1,3,5-tri-O-acetyl-4-
bromo-4-deoxy-a-L-and-P-L-, preparation
of, 28:266
Tagatose, 7:99-136
Ct-D-
crystallography of, 25:60,31:365
sweetness-structure relationship, 45:253
composition in aqueous solution, 42:65
D-, 24:366
conformation of, 23:32
cyclic acetal, 26:251
properties of, 26:273
infrared spectrum of, 23:39
preparation from o-galactose. 31:7 1
purification of, and diisopropylidene
acetal, 26:198
synthesis, 41:8
taste properties, 45:254
1-deoxy-o-, composition in aqueous solution,
42:38
1-deoxy- 1-(dibenzylarnino)-o-, preparation
and deamination of, 31:5 1
4-deoxy-4-fluoro-o-, preparation, 38:2 18
L-, conversion into L-ascorbic acid by
irradiation, 37: 107-108
liquid chromatography methods for analysis
of, 46:33
6-0-methyl-o-, composition in aqueous
solution, 42:38, 46
preparation, 36: I 1
Tagatose 6-phosphate, D-, composition in
aqueous solution, 42:46
Tagatoside, methyl OL-DL-,synthesis, 40:7 1
Tailings, definition, 36:217,229
Takaamylase
a-D-mannosidase as structural reagent for,
28:444
gas-liquid chromatographic analysis of,
28:54
Takaamylase A glycan, structure, 37: 173
Takadiastase, r-arabinanase activity of, 42:383
Talitol
2-acetamido- 1,2-dideoxy-l -nitro+-, 24: 133
1-amino-1 ,S-anhydro-l ,h-dideoxy-~-,23: I38
1,4-anhydro-5,6-dichloro-5,6-di-deoxy-o~-,
preparation of, 33535
4-azido-3-0-benzoyl-4-deoxy-~-, 22: I 18
D-
anhydridation of, 25233
crystallography of, 2 5 6 0
3,5-di-O-(acetoxymethyl)-l,6-di-O-acetyl-~-,
22: 13
3,4-dI-O-benzoyl-o-, 22: 1 17
di-0-isopropylidene-D-, dibenzoate, 22: 1 18
DL-, crystalline, 26: 14
L-
crystalline, 26: 14
crystallography of, 25:60
4-0-acetyl-3-0 benzoyh-, 22: 1 17
I ,3:2,4:5,6-tri-O-methylene-~-, acetolysis of,
22: 13,39:24
Talofuranose
5-acetamido-5,6-dideoxy-~-, 23: 177
5-amino-3-O-benzyl-5,6-dideoxy-l,2-0-
isoprpylidene-P-L-, 23: 139
1,5-anhydro-a-o-, preparation of. 34: 157
1,6-anhydro-a-o-, 39: 163
preparation of, 34: 153, 157
stability of, 34: 153
6-deoxy-2,3 -0-isopropylidene-5-O-methyl-
D-, 24: 194
3-0-benzoyl- 1,2-0-isopropylidene-5,6-di-0-
(methylsulfony1)-P-L-, sulfonate
displacement in, 33: 127
Talohranoside
methyl 5-acetamido-5,6-didieoxy-2,3-0-
isopropylidene-a-L-, 23: I 77
methyl 5-amino-5,6-dideoxy-2,3-0-
isopropylidenea-L-, deamination of,
31:56
methyl 5-amino-5,6-dideoxy-2,3-0-
isoprpyhdene-a-D-, 23: 178
methyl S-azido-5,6-dideoxy-2,3-0-
isoprpylidene-a-r, 23: 177
methyl 6-deoxy-2,3-O-isopropylidene-a-~-,
24: 189
methyl 6-deoxy-2,3-0-isopropylidene-0~-~-,
synthesis, 39: 166
methyl 5,6-dideoxy-5-iodo-2,3-0-
isopropylidene-a+-, preparation of,
28:242,282
methyl 5-0-benzoyl-6-deoxy-2,3-0-
 SUBJECT INDEX
isopropylidene-a+, 24: 155
preparation of, 28:282
methyl 5-0-benzoyl-6-deoxy-2,3-0-
isopropylidene-p-L-,preparation of,
29:s
methyl S-benzoyl-6-deoxy-2,3-0-
isopropylidene-5-thio-a+-,23:2 18,219
Talofuranosiduronic acid, methyl 2,3-0-
isopropylidene-P-oL-,methyl ester,
synthesis, 40:75-76
D-Taloiiuanosylfluoride, 2,3,5,6-tetra-0-
benzoyl-a-, 'H- and I9F-NMR data for,
46:98
Talofuranosyl fluoride per-0-benzoyl-a+,
synthesis, 38:201
Talono-1,4-lactone, L-, irradiation, 37: 123
Talopyranose
a-D-, 4%74
crysta1 structure bibliography, 3843 l a 3 2
4-amino-1,6-anhydro-4-deoxy-P-~-,
preparation of, 34:126
1,4-anhydro-, 6-deoxy-2,3-0-isopropylidene-
p-L-, synthesis, 39: 165-166
1,6-anhydro-
p-0-
acetalation of, 34:90-91
complexes, 3 4 5 5
conformation of, 34:61
deuterated and other derivatives,
synthesis of, 34:97-99
sweetness-structure relationship, 45269
p-toluenesulfonylationof, 34:82
3-C-(hydroxymethyl)-2,3-0-
isopropylidene-p-D-,preparation of,
34: 100
D-, acetolysis of, 34:65
2,4-di-0-p-tolylsulfonyl-p-~-,preparation
of, 34:82
2,3-O-isopropylidene-p-~-
formation by acetal migration, 34:205
mass spectrometry of, 3462
mass spectrum of, 29:75
3,4-O-isopropylidene-p-~-
acetal migration, in, 34:205
crystal structurebibliography, 32:361
hydrolysis and isomerization, 39:26
mass spectrometry of, 34:62
3,4-0-isopropylidene-2-0-p-tolylsulfonyl-
P-D-, reactivity of, 24:154, 163
2,3-0-isopropylidene-4-0-p-tolylsulfonyl-
49 1
p-D-,reactivity of, 24: 154, 163
per-0-substituted, 34:77
5-a-carba-a-DL-, 48:23
D-
2-deoxy-2-fluoro-
a anomer, 'H- and 19F-NMRdata for,
4688-89
p anomer, 'H-and 19F-NMRdata for,
46:89
orientation of hydroxyl groups for, in
"C,(D)conformation, 4575
6-deoxy-S-thio-~-,23:218
2,4-diamino-1,6-anhydro-2,4-dideoxy-p-~-,
preparation of, 34: 122
1,6:2,3-dianhydr0-
p-D-
mass spectrometry of, 34:62
preparation of, 34:107, 113
4-O-methyl-P-~-,as synthetic
intermediate, 34: 121
1,6:3,4-dianhydro-P-o-,preparation of,
34:107,113
4,6-o-isopropylidene-o-,synthesis, 39:73
2,3,4-tri-0-acetyl-1,6-anhydro-p-~-,
conformation of, 26:60
Talopyranose pentaacetate
5-a-carba-a-~~-,4&27
carba-P-DL-,48:34-35
Talopyranoside
D-
2-deoxy-2-fluoro-, trifluoromethyl3,4,6-
tri-0-acetyl-P-, 'H- and I9F-NMR
data for, 4689
methyl 4-deoxy-4-fluoro-a-
"C-NMR data for, 46: 164
'H-and I9F-NMR data for, 46:94
6-0-trityl-a-, IH- and I9F-NMR data
for, 46:94
methyl 4,6-dideoxy-4,6-difluoro-a-
I3C-NMR data for, 46:175
'H- and I9F-NMR data for, 4 6 150
2,3-0-isopropylidene-a-, IH- and I9F-
NMR data for, 46: 150
methyl 4,6-dideoxy-4-fluoro-a-
6-amino-, 'H-and I9F-NMR data for,
46: 120
6-azido-, 'H- and I9F-NMR data for,
46:119
2-deoxy-2-fluoro-~-,48: 164
4,6-dideoxy-4,6-difluoro-a-~-, 48: 149
492 SUBJECT INDEX
Talopyranoside (continued)
methyl 4-acetamido-4,6-dideoxy-
CI-D-, 23:187
(Y-L-,23:187
methyl 4-amino-4,6-dideoxy-2,3-0-
isopropylidene-a+, 24: 153, 190
deamination of, 31:42
methyl 2,3-anhydro-6-deoxy-4-0-methyl-a-
L-, 25: 147
methyl 3,4-anhydro-6-deoxy-2-0-methyl-a-
L-, 25147
methyl 3,4-anhydro-2-0-benzoyl-6-deoxy-~1-
D-,25:147
methyl 2,3-anhydro-4,6-0-benzylidene-~-,
25:116, 140
methyl 2,6-anhydro-3,4-0-isopropylidene-P-
D-,24: 197
methyl 2-(chloromercuri)-2-deoxy-~1-~-,
crystal structure of, 2975
methyl 6-deoxy-a-~~-, synthesis, 40:69
methyl 6-deoxy-2,3-0-isopropylidene-4-C-
(2-methyl- 1,3-dithian-2-yl)-a-~-,
chemical shift values for, 32:42
methyl 4-deoxy-2,3-0-isopropylidene-4-C-
methy1-6-O-methyl-a-~-,synthesis of,
27:281
methyl 4,6-dideoxy-4-(dimethylamino)-a-~-,
methiodide, crystal structure
bibliography, 30:452
methyl 3,4-di-0-acetyl-2,6-anhydro-p-~-,
crystal structure bibliography, 38:442
methyl 4,6-O-benzylidene-, hydrolysis of,
34:202
Talopyranosyldaunomycinone
7-0-3-amino-2,3,6-trideoxy-2-fluoro-a-~-,
48:232-233
7-0-2,6-dideoxy-2-fluoro-a-~-, 48:232-233
D-Talopyranosyl fluoride
2,3,4,6-tetra-O-acetyl-(~-,'~C-NMR data for,
46:161
3,4,6-tri-O-acetyl-2-deoxy-
2-bromo-a-, 'H- and I9F-NMR data for,
46:130
2-fluoro-P-, 'H-and I9F-NMR data for,
46:147
2-iodo-u-, 'H- and I9F-NMR data for,
46: 130
Talose
2-acetamido-
2-deoxy-o-, 24:134
2,6-dideoxy-~-,in Type 5 capsular
polysaccharide,33:302
5-acetamido-
5,6-dideoxy-~-,23: 176
5,6-dideoxy-~-,23: 176
2-amino-
2-deoxy-~-,22: 131
2,6-dideoxy-~-
biosynthesis, 44:296-298
deamination of, 31:40,44
3-amhO-
3-deoxy-~-,22: 131
3,6-dideoxy-~-,22: 128
2,5-anhydrO-D-, 25: 186
preparation of, 31:25
composition
in aqueous solution, 42:63
in nonaqueous solvent, 42:68
D-
acetonation of, 34: 184
derivatives, cyclic acetals, table, 34:
239
gel chromatographyof, 25:3 1
nonselective spin-lattice relaxation rates,
45: 148
preparation from D-galactose by
acyloxoniumrearrangement, 26: 161
proton spin-lattice relaxation rates, 45: 150
2-deoxy-, 2-fluoro-~-,labeled, 48: 192
6-deoxy-
composition in aqueous solution, 42:63
D-,21:173
ester with guanosine 5'-pyrophosphate,
28:321
L-, 21~173,179, 181,51:226
biosynthesis, 44:296-298
nucleoside, preparation of, 42:254
1,2:5,6-di-O-isopropylidene-
p-D-,reaction with triphenylphosphine-
carbon tetrachloride, 28:247
D-
formation of, 34: 184
preparation of, 34: 184
L- derivatives, cyclic acetals, Table, 34:239
mutarotation of, 23:23
Taluronic acid, 2-amino-2-deoxy-~-,bio-
synthesis, 44:296-298
Tamarind-kernelpolysaccharide
dextrinization,47:3 10-3 12
gas-liquid chromatographyof, 28:56
 SUBJECT INDEX
Tamarindus indica
cell-wall studies on, 42:287-289
polysaccharides from seed of, 24:372
Tam-Horsfall glycoprotein, 25:472,478
in urine, 24:441, 25:414415
Tangerine, 42:371
TANGO pulse, 51:21
Tannin, effect on pectinesterase, 33:337
T antigen, 45: 17 1
Tapioca, dextrins source, 47:3 17-3 18
Tara gum, uses of, 31:246
Tartaric acid
configuration of, 21:32, 25:55
nomenclature of, 21:34
D-and L-, derivatives, crystallography of,
2558
dextro-, see Threaric acid, L-
Tartronic acid, trimethylsilylated, mass
spectrometry of, 29:80
Taste
blindness, 45:3 1 1
and chemical composition, early
explanations of, 45:206
and hydrophobicity, 45:223
intensity, measurements, types of measures
used for, 45:350
perception
effect if structure on, 45:20&20 I
mechanism, 45:200
peripheral mechanisms in, 45326-328
receptor mechanism for, 45:209-2 14
factors determining response of,
45:210-211
sense, 45: 199
and sensory system, 45:325
and structure, early explanations of. 45:
205
Taste cell transduction, steps in, 45:2 12-2 12
Taste couples, 45:218
Taste receptor, 45:326-328
binding of taste stimulus to, 45:329-330
versus behavioral responses, 45:329-330,
334
binding to, 45:328-339
membranes initial interaction with taste
modifier molecules, 45:338
in sweetness, 45:237
Taste theory, evolution of, 45:200-201
Tauromerism, keto-enol, 26:6
Tautomeric forms of sugars, 42: 16
493
Taxonomy, fungal, polysaccharides as aids in,
23:414
Tay-Sachs disease, 25:478,40:27&279
hexosaminidases in, 3 1 5 6
T-domains, mucus glycoproteins, 47:353
Teichoic acids. 21:323-375
from actinemycetes, 21:363
from Bacillus .suhtilis, 21:350, 354
bacterial polysaccharides, 48:3 15-3 16
biosynthesis of, 21:372. 26:476-481, 28:334
carbon- 13 nuclear magnetic resonance
spectra, 38:82, 88
deamination and structure of, 31:76
degradation of, 21:340
dextran-antiteichoic acid cross-reactions,
30:404
discovery of, 21:326
function of, 21:371
glycerol. 21:334,346
hydrolysis of. 21:33 I , 3455346,352
interaction with concanavalin A, 35: 175-177
from Lactobacillus arabinosus, 21:334, 361
from Lactohacillus buchneri. 21:350
from Lactobacillus casei, 21:341
lipid intermediates in biosynthesis of, 26:430
location in relation to cell structure. 21:365
membrane, 21:332
polymers, hydrolysis of, 28: 16
ribitol, 21:354
alkali action on, 21:358
from Staphylococcus arahinosus. 21: 175,
363
from Staphylococcus uureus. 21:343
Copenhagen, 21 :360
H, 21:359
from Staph.vlococcus 1acti.r.21 :342, 347, 350
from Streptococci. 21:344
wall, 21:346
Telluric acid, complex with-D-fructose, 22:288
Temperature
coefficient, for anomerization, 24:5 1
effect on
P-amylase action, 23:341
on enzyme kinetics, 23:295,327
on phosphorylase action, 23:356
cyclic acetal preparation, 26:201
gel chromatography, 25: 19
solubility of sucrose. 27:89
utilization of monosaccharides by yeasts,
32230
494 SUBJECT INDEX
Terpenes, C-glycosylated, syntheses by Wittig
reaction, 27:238
Terphenyl, in gas-liquid chromatography,
28:46
2-ter&Butylanthraquinone, for enhancing
detectahility of carbohydrates, 46:67
Testes, D-fructose metabolism in, 34:298-305
Testosterone, plasma, and seminal D-frutose
values, 34:303-305
Tethered approach connection, 53:300-301
Tetra-0-acetyl- 1,5-anhydro-~-arabino-hex- 1-
enitol, synthesis, 49:85
Tetra-0-acetyl- 1-bromo-P-o-glucopyranosyl
chloride
elimination reactions, 49:89-90
synthesis, 49:61
Tetra-0-acetyl-5-hromo-~-~-glucopyranosyI
chloride, synthesis, 49:61
Tetra-0-acetyl- 1-bromo-P-o-glucopyranosyl
cyanide, synthesis, 49:58
Tetra-0-acetyl- 1-bromo-P-D-ghcopyranosyl
fluoride, synthesis, 49:6 1
Tetra-O-acetyl-5-bromo-~-~-glucopyranosyl
fluoride, synthesis, 49:61
Tetra-O-acetyl-5-bromo-~-~-xy~opyranose,
49:4748
elimination reactions, 49:87
Tetra-0-acetyl-o-ghcopyranosyl radical, 49:72
Tetraammonium 5 -p-adenyl-(3 ,5)-
thymidylyL(3 ,5)-adenylyl-(3 ,5 )-
thymidine, hydrate, crystal structure
bibliography, 38529
Tetra-O-benzoyl-2-bromo-~-glucono- 1,5-
lactone, synthesis, 49:62-63
Tetrabutylammonium fluoride, fluorinating
agent, 38:219
Tetracosanoic acid, 24:396,410
2-hydroxy-, 24:396-397,410
Tetradecanoic acid, methyl ester, esterification
of sucrose with, 33:44
Tetradeca(ribonucleotide), synthesis, 39:42
Tetradeoxynonulosonic acids, 5,7-diamino-
3,5,7,9-, 47:180-181,48:298
Tetraethyleneglycol, as matrix for f.a.b.-mass
spectrometry, 45:26
Tetrahedral-lattice model, 51:80-81
Tetrahy&ohran-2-one, as solvent for sugars,
27:106
spiro-Tetrahydro-3-methyl-2-(czs-2,3,4,6-tetra-
O-acetyl-~-glucopyranosyl)-3-fi1ranol,
crystal structure, 43:250-25 1
2,3,6,7-Tetrahydro-7-methylcyclopen[b]-
azepin-8-( lH)-one, 46:3 15
Tetralin, as reaction medium for reduction of D-
glucose, 27: 106
2,3,2,3-Tetramethoxyhenzoin,
photocyclization of, 46:201
I , 1,3,3-Tetramethylurea, as matrix for f.a.b.-
mass spectrometry, 45:27
Tetra-O-acetyl-2-acetarnido-2-deoxy-
carbahexoses, synthesis, 48:60,62
Tetra-0-acetyltrillenogenin mono-p-
bro-mobenzenesulfonate, crystal structure,
43:268-269
Tetra- 0-benzoyl-a-o-mannopyranosyl
bromide, 48:73
(+)-2-O-(Tetrahydropyran-2-yl)uridine,crystal
structure, 43:366-367
Tetraphosphoric acid, in selective
phosphorylation of Carbohydrates, 33:47
Tetraric acids, trivial names, 52: 11 1
Tetrasaccharide AX,, from arabinoxylan,
32:347
Tetrasaccharide-glycoside, synthesis, 49:228
Tetrasaccharides, 51: 151
in plant kingdom, 37:310-311
Tetrazole
I-p-D-, ribohranosyl-, crystal structure
bibliography, 34:372
derivatives, from sugar derivatives, 25393
IH-
5-amino- 1 -P-D-nbohranosyl-, crystal
structure bibliography, 37:434
1 -P-o-ribofuranosyl-, crystal structure
bibliography, 37:434
2H-, 5-amino-2-P-~-ribofuranosyl-, crystal
structure bibliography, 37:434
Tetrazolides, (arylsulfony1)-, in nucleotide
formation, 36: 158
Tetrazolium Blue, for enhancing detectability
of carbohydrates, 46:67
Tetrazolium bromide, 5-a-~-lyxofUranosyl-2,3-
diphenyl-, crystal structure bibliography,
38:470
Tetr-3-enose, 3-0-acetyl- 1,2-0-isopropylidene-
a-L-glycero-, 24:248
Tetritols
acetals of, 7:137-207
acetates, gas-liquid chromatography of,
28:92
anhydro-, 25:230
derivatives and, 25:271
 SlJBJECT INDEX
2-deoxy-
oL-glycero-. 4-diethylborinate 1.3-
ethylboronate, selective cleavage,
39:54
2-fluoro, synthesis, 40: 104-1 05
3-deoxy-~~-gfvcero-
ethylhoronate, structure, 3 5 4 3
phenylboronate, structure, 3 9 4 3
1,3:2,4-di-O-benzyIidene-, selective
hydrolysis, 39:20
halogen derivatives, 22:213
1,3-0-benzylidene-, sulfonic esters.
reduction of, 23:275
Tetritol- 1 -yl imidazoline-2-thione, 4-11-
arabino-, 1-(4-methoxyphenyl)-3-methyl-.
crystal structure bibliography, 37:397
Tetrodialdose, L-threo-, from o-glucose
radiolysis, 37:41
Tetrofuranose, 4-C-isopropyl-l.2-0-
isopropyhdene-cY-D-xyk-, proton magnetic
resonance spectra, non-equivalence of
nuclei in, 27:63
Tetrofuranoside, methyl 3-deoxy-3-C-forniyl-
a-L-threo-, 22: 171
Tetrofuranosylamine, 2-deoxy-P-~-ghvero-,
48:242-243
Tetronic acid, 4-amino-3.4-dideoxy-I -glvcrro-,
from butirosins, 30: 131
Tetronitrose
natural occurrence of, 4 2 7 3
structure of, 42:71,78
synthesis of, 423123, 125
Tetroses
3-acetamido-2,3-dideoxy-
D-glycero-,synthesis, 40: 1 17
or-glycero-, synthesis, 40: 1 17
in aqueous solution, 42: I7
branched-chain, in formose reaction
products, 29:211-212
crystallography of, 2 5 5 8
deoxy-, melting points and optical rotations
of, 26:280
2-deoxy-~-g/,vcero-, 21: 154
halogen derivatives, 22:213
polarography of, 29: 129, 150
Tetmlose
o-and L-glycero-, polarography of, 29: 129
3,4-di-O-benzoyl- I -bromo-l -deoxy-n-
glycero-, 22: 197,2 13
preparation, 38:243
3,4-di-O-benzoyl- I -chloro- I-deoxy-~-
495
glvcero-, 22:197, 213
preparation, 38:243
3,4-di-O-benzoyl- 1-deoxy- 1 -diazo+
glycero-, halogen derivatives from,
31:60
L-glycero-
polarography and electroreduction of,
29:13 1-133
preparation, 37:142
3,4-O-dibenzoyl- I -deoxy-l -diazo+
glycero-, reaction with hydrogen
fluoride, 38:243
2-Tetrulose, ni.-g/ycero-. synthesis, 40:26,
29
Textile industry, galactomannans in, 31:3 I 1
Thallium(II1) trifluoroacetate, reaction with
dithioacetals. 3260
Thallium L-ascorbate, crystal structure,
43:337
Thaumatin
antibodies, cross-reactivity, 45333-334
immunoreactivity, and relative sweetness,
45332
relative sweetness, 45:332
sweetness. 45:2 13
time-intensity relationships for, 49346
three-dimensional structure, 45:333-334
Theanderose, in honey, 25:297, 301,308
2-Thenoic acid, cellulose esters, preparation of,
29:338
Theophrastus, 45:200,201
Theophylline
7-P-~-ribofuranosyl-,5'-phosphate, 22:370
7-(6-deoxy-P-~-/yxo-hexopyranosyl-2-
ulose), biological activity of,
42:262-263
7-(3-deoxy-3-nitro-P-~-galactopyranosyl)-,
acetylation with acetic anhydride and
perchloric acid, 33:3 1
7-(3-deoxy-3-nitro-~-1~-manno-pyranosyl)-,
acetylation with acetic anhydride with
boron trifluoride, and with phosphoric
acid, 33:3 1
7-(2,4-di-O-acetyl-3,6-di-deoxy-r-etyfhro-
hex-2-enopyranosyl)-, 24:24 1
glycuronic acid conjugate, preparation,
36: 127
7-(methyl 2-acetamido-6-O-acety1-2,3,4-
trideoxy-P-~-etylhro-hex-2-
enopyranosid-4-yl),crystal structure,
43:296
496 SUBJECT INDEX
Theophylline (continued)
7-(methyl 2-acetamido-6-O-acety1-2,3,4-
tridoexy-a-o-threo-hex-2-
enopyranosid-4-yl), crystal structure,
43:294296
N-glucosyl-, 2 1 ~ 2 4
7-(3-O-acetyl-4,6-dideoxy-~-~-gl~vcero-hex-Thiazoles
3-enopyranosyl-2-ulose), antitumor
activity of, 42:263
Thermal analysis, differential, during starch
pyrolysis, 22:487,489
Thermal decomposition, 47:203-204
Thermodynamics
of gels, 24:306
for mutarotation of sugars, 24:5 I , 56
Thermogravimetric analysis, during starch
pyrolysis, 22:487
Thevetose, cardenolides containing, 21 :286
Thiabenzazole, antifungal activity, 49: 166
(E,E)-Thiacyclodeca-4,7-diene,49: 160
Thiadiazoline, derivatives, from sugar
derivatives, 25:393
Thiamine, 52:267-307
biosynthesis
from 5-amino- 1-( p-o-
ribofuranosyl)imidazole, 52:300-
303
problems in the study, 52:268-269
cleavage of bond between pyrimidine and
thiazole, 52:271-272
mass-spectrometric fragmentation,
52:274-275
pyramine degradation, 52:274
structure, 52:268
synthesis
derepression by 5-amino- 1-(P-D-
ribofuranosy1)imidazole 5 -
phosphate, 52:292-293
in spinach chloroplasts, 52:277
thiazole
degradation, 52:27 I , 273
five-carbon chain, pentulose as precursor,
52:288-291
pyruvate and glucose as five-carbon chain 1-Thioaldose derivatives, thioglycosides
precursors, 52:282-283
synthesis by E. Cali cells, 52:275-277
Thiamine diphosphate, biosynthesis, from
thiazole and pyrimidine precursors,
52:269-271
Thiamine thiazole
isolation of Carbon C-2, 52:27 1,273
from pentulose and glycine, 52:291
1,2,3,4-Thiatriazoles, model, synthesis,
44:lOl
Thiazine, derivatives, from sugar derivatives,
25:403
amino-, C-glycosylated, synthesis, of,
27:295
biosynthesis, in yeasts, 52:306
cleavage of bond with pyrimidine,
52:271-272
degradation, 52:271, 273
mass-spectrometric fragmentation, 52:274
metabolites, with probable deoxypentulose
origin, 52:284-287
precursors, biosynthesis of thiamine
diphosphate, 52:269-27 1
Thiazolidine, derivatives
preparation of, 32:20
from sugar derivatives, 25:385
Thiazolidinecarboxylic acid, 2-(o-galactitol-l-
yl)-4-, diastereomers, 46:3 17-3 18
Thiazoline, derivatives, from sugar derivatives,
25:352,386
Thietane ring, sugar derivative, 25: 157
Thin-layer chromatography, 46:28
metal cation4arbohydrate complexes
applications, 47:35-36
Thin-layer ligand-exchange chromatography,
metal-sugar complexes, 4 7 5
Thioacetals
aldofuranosides and thioaldofuranosides
from, mechanism of, 21:117
glycofuranoside preparation from di-,
21:112-113
mass spectra of, 21:85, 93
of deoxy sugars, 21:205-206
as photosensitive protecting groups, 46: 195
Thioaldofuranosides, 21:114
ethyl, melting points and specific optical
rotations of, 21: 142
mechanism of formation of, 21: 1 17
preparation, 52: I83
Thioalkoxide group, participation in sugar
reactions, 22: 155
Thiobarbituric acid
5-butyl-2-, cyclodextrin inclusion complexes
with, 46:223-224
 SUBJECT INDEX
5-hexyl-2-, cyclodextrin inclusion complexes
with, 46:223-224
5-pentyl-2-, cyclodextrin inclusion
complexes with, 46:223-224
5-propyl-2-, cyclodextrin inclusion
complexes with, 46:223-224
Thiobarbituric acid, as reagent for D-fructose
estimation, 22:239
Thiocarbamates,carbohydrate,photolysis,
38:157-158,164
Thiocarbohydroximidicacid, C-allyl-S-P-D-
glucopyranosyl-0-sulfo-, potassium salt,
monohydrate, crystal structure
bibliography, 38:440
Thiocarbonates, of carbohydrates, 15:91-158
Thiocarboxamides,synthesis, 44: 109-1 10
Thiocyanate ion, cyclodextrin inclusion
complexes with, 46:221
Thiocyanates,44:9 1
as solvents for sugars, 27:95
Thiocyanogen,reaction with tri-0-acetyl-D-
glucal, 24:209
1-Thioglycerol
cluster ions, 45:29
as matrix for f.a.b.-mass spectrometry,
45:26-28,54
Thioglycolic acid, cleavage of deaminated
thiamine, 52:271-272
Thioglycosides,52: 179-200
anomeric activatioddeactivation, 52: 190,
192
block synthesis of oligosaccharides,
52: 191-1 98
D-glucopyranosyl residues, 52: 195, 198
1-active ganglioside analogue, 52: 193-
194
conversion into other glycosyl donors,
52:183-184
direct activation, 52:187
formation from dithioacetals,32:66-70
as glycosyl acceptors in oligosaccharide
synthesis, 52: 197-198
glycosylationreactions, armed-disarmed
concept, 52: 189-193
as glycosyl donors, 50:22
in situ generation of glycosyl halides,
52:184-185
nomenclature, 52: 135-136
preparation, 52: 181, 183
promoters, 52: 185-1 89
497
stereoselectivity,52:189-190
steric activation-deactivation,52: 19&191,
193
I-Thioglycosides
3-0-glycosidic linkage formation,
50:29&292
hydrolysis of, 22:35
Thioguanine nucleosides, biological activity of,
42: 132
Thioketonucleosides,synthesis of, 42:257
Thiolanediol 1-oxide
cis-3,4-, phenylboronates, separation of
stereoisomers,3 5 5 8
3,4-, esters, thio carbohydrate substrates,
40: 101-1 04
Thiol group, 23:117,334,347
Thiol reduction, mucus glycoproteins tertiary
structure, 47: 352-3 5 3
Thiols
in dithioacetal preparation, 32: 19-20
reaction with aldoses, 21:19
1-Thiols, thioglycosidespreparation, 52: 183
Thionobenzoyl group, participation in sugar
reactions, 22: 169
Thionucleosides,preparation of, 42:245
Thionyl bromide, and hexamethylphosphoric
triamide, bromination of D-ribonucleosides
by, 28:250
Thionyl chloride
and hexamethylphosphorictriamide,
chlorination of D-ribonucleosides by,
28:250
polymerization of sugars by, 21:447
reaction with sucrose, 33:252
selective chlorination with, in N,N-
dimethylformamide,33:80
Thiopental, cyclodextrin inclusion complexes
with, 46223-224
Thiophene-2-aldehyde, 3-bromo-, Fourier
proton magnetic resonance spectroscopy
of, 27:62
Thiophenes
2-~-~-ribofuranosyl-, preparation of, 33: 160
~-thveo-3,4-dihydroxy-2,3,4,5-tetrahydro-, 2-
dimethyl acetal, 23:208
formation of, 46:3 18
tetrahydro-3,4-dimethyl-,S-oxide, as solvent
for sucrose, 27:lll
tetrahydro-I ,I-dioxide, solubility of sucrose
in, 27:87
498 SUBJECT INDEX
Thiophenes (continued)
S-oxide, as solvent for sugars, 27: 1 11
tetrahydro-3-methyl-, S-oxide, as solvent for
sucrose, 27: 1 1 1
2-(2,3,4,6-tetra-O-acetyl-P-~-
glucopyranosy1)-, synthesis of, 33:
143
Thiophenobarbital, cyclodextrin inclusion
complexes with, 46:223-224
4-Thiopseudouridine, crystal structure,
43:311-313
5-Thiopyranosides, hydrolysis and
methanolysis of, 22:37
Thiosemicarbazides, synthesis, 44: 106-109
Thio sugars
biological activity of, 42:135-137
composition in aqueous solution, 42:43,
52-54
C-S-C-H pathways, torsion angles and
vicinal coupling constants, 51:55
mutarotation of, 24:49
in solution, 49:3 I
Thiothymine, 1-(tetra-0-acetyl-P-o-glycosy1)-
2-, synthesis, 44:97-98
Thiouracil, 2,5-anhydro-l-(2,3-0-
isopropylidene-P-o-ribofuranosyl)-2-,
crystal structure, 43:325-326
Thioureido group, participation in sugar
reactions, 22:146, 164
Thiourethano group, participation in sugar
reactions, 22: 146
Thiouridine, 5,6-dihydro-2-, crystal structure,
43:36&36 1
Thiouridine hydrochloride, 2,3-0-
isopropylidene-5-(methylamino)-methyl-
2-, 43:335
8-Thioxoadenosine, monohydrate, crystal
structure, 43:318
Thomosamine, 23: 155
Thompson, Aha, obituary of, 19:1-6
Thorpe-lngold effect, 49:24
Threaric acid
L-
(+)-, 2 1 ~ 3 4
configuration of, 31:82
in L-apiose synthesis, 31: 180
precursor for sugar syntheses, 40: I 15-
1I7
2-0-(carbozymethyl)-or-, 2526 1
Threitol
1,4-anhydro-, 25:230
L-, infrared spectrum of, 25252
I -3-O-benzylidene-2,4-di-O-p-tolylsulfonyl-
L-, 23:275
I , I-bis(acetamid0)-I-deoxy-L-,preparation
of, 31:83
catalytic oxidation of, 25262
D-, gas-liquid chromatography of, 28:93
2-deoxy-2-fluoro-o~-,synthesis, 38:237,
40: 104
4-deoxy-2,3-U-isopropylidene-o-, synthesis,
40:117
1,3:2,4-di-O-benzylidene-~-, selective
hydrolysis, 39: 19
1,3:2,4-di-O-methylene-~-, dipole moment
and conformational analysis of,
26:6546
m.-, synthesis, 40:29
L-, synthesis, 40:115
Threofuranose
4-acetamido-4-deoxy-o-, 23: 196
1,2:3,3-di-O-isopropylidene-[3-C-
(hydroxymethy1)-P-L-,preparation of,
31:183
I ,2-O-isopropylidene-P-~-,in o-apiose
synthesis, 31:179
Threofuranoside
methyl 3-deoxy-3-C-formyl-a-~-,
preparation of, 31:29
methyl 2-deoxy-2-C-formyl-P-o-,
preparation of, 31:29
a-~-threo-Hex-4-enopyranosiduronic acid,
methyl 4-deoxy-2,3-di-O-methyl, methyl
ester, synthesis, 39:248
rhren- I ,4-Lactone, 2,6-di-O-benzoyl-3,5 -
dideoxy-o,r.-, 50: 172
Threonic acid
4-bromo-4-deoxy-DL-, synthesis, 40:5
4-chloro-4-deoxy-o~-,synthesis, 40:5
4-(cyclohexylamino)-4-deoxy-~-. 23: 14 1
4-deoxy-o~-,synthesis, 40:5
DL-, synthesis, 4 0 : 5 4
L-, synthesis, 40:115
o-Threonic acid, 2-C-methyl-, isolation and
characterization of, 28: 195
Threonine
P-o-glucopyranosyl-( I+~)-(Y-L-
fucopyranosyl-( I-~)-L-, isolation and
synthesis, 39:330
(9-P-o-ribofuranosylpurin-6-ylcarbamoyl)-
 SUBJECT INDEX
L-, crystal structure bibliography,
32:383
L-
a- and p-o-glycosyl derivatives,C-NMR
chemical-shifts data, 43:23
carbohydrate chains linked to, in
glycoproteins, 26:458
carbohydrate substrate, 40: 1 17
in cell-wall glycoproteins, 42:298
derivatives, glycosylation, 43: I56 - 172
in glycoprotein from sheep and ox. 33:7
in glycoprotein linkages, 25:4 I 8, 425
mass spectra of acetylated 0-glycosyl
derivatives, 29: 105
0-a+-galactosylated peptides, C-N MR
chemical shifts, 43:28, 3 I
3-0-Dg~yCOSy~, 43: 156-175
0-glycosyl derivatives, synthetic,
43:135-201
0-glycosylation, 43:27
0-glycosyl derivatives, 43:27-28
Threono- 1,4-lactone, DL-, synthesis, 40:6
Threose
4-acetarnido-4-deoxy-o-, 23: 141
D-
composition in aqueous solution, 42:31,
3637
crystallography of, 25:58
derivatives, cyclic acetals, Table, 34:2 10
from o-xylose oxidation, 33:98
polarography of, 29: 129
synthesis, 40:121-122
DL-,synthesis, 40:5-8, 90
L-
crystallography of, 25:58
derivatives, cyclic acetals, Table, 34:2 I0
L-ascorbic acid from, 37: 149-1 50
from L-sorbose by oxidation, 33:W
synthesis, 40: 1 17
4-O-methyl-o-, saccharinic acids from
alkaline degradation, 28: 195
rhreo-threo configuration, 47: 14, 145
Threuronic acid, L-, decarboxylation of, 28: 188
Thrombin, 43: 1 19
antithrombin-mediated inhibition,
43:119-121
group properties. 43: 122
Thrombocytes, desialylated, 40:222
Thrombopenia, 45: I7 1
Thromboxane, synthesis of, 42:95
499
Thulium complex, in conformational analysis
of acetals. 34: 198
Thylakoids, structure, 0-D-galactosylglycerides
in, 37:327
Thymidine
5-(2-acetamIdo-2-deoxy-a-~-galacto-
pyranosyl pyrophosphate), enzymic
synthesis of, 28:324
5 -(2-acetamido-2-deoxy-a-~-g~uco-
pyranosyl pyrophosphate), enzymic
synthesis of, 28:324, 342
5-(4-acetamido-4,6-dideoxy-~-galactosyl
pyrophosphate), and epimer, 28:323
5-(a-~-galactopyranosyl pyrophosphate),
enzymic preparation of, 28:340
isolation of, 28:322
5-(a-~-glucopyranosylpyrophosphate),
enzymic synthesis of, 28:338
epimerase action on, 28:375
isolation of, 28:322
mechanism of conversion of, 28:38 1
structure of, 28:309
5 -(a-o-mannopyranosyl pyrophosphate),
occurrence of, 28:322
5 -(2-amino-2-deoxy-a-~-glucopyranosyl
pyrophosphate), enzymic synthesis of,
28:339
3- and 5(trialkylsilyl)ethers, acid
hydrolysis, 39:65
25-anhydro-, 24: 179
3-O-(methylsulfonyl)-,displacement
reaction of, 24: 184
2.3-anhydro-
5-deoxy-5-iodo-,preparation of, 28:245
5-0-(methylsulfonyl)-, 24: 178
2,2-anhydro-2-thio-5-0-trityl-, 24: 1 8 I
5-(3-benzoylpropanoyl)-,preparation, 39:4 1
5-@-1.-rhamnopyranosyl pyrophosphate),
biosynthesis of, 28:383
isolation of. 28:323
5-bromo-5-deoxy; form B, crystal structure
bibliography, 31:370
crystal structure bibliography, 31:370
3,5-cyclic phosphate, 22:321
hydrolysis, 39:hl
5 -(6-deoxy-a-~-xylo-heptopyranosyl-4-
ulose pyrophosphate), enzymic
synthesis of, 28:323
5-(6-deoxy-~-glucosylpyrophosphate),
enzymic synthesis of, 28:323
500 SUBJECT INDEX
Thymidine (continued)
5-deoxy-5-iodo-,preparation of, 28:243
3 -deoxy-3-iOdO-5-0-(p-nitrobenzoyl)-,
preparation of, 28:248
5-(~-fucosylpyrophosphate), preparation of,
28:323,356
35-dideoxy-3,5-diiodo-, preparation of,
28:245
3 5-di-0-acetyl-, selective deacylation,
39:36
35-di-O-(methylsulfonyl)-, displacement
reaction of, 24:178
35-diphosphate, 22:308,322, 348
5-(~-ribosylpyrophosphate), occurrence of,
28:322
esterification of, 33: 13
with (p-nitrophenoxy)carbonylchloride,
33:32
glucose and D-galacturonic acid esters of 5-
pyrophosphate, 28:323
3' -0-acetyl-
5-deoxy-5-iodo-, preparation of, 28:243
5-0-(chloroacetyl)-, selective
deacylation, 39:43
5-O-(4-methoxycrotonoyl)-, selective
deacylation, 39:39
5-0-(2,2,2-tribromoethoxycarbonyl)-,
selective deacylation, 39:4 1
preparation, 39:41
4-thio-, crystal structure bibliography,
30:462
5-0-acetyl-
hydrolysis, 39:39
3-0-(2,4-dinitrophenylsulfenyl)-,
selective deacylation, 39:43
3 -0-(2,2,2- tribromoethoxycarbony1)-,
selective deacylation, 39:41
preparation, 39:41,43
3 -0-(methylsulfonyl)-5-0-trityl-,
displacement reaction of, 24: 178
3-0-(p-anisyldiphenyhnethyl)-5-0-(1-
napthyldiphenlymethy1)-,selective
cleavage, 39:48
5 -0-pivaloyl-, hydrolysis, 39:39
5-O-(p-nitrobenzoyl)-,reaction with
triphenylphosphine and iodine, 28:248
5-0-trityl-, reaction with
triphenylphosphine-carbon
tetrachloride, 28:248
3-phosphate,22:338,343
5-phosphate, 22:3 11,343
phosphorylation of, 33:4849
5 -pyrophosphateglycosyl esters, occurrence
and enzymic synthesis of, 26:356
radiolysis and free-radical-induced scission,
3 75 2 ,5 6 5 7
reaction with diethyl diazodicarboxylateand
carboxylic acids, 33:45
(-)-(5s)-5,6-dihydro-5-hydroxy-, crystal
structure bibliography, 385 12
selective acetylation of,33:33
selective chlorination with
triphenylphosphine and carbon
tetrachloride, 33:79
selective iodination with methyltri-
phenoxyphosphonium iodide, 33:77
selective oxidation of, 33:88-89
selective sulfation of, 3351
4-thio-p-~-,23:223
2-thio-5-O-trityl-, methanesulfonylation of,
24:181
Thymidine 3,5-bisphosphate, radiolysis,
31:47
Thymidine-5-carboxylicacid, crystal structure
bibliography, 32:382
Thymidine 5-diphosphate, glycosyl esters,
44:280, see also Glycosyl nucleotides
Thymidine 3,5-(N,N-
dimethylphosphoramidate),43:373
Thymidine 3 -phosphate, 5-0-(2,4,6-
trimethylbenzoy1)-, hydrolysis, 39:39
Thymidylate, disodium thymidylyL(5+3 )-5 -
,dodecahydrate, crystal structure
bibliography, 31:36 1
Thymidylic acid, calcium salt hexahydrate,
crystal structure bibliography, 31:370
Thymine
1-(6-amino-2,5,6-trideoxy-~-erythro-
hexofuranosy1)-, deamination of, 3157
1-(3,5-anhydr0-2-deoxy-p-o-,threo
pentofuranosy1)-, 24: 172
1-p-D-arabinofuranosyl-, 24: 180
crystal structure bibliography, 31:358
preparation of, 29:7
I-p-D-glucopyranosyl-,6-phosphate,22:373
1-P-D-ribonfuranosyl-
3-phosphate, 22:352
5-phosphate, 22:373
l-p-D-xylofuranosyl-, displacement reaction
of, 24: 181
 SUBJECT INDEX
1-(3-chlor0-2,3-dideoxy-5-O-trityl-o-
erythro-pentofuranosy1)-,preparation
of, 28:248
1-(2-deoxy-$-o-e?ythro-
pentohmosyluronic acid) conjugate,
preparation, 3 6 127
1 -[2-deoxy-3,4-di-0-(methylsulfonyl)-~-~-
erythro-pentofuranosyl]-,displacement
reaction of, 24: 184
1 -(2-deoxy-2-fluoro-~-~-arab~nofuranosyl)-Titanium tetrabromide, 1,6-
biological activity, 48:248-249,255
synthesis, 48:238
1-(6-deoxy-6-fluoro-~-~-gluco- and-galacto-
pyranosyl), synthesis and biological
activity, 48:266-267
2-deoxyglucosyl-, as inhibitor of pyrimidine
nucleoside phosphorylase, 27:4
1-(6-deoxy-2,3-O-isopropylidene-a-~-lyxo- humectants, gas-liquid chromatographic
hexopyranosyl-4-ulose), antitumor
activity of, 42:263
2,3 -imino-1-(2-deoxy-$-~-threo-
pentofuranosy1)-, 24: 184
1-(5-O-acety~-2,3isopropylidene-$-~-,
ribohmosyl)-5,6-(dichloromethylene)-
5,6-dihydro-3-methyl-, crystal structure
bibliography, 3 8 4 9 8 4 9 9
1 -(5-O-acetyI-2-O-p-tolylsulfonyl-p-~-
ribofuranosyl)-,23:245
1-[2-O-(methy~su~fony~)5-O-trityl-p-~- Toluene
ribofuranosyl]-,23:245
1-(2-O-p-tolylsulfonyl-5-O-trity-p-D-
ribOfuranOsyl)-, 23:245
I - ( ~ - ~ ~ ~ o - D - x ~ I o ~ ~ o2s 3~ ~I 12) 1- ,
Thymol, as reagent for D-fructose estimation,
22:238
Thyroglobulin, 25:446
a-D-mannosidase in structural studies of,
28:445
carbohydrate chain in, 26:461
sialylated oligosaccharides,fractionation,
4646
Ti F4 catalyst, glycosyl fluorides, synthesis,
48109
Tigogenin, reaction with tetra-0-acetyl-ma-,
glucopyranosylbromide in presence of
silver salts, 34:249
Tiliroside, as plant-growth substance, 21:412
Time-correlationfunction, 51:64,67-68
composite, 51:117
segmental motion, 51:79
501
total, 51:77
Timothy, hemicellulose:celluloseratio, 36:253
Tin
intermediates,see Organotin
NMR spectroscopy,53: 19-20
Tin compounds, tributyltin hydride, reduction
of chlorodeoxy sugars by, 28:303
Tinea nigra, 41:93
Tipson-Cohen reagent, 24:229,232,255
anhydrohexopyranosecleavage by, 34:67
Titanium tetrachloride
1,6-anhydrohexopyranose cleavage by, 34:67
in carbohydrateresearch, 29:4
TNantigen, 45: 171
Tobacco
cell-wall studies on, 42:284
analysis of, 28:97
smoking, levoglucosan formation in, 34:46
Tobramycin
discovery of, 30: 112
and structure of, 30: 124
mass spectrometryof, 29: 105
I-N-acyl derivatives, activity against
resistant bacteria, 30: 174
synthesis of, 30: 112, 162
TOCSY pulse, 51:23
a,-a-dihalo-, benzylidene acetals prepared
with, 34:188
2,4-diisocyano-, in neoglycoprotein
preparation, 3 2 2 5 1
as dispersing medium for reaction of sucrose
with phosgene, 27:106
0-(2,3,5-tri-O-acetyI-o-xylofuranosyl)-,
preparation of, 33: 144
Toluene-3,4-dithiol,zinc complex, as reagent in
D-fructose estimation, 22:239
p-Toluenesulfonates, 45:4
carbohydrate,photolysis, 3 8 162-163
photolysis of, 46191
p-Toluenesulfonic acid
in anhydridizationof hexoses, 3 4 4 6 4 7
esters of polysaccharides,29:337
p-Toluenesulfonic anhydride, sulfonylation of
carbohydratesby, 23:238
p-Toluenesulfonylation,53:37-38
of 1,6-anhydro-hexopyranoses,34:80
of carbohydrate boronates, 3 5 5 3
502 SUBJECT INDEX
p-Toluenesulfonylation (continued)
of dextrans, 30:41&411
of D-glucofuranose, 30:4
selective, 33:14,27,3&35,41
of maltose and derivatives, 39:227-229
of sucrose, 33:36
p-Toluenesulfonyl chloride
intermediate in nucleotide formation, 36: 157
reaction with amino group in dithioacetals,
32:55
replacement of hydroxyl group in
carbohydratesby chlorine, 22: 183
sulfonylation agent for sugars, 23:236
a-Toluenethiol, in dithioacetalpreparation,
32:17, 19
p-Toluic acid
esters of carbohydrate dithioacetals,33:41
esters of sugar dithioacetals,preparation of,
32:45
Toluidine Blue, complexes with
glycosaminoglycans,29:401
p-Toluoyloxy group, reactivity of, in
acyloxonium salt formation, 26: 131
p-Tolylboronates, stability to hydrolysis, 3 5 5 0
p-Tolylsulfonyloxy group, reactivity of, 24: 139
Tolyposamine, synthesis, 40: 106
Tomatine, as beetle repellent, 24:6
Tomato
cell wall studies on, 42:298
development physiology of, 42:340-343,
369,371-372,377,379-380
Tomato pectinesterase,see Pectinesterases
Tomato wilt, protective mechanisms for,
33:384
Tonoplast, of yeast cell, 32:141
Torsional angles, coupling of bond lengths and
bond angles to, 4296-101
Torsional potentials, Fourier component
analysis, 47:82-85
Torulopsis spp.
cundidu, transport of monosaccharidesinto,
32: 1 5 6 157
duttilu, maltose utilization by, 32: 183
galactomannans,41:92
mugnoliue, in glycerol manufacture from
sugars, 32:128
stellutu, D-fructose fermentationby, 32: 153
Toxins
binding by sialic acids, 40:230-231
from starch pyrolysis, 22:499
Toyocamycin,monohydrate, crystal structure
bibliography, 38:519
Tracers, isotopic, 3:229-250
Tracheid cell walls, 26:303-305
Tragacanth, gum, 44:247
Tragacanthic acid, 24:361
enzymic hydrolysis of, 24:340
Trumetes versicolor,a-L-arabinofuranosidase
of, 42:387
Tranquilizer, Trioxazin, 2 8 9
Transacetalation,39:78
Transaminases in fruit climacterics, 42:365
Transeliminases,depolymerizingenzymes,
33:325
Transesterification
in ammonolysis of carbohydrate acyl esters,
31:lOl
of carbohydrate esters, 33:44
of nucleosides with tris(quino1in-8-yl)
phosphate, 33:49
of sucrose, 33:272-273
Sugars, 49:235-236
Transferases
enzymic specificity,monitored by I3C-NMR
spectroscopy,43: 10
glycosylationswith, see Glycosylation
sugar and glycosyl ester nucleotide, 25469
Transfer reactions, catalyzed by glycosidases,
49:231-233
Transfemin
carbohydrate linkage in, 2542 1,444
deamination of, 31:236
N-glycosyl glycopeptide, mass spectrometric
analysis, 38:395
Transformation,the Lobry de Bruyn-Alberda
van Ekenstein, 13:63-103
Transfructosylation,of honey oligosaccharides,
25298,304
Transglucosylase,in hydrolysis of starch, 36:33
Transglucosylation,in honey oligosaccharides,
25298,304
Transglycosylase,endo-, in cellulose
microfibril creep, 42:357
Transglycosylation,22:248,490,494,23:305,
25:35,32288,42308
of 2-acetamido-2-deoxy-P-~-
glucopyranosides,31:5
in cellulose biosynthesis, 26:323
in cell-wall development, 26:348
ofo-apiose, 31:155, 172-173
 SUBJECT INDEX
and enzymic action, 30:276
Transition metals, 53:326-327
oxidation by, 37:20
reductions, 3719-20
Transition state
anomeric effect, 47: 118
slow, tight-binding inhibitors, 48:382-383
Transketolase, synthesis, 49:204207
Transmembraneelectrical potential, intact cell,
41: 174-150
Transosylation, 23:305
Transpeptidation, 26:432
Trehalase
a,-a-
6-deoxyd-fluoro-, 48:211
in yeasts, 32: 199
activity in developing systems, 30:252
distribution, specificity, and location of,
30:246-252
in human serum and urine, 30256
preparation and purification of, 30229
role in transport of sugars, 30:253
validamycin and validoxylamine activity
against, 48:88
Trehalosamine, 48:72
a,-a-
discovery of, 30:112
from Streptomyces, 30:236
synthesis of, 30: 137, 153
carba-, 48:88-89
synthesis, 48:72-73
isomer of, 28:286
a,-a-Trehalose calcium bromide trihydrate,
crystal structurebibliography, 31:359
Trehalose derivatives, sweetness, comparison
to corresponding monosaccharide analog,
by paired comparison test, 45:244245
a,-a-Trehalose 6,6-dimycolate, in
Mycobacterium, 30:235,254
a,-a-Trehalose 6,6-diphosphate,polymer,
from Mycobacterium tuberculosis, 30:236
Trehalose hexacetate, 6,6-dibromo-6,6-
dideoxy-a, a-,chloroform solvate, crystal
structure, 43:254-256
a,-a-Trehalose 6-phosphate
biosynthesis of, 30:237-245
occurrence and synthesis of, 30:236
a,-a-Trehalose 6-phosphate phosphatase
distribution, specify, and location, 30:245
possible control mechanism, 30:245
503
Trehalose 6-phosphate synthetase
in Mycobacterium smegmatis, 30:242
from Mycobacterium tuberculosis, 30:242
in Streptomyces hygroscopicus, 3024 1
of yeast, 30:238
a,-a-Trehalose phosphorylase
from Euglena gracilis, 30:254
in trehalose synthesis, 30:244
Trehaloses, 18:201-225,21:29
a,-a-, 25~301
3,6:3, 6-dianhydro-, sweetness-structure
relationship, 45:273
6-amino-6-deoxy-
preparation of, 28:286
synthesis and antibacterialactivity of,
30:153
3,6-anhydrO-
hexaacetate, conformation of, 26: 117
sweetness-structure relationship, 45x273
6-azido-6-deoxy-,preparation of, 28:286
benzylidene derivatives, reactions with N-
bromosuccinimide, 26: 164
biosynthesis of, 26369
mechanism of, 30:236-245
6-hromo-6-deoxy-, heptaacetate, reaction
with sodium azide, 28:286
calcium bromide, monohydrate, crystal
structure, 43:342-343
catabolism of, 30:245-254
conformation, 4752
6-deoxy-, preparation by photolysis of
iodo precursor, 28:305
6,6-diaminod,6-dideoxy-, synthesis and
antibacterial activity of, 30: 153
3,6:3,6-dianhydro-, conformation of,
26:117
2,2-dideoxy-, from yeasts, 30:237
4,4-dideoxy-
4,4-difluoro-, preparation, 38:222
sweetness, comparison to methyl 4-
deoxy-a-o-xylo-hexopyranoside,
45:244
sweetness threshold, determination by
triangular test, 45:245
6,6-dideoxy-6,6-difluoro-, preparation,
38:211
dihydrate, crystal structure bibliography,
30:453
6,6-di-O-hexadecanoyl-, preparation,
39:63
504 SUBJECT INDEX
Trehaloses (continued)
as energy reserve, 30:252
exo-anomeric effect, 47:70
isolation and identification of, 30:229,
232-235
metabolism of, 30:227-256
methyl derivatives, sweetness, 45262
methyl ethers, taste properties, 45262
mono- and di-deoxy derivatives,
sweetness-structure relationship,
49259-260
occurrence of, 30227,230-235
preparation of, 34:258
radiolysis and radical-induced scission,
37:52
as reserve supply of energy, 30:255
sc conformation, 47:88
as storage carbohydrate in yeasts, 32:200,
230
structure of, 32:193,39:353,358
sweetness, 45263
comparison to methyl a-D-
glucopyranoside,45244
structure relationship, 45243
threshold determination by triangular
test, 45245
4,6,4' 6'-tetradeoxy-4,6,4,'6'-tetrafluoro-,
preparation, 38:222
2,3,2',3 '-tetra-O-benzoy1-4,6:4,'6'-di-O-
benzylidene-, selective methanolysis,
39:19
utilization by yeasts, 32:147, 19k-195,
199-200,39:390-391
and associations of abilities, 32:226
a-p-
acceptor products, 51:153
2-chloro-4,6-bis(ethylamino)-, as
herbicide, 21:407
in honey, 25297,300
3-O-a-~-glucopyranosyl-, from
Streptococcusfaecalis, 30:237
synthesis and occurrence of, 30:229,237
2,4,6-tris(methoxy)-, as solvent for sugars,
27:117, 119
a,a'-galacto-, sweetness, comparison to
methyl a-D-galactopyranoside,49244
p, p-, 25:301
synthesis and occurrence of, 30:229,237
halogenation with N-halosuccinimidesand
triphenylphosphine,33:78
2,3,4,2',3,'4'-hexa-O-acetyl-6,6'-dideoxy-
6,6'-dithiocyanato-a-a, 44: 145
liquid chromatographymethods for analysis
of, 46:33
methanesulfonylation and p-toluene-
sulfonylation of, 33:35
pyrolysis of, 34:45
reaction with sulfuryl chloride, 33:77
selective chlorination with sulfuryl chloride,
33:73
selectivephosphorylation of, 33:49
synthesis of, 25: 165
carba-, 48:69-70
a,-a-Trehalose 2-sulfate, esters in
Mycobacterium tuberculosis, 30:236
Tremella, polysaccharide, 36:301
Tremellaficiformis, polysaccharide, 41:97
Tremella mesenterica, polysaccharide,
41:7&72,97
Tremuloidin, gel chromatography of, 2547
Trestatins, 48:25-26
Triacetoxonium ion, in fragmentation of
peracetylated glycosides, 2946
Tri-0-acetyl- 1,5-anhydro-2-deoxy-~-urubino-
hex-1-enitol, synthesis, 49:85
Tri-0-acetyl-p-D-xylopyranosyl chloride,
47:63
Triacontanoic acid, 2,4,6,8,10,12,14-
heptamethyl-, ester of trehalose 2-sulfate,
in Mycobacterium tuberculosis, 30:236
Trialkylsilyl group, selective removal,
39:62-70
Triamino sugars, C-branched, synthesis of,
42:109
Triazine
cellulose derivatives,preparation of, 29:349
dyes, for cellulosic materials, 29:35 1
in neoglycoprotein preparation, 32248-250
1,3,5-Triazine
2,4,6-trichloro-, reactions with alcohols and
carbohydrates, 28:258
2,4,6-trione, 1,3,5-tri-chloro-,reaction with
cyclic acetals, 39:118
s-Triazine2-chloro-4-(ethylamino)-6-
(isopropylamin0)-, as herbicide, 21:406
as-Triazine-3,5(2H,4H)-dione,2-p-0-
ribofuranosyl-, see 6-Azauridine
as-Triazin-3(2H)-one, 5-amino-2-p-~-
ribofuranosyl-, crystal structure
bibliography, 32:372
 SUBJECT INDEX
s-Triazole
3-amino-, as plant-growth substance, 21:399
3-(~-~-glucopyranosylamino)-, 21:402
1,2,3-Triazole
derivatives, from sugar derivatives,
25~387-392
1-phenyl-5-~-o-ribofuranosyl-, preparation
of, 33: 184
1,2,4-Triazole,3-amino-5-ribofuranosyl-,
synthesis, 40:77
1,2,4-Triazole-3-carboxamide,1-p-D-
ribofuranosyl-,see Virazole
Triazolides, (arylsulfony1)-, in nucleotide
formation, 36: 158
Triazolo nucleosides, synthesis of, 42:257
Tri-O-benzoyl-5-bromo-6-deoxy-~-~-xylo-hex-
4-ulopyranose, synthesis, 49:55
Tri-O-benzoyl-a-o-arabino-hex-2-
ulopyranosyl bromide, synthesis, 49:55
Tri-0-benzylfucosyl donor, 50:98, 104
2,2,2-Tribromoethoxycarbonylgroup, non-
hydrolytic removal, 39:41
Tributylstannane,49:76-77
Tributylstannylethers
as glycosyl acceptors, 53: 126-127
nomenclature, 53:19
reactions, 53:32-33
regioselectivity,53:33-36,65-68,95-97
terminal diols, 53:120-121
Tributyltin ethers, 53:25-26
Tributyltin hydride, reduction of chlorodeoxy
sugars by, 28:303
Trichloroacetaldehyde,53:365-366
Trichloroacetimidate
p-, a-selective glycosidation, 50:73, 77
method, 50:25-115
alcohols and sugars as 0-nucleophiles, see
Nucleophiles, 0-
kinetic anomeric effect, 50:29
3-0-glycosidic linkage formation,
50~289-290
0-glycosyl trichloroacetimidateformation,
50:25-30
reaction with Bronsted acids, 50:30-32
0-glycosyl, formation, 50:25-30
2-N-phthaloyl-2-, reaction with nucleophiles,
50:68,72-76
2,2,2-Trichloroethoxycarbonylgroup,
50:286-287
Trichodonin, taste properties, 45:3 12
505
Trichophytin, 23:403
Trichosporonfernentans, galactomannan,
41:92
Tridacna marima lectin, purification and
properties, 35:314
Tridacnin, purification and properties, 35:3 14
Tridecanoic acid, 3-hydroxy-, gas liquid
chromatography and mass spectrum of,
30:36
Trideoxyhexoses,21: 195
Trideoxy nucleosides, preparation of, 42:245
Trideuteriomethylgroup, in identification of
methylated monosaccharidesby mass
spectra, 21:71
Triethanolamine,as matrix for f.a.b.- mass
spectrometry, 45:26-27
Triethanolamine-l,1,3,3-tetramthylurea, as
matrix for f.a.b.-mass spectrometry,
45:54
Triethylamine
2-chloro-l-l,2-trifluoro-, replacement of
hydroxyl group by fluorine, 22: 185
dechlorinationof chlorodeoxy sugars in
presence of, 28:302
Triethylammoniumuridine 3,5-cyclic
phosphate, crystal structure bibliography,
31:369
Triethylenetetramine,as matrix for f.a.b.-mass
spectrometry,45:26
Triethyl phosphite, reactions with bromodeoxy
and deoxyiodo sugars, 28:285
Trifluoroacetates
alditols
gas-liquid chromatographyof, 28:65,
30:32
mass spectrometry of, 29:55
and nucleosides, mass spectrometry of,
30:42
in gas-liquid chromatography,28:36,50
of methylated alditols, gas-liquid
chromatographyof, 30:99
of oligosaccharides,gas-liquid
chromatographyof, 28:70
of 0-methyl sugars, gas-liquid
chromatographyof, 30536
of sugars, gas-liquid chromatography of,
28:87
Trifluoroacetic acid
hydrolysis
of glycoconjugateswith, 46:267-268
506 SUBJECT INDEX
Trifluoroacetic acid (confinued)
of polysaccharides with, monosaccharide
recoveries after, 46:261-263
pH of aqueous solutions of, 46:252
Trifluoroacetic anhydride, in acetolysis, 22: 1 1,of methylated alditols, gas-liquid
13
(Trifluoroacetyl)ation, amino sugars, 38:25 1
Trifluoroacetyl group, as blocking group,
39:36
Trifluoro(fluoroxy)methane, fluorinating agent,
38:230-233
0-(Trifluoromethy1)ated sugars, synthesis,
48: 184-1 85
Trifoliin A,44:379
Trigonellafoenum-gruecum, seeds
a-o-galactosidase in, 35365
p-o-mannanase from, 35:367
P-o-mannosidase in, 35374
components of immature, 35352,355
galactomannan
biosynthesis in, 35:352, 355
location in, 35:345
germination, galactomannan degradation
during, 35:356-361
oligo-P-o-mannosyl-( 1+4)-phosphorylase
from, 35:375
Trigonellafoenum-gruecum, galactomannans in
seeds of, 31:255,257
Trimethylacetic acid, cyclodextrin inclusion
complexes with, 46:22 1
2,3,5-Trimethylbenzoquinone,formation,
46:294
Trimethyl- I-butanol, 2,2,3-,
molecularconnectivity index, correlation Trioxabicyclo[3.3.0]octane,ring system, steric
with biological activity, 45:229-230
1,3,5-Tri(3-methylbut-2-enyl)-scyllo-inositoI, 3,6,8-Trioxabicyclo[3.2.1]octanes
47:6, 15
Trimethylenediamine-bis[guanosine5 -(methyl
phosphate)platinum(II), undecahydrate,
crystal structure, 43: 332-3 33
Trimethyl glucurone, preparation and structure
of, 33:201
3,4,5-Trimethylphenyl acetate, cyclodextrin
inclusion complexes with, 46:223-224
Trimethylpropyl ethyl ether, (S)-(+)-1,2,2-,
circular dichroism, 45:83
Trimethylsilylation
of polysaccharides, 29:329
of sugars, 28:23-33
Trimethylsilyl ethers
of alditols, gas-liquid chromatography of,
30:30
in gas-liquid chromatography of neutral
monosaccharides, 28:4 1 4 9
chromatography of, 30238
of methylated methyl glycosides, gas-liquid
chromatography of, 30:25-26.80-81
of methylated sugars, gas-liquid
chromatography of, 30:27-29,83-85
of oligosaccharides, gas-liquid
chromatography of, 28:68-70
of reducing sugars in aqueous solution,
42:22
Tri-0-acetyl-P-o-arabinopyranosylbromide,
crystal structure, 43:341-342
Tri-O-acetyl-P-o-xylopyranosyl chloride,
43:371
2,3,4-Tri-0-henzoyl-2-C-chloride, crystal
structure, 43:256-257
Triose kinase
control enzyme in o-fructose metabolism in
liver, 34:296
in metabolism of o-fructose, 34:293-335
Triose phosphate isomerase, equilibrium
catalyzed by, 49: 191
Triose-reductone, formation, 46:294
Trioses
from degradation of hexoses, 22:242
halogen derivatives, 22:2 13
polarography of, 29:129, 150
3,7,9-Trioxabicyclo[4.2.llnonanes,
hydrogenolysis, 39: 134
hindrance by, 28:241
hydrogenolysis, 39: 134
preparation and hydrogenolysis of, and
methyl derivatives, 34:148
Trioxacarcinose B
natural occurrence of, 42:73
structure of, 42:71
1,3,5,2,4-Trioxadiborepane, nomenclature,
3536
1,3,5-Trioxane, infrared spectrum of, 29: 181
Trioxazin, tranquilizer, 28:9
Triphenylmethoxy group, displacement in
carbohydrates by halogen, 22: 181
Triphenylmethyl fluoroborate
acetal oxidation, 39:85-86
 SUBJECT INDEX
cyclic acetal oxidation and halogenation.
39:107-113. 152
Triphenyl phosphate-bis(pyridin-2-yl)
diselenide, in nucleotide formation,
36: I59
Triphenylphosphine-bis(pyridin-2-yl)disulfide,
in nucleotide formation, 36: 159
Triphenylphosphine-dibenzyl hydrogen
phosphate-diethyl azodicarboxylate,
phosphorylation of thymidine and uridine
with, 33:49
Triphenylphosphite halides, replacement of
hydroxyl group by halide, 22: I84
Triple bonds, unsaturated monosaccharides,
52:95-96
Trisaccharide AX,, from arabinoxylan. 32:346
Trisaccharides, 21:28
esters with uridine 5-pyrophosphate, 28:33 I
interaction with lectins, 35: 142
mass spectrometry of trimethylsilyl
derivatives, 30:39
from mesquite gum, 24:350
permethylated, mass spectrometry of.
29:85-89,30:42
in plant kingdom, 37:290-300, 3 I 0
structure, 35:5
synthesis, 39:53,40: 126,49:22 1. 229,
236-237
from urine of genetic disease mannosidosis
patients, degradation of acetylated by
oxidation with chromium trioxide,
31:231
vicinal carbon-proton coupling constants,
51:52-53
Trisalosylactosylceramide, identification, 4 5 5 6
Tris(4-bromophenyl)ammoniumyl
hexachloroanthimonate, 52: 187
Tris(dipivalomethanat0) europium (111). and
dipyridine adduct, effect on proton nuclear
magnetic resonance spectroscopy. 29: 17,
23
Tris (1,1,1,2,2,3,3-heptafluoro-7,7-dimethyl-
4,6-octanedionato) europium (111). in
proton nuclear magnetic resonance
spectroscopy, 29:21
Trisialosylganglioside, see Gangliosides
Trisialosyllactosylceramide,44:437
Trisodium 6-O-phosphono-~-gluconate
dihydrate, crystal structure bibliography,
32:355
507
Tris(quino1in-8-yl) phosphate, in
transesterification of nucleosides, 33:49
Tris(tetramethylammonium) trimetaphosphate,
selective phosphorylation of nucleosides
with, 33:49
Triterpenoid. o-glucopyranuronic acid
conjugates, preparation, 36: 109
Tritiation
by addition to double bond of unsaturated
sugar, 27: 136
ofheparin by tritium gas, 27:138
recoil labeling, 27:138
Tritium
compounds, stability of, 27: 139
labelling, of heparin and
glycosaminoglycans, 29:350
localization and chemical degradation,
27:140
p-Tritylaminophenyl, protecting group.
36: 194- I95
Tritylation
of dithioacetals, 32:46
dithioacetals in, of pentoses, 32:61
of levoglucosan, 34235
of nucleoside boronates, 35:55
selective
of maltose and derivatives, 39:2 19-220
and reactivities of hydroxyl groups,
33:51-53
of sucrose, 33:238-243
Trityl chloride, see Methane, chlorotriphenyl-
Trityl ethers. of carbohydrates, 3:79-1 I 1
Trityl fluoroborate, cleavage of cyclic acetals
by, 34:207
Trityl groups, as protecting groups, 36: 142
Tritylone group, as protecting group, 39:4849
Trityloxy group, displacement in carbohydrates
by halogen, 22: 18 1
2-(4-Tritylphenyl)sulfonylethyl, protecting
group, 36: I94
2-(4-Tritylphenyl)thioethyl, protecting group,
36: 194
Trityl protecting group, Helferichs work on,
45:3
Trityl tetrafluoroborate, oxidation by, 37: 1 14
Tropeoleum mujus, polysaccharide from seeds
of, 24:314
Tryptophan
D-, favored conformation, 45232
in o-mannanases, 32:307
508 SUBJECT INDEX
Tryptophan (continued)
as hydrophobic binding-region of sweet-taste
receptor, 45:336
L-, cyclodextrin inclusion complexes with,
46:222, 224
Tsushimycin, inhibitor of protein glycosylation.
40:342
Tubercidin
configuration of, 24: 187
crystal structure bibliography, 31:358
reaction with 2-acetoxy-2-methylpropanoyl
halides in acrylonitrile, 33:85
Tuberculosis, incidence, 51:169-170
Tuberculostatic activity, of acylhydrazones of
akfehydo-~-g~ucurono-6,3-lactones,
33:2 I5
Tuberculostatic agents,
(glucopyranosy1amine)uronic acid
derivatives, 36: 123
Tubocurarine, sialic acid binding, 40:217
Tubulosine, 46: 13
Tumor-cell antigens, glycopeptides, liquid
chromatography separation, 46:48
Tumor-cell glycoproteins, sialylated
oligosaccharides, fractionation, 46:46
Tumor cells, see also Antitumor activity
antibodies, 53:249-250
autochthonous, effect of antitumor
polysaccharides on, 32:274-275
effect of plant polysaccharides on cell
volume and vacuolization of, 32265
glycolysis in, 33:4
glycoproteins in, 53:2 10-2 1 1
immune response, effect of polysaccharides
on, 32:26&272
lectin-binding, 35205
lectin-reactive, 35:327-333
oligosaccharides, liquid chromatography
separation, 46:4243
sialic acid masking, 40:227-228
Tumongenesis
fucolipid role, 39:309
fucosyltransferase levels, 39:33 1
glycopeptides, 39:305
Tunicamine, inhibition of protein glycosylation,
40:340
Tunicamycin
effect on cell differentiation, 40:366-369
on collagen biosynthesis, 40:365-366
on immunoglobulin secretion, 40:361
on virus infections, 40:37&371
inhibition of protein glycosylation.
40:339-342
isolation and structure, 40:340
role, 37:213
Tunicates, glycolipids, see Glycolipids
Turanose, 2:l-36, 21:30, 49:31
acetolysis of, 31: 199
composition in aqueous solution, 42:39,
66
conformational equilibria, 23:32
crystal structure bibliography, 38:445446
D-, anomeric equilibria in aqueous solution
and Fourier-transform spectra, 27:60
in honey, 25:295,300
liquid chromatography methods for analysis
of, 46:33
structure of, 32:192,39:357
taste properties, 45:254255
utilization yeasts, 32: 194
Turbidity
and activity of pectic enzymes, 33:366
of sugar products, 9:247-284
Two-state jump model, 51: 125-127
Tylosin, 21:173
biosynthesis, 35:83
Tyrosine
In o-mannanases, 32:307
L-, cyclodextrin inclusion complexes with,
46:222,224
Tyvelose, 21:187, 189-190,23:272
derivative, 26: 166
ester of cytidine pyrophosphate, isolation of,
28:316
gas-liquid chromatography of, 28:63
preparation of, 28:300
synthesis, 41: 10
U
UDP-apiose, biosynthesis of, by
decarboxylation, 31: 162-169
enzymic, 31: 169-172
UDP-o-galactose
a-r-fucose-( 1,2)-o-galactose-a-3-~-
galactosyltransferase, 44:246
N-acetyl-( 1-+4)-P-~-galactosyl transferase,
44:246
[Uridine 5 '-(a-o-galactopyranosyl
 SUBJECT INDEX
diphosphate)], biosynthesis,
37:28&287
UDP-D-glucose, biosynthesis, 37:286
UDP-u-glucuronic acid
in biosynthesis of UDP-D-apiose,
31:163-167
in cyclase, in UDP-apiose, biosynthesis,
31:169-172
UDP-glucuronic acid decarboxylase. from
Lemnaceae minor, 31: 170
UDP-glucuronic carboxy-lase, in UDP-apiose
biosynthesis, 31: 170
UDP-N-acetyl-D-galactosamine: a-L-fucosyl-
( 1,2)-o-galactose-a-3-N-acetyl-n-
galactosylaminotransferase, 44:246
Ulex europeus
11, extract, carbohydrate-binding specificity,
39224226
I lectin
carbohydrate-binding specificity, 35:290
hemagglutinating activity, 35:289
isolation and purification, 35289-290
Ultracentrifugation
enzyme purification by, 23:284,286
in enzyme purity test, 30:264
of gels, 24:3 1 1
of polysaccharides, 24:335
of urine protein-carbohydrate compounds,
24:442
Ultracetrifugation, 53:20&208
Ultrafiltration, and enzymic depolymerization.
30:273
Ultrasonic irradiation, starch modification,
51:245-247,302-303,305-307
Ultrasound, effect on D-fructose, 22:245
Ultraviolet irradiation
cleavage of carbon-iodine bonds by, 28:304
for hydrolysis of glycosidic linkage, 36:86
starch modification, 51:292-296
Ultraviolet photolysis, of dithioacetals, 32:78
Ultraviolet spectroscopy, 53:284-285
of arylated unsaturated hexitols, 27:239
1,4:3,6-dianhydrohexitols,49:99-- 100
of dithioacetals, 32:97
of ketonucleosides, 42:252
of sugars, 35:5
of sulfonic esters of carbohydrates, 23:257
Umbelactone, 50: 188-189
Umbelliferose
biosynthesis, 37:294, 349
509
occurrence, 37:293
structure, 37:293
synthesis in vitro, 37:350
Umhilicaria pustulatu. polysaccharide, 41:75
Umezawa, Hamao, obituary, 48: 1-1 7
Umezawa, S., 46:9
Undecaprenol, 44:349
Undecaprenyl (D-mannosyl phosphate) in cell-
wall polysaccharide biosynthesis,
42:323-324,330
Unrau method, of methylation of
carbohydrates, 30:13
Unsaturated acyclic compounds. 24:260
Unsaturated cyclic compounds
2,3-, furanoid, 24:226
2,3-, pyranoid, 24:231
3,4-, furanoid, 24:246
3,4-, pyranoid, 24:249
4,5-, furanoid, 24:250
4,5-, pyranoid, 24:252
5,6-, furanoid, 24:255
5.6-, pyranoid, 24:257
Unsaturated sugars, 24: 199-266
formation of, 22:202
halogen addition to, 22:193, 195
Uracil
1-[3-acetamido-4,6-O-benzylidene-3-deoxy-
2-O-(methylsu~fonyl)-P-~-
glucopyranosyl]-, displacement reaction
of, 24: 183
5-acetyl- 1-(2-deoxy-a-o-elythro-
pentofuranosy1)-, crystal structure
bibliography, 38:491492
5-acetyl- 1-(3,5-O-isopropylidene-p-~-
xylofuranosy1)-, crystal structure
bibliography, 34:376
1-allopyranosyl-, preparation of, 31:30
1-( 5-amino-5-deoxy-~-~-a~~ofuranosy~uronic
acid)-5-(hydroxymethyl)-. 23: 1 16
I -(5-amino-5-deoxy-~-~-a~~ofuranosy~uronic
acid)-5-(hydroxymethyl)-, deamination
of, 31:57
1-(3-amin0-3-deoxy-P-o-g~ucopyranosy~)-,
deamination of 2,4,6-triacetate
hydrochloride, 31:30
1-(2- and 3-O-acetyl-P-~-xyfo-furanosyl)-,
acyl migration in, 33: 105
2,2-anhydro- 1-P-D-arabinofuranosyl-
crystal structure bibliography, 31:355
selective methylation of, 33:59
510 SUBJECT INDEX
Uracil (continued)
1-(2,5-anhydro-~-o-lyxofuranosyl)-, 2520I
hemiacetal, 25212
1-(3,5-anhydro-P-~-lyxofuranosyl)-, 24: 172
I-(2,3'-anhydro-P-~-xylofuranosyl)-, 24: 179
1-(3,5-anhydro-~-~-xylofuranosyl)-, 24: 172
2,3'-anhydro- I -[2,5-di-O-(methylsuIfonyl)-
~-D-lyXOfurallOSy~]-, 24: 182
1-(2,5-anhydro-3-0-benzyl-p-o-
arabinokanosy1)-, 25:200
~ - A z A - , see 6-Azauracil
1-P-0-arabinofuranosyl-, 24: 180
5-bromo-, crystal structure bibliography,
31:358, 369
crystal structure bibliography, 31:356
3',5'-diphosphate, 22:369
S-flUOrO-, preparation of, 29:7
methylation of, 3 3 5 9
4-thio-, monohydrate, crystal structure
bibliography, 31:356
543-0-arabinofuranosyl-, synthesis of,
33: 175
1-P-D-lyxofuranosyl-, acetylation of, 33:32
5-p-~-ribofuranosyl-,see Pseudouridine
l-(P-o-ribofuranosyhronic acid) conjugate,
preparation, 36: 126-127
5-p-0- xylofuranosyl-, synthesis of, 33: 175
1-P-o-xylofuranosyl- selective acetylation
of, 33:32-33
1-(5-chloro-5-deoxy-2,3-di-U-p-
tolylsulfonyl-p-o-ribofuranosyl)-,
preparation of, 28:255
3-(5-chloro-5-deoxy-2,3-di-O-p-
tolylsu~fonyi-P-o-ribofuranosy~)-,
22: 183
1-(5-deoxy-P-D-erythro-pent-4-
enofuranosy1)-, stability of, 29:295
3-(2-deoxy-2-fluoro-~-~-nbosyl)-, 22: 190
2,2'-anhydride from, 22:202
1-(3-deoxy-3-iodo-2,5-di-O-trityl-P-~-
xylofuranosy1)-,preparation of, 28:245
1-(3-deoxy-3-iodo-5-O-trityl-p-~-
xylofuranosy1)-, preparation, 39:48
1-[2-deoxy-3-O-(methyIsulfonyl)-5-O-trityl-
P-o-fhreo-pentofuranosyl]-,24: 166
I-( 5-ethoxycarbonylfuran-2-yl)-, preparation
of, 29:295
5-fluoro-l-(2-O-tolylsulfonyl-5-O-trityl-p-~-
ribofuranosy1)-, 23:245
keto derivatives of synthesis, 42:234-235
5-nitro- 1-(-P-D-ribosyluronic acid)-.
monohydrate, crystal structure
bibliography, 37:434,38:503-504
1-(3-O-acetyl-P-~-arabino-furanosyl)-2,2'-
anhydro-, preparation of,33:84
3-(5-O-acetyl-2-deoxy-2-iodo-p-~-
ribofuranosy1)-, 22: 180
1-(2,3-O-isopropy!indene-p-o-
ribopentodialdo- 1,4-furanos-l -yl)-, p-
elimination in, 29:276-284
1-[5-O-(methy~su~fonyI)-P-~-lyxofuranosy~]-
,displacement reaction of, 24: 176
1-[2-O-(methy~su~fony~)-P-~-xylofuranosy~]-
, displacement reaction of, 24: 181
I -(2-O-tolylsulfonyl-5-O-trityl-~-~-
ribofuranosy1)-, 23:245
1-(5-thio-o-xylopyranosy~)-, 23:211
I -[2,3,5-tri-O-(methy~su~fonyl)-~-~-
arabinofuranosyl]-, displacement
reaction of, 24:182
Uracil-5-yl- disulfide, l-(2-deoxy-a-~-elythro-
pentofuranosy1)-, crystal structure
bibliography, 31:371
Uracil-5-yl- methyl sulfide, 1-(2-deoxy-a-~-
eryfhro-pentofuranosy1)- crystal structure
bibliography, 31:370
Urea
1-(2-chloroethyl)-3-
P-maltosyl-
I -nitroso-, synthesis and antitumor
activity, 39:243
synthesis, 39:243
(hepta-0-acetyl-P-maItosy1)-
I-nitroso-, synthesis and antitumor
activity, 39:243
synthesis, 39:243
and derivatives as solvents for sugars, 27: 1 12
D-ghlCOSyl-, 2 1 ~ 2 4
3-(3,4-dichlorophenyl)- I, 1-dimethyl-
effect on sugarcane, 21:427
as herbicide, 21:405
effect
on antitumor activity of polysaccharides,
32:261
on solubility of sugars in methanol, 27:97
on trimethylsilylation reactions, 28:26
glucosylthio-, 21:24
nitroso-, research, 29:2
3 4 p-chlorophenyl)- 1,l-dimethyl-
effect on sugarcane, 21:422,426
 SUBJECT INDEX
as herbicide, 21:405
tetramethyl-, as solvent for sugars. 27:1 I3
Ureides, glycosyl, 13:215-236
Ureido group, participation in sugar reactions,
22:139,146
Urethano group, participation in sugar
reactions, 22: I39
Urethans
protection as, 46:192-194
as solvents for sugars, 27:1 12
Urey-Bradley force-field, 44:39
Urey-Bradley-Schimanouchi force-field. 44:39
Uric acid, 3-P-~-ribofuranosyl-,5-phosphate.
22:324
Uridine, 24:178
a-,5-formyl-, crystal structure bibliography.
31:413
2,-deoxy-,5-phosphate disodium salt
pentahydrate, crystal structure
bibliography, 34:373
5-(2-acetamido-2-deoxy-a-o-gaIacto-
pyranosyl pyrophosphate), biosynthesis
and enzymic synthesis of, 28:342-343
isolation of, 28:327
5-(2-acetamido-2-deoxy-a-u-
glucopyranosyl pyrophosphate),
enzymic synthesis of, 28:341
fermentation production and biosynthesis
of, 28:343
isolation of, 28:327
5-(2-acetamido-2-deoxy-a-u-
glucopyranosyluronic acid
pyrophosphate), isolation of, 28:327
5-(2-acetamido-2,4,6-trideoxyhexosyl
pyrophosphate), isolation of, 28:327
acetylation of, 33:32-33
adenylyL(3-5 )-
9-aminoacridine complex,
pentadecahydrate, crystal structure
bibliography, 34:377
phosphate disodium salt dodecahydrate,
crystal structure bibliography, 31:362
sodium salt hexahydrate, crystal structure
bibliography, 37:427428
5-(a-o-galactofuranosylpyrophosphate). in
biosynthesis of galactocarolose, 28:325
5-(a-o-galactopyranosyl pyrophosphate),
enzymic synthesis and fermentation
production of, 28:34&341
isolation of, 28:325
51 1
oxidation with u-galactose oxidase,
28:344
synthesis by mixed anhydride method,
28:351
acid
5-(a-~-galactopyranosyluronic
pyrophosphate), enzymic synthesis of,
28:343
isolation of, 28:326
5-(a-~-glucopyranosyl-~~C pyrophosphate),
preparation of, 28:336
5-(a-~-glucopyranosyl pyrophosphate),
26:352
carbodiimides in synthesis of, 28:353
chemical synthesis by phosphoramidate
method, 28:345
degradation of, 28:312-313,356
enzymic preparation of, 28:33&337
isolation of, 28:325
mechanism of epimerase reaction with,
28:372
structure of, 28:309
synthesis by mixed anhydride method,
28:351
synthesis of analog with C-P bond,
28:349
discovery and occurrence of, 32:9
and -6-t
5-(a-o-glucopyranosyl-3-t,-4-/,-5-/
pyrophosphates), preparation of. 28:
337
5-(a-o-glucopyranosyluronicacid
pyrophosphate), decarboxylation of,
28:385
enzymic synthesis of, 28:343
isolation of, 28:326
5-(a-o-mannopyranosyl pyrophosphate), in
human blood-cells, 28:325
5-(a-o-ribo-hexopyranos-3-ulose
pyrophosphate), enzymic preparation of.
28:344
5-(a-~-xylopyranosylpyrophosphate),
28:325
enzymic synthesis of, 28:343
5-(a-guluclo-hexodialdosepyrophosphate),
enzymic preparation of, 28:344
5-amino-, crystal structure bibliography,
38507
5-(2-am~no-2-deoxy-a-o-galactopyranosyl
pyrophosphate)
enzymic synthesis of, 28:338
preparation of, 28:355
512 SUBJECT INDEX
Uridine (continued)
2,5- and 3,5-di-O-acetyl-, acyl migration
in, 33: 105
2,5- and 3,5-di- 0-benzoyl-, acyl
migration in, 33:105
2,5- and 3,5-di- 0-formyl-, acyl migration
in, 33: 105
2- and 3-0-pivaloyl-, acyl migration in,
33: 105
2,2-anhydro-, 24: 180
5-deoxy-5-iodo, 3 -0-(phenyl
methylphosphonate), preparation of,
28:244
35-di-O-(methylsulfonyl)-,24: 182
selective iodination with
methyltriphenoxyphosphonium
iodide, 33:77
2,5-anhydro-, 2,3-0-isopropylidene-
crystal structure bibliography, 31:361,
32:378
preparation of, 28:244
5-(barium phosphate) hydrate, crystal
structure bibliography, 31:369
5 -(P-L-arabinopyranosyl pyrophosphate),
enzymic synthesis of, 28:343
isolation of, 28:325
5 -(P-L-rhamnopyranosyl pyrophosphate),
biosynthesis of, 28:326
5-bromo-
crystal structure bibliography, 31:369
methyl sulfoxide complex, crystal
structure bibliography, 31:369
2-deoxy-, crystal structure bibliography,
31:369
5-deoxy-, preparation of, 28:253
5-(carbamoylmethy1)-, crystal structure
bibliography, 38:5 1&5 15
(carboxmethyl)-2-thio-, monohydrate, cystal
structure bibliography, 38:528
5 -(carboxymethy1)-
crystal structure bibliography, 38:5 14
5-deoxy-, synthesis of, 27:258
5-chloro-, crystal structure bibliography,
30:456
2-chloro-2 -deoxy-
crystal structure bibliography, 30:456
preparation of, 33:84
5-chloro-5 -deoxy-
2,3-0-isopropylidene-, preparation of,
28:248,253
preparation of, 28:253
5-chloro-2-deoxy-, crystal structure
bibliography, 31:355
crystal structure bibliography, 30:466,
34:363
2:3-cyclic phosphate, 22:308, 314, 355
3,5-cyclicphosphate, 22:360
hydrolysis, 39:61
2-deoxy-
5-(a-o-glucopyranosyl pyrophosphate),
enzymic synthesis of, 28:338
crystal structure bibliography, 30:457
3 ,5-di-O-(dihydrocinnamoyl)-, enzymic
hydrolysis, 39:43
5-ethynyl-, crystal structure bibliography,
3 8 5 12-513
5-fluOrO-, crystal structure bibliography,
31:369
5-fluoro-3 -0-(methylsulfonyl)-5-0-
trityl-, displacement reaction of,
24: 178
5-iOdO-
crystal structure bibliography, 31:369
Sphosphate, 22:335
3 -0-(methylsulfonyl)-5Otrityl-,
displacement reaction of, 24: 178
photochemistry, 38: 149-150
5-vinyl-, crystal structure bibliography,
385 13
5-deoxy-
5-(diphenylphosphinylmethy1)-, synthesis
of, 27:260
5 -iodo-2, 3 -0-isopropylidene-
preparation of, 28:243,248
reaction with triethyl phosphite, 28:285
2-O-p-tolylsulfonyl-, 23:245
5-(2-deoxy-a-o-urubino-hexopyranosyl
pyrophosphate), fermentation
production of, 28:341
5 -(2-deoxy-a-o-lyxo-hexopyranosyl
pyrophosphate), fermentation
preparation of, 28:341
5 -(2-deoxy-~-urubino-hexosyl
pyrophosphate), enzymic synthesis of,
28:338
5-(o-glucopyranosyluronic acid
pyrophosphate), enzymic conversion of,
32:ll
5 -(2,6-dideoxy-o-ribo-hexosyl
pyrophosphate), isolation of, 28:326
 SUBJECT INDEX
5,6-dihydro-
5 (a-o-glucopyranosyl pyrophosphate),
preparation of, 28:354
2,4-dithio-, crystal structure bibliography,
37:411
dihydro-, hemihydrate. crystal structure
bibliography, 30:458
5 -(I ,3-dihydroxy-2-propanone
pyrophosphate), isolation of. 28:334
2,3-di-O-acetyl-
5-iodo-, preparation of, 28:243
synthesis, 39:37
3,5-di-@acetyl-
crystal structure bibliography, 38:494-495
2-deoxy-2-fluoro-, crystal structure
bibliography, 32:383
2-deoxy-2-halo-, regioselective
deacylation, 39:4 1
2-O-p-tolylsulfonyl-, displacement
reaction of, 24: 180
3,S-di-O-benzoyl-, synthesis, 39: I53
2,3 -di-O-benzyl-,5 -(benzyl
phosphorochloridate), in synthesis of
nucleoside glycosyl pyrophosphates,
28:351
2,5-di-O-trityI-
reaction with
methyltriphenoxyphosphoni um
iodide, 28:245
selective detritylation, 39:48
3,5-di-O-trityI-. selective detritylation,
39:48
2,4-dithio-, monohydrate, crystal structure
bibliography, 30:457
5-fluoro-
2,3-di-O-(methylsulfonyl)-5-O-trityl-,
23:246
2-O-p-tolylsulfonyl-5-O-trityl-,
23:245-246
4-thio-, crystal structure bibliography,
34:373
5-(fructosyl pyrophosphate), isolation of,
28:326
5-glycosyl pyrophosphates, occurrence and
enzymic synthesis of, 26:354-355
glycuronic acid conjugates, preparation.
36: 127
5-hydroxy-
5-(a-~-glucopyranosylpyrophosphate),
enzymic preparation of, 28:338
513
crystal structure bibliography, 31 :356
S-iOdO-, crystal structure bibliography,
30:456
5-(~-leucylamino)-,crystal structure
bibliography, 38:495,497
5-methoxy-, crystal structure bibliography,
3 ~ 2 8
5-methyl-
hemihydrate, crystal structure
bibliography, 31:371
5-O-trityl-, methanesulfonylation of,
24: 180
6-methyl-, crystal structure bibliography,
30:461
5-(methyl 2-acetamido-2-deoxy-a-~-
gl yucopyranosyluronate
pyrophosphate), preparation and
reduction of, 28:355
5-(methyl a-D-galactopyranosyluronate
pyrophosphate), preparation of, 28:355
5-(methylaminomethyl)-2-thio-, crystal
structure bibliography, 38528
3-methyl-,3-phosphate, 22:352
4-(methylthi0)-, selective benzylation of,
3359
5-(N-acetylmuramic acid pyrophosphate),
isolation of, and derivatives, 28:328
5-(N-glycolylmuramic acid pyrophosphate),
isolation of, 28:329
5-nitro-, monhydrate, crystal structure
bibliography, 38:S27
2-O-acetyl-
3,5-monophosphatebenzyl ester, crystal
structure bibliography, 38:498
3,5-O-(tetraisopropyldisiloxane-1,3-
diyl)-, selective cleavage, 39:68
3-O-acetyl-
2-chloro-2-deoxy-5-0-( p-
nitrobenzoy1)-, preparation of, 33:84
5 -0-( tetrahydropyran-4-yl)-, selective
deacylation, 39:39
50acetyl-
acylation and sulfonylation of, 33:3 1-32
2-chloro-2deoxy-,preparation of, 28:249
deacylation rate, 39:38
3-O-p-tolylsulfonyl-, 23:245
2-O-p-tolylsulfonyl-, 23:245
displacement reaction of, 24: 180
reaction with triphenylphosphineecarbon
tetrachloride, 28:249
514 SUBJECT INDEX
Uridine (continued)
selective chlorination with
triphenylphosphine and carbon
tetrachloride, 33:79
5-O-acyl-, ammonolysis half-times, 39:38
1-(5-O-benzoy~-~-~-lyxofuranosyi)-,
benzoylation and p-toluene-
sulfonylation of, 33:32
2-0-benzyl-, esterification with pivaloyl
chloride, 33:13
2 ,3 -0-benzylidene-
bromination by N-bromosuccinimide and
triphenylphosphine, 28:249
5 -bromo-5-deoxy-, preparation of,
28:249,253
5-deoxy-5-iodo-, preparation of, 28:250
reaction with N-bromosuccinimide,
26: 166
5-O-(chloroacetyl)-, deacylation rate, 39:38
5-O-formyl-, deacylation rate, 39:38
2,3 -0-isopropylidene-, reaction with
triphenylphosphine-carbon
tetrachloride, 28:248
5 -0-(methoxyacety1)-, deacylation rate,
39:38
5-0-( 1-methoxyisopropyl)-, preparation of,
33:72
2,3 -0-(methoxymethy1ene)-, crystal
structure bibliography, 38:492493
2-0-methyl-, preparation of, 33:69
5 -0-(p-anisyldiphenyImethy1)-, hydrolysis
rate, 39:47
5 -0-(phenoxyacety1)-, deacylation rate,
39:38
5-O-(p-nitrobenzoyl)-, reaction with 2-
acetoxy-2-methylpropanoylchloride,
33:84
2,3 -0-tetraisopropyldisiloxane-I ,3-diyl)-,
preparation, 39:69
5 -0-(tri-p-anisylmethy1)-, hydrolysis rate,
39:47
5I-O-trityl-
hydrolysis rate, 39:47
selective etherification with
chlorotriisopropylsilane,33:53
2-phosphate, 22:350
3-phosphate, 22:351-352,380
3:5-phosphate,22:368
5-phosphate, 22:311,325,327,336,341,
369
preparation, 35:54
phosphoramidate, in nucleotide synthesis,
28:345
proton magnetic resonance spectroscopy of,
2233
5-pyrophosphate, 22:369
disaccharide sulfate esters, in hen oviduct,
28:329
monosaccharide sulfate esters, in hen
oviducts, 28:329
oligosaccharide esters, 28:33 1
trisaccharide esters, 28:33 1
esters Of D- glucose, o-galactose, D-xylose,
and L arabinose, in mung bean, 32:9
radiolysis and radical-induced scission,
37:52
reaction with
arsenic trichloride in N, N-
dimethylacetamide, 33232
(bromo(or ch1oro)-
methy 1ene)dimethyliminium
bromide(or chloride), 28:253
role in biosynthesis, 32: 12
selective benzylation of, 33:59
selective bromination with N-bromo-
succinimide and triphenylphosphine,
33:78
selective esterification, 33:45
selective etherification, 33:70
selective halogenation with N,N-di-
methyl(ha1omethaniminium) halides,
33:82
with triphenylphosphine and carbon
tetrahalides, 33:79
selective iodination with
methyltriphenoxyphosphoniumiodide,
33:77
selective oxidation of, 33:88
selective phosphorylation of, 33:49
selective tritylation of, 33:5 1
2-thio-, crystal structure bibliography,
38:485
4-thio-
crystal structure bibliography, 31:369
sesquihydrate, crystal structure
bibliography, 30:458
4-thio-o-, 23:223
3 -thiophosphate,methyl ester, triethyl-
ammonium salt, crystal structure
bibliography, 32:377
 SUBJECT INDEX
transacetalation of, 33:72
triethylammonium 3,5-cyclic phosphate
complex, crystal structure bibliography,
31:369
2,3,5-tri-O-acetyI-,selective deacylation,
39:36
2,3,5-tri-O-benzoyl-, selective deacylation,
39:39
2,3,5-tri-O-fomyl-, methanolysis,
selective, 39:37
2,3,5-tri-0-(methylsulfony1)-,
displacement reaction of, 24: 182
uridylyl-3+5-. 22:371
Uridine (2-acetamid0-2-deoxy-o-glucosyl
diphosphate), 44:282
Uridine S-(cu-D-glucopyranosyl
pyrophosphate), a,-a-trehalose
biosynthesis from, 30:237-241
Uridine 5-[cobalt(11) monophosphate],
heptahydeate, crystal structure
bibliography, 38:527
UridineS-(dimethylamino)-,5-phosphate,
22:312
Uridine 5-diphosphate, glycosyl esters. 44:280
Uridine diphosphate D-glucose, discovery and
action as o-glucosyl donor, 32:)
Uridine diphosphate glucose
precursor to cellulose biosynthesis,
41: 125-132
preparation, 49:213
(lb3)-P-~-glucansynthetase, in plant
extracts, 41:128
(I-+4)-p-~-glucan synthetase
assay of solubilized, 41: 146
cellulose biosynthesis, 41: 128-129, 148
Uridine diphosphate-xylose:xylosyltransferase,
41:129-130
Uridine 5-(dipotassium diposhphate),
trihydrate, crystal structure, 43:277 -278
Uridine 5-(disodium diphosphate),
hcptahydrate crystal structure, 43:3 1 1
Uridine disulfide, 4-thio-, crystal structure
bibliography, 31:371
Uridine 3-monophosphate,monohydrate,
crystal structure, 43:279-280
Uridine 5-monophosphatecopper(I1) 2,- 2-
iminodipyridine, crystal structure
bibliography, 38524-525
Uridinene, 24:228
Uridine 2,3-0-sodio 5-(methyl phosphate)
515
methanolate, crystal structure
bibliography, 38:5 10-51 1
Uridine-5-oxyacetic acid, methyl ester
monohydrate, crystal structure
bibliography, 34:369
Uridine 3-phosphate disodium salt
tetrahydrate, crystal structure
bibliography, 30:457
Uridine 2.3 -phosphorothioate,
triethylammonium salt, crystal structure
bibliography, 30:456
Uridylic acid, 22:3 13
5,6-dihydro-, 22:323
4-thio-, 22:323
Urinary glycoconjugates, hydrolysis, 46:262
Urine
gas-liquid chromatographic analysis of,
28:48. 81
glycopeptides and glycoproteins of,
25:414-415
protein-carbohydrate compounds in human,
24:435452
sugars in, identification by gas-liquid
chromatography, 28:44,46
Urine 5-(cadmium phosphate), diaquo-2,2-
dipyridylamine, pentahydrate, crystal
structure, 43:296-297
Uronates, preparative use of, with endocyclic
enolacetal linkage, 29:285-291
Uronate-sugar conjugates
p-eliminative degradation and structure of
natural, 29:254
occurrence, 29:230
selective p-eliminative cleavage of natural,
29:238-245
structural features and degradation of,
29:23 1-232
Uronic acids
acid decomposition, 46:252
alditols from, gas-liquid chromatography of
acetates, 28: 129
alkaline degradation of, 28:206
analysis of, 28:22
assay, 39:3
carbon- I 3 nuclear magnetic resonance
spectroscopy, 41:62
characterization of, 29374
decarboxylation and dehydration of,
28:186-193
definition, 52:5 1
516 SUBJECT INDEX

Uronic acids and immunity, 41:191-202

degradation of, 31:239 Vacciniin, 21:24,26
determination of, 28: 14 Vacuole, of yeast cells, 32:137, 141
esters of guanosine 5-pyrophosphate, Vacuolization, polysaccharide effect on, 32:265
28:320 Vaginidiol monoglucopyranoside, crystal
gas-liquid chromatography, 28:64,71-78 structure bibliography, 38:473475
as alditol acetates, 30:32 Valence force-field, 44:38-39
in glycoproteins, 25413,415 Validamines, 48:74
in hemicellulosic materials, 36:230,236-24 1 natural occurrence of, 42:73,76
liquid chromatography preparation of, 30: 138
analytical, 46:33-34 structure of, 42:71, 78
large-scale preparative, 4 6 6 2 synthesis of, 42:117,48:52-53,64
pre-column derivatization procedures, Validamycins
46:68 A, 48:24
mass spectrometry of, 29:54,66,30:42 microbial degradation, 48:52
of trimethylsilyl derivatives, 30:38 synthesis, 48:78-79
methanolysis of, 46:257-258 activity against
nomenclature, 52:108-110 Pellicularia sasakii, 48537
polarography of, and lactones, 29: 162 trehalase, 48:88
polysaccharide derivatives, 52: 165 B, synthesis, 48:78-80
polysaccharides containing, solvolysis, biosynthesis and structure, 35: 120-122
47:181 discovery of, 30: 112
reductic acid from, 28:209 isolation and structures of, 30:138-139
residues synthesis, 48:74-81
acid hydrolysis of, 31: 193 Validatol
p-eliminative degradation of deoxy-, preparation of, 30: 138
carbohydrates containing, natural occurrence of, 42:73, 76
29:229-303 preparation of, 30: 138
degradation of polysaccharides containing, structure of, 42:71, 78
by p-elimination, 31:214-220 synthesis of, 42: 117
synthesis of, by catalytic oxidation of Validoxylamines
hemiacetal function, 33:88 A, preparation of, 30:138
trimethylsilyl derivatives, gas-liquid activity against
chromatography of. and methyl esters, Pellicularia sasakii, 48237
28: 138- 140 trehalase, 48:88
in urine (human), 24:438439 B, synthesis, 42: 1 17,48:7677
Uronolactones, carbon- 13 nuclear magnetic structure, 35: 120-122
resonance spectroscopy, 4 1 5 2 Valienamines, 48:348
Uzarigenin, 21:274 natural occurrence of, 42:73
structure of, 42:71,78
synthesis of, 42:129-130,48:52-53, 55,64
V in validamycins, 30: 138
Valine, L-, protein linkage with, 25:420
Vaccines Valinomycin, 41: 148-149
anhydrohexitols as emulsifiers for, 25:269 Valiolamines, 48~52-53, 74,83
anticaries, 30:441 synthesis, 48:58-59, 65
artificial polysaccharide, 41: 198-199 Vallarose, 21:173
capsular polysaccharides as human, Valonia, cellulose, 52:326, 329-330
41:155-208 V-Amylose, vibrational spectra, frequency
humoral antibodies, 41:189-191 calculations, 44:5 1
 SUBJECT INDEX
Vancomycin, effect on peptidoglycan
biosynthesis, 26:430
Vancosamine
DL-, synthesis, 40: 15
natural occurrence of, 42:73
structure of, 42:70,78
synthesis of, 42:114, 122-123
Van Deemter equation, 2 5 2 1
Vanillin, 53:366
vant Hoff-Le Be1 theory, asymmetric carbon
atom, 5 0 : 3 4
Vapor-tension data, for levoglucosan, 34:52
Vargha, Laszlo, 4 5 9
obituary, 28:l-10
Varianose, 23:399, 41:lOO
Vasodilation, isobexide nitric esters,
49: 161-1 62
Vasopenton, as spasmolytic agent, 28:9
Velocity constant, of mutarotation of a-o-and
p-D-glucose, 24:14
Veratric acid, 1-ester with o-glucuronic acid,
36:104, 108
Verbascose
biosynthesis of, 26:375, 37:356-357
in endosperm during germination, 35:357
isolation, 37:306-307
Verbascotetraose, occurrence and structure,
37:3 10
Vertebrates, sialic acids occurrence, 40: I37
Verticillium duhliue, gas-liquid
chromatography of metabolites of, 28:47
Vesicular stomatitis virus
glycoproteins, effect of sugar side-chains,
4 0 ~55-356
3 erythrocyte agglutination, effect of sialyl
G protein, 44:234
VG Analytical ZAB-HF mass spectrometer,
4536-3 7
Viboquercitol, taste properties, 4 5 2 9 1-292
Vibrational degrees of freedom, 44: I 2
Vibrational frequencies. 44: 12
calculations, methods, 44:3 1-34
Vibrational spectroscopy
background, 44:lO
intensities, calculation of, 44:35-36
noncomputer results, 44:22
Vibratory hydrogen hypothesis, of sweetness,
45:205,218
Vibrio cholerue, 0-specific polysaccharides,
47: 179
Viburnumfurcutum, furcatin from, 31: 148
517
Viciu crucca lectin, isolation and properties,
35138, 304
Viciu enilia lectin, isolation composition, and
properties, 35:3 11
Viciu grumineu lectin
carbohydrate-binding specificity, 35: 145,
303
isolation, 35302
purification and composition of, 35:303
Vicinal diol, n-threo configuration, 49: I9 I
Vinelose
ester of cytidine pyrophosphate, 28:3 17
L-, biosynthesis, 35:85-89
natural occurrence of, 4272, 76
structure of, 42:70
synthesis of, 42:119
Vinylation, of methyl a-D-glucopyranoside,
reduction and gas-liquid chromatography
of, 30:26
Vinylene carbonate, see 1,3-Dioxol-2-one
Vinylog systems, p-elimination and double p-
elimination in activated, 29:283
Vinyl sulfone, see Divinyl sulfone
Viosamine, 23:153,24:159
Viral hemagglutinin, synthesis, effect of
tunicamycin, 40:378
Virazole, crystal structure bibliography,
31:359. 37:408
Virenose
natural occurrence of, 42:72
structure of. 42:70
synthesis of, 42: I 18, 123
Viruses
linkages, 40:229-230
glycosylation inhibition effect, 40:369-373
sialic acids occurrence, 40: 134, 136
Virus glycoproteins
glycopeptides, liquid chromatography
separation. 46:48
isolation of, on analytical-scale columns,
46:60
Viscoelastic putty, 24:296
Viscosity
and action pattern of enzymes, 30:27 1
and activity of pectic enzymes, 33:366
effect of carbohydrate-complex salt
formation on, 21:213
effect on gel chromatography, 25:21
sialic acid residue effect, 40:2 18
518 SUBJECT INDEX
Visible light, starch modification, 51 :292-296
Visible spectroscopy, 53:284-285
Vitamin A derivatives, role in protein
glycosylation, 40:297-299
Vitamin B,, biosynthesis, 1-deoxy-o-threo-
pentulose in, 52:287
Vitamin B,,
crystal structure bibliography, 31:371
degradation, 36:3
5-phosphate, pentadecahydrate, crystal
structure, 43:370
sialic acid effect, 40:219
spin-lattice relaxation of I3C nuclei in, 27:60
Vitamin C
history, 28:3
research of Maurice Stacey, 5 2 5 6
studies of polysaccharides of micro-
organisms, 52:6
synthesis, Garcia Gonzilez work on, 45: 10
Vitamin K, analogs, research, 29:2
Vitamin L,, biological activity and structure of,
42: 135-1 36
Vitamins, 53:37+375
crystal structures of, 2590-92
volatile products from pyrolysis of, 22:505
Volatility, of methylated polysaccharides,
effect on methylation analysis, 30: 17
Volemitol, 21: 17
von Gierkes disease, 25478
W galactomannans in, 31:31 I
Wagner-Meenvein rearrangement, 24: 193,
25:209
Walden inversion, 21:20,25:6,264
and anhydridization, 33: 121
in 1,6-anhydrohexopyranoses,34:85, 87
in fluorinations, 38:218
Waldenstroms macroglobulinemia,
glycoprotein (compounds 68,69, and
70),H-NMRspectroscopy, 41:344,
357-363
Warfarin
discovery, 39: 1
inhibition of protein glycosylation,
40:34&345
Water
action on starch, 47:303
catalysis of mutarotation by, 24: 17
as catalyst in mutarotation of sugars, 24:28
catalytic activity of, 24:22
effect on mutarotation reactions, 24:3 1
elimination reaction, from carbohydrate
radicals, by radiation, 37:9-11, 13-14
evolution from cellulose on heating,
23:428429
hydration, in carbohydrate crystals, 25:99
Raman scattering of, 44:70
role of, in intensity of sweet-taste sensation,
44238
vibrational spectroscopic studies, 44:85-86
Water-starch complex
analysis, 53:3 10-312
problems, 53:298-300
sorption, 53:304-307
starch origins, 53:307-3 10
water in, 53:300-304
Wutsonia pyramidatu
polysaccharides from corm sacs of, 24:371
xylan, crystal structure bibliography, 40:39 1
Wutsonia versveldii, polysaccharides from seed
boxes of, 24:371
Wax-bean lectin, purification and composition,
35296
Weermann reaction, for degradation of
periodate-oxidized pol ysaccharides,
31:237
of snail galactan, 31:211
Welan, 52:389,391-393,432,434
Well drilling
plant galactomannans in, 35342
Wheat
cell walls
arabinoxylans, 36:242,244
studies on, 42:271,287,291,293-294,
300,3 15,327
hemicellulose:cellulose ratio, 36:253
roots, polysaccharides, 36:245
starch
degradation parameters, variation with
microwave radiation, 51:302, 304
time-temperature curves
conduction heating, 51:299, 302
microwave heating, 51:299,301
xylans, 36:23+235
Wheat germ
agglutinin
effect on cellular transport, 40:376
 SUBJECT INDEX
sialic acid analysis, 40: 175
lectin
agglutinating activity, 35:2 14
carbohydrate-binding sites, 35:2 16, 222
carbohydrate-binding specificity, 35:220
interaction with cellular structures, 35:3 17
isolation, 35:137,214
mitogenic activity, 35:224
precipitation, 35:2 16, 224
purification, and properties, 35:2 14
structure, 35:2 I5
Wiegand, Friedrich, 45:3
Wieland, H., 46: 12
Willow cell-wall studies on, 42:28 1-283
Wilson GF method, 44:32
Wilzbach reaction, for labeling sugars with
hydrogen isotopes, 27:137-138
Wines, 1.r. spectroscopy in analysis of. 44:23
WisturiuJoriburidu lecti n
isolation, 35: 138, 3 12
purification and properties, 35:3 12
Wittig reaction, 24:260, 262
in carbohydrate chemistry, 27:227-299
of 3-deoxy-o-rnanno-2-octulosonic acid,
38:358,369,371-373
in dethiobiotin synthesis, 27:2 12
fluorination of carbohydrates, 38:246
and synthesis of C-nucleoside precursors,
33: 153-158
Woessner equation, 51: 122
Wohl degradation
acyclic sugar intermediates in, 26:9
of cellobiose. 26:8
5-deoxy pentoses by, 21: 177
Wolfrom, Melville Lawrence, 44:l-2, 45: 15,
46:4
obituary, 26: 1 4 6
Wood
hemicellulloses of, 19:247-302, 20:409483
hydrolysis of, 46:263-264
levoglucosan from, 34:38,40
polysaccharides associated with cellulose of,
10~283-333
Pulp
gas-liquid chromatography of, 28:42, 61,
74,78, 88
liquid chromatography analysis, 46:52
saccharification of, 4: 153-1 88
Woodward Reagent K, for synthesis of peptide
derivatives of muramic acid, 43: 149
519
worms
glycolipids, see Glycolipids
parasitic, a,-a-tetrahalose biosynthesis in,
30:239,244
Wort, analysis by gas-liquid chromatography,
28:46
X
Xantham gum
biosynthesis, 44:376-377
structure, 44:376
Xanthan, 52:395, 53:246-247
circular dichroism, 45:118-119
Fourier-transform infrared spectroscopy,
44:63
structure, 44:lSO-151
enzymic analysis, 44: 156-1 58
Xanthan gum
industrial production, 36:27 1-272
preparation, 36:294
properties, 36:292-294
structure, 36:293
uses, 36:295-297
Xanthates
deoxy sugars from, 21: I63
photochemical cleavage of, 46:190
of polysaccharides, preparation and uses of,
29:346
in I-thioglycosiduronic acid synthesis, 36:99
xanthides, carbohydrate, photolysis,
38: I 57-1 60
Xanthomonas
extracell ular polysaccharides, circular
dichroism, 45:118-119
polysaccharide, crystal structure
bibliography, 36:332,40:399
Xunthomonas cumpestris
capsular polysaccharide, conformation and
serological specificity, 41: 178
polysaccharide from, interaction with
galactomannans. 31:242,301-307
Xanthosine, dihydrate, crystal structure
bibliography, 37:4 14
Xenon difluoride, 48: 176-1 77
X-Ray crystallography
cellulose structure, 41:113
from characterization of an
hydrodeoxyheptitols by, 23%
520 SUBJECT INDEX
X-Ray crystallography (continued)
in conformational analysis, 26:53
of 5-deoxy-5-phosphino- and 5-phosphinyl-
L-idopyranoses, 42: 165-172
of 4-deoxy-4-phosphinylpentofuranoses,
42:183-184
of galactomannans, 31:280
glycoside hydrolases, 48:325-326
of sugars, 35:5
X-Ray diffraction, 44:87, 53:290
analysis, polysaccharides, 52:3 14-325
and carbohydrate boronate structure, 35:41
of carbohydrate crystals, 25:54
of cellulose, effect of heating on, 23:428
conformation of glycofuranosides and, 21:97
and furanoid ring structure, 34:201
by gels, 24:306
of halogenated sugars, 22:201
intensities, of carbohydrates, nucleosides,
and nucleotides, 30:446
interpretation of fiber diagrams, 22:43 1
of L-fructose, 22:233
of polyglycoses, 21:501
of polysaccharides, 22:421482
of ribonucleoside 5'-phosphates, 22:3 12
of starch during pyrolysis of, 22:486
of sulfonic esters of carbohydrates, 23:254
X-Rays irradiation, starch modification by,
51:241,263,265
Xylal
3,4-di-O-acetyl-
D-, hydroformylation of, 23:91
hydroxymethylaiton of, 23:74
0x0 reaction with, 23:66
2-nitro-o-, 24:207
di-0-acetyl-D-
reaction with benzotriazole and 5,6-
dimethyl derivative, 24:2 17
reaction with hydrogen chloride or
hydrogen bromide, 28:264
di-0-benzoyl-o-, reactions with hydrogen
halides, 28:265
hi-O-acety1-2-hydroxy-o-,conformation of,
26: 123
Xylan acetate, circular dichroism, 45:121
Xylanases, 42:379
p-D-,44:163
Schizophyllum commune, 44: 162
D-
assay and purification of, 32:328
concentration of culture solutions, 32:328
extraction of intracellular, 32:329
inhibitors of, 32:33 1-33
mode of action of bacterial, 32:334
of fungal, 32:334344
molecular weight of, 32:330, 332
physicocbemical properties of,
32:33&334
of rumen microbial origin, 32:344346
separation and purification of, 32:329-330
unit of activity of, 32:328
endo-( 1+4)-p-o-, 44: 158, 163
I r p a lacteus, 44: 159
exo-o-, isolation of, 32:334
mode of action, analysis of, 46:54
(1+4)-p-~-, 44~161
Cryptoccus albidus. 44: 160-161
definition and nomenclature of, 32:3 19
occurrence of, 32:319-328
(1 -3)-P-~-Xylanases
assay of, 32:3 17
definition of, 32:317
mode of action of, 32:3 18-3 19
occurrence of, 32:317
physicochemical properties of, 32:3 18
purification of, 32:318
Xylans, 5:269-290
acetylated, enzymic analysis, 44: 162
acidic, acid hydrolysis, 36:237
p-D-, Rhodymenia palmata. enzymic
analysis, 44: 163
biosynthesis of, 26:402
birch, degradation by p-elimination, 31:217
by Weermann rearrangement, 31:238
constitution of, 25:6
corn, structure, 36:231,236
crystallography of, 22:458
D-. 47: 18
~-urabino-(4-O-methyI-o-glucurono)-,
46:306
(4-~-methyl)-~-glucurono)-, model
compounds related to, alkaline
degradation, 46:306
rice-straw, enzymic analysis, 44: 162
Shirakamba wood, enzymic analysis,
44: 162
degradation by periodate oxidation, 31:20 1
hemicellulosic, 44: 158
larch-wood, enzymic analysis, 44: 159
linear and branched, definition, 36:217
 SUBJECT INDEX
liquid chromatography analysis, 46:39
methylation of, 30: 11-12,36:239-240
oligosaccharides, 46:305
orientational measurements in, 44:27
from plant cell walls, 44:359
in plant cell walls, 26:301, 42:269. 275
structure, 42:291-292
polysaccharides, see Polysaccharides
(1+3)-p-~-, 52:361
crystal structure bibliography, 33:397,
40:390
(1+4)-p-0-, 52~338-339,407
biosynthesis in asparagus, 32: 1 1
crystal structure bibliography, 33:397
Rhodymeniupulmutu, 44: 158
seaweed, 44:158
speargrass, gas-liquid chromatographic
analysis of, 28:62
structure, 35:7,36:229-249
Wutsoniu pyrumidutu, crystal structure
bibliography, 40:391
wheat, structure, 36:230, 235
wheat-straw, enzymic analysis, 44: 159
wood, alkaline-degradation products of,
46:305
(1+4)-p-~-Xylan xylanohydrolase, name for
D-xylanases, 32:3 19
Xylene, as dispersion medium in preparation of
sucrose esters, 27: 106
Xylitol
I -acetamido-
1,5-anhydro-l-deoxy-, 23:121
tri-0-acetyl- 1,5-anhydro- 1-deoxy, mass
spectrum of, 21:91
2,3,4-tri-U-acetyl- 1,5-anhydro- I -deoxy-,
mass spectrum of, 23:201
5-acetamido-1 ,s-deoxy-o-, 23: 167
acetates, separation of methylated, 30:23
1-amino- 1,4-anhydro-
1-deoxy-L-, 23:148
1,5-dideoxy-~-,23: 150
I-amino-I ,5-anhydro- I -deoxy-, 23: 159- 160
1,3-anhydro-, 2,4-O-methyIene-o~-,24: 174,
25:235
I ,4-anhydro-
5-chloro-5-deoxy-~~-, 25:234,257
D-
sweetness-structure relationship, 45:257
triacetate, isomenzation of, 25:258
5-deoxy-5-fluoro-, preparation, 38:242
52 1
5-deoxy-S-fluoro-~1.-,25:257
2,3-di-O-benzyl-S-O-p-tolylsulfonyI-~~-,
22: I14
i-O-methyk-o~-,infrared spectrum of,
25:250
3,5-O-methylene-i~~-. infrared spectrum
of, 25:250
reaction with dry hydrogen chloride,
25:257
ring opening and isomerization of,
25:259
conformation of, 26:69
crystalline, 26: 14
crystal structure bibliography, 31:364
D-, anhydridation of, 25:231
1,4:3,5-dianhydro-
nuclear magnetic resonance spectrum of,
25:254
2-0-methyl-~~-,236 nuclear magnetic
resonance spectrum of, 25:254
ring opening of, 25:257-258
1,4:2.5-dianhydro-~~-, 25:236
1,5-dideoxy-, phenylboronate, structure,
35:43
2-diethylborinate I ,3:4,5-bis(ethylboronate),
hydrolysis, 35:52
1,5-di-O-benzoyl-2,4-0-
benzylidene-, esterification and hydrogen-
bonding, 33: 16
methylene-esterification and hydrogen-
bonding, 33: 16
2,4:3,5-di-O-benzylidene-O-
(phenylsu1fonyl)-, displacement
reactions of, 24: 143
2,4:3,5-di-O-methylene- I-O-
(phenylsul fonyl)-, displacement
reactions of, 24: 143
DL-,4-diethylborinate 1,2:3,5-
bis(ethy1boronate). selective cleavage,
39:54
infrared spectrum, 45:294
liquid chromatography methods for analysis
of, 46:33
2,4-O-methylene- 1 -U-p-tolylsulfonyl-oL-.
displacement reactions of, 24: 174
selective oxidation with mercuric acetate,
33:99
stability constants, 47:29
sweetness-structure relationship, 45:295
syn-axial interaction on, 45:294
522 SUBJECT INDEX
Xylitol (continued)
trimethylsilyl ether, gas-liquid
chromatography of, 28:57
tri-0-acetyl- 1,4-anhydro-o-, rearrangement
in hydrogen fluoride, 26: 175
2,3,4-tn-O-benzyl- 1,5-di-O-p-tolyIsulfonyl-,
solvolysis of, 24: 196
yeast utilization of, 32: 147
Xylitol 1,3-phosphate diethylamide, 2,5-
anhydro-4-O-methyl-o-, crystal structure,
43:224-225
Xylobiase, 23:212
Xylobiose, 24:369,375
P-D-(1-4)-, hexaacetate, crystal structure
bibliography, 31:354
liquid chromatography methods for analysis
of, 46:33
Xylobiose peracetates, NMR data for, 42: 194
a-~-Xylofurano-[2,1-6]-imidazolin-2-one,
43:370
Xylofuranose
4-acetamido-
5-deoxy-4,5-dideoxy-~-,23: 196
1,2,3,5-tetra-O-acety1-4-deoxy-o-,
23: 182-1 83
5-acetamido-
5-deoxy-~-,23:167
5-deoxy-~-,23:168
5-deoxy- 1,2-O-isopropyhdene-a-o-,
23: 166
4-amino-, 4-deoxy-~-,23: 147
4,5-carbamate, 23: 147, 183
5-amino-
5-deoxy-~-,23:122
5-deoxy-l,2-O-isopropylidene-a-~-,
23: 120
deamination of, 31:55
3,5-anhydro- 1,2-0-isopropylidene-a-o-,
24~172-173
polymerization, 39:2 I 1
preparation of, 28:289-290
synthesis, 39: 173
5-benzamid0-5-deoxy-o-, 23: 169
5-(benzylamino)-l,2-O-cyclohexylidene-5-
deoxy-a-o-, 23: 140
2,5-bis(acetamido)-2,5-dideoxy-~-,23: 173
5-bromo-5-deoxy- 1,2-O-isopropylidene-3-0-
methyl-a-o-, reaction with triethyl
phosphite, 28:285
3-C-(acetoxymethyl)-5-O-acetyl-3-deoxy-3-
fluoro- 1,2-O-isopropy~idene-a-o-,
preparation, 38:250-25 1
conformation of, 34:201
D-
3-C-(acetoxymethyl)-3deoxy-3-fluoro-
5-O-acetyl-l,2-O-isopropylidene-a-,
'H- and 19F-NMR data for, 46:142
1,2,5-tri-O-acetyl-, 'H- and I9F-NMR
data for, 46: 142
3-deoxy-3-fluoro- 1,2-O-isopropylidene-a-
3-C-(ethoxyallyl)-, IH- and I9F-NMR
data for, 46: 142
3-C-(hydroxymethyl)-, IH- and I9F-
NMR data for, 46: 142
3,5-dideoxy-3,5-difluoro-1,2-0-
isopropylidene-a-, 'H- and I9F-NMR
data for, 46: 156
3-0-benzyl-5-deoxy-5-fluoro- 1,2-0-
isopropylidene-a-, IH- and I9F-NMR
data for, 46: 1 13
1,2-O-isopropylidene-3-deoxy-3 -fluoro-5-
0-p-tolylsulfonyl-a-, 'H- and I9F-
NMR data for, 46: 1 12
5-deoxy-
5-fluoro- 1,2-0-isopropylidene-a-o-,
proton magnetic resonance
spectroscopy of, 27:29
5-iodo- 1,2-O-isopropyhdene-a-o-
methylphenylphosphinate, preparation
of, 28:280
reaction with silver fluoride, 28:289
5-iodo-3-0-p-nitrobenzyl- 1,2-0-
isopropylidene-a-o-, proton magnetic
resonance spectroscopy of, 27:29,72
1,2-O-isopropylidene-a!-~-, 23:273
1,2,-O-isopropylidene-S-thiocyanato-a-~-,
44: I45
1,2:4,5-di-O-isopropylidene-~-, mass
spectrum of, 21:78
1,2-di-O-acetyl-, 3,5-di-O-p-tolylsulfonyl-~-,
22:15
2,3-di-O-acetyl-
I ,5-anhydro-P-o-, synthesis, 39: 172
5-O-(chIoroacetyl)-o-, selective
deacylation, 39:35
2,3-di-O-benzoyl- 1,5-di-O-trityI-o-, selective
cleavage, 39:47
1,2:3,5-di-O-benzylidene-a-o-,
diastereoisomers, 34: 196
hydrolysis of, 34:203
 SUBJECT INDEX
preparation of, 34: 186
1,2:3,5-di-O-cyclohexylidene-a-~-
acetal cleavage by Grignard reagent,
39: 155
hydrolysis of, 34:203
1,2:3,5-di-O-isopropylidene-a-o-
hydrolysis of, 34:203
irradiation, 39:88
1,2:3,5-di-O-methylene-a-o-
deacetalation, 39:24
oxidation by potassium permanganate,
39532
(E)-3-C-[2-(carboxamido)-
ethoxycarbonyl)ethylene]-3-deoxy-3-
fluoro- 1,2-0-isopropylidene-5-O-trityl-
a-D-, preparation, 38:25 1-252
3-0-acetyl-5-deoxy-5-iodo- 1,2-0-
isopropylidene-a-o-, reaction with
silver fluoride, 28:291
3-0-benzyl-5-deoxy-5-
fluoro-l,2-O-isopropylidene-a-~-, proton
magnetic resonance spectroscopy of,
21:29
iodo- 1,2-O-isopropylidene-a-o-, proton
magnetic resonance spectroscopy of,
27:29, 72
3,5-O-benzylidene- 1,2-O-isopropylidene-a-
D-, irradiation, 39:88
3-0-benzyl- 1- 1,2-O-isopropyIidene-5-O-p-
tolylsulfonyl-a-o-, fluorination, 38:208
3-0-crotonyl-5-deoxy- 1,2-O-isopropylidene-
a-n-,Grignard reaction with, 27:203
1,2-O-isopropylidene-
a-D-
conformation of, 26: 120,34:201
3,5-cyclic phosphate, deacetalation and
hydrolysis, 39:62
3,5-phenylhoronate, preparation, 3 5 3 8
phosphorylation of, 33:46
reaction with (2-chloro-l,l,2-tri-
fluoroethyl) diethylamine, 38:229
reaction with diphenyl
phenylphosphonite and methyl
iodide, 28:280
selective esterification of, 33:35
3,5-di-O-(methylsulfonyl)-a-~-,
displacement reaction of, 24: I73
3,5-di-O-p-( tolylsulfonyl)-a-D-.
displacement reaction of, 24: 15I ,
165
523
3,5-di-0-p-tolylsulfonyl-a-r-, acetolysis
of, 22: I5
3,5-di-O-p-tolylsulfonyl-o-, sohoiysis of,
25:203
3-O-methyl-a-o-, 24:248
3-O-(methylsuifonyl)-a-~-, displacement
reaction of. 24: 173
3-0-p-tolylsulfonyl-a-o-, displacement
reaction of, 24: 152
5-O-p-tolylsulfonyl-a-o-, displacement
reaction of, 24:172
5-seleno-a-~-,23:232
5-seleno-o-, solvolysis of, 25205
5-thio-u-, so~vo~ysis of, 25:205
Se-benzyl- 1,2-O-isoprpylidene-5-seleno-u-
D-, 23:232
tetra-O-acety1-5-thio-a-o-, 23:208
tetra-O-acetyl-5-thio-P-o-, 23:208
Xylofuranoside
D-
methyl 2,5-di-O-benzoyl-3-deoxy-3-
fluoro-a-, 'H- and I9F-NMR data for,
46:112
methyl 3-O-benzoyl-5-O-benzyl-2-deoxy-
2-fluoro-P-, IH- and I9F-NMR data
for, 46: 1 1 1
ethyl 2-acetamido-2-deoxy- 1-thio-a-o-.
21:116
methyl, isolation of anomeric
phenylboronates, 35:58
methyl, methyl ethers, separation of, 30:
18
methyl 2,-di-O-benzoyl-3-bormo-3-deoxy-
D-, synthesis, 39: 109
methyl a(and P)-D-
conformation of, 21:98
entropy of activation for hydrolysis of,
22:40
hydrolysis of, 22:38
methyl 3-amino-3-deoxy a- and-P-o-,
deamination of, 31:57
methyl 5-amino-5-dioxy-P-o-, 23: 123,208
methyl 3,5-anhydro-3-thio-c-o-, 25: 157
methyl 2-azido-3,5-bis(benzamido)-2,3,5-
trideoxy-P-o-, 23: 174
methyl P-D-, 3,5-phenylboronate, hydrolysis,
3 5 5 1-52
methyl 3,5-bis(benzarnino)-3,5-dideoxy-2-0-
p-tolylsulfonyl-P-o-, 23: 174
methyl 2-bromo-2-deoxy-
524 SUBJECT INDEX
Xylofuranoside (continued)
p-0-, monobenzoates, preparation of,
28:269
3-O-formyl-5-O-benzoy~-p-~-, synthesis,
39: 120
methyl 3-deoxy-3-C-formy1-cr-o-
hemiacetal, 24: 193
preparation of, and derivatives, 31:28, 31,
33
methyl 3-deoxy-3-C-fomy~-P-o-,formation
of, 31:44
methyl 3,5-diazido-3,5-dideoxy-2-0-p-
tolylsulfonyl-a-D-, 24: 166
methyl 2,4-di-O-benzoyl-3-p-tolylsulfony-~-, crystal structure bibliography, 37:409
22:125
methyl 1,5-dithio-B-o-, hydrolysis of,
22:38-39
methyl 5-0-acetyl-a-~-,23: 108
methyl 2-0-benzoyl-
3,4-di-S-benzoyl-3,4-dithio-a-~-, 22: 141
3-0-(methylsulfonyl)-5-0-trity-a(or P)-o-
,reaction with acetic acid, 23:262
methyl 2-0-benzyl-5-deoxy-3-0-
(methylsulfony~)-a-o-,displacement
reactions of, 24: 165
methyl 3,5-0-isopropylidene-2-O-p-
tolylsulfonyl-a-o-, displacement
reactions of, 24: 153
methyl 0 - m e t h y b , mass spectrometry of,
30:42
methyl 3,5-O,S-isopropylidene-5-thio-o-,
23:208
methyl 2-S benzyl-3-chloro-3-deoxy-2-thio-
5-0-p-tolylsulfonyl-p-o-, 22: 193
methyl 5-thio-a-D-, hydrolysis of, 22:38
methyl 1-thio-p-o-, hydrolysis of, 22:38
methyl 5-thio-P-o-, hydrolysis of, 22:38-39
methyl Sthio-o-, 23:208
Xylofuranosyladenine, 8,3 '-anhydro-8-
mercapto-9-P-o-, monohydrate, crystal
structure, 43:284-285
Xylofuranosylamine, N-acetyh-,
configuration of, 31:105-106
Xylofuranosyl bromide, 3,5-di-O-acyl-2-
bromo-2-deoxy-P-o-, methanolysis of,
34:281
Xylofuranosyl fluoride
D-
3,5-acetoxonium-2-0-methyl-P-, 'H-and Xylomannans, 41:96
"F-NMR data for, 46: 109
3,5-benzoxonium-2-0-methyl-P-, 'H-and
lyF-NMR data for, 46: I09
3,5-di-0-benzoyl-2-0-methyl-, 'H- and
IYF-NMRdata for, 46:109
2,3,5-tri-O-acetyl-, 'H- and I9F-NMR data
for, 46: 108
2,3,5-tri-O-ben~oyl-a-,'~C-NMR data for,
46: 169
2,3,5-tri-U-benzoyl-P-, 'H- and lyF-NMR
data for, 46: 109
per-0-acetyl-a-o-, synthesis, 38:20 1
per-0-acetyl-p-o-, synthesis, 38:201
Xylofuranosyluracil, 2,2'-anhydro- I-a-D-,
Xyloglucans
analogy with galactomannans, 31:267
Annona muricata enzymic analysis,
44:151-152
bamboo shoot, 44:156
enzymic analysis, 44: 155
barley, 44:155-156
cellulase digestion, 44: 152-154
interconnections of in plant cell-walls,
42:369
mung bean, enzymic analysis, 44: 154
oat coleoptile, 44: 155
pea, enzymic analysis, 44: 155
Phaseolus coccineus, 44: 155-156
from plant cell-walls, 42:275,373,44:359
biosynthesis, 42:32 1-322
interconnections, 42:302-303,306-307,
310-311,315,355-356
purification, 42:276,287
structure, 42:288-291
polysaccharides, see Polysaccharides
rice endospexm, 44:155
soybean, 44: 155- 156
structure, enzymic analysis, 44: 151-1 56
sycamore, enzymic analysis, 44: 152
Tamarindus indica, enzymic analysis,
44:151
Vigna sesquipedalis, enzymic analysis,
44: 154
o-xy~o-Hexo-l,4-furanos-5-ulose, 5(S)-5-C-
acetoxy-3,5-O-benzylidene-6-deoxy-6-
fluoro-l,2-0-isopropylidene-a-, 'H- and
"F-NMR data for, 46: 143
Xyloisosaccharinic acid, 46:305
fungal, 23:407
 SUBJECT INDEX
Xylonic acid, D-, salts, preparation of, 29: I 19
Xylononitrile
tetra-0-acetyl-
D-, ammonolysis of, effect of solvent on,
31:99
L-, ammonolysis of, effect of solvent on,
31:99
2,3,4,5-tetra-O-acetyyl-~-,reaction with
ammonia, 31:83
Xylo-oligosaccharides, 4 6 5 9
chemical shifts, 46:75
1,4:3,6-dianhydrohexitols,49: 102-1 09
di-o-fructose dianhydride derivatives, 52:264
per-0-acetyl derivatives, fructose
components, 52:265-266
dihexulose dianhydrides, 52:248-249
geminal coupling, 2J ('H,19F), 46:75
'H-I9F coupling constants, 46:75-77
long-range coupling
4J, ('H, "F). 46:76-77
5J, ('H, I9F), 46:76-77
6J. ('H, 19F),46:77
per-0-acetyl dihexulose dianhydrides,
52:250-25 I
per-0-acetyl fructose glucose, 52:252
preparative liquid chromatography, 46:60
structural-reporter-group concept, 46: 79
vicinal coupling, 3J (lH,19F), 46:75-76
from xylans, 32:347-348,350
Xylopranoside
a-D-, glucopyranosyl-a-o-, preparation of,
34:265
serine-p-o-, and copper(I1) complex, crystal
structure bibliography, 34:355
Xylopyranan, carbon-I3 nuclear magnetic
resonance spectra, 38:95
Xylopyranose
1,2,3,4-tetra-O-benzoyl-p-~-, crystal
structure, 43:265-266
2,3,4-tri-O-acetyl-a-o-, 43:37 1
a-o-Xylopyranose calcium chloride tri hydrate,
crystal structure bibliography, 31:348
Xylopyranose 1,2,3-orthobenzoate. 3 - 0 - ( p -
bromobenzoy1)-a-u-. crystal structure,
43:347-348
Xylopyranoses
4-acetamido-
4-deoxy-~-,23: 147, 180
1,2,3-tri- 0-acetyl-o-, 23: 182
5-acetamido-
525
5-deoxy-a-~-,23:126, 167, 19&192
5-deoxy-o-, 23:122, 126, 128, 148, 160,
192-1 93
synthesis, 41:9
tetra-O-acetyl-5-deoxy-o-. mass spectrum
of, 23:201
a - D - , 45:74
conformation in solution, 26:85
crystal structure bibliography, 30:447
ester of adenosine 5'-pyrophosphate,
enzymic preparation of, 28:343
of uridine 5'-pyrophosphate, enzymic
preparation of, 28:343
occurrence of. 28:325
1,2,4-orthobenzoate
crystal structure bibliography, 30:465,
34:357
3-( p-bromobenzoate), crystal structure
bibliography, 30:465
reaction with sulhryl chloride, 28:235,
33:76
taste properties. 45:242
5-amino-5-deoxy-, derivative, synthesis,
40:97
p-D-
conformation in solution, 26:85
taste properties, 45:242
tetraacetate, conformations of, 24:58
5-[(benzyloxycarbonyI)amino]-5-deoxy-a-
D-, 23:192-193
5-benzymIdo-5-deoxy-o-, 23: 169
5-d, P-D-,tetraacetate. preparation of, 27:220
D-
amino-substituted, 47:65
derivatives having N-substituents,
equilibria, 47:6465
1,3,4-tri-0-acetyl-2-deoxy-2-fluoro-a-
'IC-NMR data for, 46:167-168
'H- and I9F-NMR data for, 46: 104
5-deoxy-5-phosphino- and-5-phosphinyl-~-,
synthesis of, 42:138-145
3,4-di-O-acetyl-2-bromo-2-deoxy-~-,
reaction with (p-nitropheny1)-
hydrazine, 25:202, 28:287
1,2:3,4-di-O-isopropylidene-5-thio-a-~-,
selective hydrolysis, 39: 17
a-L-,crystal structure, 43:207-208
N-amino-5-amino-5-deoxy-o-, 23: 1 59
0-(a-u-glucopyranosyluronicacid)-( 1+2)-
0-p-o-xylopyranosyl-( 1+4)-0-. 24:37 1
526 SUBJECT INDEX
Xylopyranoses (continued)
4-O-~-~-xylopyranosyI-O-, 24:372
0-P-D-xylopyranosyl-(1+~)-P-D-
xylopyranosyl-( 1+4)-~-, 24:372
3-0-benzoyl- 1,2-0-benzylidene-4-bromo-4-
deoxy-a-L-, synthesis, 39: 112
~-(4-0-methy~-a-~-g~ucopyranosy~uronic benzyh-D-
acid)-( 1+2)-0-~-o-xylopyranosyl-
(1+4)-a-o-, trihydrate, crystal structure
bibliography, 31:354
(1+4)-~-, 24~371
per-0-acety~-2-deoxy-2-fluoi-o-~-~-,
synthesis, 38:202
phosphorus derivatives of, physical
properties, 42: 191
(R)- and-(S)-5-d, tetra-0-acetyl-, preparation
of, 21: 144
1,2,3,4-tetra-O-acetyI-
p-D-,crystal structure bibliography,
32392
5-[(benzyloxycarbonyl)amino]-5-deoxy-a-
D-, 23: 188
5-[(benzyloxycarbonyl)amino]-5 -deoxy-a-
D-, conformation of, 26:88
tetra-0-acetyl-
a-D-
conformation of, 26:93
rearrangement in hydrogen fluoride,
26: 177
P-D-,acetoxonium salt, 26: 153-1 54
5-thio-o-, sulfone, 23:212
1,2,3,4-tetra-O-benzoyl-p-~-, crystal
structure bibliography, 38:526
tetra-0-benzoyl-D-, rearrangement in
hydrogen fluoride, 26:178
5-thio-a-o-
Amadori rearrangement of, 23:211
biochemical activity of, 23:2 12
mutarotation of, 24:49
reaction with amines, 23:209
s-thio-~-,23:207
mutarotation of, 23:208
synthesis, 44:135
synthesis and structure of, 42:138-139
1,2,3-tri-O-acetyl-4-benzamido-4-deoxy-r-,
23: 182
1,3,4-tri-0-acetyl-2-deoxy-2-fluoro-a-o-,
crystal structure bibliography, 37:384
tri-O-acetyl-2-deoxy-2-fluoro-a-~-,
crystallographic analysis, 38:280
t~i-0-benzoy~-2-O-methyl-p-~-,
rearrangement in hydrogen fluoride,
26: 183
o-Xylopyranose tetraacetate, anomeric
equilibria, 47:66
Xylopyranoside
benzoylation of, 33:25
catalytic oxidation of,33:89
benzyl2-0- and 3-0-acetyl-4-0-methyl-p-
D-, methylation and acyl migration in,
33:104
benzyl4-O-methl-p-o-
relative reactivities of hydroxyl groups in,
3359
selective acetylation of, 33:26
D-
benzyl3-deoxy-3-fluoro-p-,'H- and 19F-
NMR data for, 46: 106
tdfluoromethyl3,4-di-O-acetyl-a-, IH-
and I9F-NMR data for, 46: 105
methyl 2,3,4,-tri-O-(methylsulfonyl)-a-~-,
23:249
methyl 4-acetamido-
4-deoxy-a-o-, 23: 182
4-deoxy-P-r-, 23: 180, 182
methyl 5-acetamido-
5-deoxy-a-o-, 23: 192
5-deoxy-2,3,4-tri-0-methyl-a-o-, 23: 190
conformation of, 26:88
hindered rotation of acetyl group in,
23: 1 9 4 1 9 5
mass spectrum of, 23:202
methyl a-D-, 23:192
acylation of 2,4-boronic esters, 33:24
crystal structure bibliography, 38:429
2,4-phenylboronate, oxidation, 35:57
preparation, 35:46
separation from isomers, 35:58
reaction with methanesulfonyl chloride in
N,N-dimethylformamide, 33:8 1
selective esterification of, 33:25
sulfonylation of, 23:249
methyl 3-amino-
3-deoxy-a-o-, deamination of, in
nucleoside synthesis, 31:70
3-deoxy-P-o-, deamination of, 31:29
3-deoxy-o-, 23:262
methyl 5-amino-5-deoxy-a-o-, 23: 129,
192-193
 SUBJECT INDEX
methyl 3-azido-, 3-deoxy-a-o-, selective
benzoylation of, 33:26
methyl 4-azido-
4-deoxy-
p-L-,23: 180
2,3-di-O-(methylsulfonyl)-~-r~-,
displacement reactions of, 24: I63
2,3-di-O-benzoyl-4-deoxy-a-~-, 24: I60
methyl p-D-, 23:192
acylation of 2,4-boronic esters, 33:24
carbon-I 3 nuclear magnetic resonance
spectrum, signal-to-noise ratio,
41:31-32
crystal structure bibliography, 38:429430
3-diethylborinate 2,4-ethylboronate,
selective cleavage, 39:55
hydrolysis of, trifluoroacetic acid in, 28: 17
2,4-phenylboronate, oxidation, 35:57
preparation, 35:37
relative activities of hydroxyl groups in,
33:58
selective methanesulfonylation of, 33:26
selective oxidation with chromium
trioxide, 33:99
methyl 5-[(benzyloxycarbonyI)aniino]-5-
deoxy-a-o-, 23: 192-193
methyl 4-chloro-4-deoxy-a-~-,2,3-
di(chlorosulfate), preparation of, 33:75
methyl 3-deoxy-3-fluoro-p-~-,preparation,
38:212
methyl 2,3-di-0-benzoyl-4-bromo-4-deoxy-
a-L-, synthesis, 39: 1 1 1
methyl 2,3-di-O-(methylsulfonyl)-au-r,-,
23:249
methyl 2,4-di-O-(methylsulfonyI)-a-i~-,
23:249
methyl 1,5-dithio-p-~-,23:209
methyl 4-0-benzyl-3-deoxy-3-iodo-2-0-p-
tolylsulfonyl-p-L-, reaction with sodium
iodide, 28:293
methyl 2-0-(methylsulfonyl)-a-~-,23:249
methyl 2-O-p-tolylsulfonyl-a-~-,23:249
methyl 3-O-p-tolylsulfonyl-a-~-, 23:249
methyl 4-0-p-tolylsulfonyl-a-~-, 23:249
methyl 5-thio-a-o-, 23:208
sulfone, 23:212
methyl I-thio-P-D-
crystal structure of, 25:58,31:365
synthesis of, 25:58
methyl 5-thio-P-o-, 23:208-209
527
methyl tri-0-methyl-P-o-, mass spectrum of,
21:60
methyl 2,3,4-tri-O-
acetyl-
(Y-D-. crystal structure bibliography,
32365
5-thio-a-o-, sulfoxide, 23:213
5-thio-D-, sulfone, 23:212
methyl-P-D-, identification of, 30:24
methyl tri-O-(methylsulfony1)-a-o( and p-
D)-, displacement reactions of, 24:161
methyl 2,3,4-tri-O-methyl-5-thio-o-, mass
spectrum of, 23:202
p-nitrophenyl p-D, crystal structure
bibliography, 37: 384
XyIopyrano~ide-5-~*0, methyl a-o-and p-D-,
preparation, 35:58
Xylopyranosylamine
N-acetyl-o-, configuration of, 31: 104
5-thio-N-p-tolyl-o- Amadori rearrangement
of, 23:2 1 1
2,3,4-tri-O-acetyl-N-phenyl-5-thio-p-~-,
23:2 1 1
Xylopyranosyl azide, tri-0-acetyl-p-o-, crystal
structure bibliography, 37:385
Xylopyranosyl bromide
2,3,4-tri-O-acetyl-
a-D-, solvolysis of, 22:37
5-thio-a-o-. solvolysis of, 22:38
tri-0-acetyl-P-o-, conformation of, 24:58
tri-0-benzoyl-P-D-, crystal structure
bibliography, 32:370-37 1
Xylopyranosyl chloride
2-chloro-2-deoxy-a-o-,3,4-di( chlorosulfate),
preparation of, 28:236-237
D-, 2,3,4-tri-(chlorosulfate), preparation and
reactions of, 28:235-236
tri-0-acetyl-a-D-, acetoxonium salt,
26: 153-1 54
2,3,4-tri-O-acetyl-P-o-, crystal structure
bibliography, 32:362-363
tri-0-acetyl-p-o-
acetoxonium salt, 26: 153-154
conformation of, 26:88
2,3,4-hi-O-benzoyl-p-~-, crystal structure
bibliography, 37:405
Xylopyranosyl fluorides
D-
2-deoxy-2-fluoro-, p anomer, 'H- and "F-
NMR data for, 46: 155
528 SUBJECT INDEX

Xylopyranosyl fluorides (continued) 4,5-dideoxy-~-,23: 183

3,4-di-O-acetyl-2-deoxy- 5-acetamido-
2-bromo-, 'H- and I9F-NMR data for, 5-deoxy-o-, composition in aqueous
46: 136 solution, 42:49
2-fluoro-a-, 'H- and IyF-NMR data for, 5-deoxy-~-,preparation from paramose
46:155 dithioacetal, 32:85
2-iodo-, IH- and j9F-NMR data for, acyloxonium rearrangement of, 26: 153
46:137 D-
2,3,4-tri-O-acetyI-, IH- and I9F-NMR diethyl dithioacetals, conformation of,
data for, 46:102-103 26:72
2,3,4-tri-O-benzoyl-, 'H- and I9F-NMR diphenyl dithioacetal, conformation of,
data for, 46: 103 26:72
2,4-di-O-acetyl-3-deoxy-3-fluoro-~-, 'H- a-D-
and I9F-NMR data for, 46: 155 I ,2:3,5-bis(phenylboronate)and 1,2:3,5-
3,4-di-O-benzoyl-2-0-methyl-, 'H- and bis(butylboronate), preparation,
IyF-NMR data for, 46: I03 3543
2,3,4-tri-O-acetyl-, p anomer, 13C-NMR mutarotation of, 23:22
data for, 46: 167 a-L-, 2-(hydroxymethyl) derivatives, circular
valence geometry parameters, 47:73 dichroism, 4 9 7 9
per-0-acetyl- 2-amino-, 2-deoxy-o-
p-D-,synthesis, 38:202 deamination of, 31:26
2-deoxy-2-fluoro-a-~-,synthesis, 38:204 derivatives, preparation of, 32:81
3-deoxy-3-fluoro-p-~-,synthesis, 38:204 4-amino-
per-0-benzoyl- 4-deoxy-o-, 24: 160
a-D-,preparation, 38:20 1 4-deoxy-~-,23: 147, 181
p-D-,preparation, 38:201 4,5-dideoxy-~-,23: 148
tri-0-acetyl- 5-amino-, 4,5-dideoxy-~-,23: 120
a,(3-D-. 26: 177 3- and 5-phosphate, phosphono migration in,
p-D-,conformation of, 26:88 33: 108
tri-0-benzoyl- 2,5-anhydro-
a, p-D-.26:178 D-, diisobutyl dithioacetal, 24: 175
p-D-, conformation of, 26:88 3,4-di-0-p-tolylsu~fonyl-o-, diisobutyl
(3-D-Xylopyranosyl halides, isomer equilibrium, dithioacetal, preparation of, 32:5 1
47:6243 reaction with sodium iodide-
Xylopyranosyl-5-methylfuran,4-acetyl-2-3- dimethylformamide-zinc dust, 3 2 5 2
deoxy-3-C-nitro-p-o-, crystal structure, L-, 2.5~209
43~227-228 3-0-p-tolylsulfonyl-~-,dimethyl acetal,
Xylopyranosylurea, 3-methyl- 1-P-D-, crystal 25:203
structure, 43:339 5-seleno-o-, diamethyl acetal, 23:232
Xylopymosyl fluoride, 2,3,4-tri-O-acetyI-P-o-, p-D-,proton spin-lattice relaxation rates,
43:225 45:152
o-Xylosaccharinic acid 2,5-bis(acetamido)-2,5-dideoxy-o-,23: 173
a-and p-, formation from o-xylose, 28: 195 4,5-bis(acetamido)-4,5-dideoxy-~-, 23: 173
uracil, 2-0-acetyl-3-0-p-tolylsulfonyl-, diethyl dithioacetal, mass spectrometry of,
methyl ester, preparation, 36: 129-130 32:96
Xylose 5-bromo-5-deoxy-~~-, synthesis, 28:304,
4-acetamido- 40:90
4-deoxy-~-,23: 180 composition in nonaqueous solvents, 42:62,
4,5-dideoxy-o-, 23: 183 68
composition in aqueous solution, 4 2 5 1 5-(cyclohexylamino)-5-deoxy-~-, 23: 140
 SUDJEC'T INDEX
2-(hydroxymethyl) derivatives. circular
a-D-,
dichroism, 45:79
D-, 47: 18
absorptive rate by human jejunum, 34:289
benzylidenation of, 34: 186
derivatives, cyclic acetals, table.
34:2 16
2- and 0-methyl-, gas-liquid
chromatography as nitriles, 30:33
mass spectrometry of trimethylsilyl
derivatives of, 30:38
trimethylsilylation and separation by
gas-liquid chromatography of, 30:27,
31
in aqueous solution composition. 42:26.
62,64
polarography, 42:2 I
boronates, hydrolysis, 35:5 1
a and p pyranose anomers, circular
dichroism, 45:79-80
catabolism by yeasts, 32:210
diethyl dithioacetal, methylation of,
3247
diisobutyl dithioacetal, reaction with p -
toluenesulfonyl chloride, 32:5 1
diphenyl dithioacetal, proton magnetic
resonance spectrum of, 32:89
dithioacetals, hydrolysis of, 32:67
reaction with sulfonyl chloride ion
pyridine, 32:48
mercaptalation of, 32:23
transport into Rhodotorzrlu glrrtini.~,
32156
uridine 5'-pyriphosphare ester, i n inung
bean, 32:9
utilization by yeasts, 32:227
catalytic oxidation of, 33:87
diethyl dithioacetal, selective
benzoylation of, 33:4 I
dithioacetals, selective esterification of,
33:404 I
selective methylation of, 33:66
dehydration of, 28: 176, 188
o-gulono- 1,4-lactone synthesis.
38:294-295
1,2:3,5-diacetal, selective hydrolysis,
39:16
diethyl dithioacetal, irradiation, 39:94
dialkyl dithioacetal, reaction with p -
toluenesulfonyl chloride. 25: I98
529
electrophoretic migration of, 21:234
enantionieric carba-sugars, synthesis,
48:44
enzymic isomerization. 36:46
formation
of-and xylometasaccharinic acids
from. in base, 46:281-282
of 2-furaldehyde from, 46:275-276
of saccharinic acids from, 46:281-282
gas-liquid chromatography of. 28:46
glycoenzyme constituent, 27:302, 307,
32 1
in glycoproteins, 25:4 I3
high-temperature transformation
acidic conditions, 46:276-277
basic conditions, 46:28 1-283
methyl ethers, separation of. 30: I8
monosaccharides, circular dichroism.
45:82
mutarotation
and gas -liquid chromatography of,
28:40
in pyrtdine, 28:39
nonselectivc spin-lattice relaxation rates,
45: 148
N-phenylosotriazole acetate, mass
spectrometry of, 29: I02
pemicotinate, ammonolysis of, 31:89
in pituitary glycoprotein, gas-liquid
chromatographic analysis of,
28:67-68
in plant cell-wall hydrolyzates, liquid
chromatography analysis. 46:55
polarography of. 29: 127
polymerization by hydrogen chloride,
21:463
protein linkage with, 25:4 I8
proton spin-lattice relaxation rates, 45: 152
radiation chemistry, 37:33
reaction with sulfuryl chloride, 28:235
saccharinic acids from, 28: 195
structure, 35:4
sulfur-containing. 35:8
3-deoxy-, 3-fluoro-~-,22:207
preparation, 38:212
S-deoxy-r)-, synthesis of. 21: 177
2-deoxy-2-fluoro-a-o-, preparation. 38:2 13
4,S-deoxy-5-hydrazino-~-, 23: I50
4,5-diazido-4.5-dideoxy-2,3-0-
isopropyl idene-L-
530 SUBJECT INDEX
Xylose (continued)
diethyl dithioacetal, 22: 155
preparation of, 32:5 1
3,5-dideoxy-3,5-difluoro,preparation+-,
38:244
4,5-dideoxy-4-hydrazino-~-, 23: 1 62
3,4-di-O-acety1-2,5-anhydro-o-, (p-
nitrophenyl)hydrazone, 25202
preparation of, 28:287
2,4:3,5-di-O-benzylidene-o-
diethyl dithioacetal, selective hydrolysis,
39:22
dithioacetal, preparation of, 32:53
2,3:4,5-di-O-cyclohexylidene-~-, ethylene
acetal, synthesis, 39:76
2,4:3,5-di-O-ethylidene-aldehydo-~-
polarography of, 29: 142
2,3 :4,5-di-O-kopropylidene-o-
dialkyl dithioacetals, selective hydrolysis,
39:22
diethyl dithioacetal
methylation of, 32:54
reaction with bases, 32:58
preparation of, 32:53
selective hydrolysis, 39:24
diphenyl dithioacetal
elimination reactions of, 29:298
reaction with bases, 32:58
dithioacetals, preparation of, 32:53
2,3-di-O-rnethyl-o-, dimethyl dithioacetal,
reaction with p-toluenesulfonyl
chloride, 32:50
4,5-dithio-~-,23:226
DL-,synthesis, 40:8-9, 73, 91
in fungal cell walls, 23:4 13
halogen derivatives of, 22:2 16
L-
derivatives, cyclic acetals, Table, 34:2 16
1,2:3,5-di-diacetal, selective hydrolysis,
39:16
utilization by yeasts, 32: 147, 2 18
liquid chromatography, 46:33,52-53
3-0-a- and-P-D-xyiopyranosy~-D-, synthesis,
35:55
~-O-(Y-L-, hcopyranosyl-o-, 24:362
2-O-f3-~-galactopyranosyl-~-, 24:362,373
4-O-P-~-galacto~yl-~-, 25:34
3-O-~-D-galactosyl-4-O-b-D-galactosyl-D-,
2534
2-O-f3-o-glucopyranosyl-o-, synthesis, 41 :9
3-O-P-o-glucopyranosyl-o-, synthesis, 3 9 5 5
5-O-P-D-glucopyranosyI-o-, synthesis, 41 :9
3-O-P-o-xylopyranosyl-~-, synthesis, 41 :9
~-O-P-D-X~IOPYIWIOS~I-D-, 24:369,375
5-O-benzoyI-3,4-O-isopropylidene-o-,
dimethyl dithioacetal, preparation of,
32:5 1
5-O-benzoyl-4-
deoxy-4-iodo-2,3-0-isopropylidene-o-,
diethyl dithioacetal, preparation of,
28:242
deoxy-4-deoxy-4-iodo-2,3-0-
isopropylidene-, diethyl dithioacetal,
22: 185
2,4-O-benzylidene-
D-, diethyl dithioacetal, oxidation of,
32:80
L-, composition in aqueous solution, 42:60
3,4-O-isopropylidene-
D-, dimethyl dithioacetal, preparation of,
32:s 1
5-O-p-tolylsulfonyl-~-,dimethyl
dithioacetal, preparation of, 32:
5 1-52
4,5-O-isopropylidene-o-,dithioacetals,
preparation of, 32:54
1,2-O-isopropylidene-5-9methyl-5-thio-~-,
23:235
oligomers of
I3C-NMR data for, 42:207-208
methyl glycosides of, I3C-NMR data for,
42:2 13-214
peracetates of, 42:215-216
2-O-methyb
diethyl dithioacetal, reaction with p-
toluenesulfonyl chloride, 32:50
in plant cell-wall polymer, 42:280-281,
287
3-O-methyl-o-, from Myxococcus,fulvus
lipopolysacharide, 29:67
5-O-methyb, composition in aqueous
solution, 42:45
3-O-methyl-~-,from Rhodopseudomonas
viridis lipopolysaccharide, 29:67
5-phosphate, synthesis of, 33:46
reaction with sulfuryl chloride, 33:76
selective oxidation with silver carbonate-on-
celite, 33:97
2,3,4,5-tetra-O-acetyyl-aldehydo-o-,
preparation of, 32:62
 SUBJECT INDEX 53 1

I-thio-o-, composition in aqueous solution, Y

4253
5-thio-~-,composition in aqueous solution,
42:52
UDP-D-, in polysaccharide biosynthesis,
42:32 1-322
5,5,5-trichloro-5-deoxy-, synthesis. 4 0 9 2
3,4,5-tri-O-benzoyl-
o-, diethyl dithioacetal, preparation of,
32:45
2-9ethyl-2-thio-o-, diethyl dithioacetal,
dimethyl acetal from, 32:65
2.3.4-tri-0-methyl-D-
dehydration of, 28: 181
diethyl dithioacetal, reaction with p-
toluenesulfonyl chloride, 32: 50
2,3,5-tri-O-methyl-o-, dehydration of,
28:181
Xylose antibodies, 53:226-227
D-xylOSe isomerase, sources and activity,
36:46-50
Xylose 5-phosphate, composition in aqueous
solution, 42:46
Xylosidase, p-D-,23:212,44:159, 162-163
in plant cell-walls, 42:301, 376, 379
Xylosides
methyl, lack of effect by emulsin, 50: I3
methyl p-D-
crystal structure bibliography, 31:365
selective periodate oxidation of, 33:95
methyl D-
catalytic oxidation of, 33:89
ring structure of, 23: 15
methyl 2,3,4-tri-O-methyl-o-,effect of
volatility on methylation analysis of,
30:17
Xylosucrose, 51: 150
Xylosylceramide, isolation, 40:238
o-Xylosyltransferase, 44:202-203
Xylopyranosyl fluoride, 2,3,4-tri-O-benzoyl-p-
D-, crystal structure, 43:257-258
Xylulose, D-
cyclic acetals, properties of, 26:257
preparation from xylose, 28:39
L-, synthesis of, 28:4
preparation of, 26:237
purification of, and isopropylidene acetal,
26:198
Xyluronic acid, D-, decarboxylation of, 28:
187
Yajima, T., 46:6
Yamada, Yukari, 46:3
Yamakawa, T., 46:9
Yarovenko-Rashka reagent, fluorinating agent,
3~27-229
Yeast glucan, 23:380
Yeast gum, 26:394
Yeast mannan, 53:254-255
Yeasts
&,a-trehalose in, 30:230,234, 244
aerobic growth of, in presence of sugar,
32:142
aerobic respiration of, 32:143-144, 23 1
anaerobic fermentation by, 32: 144
1,4-anhydro-, catalytic oxidation of.
25261
2,5-anhydro-, 25:202
associations of abilities to utilize glycosides,
32:222-226
cells
anatomical structures of, 32: 137-142
sugar entry into, 32: 147-1 59
walls, 32:138-140
D-glucan formation in, 32:229
diagram, 39:368
D-mannan formation in, 32:228
structure of, 32: 188-1 89
1,4:3,6-dianhydro-o-
catalytic oxidation of, 25:261
infrared spectra of, and nitrates, 25:
252
isomerization of, 25:260
ring opening of, 25:257
enzyme presence, 50: 1 I
fermentation of, 33:4, 50:7-9
galactomannans from, 31:243
gas-liquid chromatographic analysis of,
2 8 : I~
in honey fermentation, 32: 129
identification and classification of,
32: 129-137
mannans, 41:82-84,99
osmophilic, in honey, 25303
phosphonomannan, 41:86
protein glycosylation in, 42:329
pyramine synthesis, 52:303-306
rates of oxidative respiration and non-
oxidative fermentation by, 32: 172
532 SUBJECT INDEX

Yeasts (continued) Zemplen, Geza, obituary of, 14:l-8

spin-lattice relaxation of I3C nuclei in
thermally denatured, 27:60
sugar utilization, 32: 125-234, 145-147,
39:347404
thiamine, thiazole five-carbon chain,
pentulose as precursor, 52:288-291
trehalase from, 30:247
Yellow farina dextrin, alkali-lability, 47:293,
295
Yersiniu enterocoliticu, 0-specific
polysaccharides, 47: 179
Yersiniose A and B, 48:288
Yoshimura, Juji, 46: I , 9
Yoshizawa, Z.. 46:9
Yuccoside C
occurrence, 37:328
structure, 37:329
Yuccoside E
occurrence, 3 7 :32 8
structure. 37:329
2 Zymosan
Zanflo, Erwiniu tuhitica polysaccharide,
preparation, properties, and uses, 36:297
Z-Enzyme, 23:33 I , 336
Zimm-plot technique, mucus glycoproteins,
47:357-358
Zinc chloride
in anhydridization of hexoses, 34:46
effect on sugar solubility in acetone, 27:95
Zinc chloride-acetic anhydride, rearrangements
of saccharides in, 26: 192
Zinc ion, effect on a-o-mannosidase, 28:424
Zinc oxide, as photoxidation sensitizer, 51:293
Ziziphins, as sweet-taste inhibitors, 45:336-339
Zizyphus,jujubu h i t , cyclic AMP in, 42:367
Zone electrophoresis, of carbohydrates,
12:81-115
Zooglycosphingolipids, 24:382
Zorbach, William Werner, obituary, 27: 1-6
Zorbach Memorial Prize, 27:6
Zosteru, galacturonan of, 42:28 1
Zosteruceue, apiose-containing polysaccharides
from, 31: 1 5 1
Zosterine, from Zosteruceue and Phyllospudix,
31:151
antitumor activity of, 32:249, 267-268, 271
effect on properdin level, 32:271
 CONTRIBUTOR INDEX

Boldface numerals indicate volume numher.

A Biermann, Christopher J., 46:251

Binkley, Roger W., 38:105
Adams, Mildred, 5:229 Binkley, Wendell W., 8:291, 10:55,36:9
Alexeev, V. G., 27:227 Birch, Gordon G., 18:201
Alexeev, Yu. E., 27:227 Bishop, C. T.. 19:95
Anderson, Ernest, 1:329 Blair, Mary Grace, 9:97
Anderson, Laurens, 14: 135 Bleha, Tombs, 47:45
Anet, E. F. L. J., 19:181 Bobbitt. J. M., 11:l
Angyal, Stephen J., 14:135,36:1,42: 15, 47:1, Bock, Klaus. 41:27,42: 193
49: 19 Boeseken, J.. 4:189
Antonakis, Kostas, 42:227 Bonner, T. G., 16:59
Archibald, A. R., 21:323 Bonner, William A,, 6:25 1
Aronson, N. N. Jr., 27:301 Bourne, E. J., 5:145, 7:137
Aspinall, Gerald0 O., 8:217,9: 13 I , 14:429, Bouveng, Hans O., 1 5 5 3
24:333,51:169 Brady, Robert F. Jr., 26: 197
Auge, Claudine, 49: 176 Bray, H. G., 4:37,8:251
Brennan, Patrick J., 51: 169
Brimacombe, J. S., 19:303
B Brinson, Ken. 42:265
Bushway, Alfred A,, 32:235
Bacon, John Stanley Durrant, 30: I Buttenvorth, Roger F., 26:279
Baddiley, J., 21:323
Baer, Hans H., 24: 1; 67
Bailey, R. W., 17:121 C
Ball, D. H., 23:233,24: 139
Ballou, Clinton E., 9:59,32:1.39: I Cadenas, Raul A., 31:81
Banaszek, Anna, 40: 1 Caesar, George V., 13:331
Banks, W., 18:357 Caldwell, Mary L., 5:229
Barker, G. R., 11:285 Cantor, Sidney M., 6:23 1, 20: 1
Barker, Horace A,, 32: 1 Capon, B., 15: 11
Barker, S. A,, 7:137 Cam, C. Jelleff, 1:175
Barnett, J. E. G., 22:177, 27: 127 Carter, R. Douglas, 47: 125
Barnett, James A,, 32: 125,39:347 Cam, Benito. 43:51
Barreto-Bergter, Eliana, 4 1 5 7 Cerny, Miloslav, 34:23
Barren, Elliott P., 6:205 Chandrasekaran, Rengaswami, 52:3 1 I
Barry, C. P., 7:53 Chatterjee, Delphi, 51:169
Bayne, S., 11:43 Chen, Minshen, 34:285
BeClik, Andrew. 11:145 Chizhov, 0. S.. 21:39
Bell, D. J., 6:ll Clamp, John R., 16: I59
BeMiller, J. N., 13:289, 22:25 Clarke, Margaret A,, 52:441
Berman, Elisha, 43: 1 Clarke, Ronald J., 46:205; 333
Bhat, K. Venkatramana, 21:273 Coates, John H., 46:205: 333

533
534 CONTRIBUTOR INDEX
Compton, Jack, 3: 185
Conchie, J., 12: 157
Corina, D. L., 27: 127
Courtois, Jean Emile, 18: 1
Coxon, Bruce, 27:7
Crawford, Sally Ann, 37:79
Crawford, Thomas C., 37:79,38:287
Crum, James D., 13:169
Csuk, Rene, 46:73; 33 1
Czernecki, Stanislas, 53: 143
D Ferrier, Robert J., 20:67,24:199,35:31,
Dais, Photis, 45:125,51:63
Daleo, Gustavo R., 44:341
Datema, Roelf, 40:287
David, Serge, 49:176,52:267
Davies, D. A. L., 15271
Dax, Karl, 33: 189
De Belder, Anthony N., 20:219,34:179
de Lederkremer, Rosa M., 46:11,50:125
Dea, Iain C. M., 31:241
Dean, G. R., 5:127
DeFaye, J., 25:181
Deitz, Victor R., 9:247
Dekker, Robert F. H., 32:277
Dell, Anne, 45: 19
Delmer, Deborah P., 41: 105
Deuel, Harry J. Jr., 2:119, 16:335
Deulofeu, Venancio, 4: 119
Dey, Prakash M., 35:341,37:283,42:265,
44:341
Dill, Kilian, 43: 1,45: I69,47: 125
Dimler, R. J., 7:37
Dorland, Lambertus, 41:209
Doudoroff, M., 5:29
Dubach, P., 16:335
Durette, Philippe L., 26:49
Dutcher, James D., 18:259
Dutton, Guy G. S., 28: 1 1,30:9
E Gottfried, J. B., 5:127
Edye, Leslie A,, 52:441
Eggleston, Gillian, 52:441
El Khadem, Hassan S., 18:99,20:139,25:351,
38:1,51:1, 53:13
Elbein, Alan D., 30:227
Elderfield, Robert C., 1:147
Ellis, G . P., 10:95,14:63
Estramareix, Bernard, 52:267
Evans, Taylor H., 2:203
Evans, W. L., 6:27
F
Feather, Milton S., 28:161,53:1
Fedoronko, Michal, 29:107
Fernandez-Bolafios, Jose, 4 5 7
49:37
Fewster, J. A,, 11:43
Finch, Paul, 52: 1
Finne, Jukka, 38:389
Fletcher, Hewitt G. Jr., 3:45,5:1,6:135
Flowers, Harold M., 39:279
Fordyce, Charles R., 1:309
Foster, A. B., 7:247,10:335,12:81,14:213,
15:371
Fox, Jack J., 14:283,22:307
French, Dexter, 9:149,12: 189
Freudenberg, Karl, 21: 1
G
Garegg, Per J., 52: 179
Garg, Hari G., 43:135,49:239,50:277
Gautheron, Chnstine, 49: 176
Gelas, Jacques, 39:71
Gelpi, Maria E., 31:81
Glanzer, Brigitte I., 46:73; 331
Glaudemans, Cornelis P., 31:l; 313
Goepp, R. M. Jr., 4:211
Goldstein, Irwin J., 21:431,35:127
Gomez-Sanchez, Antonio, 4 5 7
Gonzalez, F. Garcia, 11:97,20:303
Goodman, Irving, 13:2 15
Goodman, Leon, 22: 109,29: 1
Gorin, Philip A. J., 23:367,38:13,41:67
Gottschalk, Alfred, 5:49
Green, John W., 3:129,21:95
Greenwood, C. T., 7:290, 11:335, 18:357,
22:483,23:281
Grindley, T. Bruce, 53: 17
Grisebach, Hans, 3 5 8 1
 CONTRIBUTOR INDEX 535

Gros, Eduardo G., 46: 11 J

Grynkiewicz, Grzegorz, 40: I
Gurin, Samuel, 3:229 Jamieson, G. A,, 27:l
Guthrie, R. D., 16:105,22:11 Jamefelt, Johan, 38:389
Jeanloz, Roger W., 6:135, ll:xiii, 13:189,
43:135
H Jeffrey, George A,, 19:7,30:445,31:347,
32:353,34:345,37:373,38:417.43:203
Haggard, A. J., 10:335 Jennings, Harold J., 41:155
Haines, Alan H., 33:11,39:13 Johnson, W. Curtis Jr., 4 5 7 3
Hall, Laurance D., 19:5 1, 29: 1 1 Jones, David M., 19:219
Hanessian, Stephen, 21:143,26:279,33: I 1 1 Jones, J. K. N., 2:235,4:243,11:185
Harding, Stephen E., 47:345 Jonsen, J., 15201
Hams, Elwin E., 4:153
Hams, John F.,28:161
Haskins, Joseph F.,2:279 K
Hassid, W. Z., 5:29, 18:309, 26:35 1
Hay, George W., 41:l Kaji, Akira, 42:383
Hayes, Colleen E., 35: 127 Karabinos, J. V.,7:99, 9:285
Haynes, L. J., 10:207, 18:227,20:357 Karkkainen, Jonna, 38:389
Hehre, Edward J., 8:277 Kashimura, Naoki, 46: 1
Helferich, Burckhardt, 3:79, 7:209 Keglevic, Dina, 36:57
Hemmer, Reinhard, 49:93 Kennedy, John F.,29:305
Herp, Anthony, 37: 1 Kent, P. W., 3:311
Heyns, K., 17: 169 Kertesz, Z.I., 5 7 9
Hibbert, Harold, 2:203 Khan, Riaz, 33:235,39:213
Hicks, Kevin B.,46:327 Kicks, Kevin B., 46:17
Hickson, John L.,16:159 Kinzy, Willy, 50:21
Hilton, H. W., 21:377 Kiss, Joseph, 24:38 I , 29:229
Hindert, Marjorie, 9:285 Klemer, Alrnuth, 16:85
Hirst, E. L., 2:235, 6:l Knirel, Yuriy A,, 47: 167
Hodge, John E., 10: 169 Kochetkov, Nicolai K., 21:39, 28:307,
Honeyman, John, 7:53,10:95, 12: 1 1 7 44:387
Horton, Derek, 14:213, 15:159, 18:123, 19:l, Koenig, Jack L., 44:7
26:l; 49,32:15,48:1, 5O:xiii Komano, Tohru, 46: I
Hough, L., 11:185, 1591, 16:159 Kort, M. J., 25:3 1 1
Hounsell, Elizabeth F.,50:311 Kowkabany, George N., 9:303
How, M. J., 19:303 Krantz, John C. Jr., 1:175
Hudson, Claude S., 1:1,2:1,3:1,4:57 Krusius, Tom, 38:389
Hullar, T. L., 21:431 Kunz, Horst, 50:277
Hutson, D. H., 18:123 Kuszmann, Janos, 28: I

I L

Igarashi, Kikuo, 34:243 Laidlaw, R. A., 7: I

Ikehara, Morio, 36:135 Laland, S., 15:201
Inch, T. D.,27:191 L a m , Olle, 33:295
Inokawa, Saburo, 42: 135 Lederer, Edgar, 16:207
Isbell, Horace S., 23:11,24:13 Lee, Cheang-Kuan, 45: 199
536 CONTRIBUTOR INDEX
Lee, Yuan Chuan, 37:225
Legler, Giinter, 48:3 19
Lemieux, Raymond U., 3:337,9: 1,50: 1
Lespieau, R., 2:107
Levi, Irving, 4: 1
Levvy, Guildford A., 12:157, 14:381, 28:401
Lezica, Rafael Pont, 44:341
Li, Su-Chen, 40:235
Li, Yu-Teh, 40:235
Liggett, R. W., 9:247
Lincoln, Stephen F., 46:205; 333
Lindberg, Bengt, 15:53,31:185,33:295,
48:279
Lindner, Buko, 50:2 1 1
Liptak, Andras, 49:3
Lohrnar, Rolland, 4:211
Lonngren, Jorgen, 29:41,31:185
Lyon, Nancy, 49:239
M Nakahara, Waro, 32:235
MacAllister, Robert V., 36:15
Maeda, Kenji, 48: 1
Maher, George G., 10:257
Malhotra, Om Prakash, 16:239
Manley-Hams, Merilyn, 52:207
Manners, David J., 12:261,17:371,30:1,
35: 1
Marchessault, Robert H., 22:421,33:387.
35:337, 36:315,40:381
Markham, Alexander F., 36: 135
Markovic, Oskar, 33:323
Marsh, C. A,, 12:157, 14:381
Marshall, J. John, 30:257
Marshall, R. D., 25:407
Matheson, Norman K., 44: 147
Mathlouthi, Mohamed, 44:7
McCarthy, J. F., 22: 1 1
McCasland, G. E., 20:ll
McCleary, Barry V., 44:147
McCloskey, Chester M., 12:137
McColloch, R. J., 5:79
McDonald, Emma J., 2:253
McGale, E. H. F., 24:435
McGinnis, Gary D., 26:297,44: 1
Mehltretter, C. L., 8:23 1
Mehta, N. C., 16:335
Mester, L., 13:105, 14:l
Micheel, Fritz, 16%
Miller, Robert Ellsworth, 6:23 1
Mills, J. A., 1O:l
Milne, E. A,, 23:281
Mizuno, Takashi, 29:173
Montgomery, John A,, 17:301
Montgomery, Rex, 22: 1
Montreuil, Jean, 37:157
Moody, G. J., 19:149
Morehouse, Margaret G., 2: 1 19
Morgan, J. W. W., 12:117
Mori, T., 8:3 15
Momson, Anthony, 31:241
Mort, Andrew J., 47: I67
Moye, C. J., 27535
Muetgeert, J., 16:299
Myrback, Karl, 3:25 1
N
Nanasi, Pal, 49:3
Neely, W. Brock, 12:13, 15341
Nelson, David A,, 46:273
Neuberg, Carl, 4:75
Neuberger, Albert, 25:407,33: 1
Neufeld, Elizabeth F., 18:309
Newth, F. H., 6:83, 10:207
Nickerson, R. F., 5:103
Nikaido, H., 26:351
Nord, F. F., 13:l
0
Ogawa, Seiichiro, 48:2 1
Ohtsuka, Eiko, 36:135
Olson, E. J., 12:299
Orenstein, Neil S., 31:135
Overend, W. George, 8:45, 1 5 1 1, 52:l
P
Pacsu, Eugene, 1:78
Palasinski, Mieczyslaw, 47:203; 279
Pamsh, F. W., 23:233,24:139
Paulsen, Hans, 17:169,23:115,26:127
Pavia, Andre A,, 43:l
Pazur, John H., 27:301,39:405,42:1, 53:201
 CONTRIBUTOR INDEX
Peat, Stanley, 2:37,5:145
Pedersen, Christian, 41:27,42: 193
Pedersen, Henrik, 42: 193
Penglis, Anna A. E., 38: 195
Percheron, Franqois, 49: 1 I
Percival, E. G. V., 3:23, 7: 1
Perlin, Arthur S., 14:9,23:1,45:125
Pemet, Andre G., 33:lll
Phillips, Glyn O., 16:13, 18:9
Pigman, Ward, 23: 1 I , 24: 13
Polglase, W. J., 103283
Priddle, J. E., 15:91
Pridham, J. B., 17:121,20:371
Purves, Clifford B., 4:l
R StanEk, Jan Jr., 34:23
Rauvala, Heikki, 38:389
Raymond, Albert L., 1:129
Rees, D. A,, 24:267
Reeves, Richard E., 6: 107
Reichstein, T., 17:65
Rendleman, J. A. Jr., 21:209
Rexova-Benkova, Lubomira, 33:323
Reynolds, D. D., 6:27
Richards, Geoffrey N., 32:277,52:207
Richtmyer, Nelson K., 1:37,5:1, 6: 175
Rietschel, Emst Th., 50:211
Robyt, John F., 51:133
Roscher, Nina M., 53:7
Rosenstein, R. D., 19:7
Rosenthal, Alex, 23:59
S Talky, E. A,, 6:27
Sanchez, A. Gomez, 20:303
Sandford, Paul A,, 36:265, 53:7
Sands, Lila, 1:329
Sarko, A,, 2 2 4 2 1
Sattler, Louis, 3: 1 13
Schauer, Roland, 40: 13 1
Schilling, Christopher H., 53:263; 345
Schmidt, Richard R., 50:21
Schoch, Thomas John, 1:247
Schuerch, Conrad, 39: 157
Schwarz, Ralph T., 40:287
Shafizadeh, F., 11:263,13:9,23:419. 26:297
Shibaev, Vladimir N., 28:307,44:277
537
Siddiqui, I. R., 25:285
Sidebotham, Ramon L., 30:371
Singh, Prem P., 32:235
Smimova, Galina P., 44:387
Smith, F., 2:79,4:243
Snaith, Sybil M., 28:401
Soltzberg, S., 25:229
Somsak, Laszl6,49:37
Sowden, John C., 6:291, 12:35, 17:l
Speck, John C. Jr., 13:63
Spedding. H., 19:23
Spencer, J. F. T., 23:367
Spohr, Ulrike, 50: 1
Sprinson, David B., 15:235
Stacey, Maurice, 2:161,3:31 I , 4:37, 7:247,
8:45, 19:303,35:1,41:1
Stetter, Hermann, 45: 1
Stoloff, Leonard, 13:265
Stoss, Peter, 49:93
Stowell, Christopher P., 37:225
Strahs, Gerald, 25:53
Suami, Tetsuo. 48:21
Sugihara, James M., 8: 1
Sundaralingam, Muttaiya, 30:445,31:347,
32:353,34:345,37:373,38:417,43:203
Sundararajan, Pudupadi R., 33:387,35:377,
36:315,40:381
Svensson, Sigfiid, 29:41,31:185
Szarek, Walter A,, 28:225,41:1
Sztaricskai, Ferenc, 49:3
T
Taravel, Francois R., 51: I5
Teague, Robert S., 9: I85
Theander, Olof, 17:223.46:273
Theobald. R. S., 15:91
Thomas, H. Jeanette, 17:301
Timell, T. E., 19:247,20:409
Tipson, R. Stuart, 1: 193,s: 107, 12: I. 16: 1
Todt, K., 23: 1 15
Tokuzen, Reiko, 32235
Tomasik, Piotr, 47:203; 279, 51:243, 53:263;
345
Tsuchiya, Tsutomu, 48: 1; 91
Turvey, J. R., 20: 183, 25: 1
Tvaroska, Igor, 47:45,51:15
538
U Wempen, I., 14:283
Ueda, Tohru, 22:307
Umezawa, Hamao, 30: 183
Urnezawa, Sumio, 30: 1 1 1
Unger, Frank M., 38:323
V Williams, Neil R., 25: 109
van Halbeek, Herman, 41:209
Varela, Oscar, 50: 125
Verstraeten, L. M. J., 22:229
Vinogradov, Evgeny V., 47:167
Vliegenthart, Johannes F. G., 41:209
van dem Bruch, Karsten, 50:277
von Sonntag, Clemens, 37:7
W
Wallenfels, Kurt, 16:239
Wander, Joseph D., 32: 15
Watson, Ronald R., 31:135
Webber, J. M., 15:371, 17:15
Weidmann, Hans, 33: I89
Weigel, Helmut, 18:61,34:1
Weiss, Alvin H., 29:173
Weiss, Ekkehard, 17:65
CONTRIBUTOR INDEX
Whistler, Roy L., 1:279,5:269, 12:299,
13:289, 16:159,32:235,34:285
Whitehouse, M. W., 13:237
Wiejak, Stanislaw, 47:; 203; 279
Wiggins, L. F., 4:293,5:191
Wilkie, Kenneth C. B.. 36:215
Williams, J. Michael, 31:9
Wise, Louis E., 15:l
Witczak, Zbigniew J., 44:91,53:143
Wolfram, Melville L., 3:337,8:291
Y
Yamamoto, Hiroshi, 42: 135
Yoshimura, Juji, 42:69
Z
Zahringer, Ulrich, 50:211
Zamojski, Aleksander, 40: 1
Zaranyika, Mark F., 51:243
Zehavi, Uri, 46: 179
Zhdanov, Yu. A,, 27:227
Zilliken, F., 13:237
Zorbach, W. Werner, 21:273
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