Carbohydrates :

Physical and Chemical Properties

By
drg. Prasetyo Adi, MS
Objectives
To Understand :
• The importance of carbohydrates for
organisms
• The classification of carbohydrates
• The physical and chemical
properties of carbohydrates
Reference :
• March and Bettelheim,1995;
Introduction to General,Organic &
Biochemistry, 4th edition, Saunders
College
What’s carbohydrate ?

• Compound containing C, H, O
• General formula : Cx (H2O)y
• Polyhydroxylated aldehydes 
aldose
• Polyhydroxylated ketones 
ketose
• In plants, simple carbohydrate
(glucose) is synthesized from
carbon dioxide and water by
photosynthesis
CARBOHYDRATES:
• POLYHYDROXY ALDEHYDES OR KETONES

• SIMPLE CARBOHYDRATES MOLECULES ARE SYNTHESIZED

CHIEFLY BY CHLOROPHYL-CONTAINING PLANTS AS LONG
AS THE SUN IS SHINING

PHOTOSYNTHESIS

LIGHT
6 CO2 + 6 H2O C6H12O6 + 6 O2
KHOLOROFIL
The Importances of carbohydrates
• Give structure to cell walls and cell
membrane (e.g. cellulose)
Humans:
• Provide the majority of energy
• A source of carbon atoms for
synthesis of many compounds
nucleic acids and connective
tissue
• Comprise large portions of nucleic
acids that form DNA and RNA (e.g.
ribose, deoxyribose)
• Comprise some portions of
connective tissues
 Classification
Based on :
1. Number of sugar units in total chain
2. Number of carbon atoms in the chain
3. Stereochemistry
Classification of carbohydrate based on the
number of sugar units :

• Monosaccharides : single sugar unit

e.g. glucose, fructose, galactose
• Disaccharides : 2 sugar units
e.g. lactose, sucrose
• Oligosaccharides : 3-10 sugar units
e.g. maltotriose
• Polysaccharides : > 10 sugar units
e.g. starch, cellulose
Monosaccharides classifisation based on the number
of carbon atoms
 Stereoisomer
• Stereochemistry : study of the spatial
arrangement of the molecules
• Stereoisomers have :
- the same order and types of bonds
- different spatial arrangements
- different properties
• Many biologically important chemicals, like
sugars, exist as stereoisomers.
 Enantiomers
• Pairs of isomers
(stereoisomers)
H
• that are
nonsuperimpossable
mirror images of each
other C
• It must have at least 1 Br
assymmetric carbon F
( a chiral carbon) OH
 Mirror
CH3CH2 CH3CH2

Br
H Br
H

H H

CH3CH2
CH3CH2

a non chiral C H Br
H Br

H
H
 Mirror
CH3CH2 CH3CH2

Br
CH3 Br CH3

H H

CH3CH2
CH3CH2

Chiral C H Br
CH3 Br

H
CH3
 Functional groups
Double bond C C

Hydroxyl OH

Carbonyl C O
O
Carboxyl C
OH

Sulfhidril
SH

Amine NH2
 O
C H H2C OH

H C OH C O

H C OH H C OH

H H

D(+) GLISERALDEHID DI HIDROKSIASETON

Aldehyde ( aldose )
O
derivates :
C H

H C
C OH

H C OH

H
D(+) GLISERALDEHID

O O
C H C H

H C OH HO C
C H

H C OH H C
C OH

CH2OH CH2OH
D(-) ERITHROSE D(-) THREOSE
 O O O O
C H C H C H C H

H C
C OH HO C
C H H CC OH HO C
C H

H C
C OH H C
C OH HO CC H HO C
C H

H C
C OH H C
C OH H CC OH H C
C OH

CH2OH CH2OH CH2OH CH2OH

D-ARABINOSE D-XILOSE D-LIXOSE

D-RIBOSE

D - Glukosa D - Gulosa D - Galaktosa

D - Alosa

D - Idosa D - Talosa
D - Manosa
D - Altrosa
 Structure of carbohydrates
• Open Chain Forms • Cyclic Forms

CH2OH

H O H
H
OH H

OH OH

H OH

Glucose
PHYSICAL PROPERTIES OF MONOSACCHARIDES

• sweetness
• solubility
• optical rotation
Table. Comperative Sweetness of Some Sugars and
Artificial Sweeteners.
Sugar or Artificial Sweetness Type
Sweetener Relaitive to Sweeteners
Lactose 0,16 Disaccharide
Galactose 0,32 Monoccharide
Maltose 0,33 Disaccharide
Glucose 0,74 Monoccharide
Sucrose 1,00 Disaccharide
Invert sugar 1,25 Mixture of Glucose and
Fructose
Fructose 1,74 Monoccharide
Aspartame 100 –150 Artificial sweetener
Acesulfame-K 200 Artificial sweetener
Saccharin 450 Artificial sweetener
Solubility
• At room temperature : carbohydrates are solids
• Because of the many –OH groups as well as the oxygen
of the aldehyde or ketone groups
 carbohydrates are soluble in water
 these groups form hydrogen bonds with the solvating
water molecules
 Optical Rotation
• All three forms of D-glucose (alpha, beta, and
open-chain) rotate the plane of polarized
ligth to the right  D-(+)-glucose
• L-glucose rotate the plane of polarized ligth
to the left  L-(-)-glucose
• There is no simple relationship between
configuration and rotation
• D-(+)-glucose = dextrose
• D-(-)-glucose = levulose
CHEMICAL PROPERTIES OF MONOSACCHARIDES

• Cyclic forms
• Oxydation
• Glycoside formations
 O
C H CH2OH

H C OH C O

HO C H HO C H

H C OH H C OH

H C OH H C OH

CH2OH CH2OH

D(+) Glucose D-Fructose

CH2OH CH2OH
CH2OH
O O
H H
H H OH
OH H
OH H OH
OH
OH H
H OH
Pyranose Furanose
 CH2OH
H
CH2OH OH H
H Rotate C4 - C5
H
H H
HO
H C O OH H C O
OH
OH OH

H OH H OH

CH2OH
O H
OH
O β
H
H
OH H O
OH
OH OH
H OH
α
 Oxidation
• All of monosaccharides are reducing
sugars
• Aldehydes and –OH groups are easily
oxidized
• Aldehydes are oxidized to carboxylic acids
Dissaccharides
• 2 units of monosaccharides
• Glycoside bonds • From carbon 1 to - OH groups (C4 position).

• α or β position from C1 of 1st unit 1 to –OH

group C4 of 2nd unit

1,4’- α or 1,4’- β linkage

H OH
6 H OH
4 H O 6
5
4 H O
HO 2 5
HO 3 1 O 2
H HO 3 1
OH OH
H OH
H H
1,4’- β linkage H
Maltose.
• It is a dissaccharide
• Contains 2 glucose units connected in a 1 4 linkage, from hydrolisis
of starch by enzymes/acid
• Ex. : • Enzyme α 1,4 - glukan 4- glucanohydrolase in saliva
• Enzyme α 1,4 - glukan maltohydrolase in malt

α - glukosidase
1 Maltose 2 D-Glucose
H 6
HOH 2C
4 H
5 O
HO 2 H
H 6
HO 3 1 HOH 2C
H 4 H
OH 5 O
O 2
H 3 1
HO
H OH
1,4’- a linkage OH

H
Cellubiose
• A dissaccharide
• From hydroliysis of cellulose by enzyme β-glukosidase
• Connected by 1,4 β glycoside linkage
• Cellubiose hydroliysis with acid produces α and β-D-glucose

H H
HOH 2C
HOH 2C
H O
H O
HO
O
HO HO
H OH OH
H OH
H H
H
Lactose
• A dissaccharide
• Connected by 1,4 β glycoside linkage
• Lactose hydrolysis  D - glucose and D - galactose,
D - glucose
• Source : * mammalian milk  5% Lactose

OH
H
HOH 2C H O HOH 2C H O
H
O
HO
H HO H
OH H OH
H H
H OH
Sucrose.
• Contains : glucose and fructose.
• The glycoside linkage is from C-1 of D-glucose (an aldose)
to C-2 of D-fructose (a

• The differences of sucrose from other dissaccharides are :

1. There are 2 anomeric carbon that used for glycoside
linkage.

2. Glucose and fructose in sucrose have no hemiacetal

group, because sucrose isn’t an equilibrium state with
forms aldehyde or keton in water .

3. Sucrose have no mutarotation and isn’t reducing sugar.

 H2OH

H O H
ALPHA-GLUKOPIRANOSE

OH H

OH

H OH O
BETA-FRUKTOFURANOSE
CH2OH
O
H OH

H CH2OH
OH H
Poly saccharide
1. Amylose • Repeated condensation of 1,4 a-D-glucose
• Polyglucose
• Contains 1000 to 2000 glucose units
• It has α 1,4 glycoside linkage
• It has flexibility to form conformation

O
O
O O Coil / helix
O O

HO o

Amylose
O

O
O
2. Amylopectin. • A polymer of α -D- glucose

• It isn’t entirely a straight-chain

molecule, but has random branches
with α 1,6 glycoside linkage

• There are 20 – 25 glucose units

in the straigth chain form with α
1,4 glycoside linkages

• A Macromolecule contains 105

to 106 glucose units

• Test with Iodine ( I2 ) gives deep

purple colour.
 CH2OH CH2OH
O O

OH OH Amylopectin
O O

OH n OH
O
CH2OH CH2
O O
OH OH
O O O

OH n OH
Glycogen ( also called animal starch)
Glycogen is similar to amylopectin, has α 1,6 glycosidic linkage at
branching points and α 1,4 glycosidic libjkage at the straigth-chain
portions.
The structural difference between glycogen and amylopectin is in the
degree of branching. There are 10 to 12 glucose units at straight chain.
It is a “giant molecule”, containing about 106 glucose units.
Cellulose.
• A linear polymer containing D-glucose units, all in
the 1,4 glycosidic linkage
• The structural difference between cellulose and
amylose : in cellulose all the 1,4 glycosidic linkages
are β.
• Cellulose is the most abundant molecule in living tissues.

CH2OH
O OH
CH2OH
OH
O O
CH2OH OH OH
O O

OH OH
n
OH Cellulose
OH
Acidic Polysaccharides
• The important role : in the structure and function of connective tissue
•The tissues are matrix between organs and cells that provides:

• mechanical strength
• filters the flow of molecular information
between cells.
Specialized
form

Examples :
Cartilage, bone, synovial fluid, skin, tendons, blood
vessel walls, intervertebral disks and cornea.
Hyaluronic acid.

• A typical and the simplest (structurally) acidic

polysaccharide of connective tissue

• A “ giant molecul “ : molecular weigth 105 – 107,

contains from 300 to 100 000 repeating units,
depending the organ in which it occur.

• Most abundant in embryonic tissue and in specialized

connective tissues such as :

- The synovial fluid : acts as lubricant

- The vitreous of the eye : its function is to provide a clear,
elastic gel that maintains the retina in its proper position.
Molecular structure of hyaluronic acid :
Composed of D – glucuronic acid linked to N – acetyl
glucosamine by β 1,3 linkage, the latter in turn is linked to
the next glucuronic acid by β 1,4 linkage.

N-Acetylglucosamine CH2OH
O
O
CH2OH
OH
O O
OH
OH
CH2OH Glucoronic acid
O NH
O n
C O
OH CH3
O
OH
Glucoronic acid
Hyaluronic acid
Heparin.
• It is one of the most acidic polysaccharides, ocuurs in
such tissues as lung, liver, skin and intestinal mucosa

• Biological function : anticoagulant activity  prevents

blood clotting.

O
C O- CH2OSO3H CH2OSO3-
O O O
COO-
OH OH OH OSO3-
O O O O
O

OSO3- NHSO3H OSO3- NH

C O n
CH3

HEPARIN
THANK YOU
!!!