Carbohydrates: Monosaccharides, Disaccharides and Polysaccharides

LEC
NOTES 4 – CARBOHYDRATES

Monosaccharides
§ Fischer Projection formula – open & linear structural formula of monosaccharides
§ C5 (the carbon atom next to a primary alcohol) is the basis in determining whether the
monosaccharide is in the D or L configuration
§ D isomer – OH on the right
L isomer -‐ OH on the left
§ a “free carbonyl group” gives the sugars its reducing property, i.e., these sugars are
“reducing sugars” & therefore will give positive results in all oxidizing tests
(e.g. siver mirror for Tollen’s, brick-‐red ppt. for Fehling’s & Benedicts, yellow ppt. for
Phenylhydrazine test)
§ open structure of sugars gives a “free carbonyl” group & is only obtained if the sugar is
in aqueous solution
Aldohexose Ketohexose

§ Haworth formula – closed ring structure of monosaccharides
§ for an aldohexose, it is the hemiacetal formation between C1 (aldehyde functional
group) & C5 (alcohol functional group) to give the closed-‐hexagon ring structure

§ for a ketohexose, it is the hemiketal formation between C2 (ketone functional group) &
C5 (alcohol functional group) to give the closed-‐pentagon ring structure

§ closed-‐ring structures of sugars DO NOT give a “free carbonyl” group since there is a
C1-‐C5 oxide linkage for aldohexoses & a C2-‐C5 oxide linkage for ketohexoses,
therefore, NO REDUCING PROPERTY
§ in aqueous solutions, water hydrolyzes these oxide linkages, liberates the carbonyl
group & thus, these sugars become REDUCING SUGARS
Disaccharides
§ a glycosidic linkage is the bond that links two monosaccharide units
§ for maltose (glucose-‐glucose), it is the acetal formation between C1 of the 1st glucose
molecule and C4 of the 2nd glucose molecule therefore maltose has a 1,4-‐glycosidic
bond
§ maltose is a REDUCING SUGAR because even though C1 (from the 1st glucose mol) is
bound by both oxide & glycosidic bonds, C4 (from the the 2nd glu mol) is bound
only by an oxide linkage thus, in an aqueous solution,water can still hydrolyze this oxide
linkage & yield a free carbonyl group
§ for lactose (galactose-‐glucose), it is the acetal formation between C1 of the 1st galactose
molecule and C4 of the 2nd glucose molecule therefore lactose has a 1,4-‐glycosidic
bond
§ lactose is a REDUCING SUGAR because even though C1 (from the 1st gal mol) is bound by
both oxide & glycosidic bonds, C4 (from the the 2nd glu mol) is bound only by an oxide
linkage thus, in an aqueous solution,water can still hydrolyze this oxide linkage & yield
a free carbonyl group

§ for sucrose (glucose-‐fructose), it is the ketal formation between C1 of the 1st glucose
molecule and C2 of the 2nd fructose molecule therefore sucrose has a 1,2-‐glycosidic
bond
§ sucrose is the only NON REDUCING SUGAR because C1 (from the 1st glu mol) and C2
(from the the 2nd fru mol) are both bound by oxide & glycosidic linkages, therefore,
NO FREE CARBONYL GROUP
§ sucrose can give a false-‐positive result in an oxidation test if the 1,2-‐glycosidic bond
undergoes hydrolysis due to to prolong heating

Polysaccharides
§ starch – a polymer of glucose
§ a starch granule has a hard, outer covering known as amylopectin (the branched 1,6-‐
glycosidic structure) & a soft inner layer, amylose (the linear 1,4-‐glycosidic structure)
§ uncooked, aqueous solution of starch gives a violet solution w/ I2 test (amylopectin)
and cooked or heated starch, gives a blue solution (amylose)
§ I2 Test (General Test for Starch)
Principle Involved: formation of starch-‐iodo complex
1) starch, being a polymer, traps the I2 in its helical structure giving a blue-‐colored
complex
2) on heating, the helical structure opens up, becomes linear & releases the iodine,
thus, solution turns colorless
3) on cooling, starch assumes the same helical structure & traps again the I2 molecule
(blue solution)

-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐-‐
EXERCISE 4 – CARBOHYDRATES
1) a. Given the monosaccharide hemiacetal, identify the anomeric carbon (C1 – C6) and
identify it as α or β anomer.
CH2OH
OH
O
OH
CH2OH
OH
b. How many chiral carbons are there?

c. Identify the carbons involved in forming the oxide linkage (C1 – C6).
d. Give the physical state of the hemiacetal monosaccharide.
2) a. Given the monosaccharide hemiacetal, identify the anomeric carbon (C1 – C6) and
identify it as α or β anomer.
CH2OH
OH
O OH
OH

OH

b. How many chiral carbons are there?
c. Identify the carbons involved in forming the oxide linkage (C1 – C6).
d. Give the physical state of the hemiacetal monosaccharide.
3) a. Is the disaccharide a reducing or a non-‐reducing sugar?
b. Which bond needs to be hydrolyzed for it to have a reducing property? (oxide or
glycosidic linkage)
c. Identify the carbons (C1 – C6) involved in producing a “free C=O” group & in what
sugar unit (1st or 2nd structure)
CH2OH
O CH2OH
H O O
O OH
HO
OH OH
HO
4) a. Is the disaccharide a reducing or a non-‐reducing sugar?
b. Which bond needs to be hydrolyzed for it to have a reducing property? (oxide or
glycosidic linkage)
c. Identify the carbons (C1 – C6) involved in producing a “free C=O” group & in what
sugar unit (1st or 2nd structure)
CH2OH
HO O

HO
HO

CH2OH
O O
CH2OH
HO
OH
5) a. If the two segments are to be joined to represent a fragment of a polysaccharide,
identify those carbons involved in forming this glycosidic bond (C1 – C6).
b. Which bond is responsible for a (+) Fehling’s test if it is going to be hydrolyzed?
(A or B)
A
CH2OH CH2OH
O CH2OH O CH2OH
HO O HO O
O OH O OH
HO HO
OH OH OH OH
HO HO
B

Segment 1 Segment 2

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b. How many chiral carbons are there?

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