CHAPTER 14

CARBOHYDRATES
Carbohydrates
ALDOSES
KETOSE
Cyclic Structures of Monosaccharides-
Haworth Structure
• Anomeric carbon = the hemiacetal carbon
of the cyclic form of a monosaccharide.
• Anomers = monosaccharides that differ in
configuration anly at their anomeric
carbons
 Reaction of Monosaccharides
A) Oxidation of Carbohydrates
- sugars can be classified as reducing and non-reducing
- if a sugar is oxidized by Fehling’s reagent (tartarate copper
complex) or Benedict (citrate copper complex) -reducing sugar -
CuO is formed as precipitate.
O O

RCH + 2Cu2+ + 5OH- RCO- + Cu2O + 3H2O

O H
C O O-
C
H OH
H OH
HO H [O]
HO H
H OH
H OH
H OH
H OH
CH2OH
CH2OH

D-glucose
D-gluconate
 O H O H
C C

H OH H OH

HO H [O] HO H
enzym-catalyzed
H OH H OH

H OH H OH

CH2OH COOH
D-glucose D-glucuronic acid
A) Reduction of monosaccharides
NaBH4 is used to reduce the monosaccharides to corresponding
sugar alcohol

CHO CH2OH

H OH H OH

HO H NaBH4 HO H

H OH H OH

H OH H OH

CH2OH CH2OH

D-glucose D-glucitol/D-sorbitol
 DISSACHARIDES
• Lactose = β-D-galactose + α- or β-D-glucose
= β-1,4-glycosidic bond
b) Sucrose = α-D-glucose + β-D-fructose
= α,β−1,2 glycosidic bond
 POLISACCHARIDES
A) Starch
amylose = α-1,4-glycosidic bonds
amylopectin = α-1,6-glycosidic bonds – for every 25
units of glucose.
B)Glycogen
amylose = α-1,4-glycosidic bonds
amylopectin = α-1,6-glycosidic bonds – for every 8-10 units
of glucose.
c) Cellulose = β-1,4-glycosidic bonds