BIOCHEMISTRY

CARBOHYDRATES
DEFINITION

▪ Carbohydrates are the most

abundant biomolecules on Earth.

▪ Many, but not all, carbohydrates

have the empirical formula
(CH2O)n; some also contain
nitrogen, phosphorus, or sulfur.
ROLES OF CARBOHYDRATES

1. Energy storage
2. Structural framework of RNA and DNA
3. Structure and protection of plants
STRUCTURE OF CARBOHYDRATES

Carbohydrates can be drawn using:

1. Fischer projection 2. Haworth projection 3. Chair conformation

STRUCTURE OF CARBOHYDRATES

Consider the structure of D-Galactose. Draw its Haworth and chair conformation.
ISOMERISM IN CARBOHYDRATES

1. Aldose-ketose isomerism
2. Enantiomers
3. Epimers
4. Pyranose and furanose ring structures
5. α and β- anomers
ISOMERISM IN CARBOHYDRATES

1. Aldose-ketose isomerism
ISOMERISM IN CARBOHYDRATES

2. Enantiomers (D vs L)
ISOMERISM IN CARBOHYDRATES

3. Epimers
Diastereomers of carbohydrates which differ only in the orientation
of one carbon.

D-Mannose is a C2 epimer of D-Glucose

ISOMERISM IN CARBOHYDRATES

4. Pyranose and furanose ring structures

Furanose – 5-membered ring structure
Pyranose – 6-membered ring structure
ISOMERISM IN CARBOHYDRATES

5. α and β- anomers
α-anomer – the -OH at C1 is trans to the C6 group
β-anomer – the -OH at C1 is cis to the C6 group
THREE MAJOR CLASSES OF CARBOHYDRATES

1. Monosaccharides
2. Oligosaccharides
3. Polysaccharides

(the word “saccharide” is derived from the Greek sakcharon,

meaning “sugar”).
MONOSACCHARIDES

▪ Simple sugars
▪ The most abundant monosaccharide in nature is the six-carbon
sugar D-glucose, sometimes referred to as dextrose.
TWO FAMILIES OF MONOSACCHARIDES

Aldoses: If the carbonyl group is at an Ketoses: If the carbonyl group is at any

end of the carbon chain (that is, in an other position (in a ketone group) the
aldehyde group) the monosaccharide is monosaccharide is a ketose.
an aldose.
D-ALDOSES

Triose Tetroses Pentoses

(3 carbons) (4 carbons) (5 carbons)
D-ALDOSES

Hexoses
(6 carbons)
D-KETOSES

Triose Tetrose Pentoses

(3 carbons) (4 carbons) (5 carbons)
D-KETOSES

Hexoses
(6 carbons)
OLIGOSACCHARIDES

• Consist of short chains of monosaccharide units, or residues, joined by

characteristic linkages called glycosidic bonds.
• The most abundant are the disaccharides, with two monosaccharide
units.
• Disaccharides contain a glycosidic bond
• O-glycosidic bond formed when a hydroxyl group of one sugar reacts
with the anomeric carbon of the other
DISACCHARIDES
DISACCHARIDES

In describing disaccharides or polysaccharides, the end of a chain with a free anomeric

carbon (one not involved in a glycosidic bond) is commonly called the reducing end.
POLYSACCHARIDES

• Sugar polymers containing more than 20 or so monosaccharide units,

and some have hundreds or thousands of units.
• Polysaccharides, also called glycans, differ from each other in the
identity of their recurring monosaccharide units, in the length of their
chains, in the types of bonds linking the units, and in the degree of
branching.
• Homopolysaccharides contain only a single type of monomer
Ex. starch and glycogen
cellulose and chitin
• Heteropolysaccharides contain two or more different kinds
POLYSACCHARIDES
POLYSACCHARIDES

1. Starch – energy reservoir of plant cells; made up of two

polysaccharides (amylose and amylopectin).

o Amylose – long, unbranched chains of D-glucose residues connected

by α(1->4) linkages.
POLYSACCHARIDES

o Amylopectin – branched polymer

– glycosidic linkages joining successive glucose residues
in amylopectin chains are α(1->4); the branch points
(occurring every 24 to 30 residues) are α(1->6) linkages.
POLYSACCHARIDES

Starch
POLYSACCHARIDES

2. Glycogen – main storage polysaccharide of animal cells.

– polymer of α(1->4)-linked subunits of glucose, with α(1->6)-linked
branches
– extensively branched (on average, every 8 to 12 residues) and compact

Glycogen phosphorylase – cleaves one glucose at a time from the nonreducing end of
a branch to produce glucose-1-phosphate, which then enters the metabolic pathways
of carbohydrate breakdown.
POLYSACCHARIDES

3. Cellulose – fibrous, tough, water-insoluble substance, found in the

cell walls of plants
– linear, unbranched homopolysaccharide, consisting of
10,000 to 15,000 D-glucose units
– glucose residues are linked by β(1->4) glycosidic bonds
POLYSACCHARIDES

4. Chitin – linear homopolysaccharide with all the residues linked in

β(1->4) glycosidic bonds.
– similar to cellulose in both structure and function
– the monomer is N-acetyl-β-D-glucosamine
REACTIONS OF MONOSACCHARIDES

1. Oxidation

▪ Aldonic acid – oxidation of the

carbonyl (aldehyde) carbon
▪ Uronic acid – oxidation of the
terminal CH2OH group
▪ Aldaric acid – oxidation of
both aldehyde and terminal
CH2OH group
REACTIONS OF MONOSACCHARIDES

2. Reduction
Alditol – can be prepared by the mild reduction (with NaBH4 or similar
agents) of the carbonyl groups of aldoses and ketoses.

NaBH4
END