CHEMISTRY OF

CARBOHYDRATES
Lecture 2
GINNETHON SHANDELE

LEVY MWANAWASA MEDICAL

UNIVERSITY
 Anomers
O Isomeric forms of monosaccharides that differ
only in their configuration about the
hemiacetal or hemiketal carbon atom are
called anomers.

O For instance, the α and β anomers of D-

glucose interconvert in aqueous solution by a
process called mutarotation.
Muta-rotation
Anomeric Forms
 Continued….

O Thus, a solution of α-D-glucose and a solution

of β -D-glucose eventually form identical
equilibrium mixtures having identical optical
properties.
 Dissacharide
O Disaccharides are condensation products of
two monosaccharide units.

O Examples are maltose, lactose and sucrose.

Examples
More Examples
 Summary
O The disaccharide lactose, which yields D-
galactose and D-glucose on hydrolysis, occurs
naturally only in milk.

O The anomeric carbon of the glucose residue is

available for oxidation, and thus lactose is a
reducing disaccharide.
 Summary
O Sucrose (table sugar) is a disaccharide of
glucose and fructose. It is formed by plants but
not by animals.

O Sucrose contains no free anomeric carbon

atom; the anomeric carbons of both
monosaccharide units are involved in the
glycosidic bond). Sucrose is therefore a non-
reducing sugar
 Polysaccharides
O Most carbohydrates found in nature occur as
polysaccharides, also called glycans.

O Homopolysaccharides: contain only a single

type of monomer;

O Heteropolysaccharides: contain two or more

different kinds.
 Polysaccharides
O Some homopolysaccharides serve as storage
forms of monosaccharides that are used as
fuels. (starch & glycogen)

O Other homopolysaccharides (cellulose and

chitin, for example) serve as structural
elements in plant cell walls and animal
exoskeletons
 Homo-polysaccharides
O The most important storage polysaccharides
are starch in plant cells and glycogen in animal
cells.

O Starch and glycogen molecules are heavily

hydrated, because they have many exposed
hydroxyl groups available to hydrogen-bond
with water.
 Starch
O Found in in tubers, such as potatoes, and in seeds.
O It contains two types of glucose polymer, amylose and
amylopectin.

O Amylose consists of long, unbranched chains of D-

glucose residues connected by (α1,4) linkages.

O Amylopectin is highly branched. The glycosidic

linkages joining successive glucose residues (α1,4); the
branch points (occurring every 24 to 30 residues) are
(α1, 6) linkages.
Amylose
Amylopectin
 Glycogen
O Glycogen is the main storage polysaccharide
in animal cells.

O It is a polymer of (α1, 4)-linked subunits of

glucose, with (α1, 6) linked branches, but
glycogen is more extensively branched (on
average, every 8 to 12 residues) and more
compact than starch
Structure
 Dextran
O Dextran are bacterial and yeast polysaccharides
made up of (α1, 6) linked poly-D-glucose; all have
(α 1,3) branches, and some also have (α 1, 2) or
(α 1,4) branches.

O Dental plaque, formed by bacteria, is rich in

dextrans.

O Synthetic dextrans are used in several commercial

products (for example, Sephadex) that serve in the
fractionation of proteins by size-exclusion
chromatography.
 Peptidoglycans
O Hetero-polysaccharide:

O The rigid component of bacterial cell walls is a

heteropolymer of alternating (β1-4) linked N-
acetylglucosamine and N-acetylmuramic acid
residues.

O The linear polysaccharides lie side by side in

the cell wall, cross-linked by short peptides