Fundamentals of Medicinal Chemistry

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The stereochemical nature of these oxygen glycosidic links is important in the

control of the metabolism of polysaccharides. Enzymes that catalyse the aque-

ous hydrolysis of the glycosidic links of polysaccharides will only usually cata-

lyse the cleavage of a link formed by a particular anomer or anomers. For

example, ana-glucosidase catalyses the hydrolysis of glycosidic links formed by

ana-glucose residue acting as a glycone in the polysaccharide chain.

1.4.5 The nomenclature of polysaccharides


Trivial names are normally used for all types of polysaccharide. Systematic

names may be used for small polysaccharides. These names are based on the

systematic names of the monosaccharides corresponding to the residues. How-

ever, the suffix-osylis used for a substituent residue joined through its anomeric

carbon to the next residue in the chain and the suffix-osideis used for the last

residue in the chain (Figure 1.19). Appropriate locants may or may not be used

in systematic names.

1.4.6 Naturally occurring polysaccharides


Naturally occurring polysaccharides can occur either as individual carbohy-

drate molecules or in combination with other naturally occurring substances,

such as proteins (glycoproteins) and lipids (glycolipids). In all cases the poly-

saccharide section may have linear or branched chain structures, which often

contain the derivatives of both monosaccharides and aminosugars (Figure 1.20).

HO OH

HO O

H

H

OH
H

H

H

COOH

CO

HO
O

CH 3 CH

COOH

OH

H

O

H

H

H

CH 2 OH

NH

CH 3

H

HO

O

HO
H

H

H

CH 2 OH

NH
CO

OH

CH 3

H

H

N-Acetyl-β-D-glucosamine (NAG) β-N-Acetylmuramic acid (NAM) β-D-Glucuronic acid


Figure 1.20 Some derivatives of monosaccharides and amino sugars commonly found in poly-
saccharides

Polysaccharides and molecules whose structures contain polysaccharide resi-

dues have a wide variety of biochemical roles. They occur as integral parts of the

structures of specific tissues: the mureins, for example, (Figure 1.21(a)) are

18 BIOLOGICAL MOLECULES

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