Fundamentals of Medicinal Chemistry

links), sulphide (sulphur glycosidic links) and carbon to carbon links

(carbon glycosidic links) are known (Figure 1.17). Each type of glycosidic

link will exhibit the characteristics of the structure forming the link.

For example, oxygen glycosidic links are effectively acetals and so undergo

hydrolysis in aqueous solution. Both trivial and systematic nomenclature

is used for glycosides (Figure 1.17). In systematic nomenclature the radical

name of the aglycone preceeds the name of the glycone, which has the

suffix-oside.

N

N

N N

NH 2

O

H

OHOH

H

CH 2

H

HO P O P O P O

OH OH OH

OOO

H

CH 2 OH

OH

O

OH

O

HO

CH 2 OH

H

OH

H

H

OH

H

O NH

HO

SO 2 NH 2

CH 2 OH

H

OH

H

H

OH

H

O

HO

OCH 3

CH 2 OH

H

OH

H

H

OH

H

Methylβ-D-glucoside

4 1

N 4 -(β-D-Glucopyranosyl)sulphanilamide

(a)

(b)

5-(β-D-Ribofuranosyl)uracil

5

H

H O

H

NH

O

HN

OH

HOCH 2 O

H

OH

1

O O C

CN

HO

CH 2 OH

H

OH H

H

H

OH

H

Prunasin, ex wild cherry bark

H

OCH 2 CH 3

H

H

H

HOCH (^2) O
H
OH
Ethylβ-D-deoxyriboside
Adenosine triphosphate (ATP), ex mammals
Aloin, ex aloes
(c)
Figure 1.17 Examples of (a) oxygen glycosides, (b) nitrogen glycosides and (c) carbon glycosides.
The shaded parts of the structures are the aglycone sections

Glycoproteins are glycosides that have a protein aglycone. The protein is

usually linked to a polysacharide (See section 1.4.4) by an O or N glycosidic

link. Glycoproteins are found in all forms of life. They exhibit a wide range of

biological activities. For example, they may act as receptors, hormones and

enzymes.

16 BIOLOGICAL MOLECULES