Fundamentals of Medicinal Chemistry

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Polysaccharide chains Polysaccharide chains

NH
CO

NH

NH

CO

NH

CO

CO

NH NH

NH
CO NH

NH
CO

CO

NHCO NH

CO

CO

NAG

NAG NAG
NAG

NAG NAG

NAM

NAM NAM NAM

NAM NAM

CO

NH
CO

NH
CO

NH

NH

CO

CO

NH
CO

Amide (peptide
bond) cross links

Tetrapeptide
chains

NAM

NAM NAM NAM

NAG NAG
NAG

NAG NAG
NAG

NAM NAM

Pentaglycine
cross links

Tetrapeptide
chains

(a) (b)


Figure A2.3 A schematic representation of the structure of the peptidoglycans of (a) Gram-
positive and (b) Gram-negative bacteria

OO

O

O

OO

O

Glucose X Glucose X

OO

Glucose X

XX

O

X

O P

O

O−

O P O

O

O−

O O−

O P O

O

O−

O P

O

O−

(a)

(b)

P O

O O
O O

O

O−

O P O

O

O−

O P O

O

O−

O P

O

O P

NAG

NH 3 NH 3

COCHCH 3 COCHCH 3

O

NAG

O O

CH 2 OH

CHOH

CH 2 OH

Glycerol A glycerol
residue

+ An alanine +
residue

Ribitol

CH 2 OH

CHOH

CHOH

CHOH

CH 2 OH X is either H or an
alanine residue

A ribitol
residue

Figure A2.4 (a) A glycerol based teichoic acid. (b) A ribitol based teichoic acid. In many teichoic
acids the monosaccharide residues are glucose and N-acetylglucosamine

The exterior surface of Gram-negative bacteria is more complex than that

of the Gram-positive bacteria. It is coated with lipopolysaccharides, which

largely consist of long chains of repeating oligosaccharide units that are

attached to the outer membrane by a core oligosaccharide (Figure A2.5).

242 APPENDIX 2 BACTERIA

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