Page 264 - Color Atlas of Biochemistry

Antibiotics 255

A. Antibiotics: overview

H 3 C CH 3 6 Transport antibiotics O S
N
HO CH 3 H H 2 N S NH
OH
O N
Sulfathiazole
NH 2
C
OH Ion channel
HO O OH O O
Tetracycline DNA 5Sulfonamides

Proteins
Folate
2 Gyrase
inhibitors synthesis
3 Aminoglycosides
Tetracyclines Replication
Erythromycin Precursors
Puromycin Translation THF
Chloramphenicol

Cell wall
synthesis
Transcription
4 Penicillins
Cephalosporins
OH mRNA
O DNA
H
HO C 1 Rifamycin
N CHCl 2 Actinomycin D
H H Daunomycin NH 3 H
C N S
Outer Inner C CH 3
Nitro membrane Murein membrane H
group O C N CH 3
O COO
NO 2 H
Chloramphenicol Ampicillin

B. Intercalators C. Penicillin as “suicide substrate”

R''
O OH O
C R''-D-Ala-
D-Ala
CH 3
OH
(substrate)
H O
H 3 CO O OH
H
Daunomycin H O
CH 3 R'
H H
HO H
H N H Penicillin
3
(inhibitor)

R R
S S
CH 3 CH 3
C N CH 3 C HN CH 3
C/G pair O
O COO O COO
HO H H
G/C pair Serine residue
Enzyme-inhibitor Covalent acyl enzyme
Daunomycin-DNA complex complex

Koolman, Color Atlas of Biochemistry, 2nd edition © 2005 Thieme
All rights reserved. Usage subject to terms and conditions of license.