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Chloramphenicol

  • O. Pongs
Part of the Antibiotics book series (ANTIBIOTICS, volume 5 / 1)

Abstract

Chloramphenicol is a broad-spectrum antibiotic which acts chiefly as a bacteriostatic agent. Chloramphenicol was isolated in 1947 from Streptomyces venezuelae. Soon afterwards, its structure was elucidated and it became the first antibiotic to be synthesized by chemical means (Controulis et al., 1949). The chemical structure of chloramphenicol is given in Fig. 1. It is one of the rare natural compounds which carry a nitro group. Nevertheless, the molecule has a structure which is one of the simplest of the known antibiotics (Rebstock etal., 1949; Dunitz, 1952). Subsequently, a large number of chloramphenicol derivatives was prepared, which exceeds more than 500 compounds (Kolosov et al., 1961). The molecule of chloramphenicol (Fig. 1) is composed of three parts: (I) a p-nitrobenzene moiety, (II) a dichloracetyl moiety, and (III) a 2-amino-propanediol moiety. In more general terms, part I represents an aromatic ring system and part II an aliphatic haloacetyl side-chain. The propanediol moiety possesses two asymmetric carbon atoms (indicated by an asterix in Fig. 1). Accordingly, four stereoisomers of chloramphenicol theoretically exist. The Newman projections of these four stereoisomers are depicted in Fig. 2. Two of these, the D-threo and the L-threo enantiomers, carry the amide side-chain (part II) and the hydroxyl on carbon 1 on opposite sides of the plane of the two asymmetric centers (Fig. 2C and D). The other two stereoisomers, the D-erythro and L-erythro enantiomers, carry the two substituents on the same side of the plane of the two asymmetric centers (Fig. 2 A and B).

Keywords

Peptide Bond Formation Amino Acid Incorporation Peptidyl Transferase Asymmetric Carbon Atom Affinity Label 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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