Chloramphenicol

Abstract

Chloramphenicol was isolated and crystallized at about the same time in three laboratories from the cultures of Streptomyces venezuelae and S. phleochromogenes var. chloromyceticus (Ehrlich et al., 1947; Gottlieb et al., 1948; Carter et al., 1948; Umezawa and Kanari, 1948). As shown in Fig. 1a, its structure is D-(—)-threo-2-dichloroacetamido-l-p-nitrophenyl-1,3-propandiol (Controulis et al., 1949; Rebstock et al., 1949). The compound is thus relatively simple but interesting, for it is one of the few natural products with both an aryl nitro group and organic halogen. Of the six isomers possible in a molecule of this structure, only the naturally occurring form is biologically active. The other isomers have been synthesized in the laboratory but have not been detected among the fermentation products of the streptomycete.