Capreomycin

Capreomycin is synthesized by Saccharothrix mutabilis subsp. capreolusa as a mixture of four related cyclic pentapeptides, capreomycins IA (Fig. 9; 6b), IB (Fig. 9; 6c), IIA (6d), and IIB (6e). The peptide backbone is made up of 15 unnatural

Fig. 9 Capreomycin

Capreomycin 6b R,= OH, R2

6c R1= H, R2 = ß-lysyl 6d R1=OH, R2 =H 6e R1=H, R2 =H

Capreomycin 6b R,= OH, R2

6c R1= H, R2 = ß-lysyl 6d R1=OH, R2 =H 6e R1=H, R2 =H

amino acids and either l-serine or l-alanine, known as Capreomycin A and B, respectively.

A few limited SAR studies [122, 123] have shown that both alanine and serine at position 1 have antitubercular activity, that small ureido modifications such as N-methyl groups (but not N, N-dimethyl) are acceptable, whereas N-aryl ureido substitution increases general antibacterial activity. Capreomycin inhibits protein synthesis by binding at the interface between helix 44 of the 30S subunit and helix 69 of the 50S subunit of the bacterial ribosome [124]. Like the aminoglycosides with which it is often confused, capreomycin has both nephro- and ototoxic side effects.

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