INACTIVATED PRODUCTS OF RIFAMPICIN BY PATHOGENIC Nocardia spp.: STRUCTURES OF GLYCOSYLATED AND PHOSPHORYLATED METABOLITES OF RIFAMPICIN AND 3-FORMYLRIFAMYCIN SV

Abstract

Rifampicin (1) was converted into four inactivated products by pathogenic Nocardia, RIP-1 and RIP-2 by N. brasiliensis and RIP-3 and RIP-4 by N. otitidiscaviarum. MS and NMR analysis showed the compounds to be 3-formyl-23-[O-(β-D-glucopyranosyl)]rifamycin SV (2), 23-[O-(β-Dglucopyranosyl)]rifampicin (3), 21-(O-phosphoryl)rifampicin (4) and 3-formyl-21-(0-phosphoryl)-rifamycin SV (5), respectively.