Inactivated products of rifampicin by pathogenic Nocardia spp.: structures of glycosylated and phosphorylated metabolites of rifampicin and 3-formylrifamycin SV.
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-(beta-D-glucopyranosyl)]rifamycin SV (2), 23-[O-(beta-D-glucopyranosyl)]rifampicin (3), 21-(O-phosphoryl)rifampicin (4) and 3-formyl-21-(O-phosphoryl)-rifamycin SV (5), respectively.
Morisaki
N
N
Institute of Molecular and Cellular Biosciences, University of Tokyo, Japan.
Iwasaki
S
S
Yazawa
K
K
Mikami
Y
Y
Maeda
A
A
D004351:Drug Resistance; D009615:Nocardia / Q000378:metabolism*; D012293:Rifampin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*
C084371:21-(O-phosphoryl)rifampicin; C084370:23-(O-(beta-glucopyranosyl))rifampicin; C084372:3-formyl-21-(O-phosphoryl)rifamycin SV; C084369:3-formyl-23-(O-(beta-glucopyranosyl))rifamycin SV; D012293:Rifampin