Structure determination of ribosylated rifampicin and its derivative: new inactivated metabolites of rifampicin by mycobacterial strains.
Rifampicin (I) was converted into two inactivated products RIP-Ma and RIP-Mb by Mycobacterium smegmatis DSM43756. MS, NMR and chromatographic analysis showed the compounds to be 3-formyl-23-[O-(alpha-D-ribofuranosyl)]rifamycin SV (6) and 23-[O-(alpha-D-ribofuranosyl)]rifampicin (7), respectively.
Morisaki
N
N
Institute of Molecular and Cellular Biosciences, University of Tokyo, Japan.
Kobayashi
H
H
Iwasaki
S
S
Furihata
K
K
Dabbs
E R
ER
Yazawa
K
K
Mikami
Y
Y
D000904:Antibiotics, Antitubercular / Q000737:chemistry / Q000378:metabolism; D001711:Biotransformation; D004352:Drug Resistance, Microbial; D007917:Leprostatic Agents / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009161:Mycobacterium / Q000378:metabolism*; D012266:Ribose / Q000737:chemistry / Q000378:metabolism*; D012293:Rifampin / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism*
C097824:23-(O-ribofuranosyl)rifampicin; C097823:3-formyl-23-(O-ribofuranosyl)rifamycin SV; D000904:Antibiotics, Antitubercular; D007917:Leprostatic Agents; D012266:Ribose; D012293:Rifampin