Structure determination of ribosylated rifampicin and its derivative: new inactivated metabolites of rifampicin by mycobacterial strains
- PMID: 8557572
- DOI: 10.7164/antibiotics.48.1299
Structure determination of ribosylated rifampicin and its derivative: new inactivated metabolites of rifampicin by mycobacterial strains
Abstract
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.
Similar articles
-
Structures of ADP-ribosylated rifampicin and its metabolite: intermediates of rifampicin-ribosylation by Mycobacterium smegmatis DSM43756.J Antibiot (Tokyo). 2000 Mar;53(3):269-75. doi: 10.7164/antibiotics.53.269. J Antibiot (Tokyo). 2000. PMID: 10819298
-
Inactivated products of rifampicin by pathogenic Nocardia spp.: structures of glycosylated and phosphorylated metabolites of rifampicin and 3-formylrifamycin SV.J Antibiot (Tokyo). 1993 Oct;46(10):1605-10. doi: 10.7164/antibiotics.46.1605. J Antibiot (Tokyo). 1993. PMID: 8244890
-
Identification and characterization of a new intermediate in the ribosylative inactivation pathway of rifampin by Mycobacterium smegmatis.Microb Drug Resist. 1999 Winter;5(4):259-64. doi: 10.1089/mdr.1999.5.259. Microb Drug Resist. 1999. PMID: 10647083
-
Phosphorylative inactivation of rifampicin by Nocardia otitidiscaviarum.J Antimicrob Chemother. 1994 Jun;33(6):1127-35. doi: 10.1093/jac/33.6.1127. J Antimicrob Chemother. 1994. PMID: 7928806
-
Rifapentine.Tuberculosis (Edinb). 2008 Mar;88(2):155-8. doi: 10.1016/S1472-9792(08)70025-8. Tuberculosis (Edinb). 2008. PMID: 18486059 Review. No abstract available.
Cited by
-
A rifampin-hypersensitive mutant reveals differences between strains of Mycobacterium smegmatis and presence of a novel transposon, IS1623.Antimicrob Agents Chemother. 2003 Oct;47(10):3208-13. doi: 10.1128/AAC.47.10.3208-3213.2003. Antimicrob Agents Chemother. 2003. PMID: 14506032 Free PMC article.
-
Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr.Proc Natl Acad Sci U S A. 2008 Mar 25;105(12):4886-91. doi: 10.1073/pnas.0711939105. Epub 2008 Mar 18. Proc Natl Acad Sci U S A. 2008. PMID: 18349144 Free PMC article.
-
ADP-ribosylation as an intermediate step in inactivation of rifampin by a mycobacterial gene.Antimicrob Agents Chemother. 1999 Jan;43(1):181-4. doi: 10.1128/AAC.43.1.181. Antimicrob Agents Chemother. 1999. PMID: 9869590 Free PMC article.
-
Integrative metagenomic and biochemical studies on rifamycin ADP-ribosyltransferases discovered in the sediment microbiome.Sci Rep. 2018 Aug 14;8(1):12143. doi: 10.1038/s41598-018-30547-x. Sci Rep. 2018. PMID: 30108275 Free PMC article.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Molecular Biology Databases
Miscellaneous