Structures of ADP-ribosylated rifampicin and its metabolite: Intermediatesof rifampicin-ribosylation by Mycobacterium smegmatis DSM43756

Authors
Morisaki, N Hashimoto, Y Furihata, K Imai, T Watanabe, K Mikami, Y Yazawa, K Ando, A Nagata, Y Dabbs, ER
Citation
N. Morisaki et al., Structures of ADP-ribosylated rifampicin and its metabolite: Intermediatesof rifampicin-ribosylation by Mycobacterium smegmatis DSM43756, J ANTIBIOT, 53(3), 2000, pp. 269-275
Citations number
20
Categorie Soggetti
Microbiology
Journal title
JOURNAL OF ANTIBIOTICS
ISSN journal
00218820 → ACNP
Volume
53
Issue
3
Year of publication
2000
Pages
269 - 275
Database
ISI
SICI code
0021-8820(200003)53:3<269:SOARAI>2.0.ZU;2-2
Abstract
23-(O-ADP-Ribosyl)rifampicin [RIP-TAs (3, Na+ form), RIP-TAf (4, H+ form)] was obtained as an intermediate in the conversion process of rifampicin (1) to RIP-Mb (2) that is mediated by cell homogenates of Mycobacterium smegma tis DSM43756 or of Escherichia coli carrying a mycobacterial mono(ADP-ribos yl) transferase gene, in the presence of NADH. 23-[O-(5'-Phosphoribosyl)] r ifampicin (5, RIP-TAp) was also obtained by the reaction of rifampicin with NADH in the presence of a homogenate of M. smegmatis. The structures of 3, 4, and 5 were determined by means of MS and NMR analyses.