Structures of ADP-Ribosylated Rifampicin and Its Metabolite: Intermediates of Rifampicin-ribosylation by Mycobacterium smegmatis DSM43756

NAOKO MORISAKI; YUICHI HASHIMOTO; KAZUO FURIHATA; TAMAE IMAI; KAYO WATANABE; YUZURU MIKAMI; KATSUKIYO YAZAWA; AKIKAZU ANDO; YOSHIHO NAGATA; ERIC R. DABBS

doi:10.7164/antibiotics.53.269

Structures of ADP-Ribosylated Rifampicin and Its Metabolite: Intermediates of Rifampicin-ribosylation by Mycobacterium smegmatis DSM43756

NAOKO MORISAKI, YUICHI HASHIMOTO, KAZUO FURIHATA, TAMAE IMAI, KAYO WATANABE, YUZURU MIKAMI, KATSUKIYO YAZAWA, AKIKAZU ANDO, YOSHIHO NAGATA, ERIC R. DABBS

Author information

NAOKO MORISAKI
Institute of Molecular and Cellular Biosciences, The University of Tokyo
YUICHI HASHIMOTO
Institute of Molecular and Cellular Biosciences, The University of Tokyo
KAZUO FURIHATA
Division of Agriculture and Agricultural Life Sciences, The University of Tokyo
TAMAE IMAI
Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University
KAYO WATANABE
Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University
YUZURU MIKAMI
Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University
KATSUKIYO YAZAWA
Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University
AKIKAZU ANDO
Department of Biotechnology, Graduate School of Science and Technology, Chiba University
YOSHIHO NAGATA
Department of Biotechnology, Graduate School of Science and Technology, Chiba University
ERIC R. DABBS
Molecular and Cell Biology Department, University of the Witwatersrand

JOURNAL FREE ACCESS

2000 Volume 53 Issue 3 Pages 269-275

DOI https://doi.org/10.7164/antibiotics.53.269

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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 smegmatis DSM43756 or of Escherichia coli carrying a mycobacterial mono(ADP-ribosyl) transferase gene, in the presence of NADH. 23-[O-(5'-Phosphoribosyl)]rifampicin (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.

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