Literature DB >> 10819298

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

N Morisaki1, Y Hashimoto, K Furihata, T Imai, K Watanabe, Y Mikami, K Yazawa, A Ando, Y Nagata, E R Dabbs.   

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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Year:  2000        PMID: 10819298     DOI: 10.7164/antibiotics.53.269

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  4 in total

1.  Characterization of a rifampin-inactivating glycosyltransferase from a screen of environmental actinomycetes.

Authors:  Peter Spanogiannopoulos; Maulik Thaker; Kalinka Koteva; Nicholas Waglechner; Gerard D Wright
Journal:  Antimicrob Agents Chemother       Date:  2012-07-16       Impact factor: 5.191

2.  Characterization of In53, a class 1 plasmid- and composite transposon-located integron of Escherichia coli which carries an unusual array of gene cassettes.

Authors:  T Naas; Y Mikami; T Imai; L Poirel; P Nordmann
Journal:  J Bacteriol       Date:  2001-01       Impact factor: 3.490

3.  Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr.

Authors:  Jennifer Baysarowich; Kalinka Koteva; Donald W Hughes; Linda Ejim; Emma Griffiths; Kun Zhang; Murray Junop; Gerard D Wright
Journal:  Proc Natl Acad Sci U S A       Date:  2008-03-18       Impact factor: 11.205

4.  Kanglemycin A Can Overcome Rifamycin Resistance Caused by ADP-Ribosylation by Arr Protein.

Authors:  John Harbottle; Hamed Mosaei; Nicholas Allenby; Nikolay Zenkin
Journal:  Antimicrob Agents Chemother       Date:  2021-10-04       Impact factor: 5.938

  4 in total

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