Structures of ADP-ribosylated rifampicin and its metabolite: intermediates of rifampicin-ribosylation by Mycobacterium smegmatis DSM43756.
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.
Morisaki
N
N
Institute of Molecular and Cellular Biosciences, The University of Tokyo, Japan.
Hashimoto
Y
Y
Furihata
K
K
Imai
T
T
Watanabe
K
K
Mikami
Y
Y
Yazawa
K
K
Ando
A
A
Nagata
Y
Y
Dabbs
E R
ER
D036002:ADP Ribose Transferases; D004926:Escherichia coli / Q000201:enzymology / Q000235:genetics; D009682:Magnetic Resonance Spectroscopy; D020102:Mycobacterium smegmatis / Q000235:genetics / Q000378:metabolism*; D009243:NAD / Q000378:metabolism; D011065:Poly(ADP-ribose) Polymerases / Q000235:genetics / Q000378:metabolism*; D012293:Rifampin / Q000737:chemistry* / Q000378:metabolism*
D009243:NAD; D036002:ADP Ribose Transferases; D011065:Poly(ADP-ribose) Polymerases; D012293:Rifampin