Glycosylative inactivation of chalcomycin and tylosin by a clinically isolated Nocardia asteroides strain.
Studies on the susceptibility of pathogenic Nocardia to macrolide antibiotics, chalcomycin and tylosin, showed that most of the Nocardia species examined were highly resistant to both antibiotics, although N. nova was moderately susceptible. N. asteroides IFM 0339 converted these macrolides into inactive metabolites by glycosylation at 2'-OH or glycosylation and reduction of the 20-formyl group. The structures of the metabolites were determined from NMR and MS data to be 2'-[O-(beta-D-glucopyranosyl)]chalcomycin (2), 2'-[O-(beta-D-glucopyranosyl)]tylosin (5) and 20-dihydro-2'-[O-(beta-D-glucopyranosyl)]tylosin (4).
Morisaki
N
N
Institute of Molecular and Cellular Biosciences, The University of Tokyo, Japan.
Hashimoto
Y
Y
Furihata
K
K
Yazawa
K
K
Tamura
M
M
Mikami
Y
Y
D000900:Anti-Bacterial Agents / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D006031:Glycosylation; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009616:Nocardia asteroides / Q000502:physiology*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D015645:Tylosin / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism
D000900:Anti-Bacterial Agents; D018942:Macrolides; C002018:chalcomycin; D015645:Tylosin