2-Epimutalomycin and 28-epimutalomycin, two new polyether antibiotics from Streptomyces mutabilis. Derivatization of mutalomycin and the structure elucidation of two minor metabolites.
A number of derivatives of mutalomycin (1), a naturally occurring polyether antibiotic, have been synthesized. In the desulfurization reaction of the ethylthio derivative (5) of mutalomycin (1) with Raney-nickel we observed an unusual course of the reaction, namely the introduction of a hydroxy group instead of the usual exchange against hydrogen, leading to two reaction products, mutalomycin (1) and 28-epimutalomycin (3). The structure of 3 and 2-epimutalomycin (2), both minor metabolites from the mutalomycin fermentation, were elucidated by X-ray analysis.
Fehr
T
T
Microbiological Research, Pharmaceutical Division, Sandoz Ltd., Switzerland.
Kuhn
M
M
Loosli
H R
HR
Ponelle
M
M
Boelsterli
J J
JJ
Walkinshaw
M D
MD
D000900:Anti-Bacterial Agents / Q000378:metabolism*; D002850:Chromatography, Gel; D002855:Chromatography, Thin Layer; D003460:Crystallization; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009550:Nigericin / Q000031:analogs & derivatives / Q000032:analysis / Q000138:chemical synthesis / Q000378:metabolism*; D014961:X-Ray Diffraction
D000900:Anti-Bacterial Agents; C060110:28-epimutalomycin; C060111:2-epimutalomycin; C016007:mutalomycin; D009550:Nigericin