Novel 26-oxygenated products in microbial degradation of ergosterol.
In order to investigate the effect of the different stereochemistry of C-24 on the microbial C-26 oxidation of sterol side-chain the genetically modified Mycobacterium sp. BCS 396 strain was used to transform erogsterol. Ergosterol was converted to 3-oxo-4,22-ergostadien-26-oic acid methyl ester, 3-oxo-1,4,22-ergostatrien-26-oic acid methyl ester, and 3-oxo-1,4,22-ergostatrien-26-oic acid, the structures of which have been determined by IR, 1H NMR, 13C NMR, and mass spectroscopy. The X-ray structure of 3-oxo-4,22-ergostadien-26-oic acid methyl ester revealed that oxidation at C-26 of the ergostane side-chain generates a chiral center with S-configuration at C-25 as a result of chiral induction of the C-24 center.
Institute for Drug Research, Budapest, Hungary.
G
G
Ambrus
A
A
Jekkel
E
E
Ilköy
G
G
Horváth
Z
Z
Böcskei
D004875:Ergosterol / Q000737:chemistry* / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009161:Mycobacterium / Q000378:metabolism*; D010084:Oxidation-Reduction; D017550:Spectroscopy, Fourier Transform Infrared; D013261:Sterols / Q000737:chemistry; D013329:Structure-Activity Relationship
D013261:Sterols; D004875:Ergosterol