Steroids p. 626 - 629 (1995)
Update date:2022-08-16
Topics:
Ambrus, Gabor
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 ergosterol. 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-oxol-1,4,22- erogstatrien-26-oic acid, the structures of which have been determined by 1R, 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.
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