Novel 26-oxygenated products in microbial degradation of ergosterol

  • Ambrus G
  • Jekkel A
  • Ilkoy É
 et al. 
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Abstract

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-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. © 1995.

Author-supplied keywords

  • ergosterol
  • mechanism of microbial 26-oxidation

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Authors

  • Gábor Ambrus

  • Antónia Jekkel

  • Éva Ilkoy

  • Gyula Horváth

  • Zsolt Böcskei

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