Enantioselective dynamic process reduction of α- and β-tetralone and stereoinversion of resulting alcohols in a selected strain culture

Curr Microbiol. 2012 Aug;65(2):189-94. doi: 10.1007/s00284-012-0143-2. Epub 2012 May 22.

Abstract

α-Tetralone and β-tetralone were subjected to biotransformation by 14 fungal strains. Enantiomeric purity of the products depended on the reaction time. 3-Day transformation of α-tetralone in Absidia cylindrospora culture gave S-(+)-1,2,3,4-tetrahydro-1-naftol of 92 % ee, whereas longer biotransformation time resulted in decrease of ee value. 3-Day transformation of β-tetralone by the same strain gave predominantly S-(-)-1,2,3,4-tetrahydro-2-naftol, whereas after 9 days of the reaction, the R-enantiomer with 85 % ee was isolated. Transformation of β-tetralone by Chaetomium sp. KCh 6651 gave pure (S)-(-)-1,2,3,4-tetrahydro-2-naftol in high yield at the concentration of 1 g/l. In this process, a non-selective carbonyl reduction was observed, followed by a selective oxidation of the R-alcohol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / metabolism*
  • Biotransformation
  • Fungi / metabolism*
  • Oxidation-Reduction
  • Stereoisomerism
  • Tetralones / metabolism*
  • Time Factors

Substances

  • Alcohols
  • Tetralones