Applied Microbiology and Biotechnology

, Volume 27, Issue 2, pp 152–158

Enantioselective reduction of acetyldimethylphenylsilane by Trigonopsis variabilis (DSM 70714)

  • Christoph Syldatk
  • Hannelore Andree
  • Andrea Stoffregen
  • Fritz Wagner
  • Burghard Stumpf
  • Ludger Ernst
  • Harald Zilch
  • Reinhold Tacke
Biotechnology

DOI: 10.1007/BF00251938

Cite this article as:
Syldatk, C., Andree, H., Stoffregen, A. et al. Appl Microbiol Biotechnol (1987) 27: 152. doi:10.1007/BF00251938

Summary

Growing and resting cells of the yeast Trigonopsis variabilis (DSM 70714) can be used for the enantioselective reduction of the organosilicon compound acetyldimethylphenylsilane (1) to give optically active (R)-(1-hydroxyethyl)dimethylphenylsilane [(R)-2] in good yields. The enantiomeric purity of the isolated product was determined to be 62–86% ee depending on the substrate concentration used. Both substrate and product caused an inhibition of the reaction at concentrations higher than 0.35 and 0.5 g/l, respectively. Besides, higher substrate and product concentrations led to increased formation of the by-product 1,1,3,3-tetramethyl-1,3-diphenyldisiloxane. Considering the limiting substrate and product concentrations, it was possible to use the same biomass at least 5 times without significant loss of enzyme activity. 3-Methyl-3-phenyl-2-butanone (5) and acetyldimethylphenylgermane (7), which represent carbon and germanium analogues of 1, were also found to be accepted as substrates by Trigonopsis variabilis (DSM 70714). The reduction rates of the silicon (1) and germanium compound (7) were much higher than the transformation rate of the corresponding carbon analogue 5.

Copyright information

© Springer-Verlag 1987

Authors and Affiliations

  • Christoph Syldatk
    • 1
  • Hannelore Andree
    • 1
  • Andrea Stoffregen
    • 1
  • Fritz Wagner
    • 1
  • Burghard Stumpf
    • 2
  • Ludger Ernst
    • 2
  • Harald Zilch
    • 3
  • Reinhold Tacke
    • 3
  1. 1.Institute of Biochemistry and BiotechnologyTechnical University of BraunschweigBraunschweigFederal Republic of Germany
  2. 2.Gesellschaft für Biotechnologische Forschung mbH (GBF)BraunschweigFederal Republic of Germany
  3. 3.Institute of Inorganic and Analytical ChemistryTechnical University of BraunschweigBraunschweigFederal Republic of Germany