Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750

Appl Environ Microbiol. 1991 Oct;57(10):3028-32. doi: 10.1128/aem.57.10.3028-3032.1991.

Abstract

R-(-)-Mandelic acid was produced from racemic mandelonitrile by Alcaligenes faecalis ATCC 8750. Ammonium acetate or L-glutamic acid as the carbon source and n-butyronitrile as the inducer in the culture medium were effective for bacterial growth and the induction of R-(-)-mandelic acid-producing activity. The R-(-)-mandelic acid formed from mandelonitrile by resting cells was present in a 100% enantiomeric excess. A. faecalis ATCC 8750 has an R-enantioselective nitrilase for mandelonitrile and an amidase for mandelamide. As R-(-)-mandelic acid was produced from racemic mandelonitrile in a yield of 91%, whereas no S-mandelonitrile was left, the S-mandelonitrile remaining in the reaction is spontaneously racemized because of the chemical equilibrium and is used as the substrate. Consequently, almost all the mandelonitrile is consumed and converted to R-(-)-mandelic acid. R-(-)-Mandelic acid was also produced when benzaldehyde plus HCN was used as the substrate.

MeSH terms

  • Acetonitriles / metabolism*
  • Alcaligenes / enzymology
  • Alcaligenes / growth & development*
  • Alcaligenes / metabolism
  • Amidohydrolases / metabolism
  • Benzaldehydes / metabolism
  • Carbon / pharmacology
  • Hydrogen Cyanide / metabolism
  • Hydrolysis
  • Isomerism
  • Kinetics
  • Mandelic Acids / metabolism*
  • Substrate Specificity

Substances

  • Acetonitriles
  • Benzaldehydes
  • Mandelic Acids
  • Hydrogen Cyanide
  • mandelonitrile
  • Carbon
  • Amidohydrolases
  • mandelic acid
  • benzaldehyde