Production of a chiral alcohol, 1-(3,4-dihydroxyphenyl) ethanol, by mushroom tyrosinase

Biotechnol Lett. 2013 May;35(5):779-83. doi: 10.1007/s10529-013-1148-z. Epub 2013 Jan 25.

Abstract

1-(3,4-Dihydroxyphenyl) ethanol was produced biocatalytically for the first time using mushroom tyrosinase. 4-Ethylphenol at 1 mM was consumed over 12 min giving 0.23 mM 4-ethylcatechol and 0.36 mM (R/S)-1-(3,4-dihydroxyphenyl) ethanol (ee 0.5 %). Mushroom tyrosinase consumed 4-ethylphenol at 6.7 μmol min(-1) mg protein(-1) while the rates of formation of 4-ethylcatechol and 1-(3,4-dihydroxyphenyl) ethanol were 1.1 and 1.9 μmol min(-1) mg protein(-1). Addition of the ascorbic acid, as a reducing agent to biotransformation reactions, increased 4-ethylcatechol formation by 340 %. However, accumulation of 1-(3,4-dihydroxyphenyl) ethanol was not observed in the presence of ascorbic acid. While the 1-(3,4-dihydroxyphenyl) ethanol was racemic, it is the first chiral product produced by tyrosinase starting from a non-chiral substrate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / enzymology*
  • Biotransformation
  • Chromatography, High Pressure Liquid
  • Monophenol Monooxygenase / metabolism*
  • Oxidation-Reduction
  • Phenols / analysis
  • Phenols / metabolism
  • Phenylethyl Alcohol / analogs & derivatives*
  • Phenylethyl Alcohol / analysis
  • Phenylethyl Alcohol / metabolism
  • Plant Proteins / metabolism*
  • Stereoisomerism

Substances

  • Phenols
  • Plant Proteins
  • 3,4-dihydroxyphenylethanol
  • 4-ethylphenol
  • Monophenol Monooxygenase
  • Phenylethyl Alcohol