Biotransformation of phenylacetonitrile to 2-hydroxyphenylacetic acid by marine fungi

Mar Biotechnol (NY). 2013 Feb;15(1):97-103. doi: 10.1007/s10126-012-9464-1. Epub 2012 Jul 12.

Abstract

Marine fungi belonging to the genera Aspergillus, Penicillium, Cladosporium, and Bionectria catalyzed the biotransformation of phenylacetonitrile to 2-hydroxyphenylacetic acid. Eight marine fungi, selected and cultured with phenylacetonitrile in liquid mineral medium, catalyzed it quantitative biotransformation to 2-hydroxyphenylacetic acid. In this study, the nitrile group was firstly hydrolysed, and then, the aromatic ring was hydroxylated, producing 2-hydroxyphenylacetic acid with 51 % yield isolated. In addition, the 4-fluorophenylacetonitrile was exclusively biotransformed to 4-fluorophenylacetic acid by Aspergillus sydowii Ce19 (yield = 51 %). The enzymatic biotransformation of nitriles is not trivial, and here, we describe an efficient method for production of phenylacetic acids in mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / metabolism*
  • Biotransformation / physiology*
  • Catalysis
  • Fungi / growth & development
  • Fungi / metabolism
  • Fungi / physiology*
  • Hydrolysis
  • Hydroxylation
  • Marine Biology
  • Phenylacetates / isolation & purification
  • Phenylacetates / metabolism*

Substances

  • Acetonitriles
  • Phenylacetates
  • benzyl cyanide
  • 2-hydroxyphenylacetic acid