Enantioselective synthesis of non-natural amino acids using phenylalanine dehydrogenases modified by site-directed mutagenesis

Org Biomol Chem. 2004 Sep 21;2(18):2684-91. doi: 10.1039/B406364C. Epub 2004 Aug 25.

Abstract

The substrate scope of three mutants of phenylalanine dehydrogenase as biocatalysts for the transformation of a series of 2-oxo acids, structurally related to phenylpyruvic acid, to the analogous alpha-amino acids, non-natural analogues of phenylalanine, has been investigated. The mutant enzymes are more tolerant than the wild type enzyme of the non-natural substrates, especially those with substituents at the 4-position on the phenyl ring. Excellent enantiocontrol resulted in all cases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Oxidoreductases / chemistry
  • Amino Acid Oxidoreductases / genetics*
  • Amino Acid Substitution
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Molecular Structure
  • Mutagenesis, Site-Directed*
  • Stereoisomerism

Substances

  • Amino Acids
  • Amino Acid Oxidoreductases
  • phenylalanine oxidase