A new chemo-enzymatic route to chiral 2-hydroxy-4-phenylbutyrates by combining lactonase-mediated resolution with hydrogenation over Pd/C

Chem Commun (Camb). 2010 Apr 28;46(16):2754-6. doi: 10.1039/b925402a. Epub 2010 Feb 25.

Abstract

A new chemo-enzymatic route to both isomers of 2-hydroxy-4-phenylbutyric acid is reported. The key step is the lactonase-catalyzed hydrolysis of cis- and trans-2-hydroxy-4-phenyl-4-butyrolactones followed by hydrogenation over Pd/C to afford optically pure 2-hydroxy-4-phenylbutyric acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry*
  • Carboxylic Ester Hydrolases / chemistry*
  • Catalysis
  • Hydrogenation
  • Molecular Structure
  • Palladium / chemistry*
  • Phenylbutyrates / chemical synthesis
  • Phenylbutyrates / chemistry*
  • Stereoisomerism

Substances

  • Phenylbutyrates
  • 2-hydroxy-4-phenylbutyric acid
  • Palladium
  • Carbon
  • Carboxylic Ester Hydrolases
  • delta-lactonase