Enantiomerically pure 3-aryl- and 3-hetaryl-2-hydroxypropanoic acids by chemoenzymatic reduction of 2-oxo acids

J Org Chem. 2015 Mar 6;80(5):2554-61. doi: 10.1021/jo502529g. Epub 2015 Feb 20.

Abstract

Phenyllactic acids are found in numerous natural products as well as in active substances used in medicine or plant protection. Enantiomerically pure phenyllactic acids are available by transition-metal-catalyzed hydrogenations or chemoenzymatic reductions of the corresponding 3-aryl-2-oxopropanoic acids. We show here that d-lactate dehydrogenase from Staphylococcus epidermidis reduces a broad spectrum of 2-oxo acids, which are difficult substrates for transition-metal-catalyzed reactions, with excellent enantioselectivities in a simple experimental setup.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrogenation
  • Lactate Dehydrogenases / chemistry*
  • Lactate Dehydrogenases / metabolism
  • Molecular Structure
  • Propionates / chemistry*
  • Staphylococcus / chemistry*
  • Stereoisomerism
  • Transition Elements / chemistry*

Substances

  • Propionates
  • Transition Elements
  • Lactate Dehydrogenases
  • D-lactate dehydrogenase