Switching from (R)- to (S)-selective chemoenzymatic DKR of amines involving sulfanyl radical-mediated racemization

Org Biomol Chem. 2010 Sep 21;8(18):4165-8. doi: 10.1039/c0ob00054j. Epub 2010 Jul 27.

Abstract

Chemoenzymatic dynamic kinetic resolution (DKR) of amines involving sulfanyl radical-induced racemization happened to be the very first switchable DKR process allowing the synthesis of either (R)- or (S)-amides, in good yield and high enantiomeric excess, depending on the nature of the enzyme; the different steps of the development of (S)-selective DKR are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amines / chemistry*
  • Bacterial Proteins / chemistry
  • Bacterial Proteins / metabolism*
  • Biocatalysis
  • Endopeptidases / chemistry
  • Endopeptidases / metabolism*
  • Free Radicals / chemistry
  • Kinetics
  • Nitriles / chemistry
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*

Substances

  • Amides
  • Amines
  • Bacterial Proteins
  • Free Radicals
  • Nitriles
  • Sulfhydryl Compounds
  • Endopeptidases
  • alkaline protease
  • azobis(isobutyronitrile)