Enantioconvergent Biocatalytic Redox Isomerization

Angew Chem Int Ed Engl. 2018 Sep 10;57(37):12151-12156. doi: 10.1002/anie.201804911. Epub 2018 Aug 20.

Abstract

Alcohol dehydrogenases can act as powerful catalysts in the preparation of optically pure γ-hydroxy-δ-lactones by means of an enantioconvergent dynamic redox isomerization of readily available Achmatowicz-type pyranones. Imitating the traditionally metal-mediated "borrowing hydrogen" approach to shuffle hydrides across molecular architectures and interconvert functional groups, this chemoinspired and purely biocatalytic interpretation effectively expands the enzymatic toolbox and provides new opportunities in the assembly of multienzyme cascades and tailor-made cellular factories.

Keywords: asymmetric synthesis; biocatalysis; enantioconvergent processes; heterocycles; redox isomerization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohol Dehydrogenase / genetics
  • Alcohol Dehydrogenase / metabolism*
  • Biocatalysis
  • Escherichia coli / metabolism
  • Hydrogen / chemistry
  • Isomerism
  • Lactones / chemical synthesis
  • Lactones / chemistry*
  • Oxidation-Reduction
  • Oxidoreductases
  • Recombinant Proteins / genetics
  • Recombinant Proteins / metabolism
  • Stereoisomerism

Substances

  • Lactones
  • Recombinant Proteins
  • Hydrogen
  • Oxidoreductases
  • Alcohol Dehydrogenase