Asymmetric Ketone Reduction by Imine Reductases

Chembiochem. 2017 Feb 1;18(3):253-256. doi: 10.1002/cbic.201600647. Epub 2016 Dec 30.

Abstract

The rapidly growing area of asymmetric imine reduction by imine reductases (IREDs) has provided alternative routes to chiral amines. Here we report the expansion of the reaction scope of IREDs by showing the stereoselective reduction of 2,2,2-trifluoroacetophenone. Assisted by an in silico analysis of energy barriers, we evaluated asymmetric hydrogenations of carbonyls and imines while considering the influence of substrate reactivity on the chemoselectivity of this novel class of reductases. We report the asymmetric reduction of C=N as well as C=O bonds catalysed by members of the IRED enzyme family.

Keywords: asymmetric catalysis; biocatalysis; carbonyl compounds; promiscuity; reduction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacterial Proteins / chemistry
  • Bacterial Proteins / metabolism*
  • Biocatalysis
  • Imines / chemistry
  • Imines / metabolism
  • Ketones / chemistry
  • Ketones / metabolism*
  • NADP / chemistry
  • NADP / metabolism
  • Oxidoreductases / chemistry
  • Oxidoreductases / metabolism*
  • Paenibacillus / enzymology
  • Streptomyces / enzymology
  • Thermodynamics

Substances

  • Bacterial Proteins
  • Imines
  • Ketones
  • NADP
  • Oxidoreductases