Stereocomplementary bioreduction of β-ketonitrile without ethylated byproduct

Org Lett. 2013 Nov 1;15(21):5408-11. doi: 10.1021/ol402733y. Epub 2013 Oct 21.

Abstract

α-Ethylation is competing with the biocatalytic reduction of aromatic β-ketonitriles in a whole-cell system. Use of two newly mined robust and stereocomplementary carbonyl reductases in a biphasic system has completely eliminated the competing byproduct. For the first time, both enantiomers of fluoroxetine precursors were obtained at 0.5 M with >99% ee and excellent chemoselectivity, without addition of any external cofactors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohol Oxidoreductases / chemistry*
  • Biocatalysis
  • Ketones / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Ketones
  • Nitriles
  • Alcohol Oxidoreductases