Kinetic Resolution and Deracemization of Racemic Amines Using a Reductive Aminase

Research output: Contribution to journalArticle

  • External authors:
  • Godwin A. Aleku
  • Juan Mangas-Sanchez
  • Joan Citoler
  • Scott P. France
  • Sarah L. Montgomery
  • Rachel S. Heath
  • Matthew P. Thompson

Abstract

The NADP(H)-dependent reductive aminase from Aspergillus oryzae (AspRedAm) was combined with an NADPH oxidase (NOX) to develop a redox system that recycles the co-factor. The AspRedAm-NOX system was applied initially for the kinetic resolution of a variety of racemic secondary and primary amines to yield S-configured amines with enantiomeric excess (ee) values up to 99 %. The addition of ammonia borane to this system enabled the efficient deracemization of racemic amines, including the pharmaceutical drug rasagiline and the natural product salsolidine, with conversions up to >98 % and >99 % ee Furthermore, by using the AspRedAm W210A variant it was possible to generate the opposite R enantiomers with efficiency comparable to, or even better than, the wildtype AspRedAm.

Bibliographical metadata

Original languageEnglish
Pages (from-to)515-519
Number of pages5
JournalChemCatChem
Volume10
Issue number3
Early online date15 Sep 2017
DOIs
Publication statusPublished - 7 Feb 2018