One-Pot Transformation of Ketoximes into Optically Active Alcohols and Amines by Sequential Action of Laccases and Ketoreductases or ω-Transaminases

Raquel S. Correia Cordeiro, Nicolás Ríos-Lombardía, Francisco Morís, Robert Kourist, Javier González-Sabín

Research output: Contribution to journalArticleResearchpeer-review

Abstract

An enzymatic one-pot process for asymmetric transformation of prochiral ketoximes into alcohols or amines was developed by sequential coupling of a laccase-catalyzed deoximation either with a ketone reduction (ketoreductase, KRED) or bioamination (ω-transaminase, ω-TA) in aqueous medium. An accurate selection of biocatalysts provided the corresponding products in excellent enantiomeric excesses and overall conversions ranging from 83 to >99 % for alcohols and 70 to >99 % for amines. Likewise, the employment of exclusively 1 % (w/w) of Cremophor®, a polyethoxylated castor oil, as co-solvent enabled to reach concentrations up to 100 mM in the chiral alcohols cascade.

Original languageEnglish
Pages (from-to)1272-1277
Number of pages6
JournalChemCatChem
Volume11
Issue number4
DOIs
Publication statusPublished - 20 Feb 2019

    Fingerprint

Keywords

  • alcohol dehydrogenase
  • enzymatic cascade
  • one-pot reaction
  • oxime
  • transaminase

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this