Control of enantioselectivity in the enzymatic reduction of halogenated acetophenone analogs by substituent positions and sizes

Afifa Ayu Koesoema, Daron M. Standley, Shusuke Ohshima, Mayumi Tamura, Tomoko Matsuda

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

We utilized acetophenone reductase from Geotrichum candidum NBRC 4597 (GcAPRD), wild type and Trp288Ala mutant, to reduce halogenated acetophenone analogs to their corresponding (S)- and (R)-alcohols beneficial as pharmaceutical intermediates. Reduction by wild type resulted in excellent (S)-enantioselectivity for all of the substrates tested. Meanwhile, reduction by Trp288Ala resulted in high (R)-enantioselectivity for the reduction of 4′ substituted acetophenone and 2′-trifluoromethylacetophenone. In addition to that, we were able to control the enantioselectivity of Trp288Ala by the positions and sizes of the halogen substituents.

Original languageEnglish
Article number151820
JournalTetrahedron Letters
Volume61
Issue number18
DOIs
Publication statusPublished - Apr 30 2020
Externally publishedYes

Keywords

  • Alcohol dehydrogenase
  • Asymmetric reduction
  • Enantioselectivity control
  • Halogenated acetophenone analogs

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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