Synthesis of enantiomerically enriched drug precursors and an insect pheromone via reduction of ketones using commercially available carbonyl reductase screening kit “Chiralscreen® OH”

Toshiya Nagai, Saki Sakurai, Naoki Natori, Manaka Hataoka, Takako Kinoshita, Hiroyoshi Inoue, Kengo Hanaya, Mitsuru Shoji, Takeshi Sugai

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

Commercially available “Chiralscreen® OH” starter kit containing five types of carbonyl reductases (E001, E007, E031, E039, and E078) was used for the reduction of several aromatic and aliphatic ketones to obtain enantiomerically enriched drug precursors and an insect pheromone. Almost stereochemically pure secondary alcohols, used in the synthesis of drugs such as (R)-rasagiline mesylate, (S)-rivastigmine, (R)-chlorphenesin carbamate, and (R)-mexiletine, and the insect pheromone (4S,5R)-sitophilure, were conveniently obtained. The enzymes worked well with ketones containing at least one non-bulky substituent at the carbonyl group. The diverse stereochemical preference of the above five carbonyl reductases was clarified.

Original languageEnglish
Pages (from-to)1304-1313
Number of pages10
JournalBioorganic and Medicinal Chemistry
Volume26
Issue number7
DOIs
Publication statusPublished - 2018 Apr 1

Keywords

  • Asymmetric reduction
  • Carbonyl reductase
  • Enzyme library
  • “Chiralscreen® OH”

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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