Enantioselective reduction of aryl and hetero aryl methyl ketones using plant cell suspension cultures of Vigna radiata

Abstract

Vigna radiata was investigated as whole cell catalyst for the bioreduction of aryl and heteroaryl prochiral ketones into optically active alcohols. The study indicates selective bioreduction of different substituted aryl and heteroaryl ketones (1a–12a) to their respective (S) – chiral alcohols (1b–12b) in good to high enantioselectivity (77.7–97.5%) with very good yields (73–82%). The results obtained confirm that the keto reductase has broad substrate specificity and selectivity in catalyzing both six and five-membered heteroaryl methyl ketones. The current methodology substantiates a promising and alternative green approach for the synthesis of secondary chiral alcohols of biological importance in a mild, cheap and environmentally benign process.

Keywords:

• Plant cell suspension culture
• (S)-1-arylethanols
• arylketones
• enantioselective bioreduction
• prelog bioreduction

Acknowledgements

B. Baskar thanks Dr. Anju Chadha, Professor, Department of Biotechnology, Indian Institute of Technology (IIT Madras), Chennai, India, for her generous support to use instrumentation facilities in her laboratory.

Disclosure statement

The authors report no conflicts of interest. The authors alone are responsible for the content and writing of this article.