Production of enantiopure chiral aryl heteroaryl carbinols using whole‐cell Lactobacillus paracasei biotransformation

Abstract

Aryl and heteroaryl chiral carbinols are useful precursors in the synthesis of drugs. Lactobacillus paracasei BD87E6, which is obtained from a cereal based fermented beverage, was investigated as whole cell biocatalyst for the bioreduction of different ketones (including aromatic, hetero-aromatic and fused bicyclic ketone) into chiral carbinols, which can be used as a pharmaceutical intermediate. The study shows that bioreduction of aryl, heteroaryl and fused bicyclic ketone (1-5) to their corresponding chiral carbinols (1a-5a) in excellent enantioselectivity (>99%) with high yields. This study gave the first example for an enantiopure production of (S)-6-chlorochroman-4-ol (3a), which has many antioxidant activity, by a biological method. For asymmetric bioreduction of other prochiral ketones, these results open way to use of L. paracasei BD87E6 as biocatalysts. Also, the present process shows a hopeful and alternative green synthesis for the production of enantiopure carbinols in a mild, inexpensive and environmentally friendly process.

GRAPHICAL ABSTRACT

Keywords:

• Biotransformation
• chiral heteroaryl carbinol
• enantioselective bioreduction
• (S)-6-chlorochroman-4-ol
• whole-cell biocatalyst

Acknowledgments

The author thanks Dr. Enes DERTLİ (Bayburt University) for supplying L. paracasei BD87E6 strain used in this study.

Availability of data

The data that support the findings of this study are openly available in https://doi.org/10.1002/cbdv.201800028, reference number [38].