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Synthesis of enantiopure ( S )‐6‐chlorochroman‐4‐ol using whole‐cell Lactobacillus paracasei biotransformation
Author(s) -
Şahin Engin
Publication year - 2020
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23177
Subject(s) - enantiopure drug , biocatalysis , chemistry , lactobacillus paracasei , environmentally friendly , enantiomeric excess , enantioselective synthesis , biotransformation , enantiomer , organic chemistry , combinatorial chemistry , stereochemistry , fermentation , lactobacillus , catalysis , enzyme , reaction mechanism , ecology , biology
Chromane, which has a fused cyclic structure, is a significant molecule that can be found in the structure of many important compounds. Lactobacillus paracasei BD101 was demonstrated as whole‐cell biocatalyst for the synthesis of ( S )‐6‐chlorochroman‐4‐ol with immense enantioselectivity. The conditions of asymmetric reduction were optimized one factor by one factor using L paracasei BD101 to achieve enantiomerically pure product and complete conversion. Using these obtained optimization conditions, asymmetric reduction of 6‐chlorochroman‐4‐one was performed under environmentally friendly conditions; 6‐chlorochroman‐4‐one, having a fused cyclic structure as previously noted to be difficult to asymmetric reduction with biocatalysts, was enantiomerically reduced to ( S )‐6‐chlorochroman‐4‐ol with an enantiomeric excess >99% on a high gram scale. This study is the first example in the literature for the enantiopure synthesis of ( S )‐6‐chlorochroman‐4‐ol using a biocatalyst. Also notably, the optical purity of ( S )‐6‐chlorochroman‐4‐ol obtained in this study through asymmetric bioreduction using whole‐cell biocatalyst is the highest value in the literature. In this study, ( S )‐6‐chlorochroman‐4‐ol was produced on a gram scale by an easy, inexpensive, and environmentally friendly method, which has shown the production of valuable chiral precursors for drug synthesis and other industrial applications. This study provides a convenient method for the production of ( S )‐6‐chlorochroman‐4‐ol, which can meet the industrial green production demand of this chiral secondary alcohol.