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Highly Enantioselective Production of Chiral Secondary Alcohols Using Lactobacillus paracasei BD 101 as a New Whole Cell Biocatalyst and Evaluation of Their Antimicrobial Effects
Author(s) -
Yılmaz Durmuşhan,
Şahin Engin,
Dertli Enes
Publication year - 2017
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201700269
Subject(s) - lactobacillus paracasei , enantiopure drug , chemistry , antimicrobial , biocatalysis , enantioselective synthesis , enantiomer , organic chemistry , enantiomeric excess , lactobacillus , combinatorial chemistry , catalysis , fermentation , reaction mechanism
Chiral secondary alcohols are valuable intermediates for many important enantiopure pharmaceuticals and biologically active molecules. In this work, we studied asymmetric reduction of aromatic ketones to produce the corresponding chiral secondary alcohols using lactic acid bacteria ( LAB ) as new biocatalysts. Seven LAB strains were screened for their ability to reduce acetophenones to their corresponding alcohols. Among these strains, Lactobacillus paracasei BD 101 was found to be the most successful at reducing the ketones to the corresponding alcohols. The reaction conditions were further systematically optimized for this strain and high enantioselectivity (99%) and very good yields were obtained. These secondary alcohols were further tested for their antimicrobial activities against important pathogens and significant levels of antimicrobial activities were observed although these activities were altered depending on the secondary alcohols as well as their enantiomeric properties. The current methodology demonstrates a promising and alternative green approach for the synthesis of chiral secondary alcohols of biological importance in a cheap, mild, and environmentally useful process.