Highly Enantioselective Production of Chiral Secondary Alcohols Using Lactobacillus paracasei BD101 as a New Whole Cell Biocatalyst and Evaluation of Their Antimicrobial Effects

Abstract

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 BD101 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.

Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)‐cyclohexyl(phenyl)methanol

“…16 Therefore, highly selective and environmentally friendly biocatalytic process to synthesis optically active carbinols is the utilization of isolated enzymes and whole cell microorganisms. 37,38 In this study, we report the asymmetric reduction of cyclohexyl(phenyl)methanone 1 to the (S)cyclohexyl(phenyl)methanol 2 by L paracasei BD101 with >99% ee and 92% yields. Whole cells contain various dehydrogenases that are able to accept a wide range of unnatural substrates.…”

Synthesis of enantiopure (S)‐6‐chlorochroman‐4‐ol using whole‐cell Lactobacillus paracasei biotransformation

“…The reason is that too much acid or base can decrease the activity of the enzyme . These data are suitable with previous studies using this biocatalyst for the bioreduction of prochiral ketones . In biocatalytic reaction, the activity and stability of the enzyme are affected by temperature .…”

“…The synthesis of 6‐chlorochroman‐4‐ol as an enantiopure form using a biocatalyst is not known in the literature. In previous study, Lactobacillus paracasei BD101 obtained from boza, a cereal‐based fermented beverage, was shown as a very effective and selective whole‐cell biocatalyst for production of enantiopure chiral secondary alcohols, which are important precursors for the synthesis of several drugs . This study has reported a method where a fused cyclic ketone can be reduced using an inexpensive and simple process with L paracasei BD101 as the biocatalyst.…”

Production of (R)‐1‐(1,3‐benzodioxol‐5‐yl)ethanol in high enantiomeric purity by Lactobacillus paracaseiBD101

“…26 Recently, we performed asymmetric reduction of acetophenone and its derivatives by high enantioselectivity and conversion using Lactobacillus paracasei BD101 as biocatalyst. 27 Herein, we report the asymmetric reduction of piperonyl methyl ketone 1 to the (R)-1-(1,3-benzodioxol-5-yl)ethanol 2 by L paracasei BD101 with >99% ee and 89% yields. Moreover, to the best of our knowledge, this is the first report on asymmetric reduction of piperonyl methyl ketone using biocatalyst.…”