Premium
Synthesis of Enantiomerically Enriched Drug Precursors by Lactobacillus paracasei BD 87E6 as a Biocatalyst
Author(s) -
Öksüz Selda,
Şahin Engin,
Dertli Enes
Publication year - 2018
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.201800028
Subject(s) - lactobacillus paracasei , chemistry , biocatalysis , yield (engineering) , ketone , lactobacillus , enantiomeric excess , enantioselective synthesis , enantiomer , alcohol , organic chemistry , fermentation , catalysis , reaction mechanism , materials science , metallurgy
Global sales of single enantiomeric drug products are growing at an alarming rate every year. A total of 7 bacterial strains were screened for their ability to reduce acetophenones to its corresponding alcohol. Among these strains Lactobacillus paracasei BD 87E6 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent Lactobacillus paracasei BD 87E6, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of 3‐methoxyacetophenone ( 1h ) by Lactobacillus paracasei BD 87E6 gave ( R )‐1‐(3‐methoxyphenyl)ethanol ( 2h ) with 92% yield and 99% enantiomeric excess. Compound 2h could be used for the synthesis of ( S )‐rivastigmine which has a great potential for the treatment of Alzheimer's disease. This study demonstrates that Lactobacillus paracasei BD 87E6 can be used as a biocatalyst to obtain chiral carbinol with excellent yield and selectivity. The whole cell catalyzed the reductions of ketone substrates on the preparative scale, demonstrating that Lactobacillus paracasei BD 87E6 would be a valuable biocatalyst for the preparation of chiral aromatic alcohols of pharmaceutical interest.