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An Enzymatic and Environmentally Friendly Route for the Synthesis of Chiral β‐Hydroxy Ketones
Author(s) -
Yıldız Tülay
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201901718
Subject(s) - environmentally friendly , lipase , chemistry , organic chemistry , biocatalysis , aspergillus niger , hydrolysis , yield (engineering) , enantioselective synthesis , enzyme , catalysis , solvent , enzymatic hydrolysis , enzyme catalysis , aqueous medium , aqueous solution , reaction mechanism , materials science , biochemistry , ecology , metallurgy , biology
Abstract The present study deals with the biocatalytic enantioselective synthesis of chiral β‐hydroxy ketones. For the first time, we report that among many enzymes, the lipase AL‐AN ( Amano Lipase A from Aspergillus niger ) catalyzed the enzymatic hydrolysis of racemic 1,3‐keto acetates in aqueous media. Optimum reaction conditions were determined by changing the enzyme, solvent, temperature, pH and amounts of enzymes. After AL‐AN was determined to be the best enzyme in this study, we examined fifteen substrates with different structures in this reaction and obtained chiral β‐hydroxy ketones with good yield, high enantioselectivity and S configuration. This study presents an environmentally friendly and green method for the synthesis of ( S )‐β‐hydroxy ketones.