Green methodology for enzymatic hydrolysis of acetates in non-aqueous media via carbonate salts

Herein we report a new approach to enantiomerically enriched acetates using a lipase-catalyzed hydrolysis in non-aqueous media by alkaline carbonate salts. The use of sodium carbonate in the enzymatic hydrolysis with Candida antarctica lipase B (CAL-B) of racemic acetates shows a large enhancement o...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: Merabet-Khelassi , M., Houiene, Z., Aribi-Zouioueche, L., Riant, Olivier
Other Authors: UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Format: Article in Journal/Newspaper
Language:English
Published: Pergamon 2012
Subjects:
Acetic acid derivative
Enantiomer
Enzyme activity
Enzyme kinetics
Enzyme mechanism
Hydrolysis
Nonhuman
Priority journal
Racemic mixture
Alcohol derivative
Alkaline earth metal
Fungal enzyme
Lipase B
Sodium carbonate
Article
Candida antarctica
Controlled study
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2078.1/126147
https://doi.org/10.1016/j.tetasy.2012.06.001
Description
Summary:Herein we report a new approach to enantiomerically enriched acetates using a lipase-catalyzed hydrolysis in non-aqueous media by alkaline carbonate salts. The use of sodium carbonate in the enzymatic hydrolysis with Candida antarctica lipase B (CAL-B) of racemic acetates shows a large enhancement of the reactivity and selectivity of this lipase. The role of the carbonate salts, the amount and the nature of the alkaline earth metal on the efficiency of this new pathway are investigated. The enzymatic kinetic resolution of acetates 1a-9a, by enzymatic-carbonate hydrolysis under mild conditions is described. In all cases, the resulting alcohols and remaining acetates were obtained in high ee values (up to >99%) while the selectivities reached E >500. © 2012 Elsevier Ltd. All rights reserved.

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