The effect of the migrating group structure on enantioselectivity in lipase-catalyzed kinetic resolution of 1-phenylethanol

• Published in: Comptes Rendus Chimie
• Main Authors: Melais, Nedjma, Aribi-Zouioueche, Louisa, Riant, Olivier
• Other Authors: UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
• Format: Article in Journal/Newspaper
• Language: English
• Published: Elsevier 2016
• Subjects: Antarc*; Antarctica
• Online Access: http://hdl.handle.net/2078.1/181250; https://doi.org/10.1016/j.crci.2016.05.002

We have studied the effects of the acyl moiety on the enantioselectivity of three lipases: Candida antarctica B, Pseudomonas cepacia and Candida cylindracea, frequently used in kinetic resolutions by acylation or hydrolysis. The size of the acyl group was examined using various enol esters during the transesterification of 1-phenylethanol and the hydrolysis of the corresponding phenylethylesters. C.antarctica-B lipase showed the highest selectivity in the transesterification of 1-phenylethanol with isopropenyl and vinyl acetate, vinyl decanoate, vinyl laurate, (E > 200). The esters 1-phenyl -ethyl-acetate, decanoate and laurate are also hydrolyzed with high selectivities (E > 150) with CAL-B. The results can be correlated to the three-dimensional form of each lipase. The effect of the migrating group on the reactivity and selectivity of the lipases are discussed for both reactions.