Investigation of the Impact of Water on the Enantioselectivity Displayed by CALB in the Kinetic Resolution of δ‐Functionalized Alkan‐2‐ol Derivatives

Abstract It is shown that the low enantioselectivity of Candida antarctica lipase B (CALB)‐catalyzed transesterification of a δ‐functionalized alkan‐2‐ol to its acetate does not correlate at all with the high enantioselectivity of the CALB‐catalyzed hydrolysis of the corresponding acetate in water....

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Bibliographic Details
Published in:Chemistry – A European Journal
Main Authors: Yang, Bin, Lihammar, Richard, Bäckvall, Jan‐E.
Other Authors: Swedish Natural Science Research Council, Knut and Alice Wallenberg Foundation
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 2014
Subjects:
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1002/chem.201404233
https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.201404233
https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.201404233
https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.201404233
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Summary:Abstract It is shown that the low enantioselectivity of Candida antarctica lipase B (CALB)‐catalyzed transesterification of a δ‐functionalized alkan‐2‐ol to its acetate does not correlate at all with the high enantioselectivity of the CALB‐catalyzed hydrolysis of the corresponding acetate in water. This lack of correlation is unusual and for unfunctionalized alkan‐2‐ol derivatives there is a very good correlation between the enantioselectivity of transesterification of the alcohol and hydrolysis of the corresponding acetate ( E >200 in both cases). The results confirm previous predictions from molecular modeling. The water effect was mimicked by CALB variant Ala281Ser, which showed an enhanced enantioselectivity in transesterification of δ‐functionalized alkan‐2‐ols compared to wild‐type CALB.

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