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

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...

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Bibliographic Details
Published in:Chemistry – A European Journal
Main Authors: Yang, Bin, Lihammar, Richard, Bäckvall, Jan-Erling
Format: Article in Journal/Newspaper
Language:English
Published: Stockholms universitet, Institutionen för organisk kemi 2014
Subjects:
CALB
enantioselectivity
hydrolysis
lipase
transesterification
Organic Chemistry
Organisk kemi
Antarc*
Antarctica
Online Access:http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-108352
https://doi.org/10.1002/chem.201404233
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Summary: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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