Original enzyme-catalyzed synthesis of chalcones: Utilization of hydrolase promiscuity

Yavor N Mitrev, Aleksander Y Mehandzhiyski, Daniela I Batovska, Andreas Liese, Boris Galunsky

Abstract


An E-chalcone was obtained with very high stereoselectivity for the first time by an enzyme-catalyzed Claisen–Schmidt condensation between benzaldehyde and acetophenone. From a set of lipases, only that from hog pancreas demonstrated promiscuity, catalyzing the reaction in the presence of imidazole as a promoter. Another enzyme, acylase from Aspergillus melleus (EC 3.5.1.14) also proved to be active in the synthesis of E-chalcone under the same reaction conditions. This acylase along with the recombinant D-amino­acylase (EC 3.5.1.81) also catalyzed the reaction between acetophenone and p-nitrobenzaldehyde. Such a “green” approach to the synthesis of chalcones is of great interest because of the important applications of chalcones as formula ingredients in the pharmaceutical, food and cosmetic industries.


Keywords


Claisen–Schmidt condensation; enzyme promiscuity; lipase-cata¬ly¬zed synthesis

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DOI: https://doi.org/10.2298/JSC160422069M

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