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

Main Article Content

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.

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How to Cite
[1]
Y. N. Mitrev, A. Y. Mehandzhiyski, D. I. Batovska, A. Liese, and B. Galunsky, “Original enzyme-catalyzed synthesis of chalcones: Utilization of hydrolase promiscuity”, J. Serb. Chem. Soc., vol. 81, no. 11, pp. 1231–1237, Nov. 2016.
Section
Biochemistry & Biotechnology
Author Biography

Aleksander Y Mehandzhiyski

Bulgarian Academy of Sciences, Institute of Organic Chemistry with Centre of Phytochemistry

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