Original enzyme-catalyzed synthesis of chalcones: Utilization of hydrolase promiscuity
Author(s) -
Yavor Mitrev,
Aleksandar Y. Mehandzhiyski,
Daniela Batovska,
Andreas Liese,
Boris Galunsky
Publication year - 2016
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc160422069m
Subject(s) - acetophenone , chalcone , chemistry , benzaldehyde , catalysis , imidazole , enzyme , stereochemistry , organic chemistry , combinatorial chemistry
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 (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 (3.5.1.81) catalyzed also the reaction between acetophenone and p-nitrobenzaldehyde. Such “green” approach to synthesis of chalcones is of great interest, because of their important applications as formula ingredients in pharmaceutical, food and cosmetic industry
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