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Enzyme-assisted Cyclization of Chalcones to Flavanones

[ Vol. 17 , Issue. 12 ]

Author(s):

Mariana Macías Alonso*, Carlos José Boluda , Gabriela Díaz Barajas, Nallely Caldera Sánchez, Iván Córdova-Guerrero and Joaquín González Marrero*   Pages 926 - 931 ( 6 )

Abstract:


Enzyme catalyzed synthesis is an eco-friendly technique in organic synthesis, having several benefits over conventional methods. In the present work, we describe a simple process of laccase and chloroperoxidase assisted cyclization of chalcones, leading to the formation of flavanones. The reaction proceeds in a mixture of phosphate buffer and ethanol, under oxygen atmosphere at room temperature, yielding the corresponding flavanone in good to moderate yield. The relative configuration of the products at C2 is tentatively assigned as S*-flavanone based on the coupling constants with the methylenic protons H3α,β. In comparison to the chemical methods, we describe a process which can be achieved efficiently under mild conditions using oxygen as oxidant.

Keywords:

Enzyme, Laccase, Chloroperoxidase, chalcone, flavonoids, flavanone, mediator.

Affiliation:

Instituto Politecnico Nacional, UPIIG, Av. Mineral de Valenciana, No. 200, Col. Fracc, Industrial Puerto Interior, C.P. 36275 Silao de la Victoria, Guanajuato, Instituto Tecnologico de Santo Domingo (INTEC), Area de Ciencias Basicas y Ambientales. Avenida de Los Proceres 49, Los Jardines del Norte 10602, Santo Domingo, Instituto Politecnico Nacional, UPIIG, Av. Mineral de Valenciana, No. 200, Col. Fracc, Industrial Puerto Interior, C.P. 36275 Silao de la Victoria, Guanajuato, Instituto Politecnico Nacional, UPIIG, Av. Mineral de Valenciana, No. 200, Col. Fracc, Industrial Puerto Interior, C.P. 36275 Silao de la Victoria, Guanajuato, Facultad de Ciencias Quimicas e Ing, Universidad Autonoma de Baja California, Clz. Universidad 14418, Parque Industrial Internacional, Tijuana, B.C. CP 22390, Instituto Politecnico Nacional, UPIIG, Av. Mineral de Valenciana, No. 200, Col. Fracc, Industrial Puerto Interior, C.P. 36275 Silao de la Victoria, Guanajuato

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