R-stereopreference analysis of lipase Novozym 435 in kinetic resolution of flurbiprofen.

Zhang, Hua Yun; Wang, Xin; Ching, Chi Bun

Zhang, Hua Yun; Wang, Xin; Ching, Chi Bun.

Afiliación

Zhang HY; Department of Chemical and Biomolecular Engineering, National University of Singapore, Singapore 117576.

Chirality ; 19(4): 245-9, 2007 May 05.

Article en En | MEDLINE | ID: mdl-17094073

RESUMEN

Immobilized lipase from Candida antarctica (Novozym 435) was employed in the kinetic resolution of racemic flurbiprofen by enantioselective esterification with methanol. It was found that the lipase has the R-stereopreference and the reaction matches Bi Bi Ping Pong mechanism with dead-end inhibition of methanol. Furthermore, the R-stereopreference was analyzed in details from the aspects of enzymatic kinetic mechanism and reaction activation energy of both enantiomers. The R-enantiomer shows lower activation energy and higher maximum reaction rate than the S-enantiomer, which implies the R-stereopreference of the lipase and makes the kinetic resolution of flurbiprofen via enzymatic reaction feasible.

Asunto(s)

Flurbiprofeno/química; Lipasa/química; Candida/enzimología; Inhibidores de Anhidrasa Carbónica/química; Relación Dosis-Respuesta a Droga; Enzimas Inmovilizadas/química; Esterificación; Proteínas Fúngicas; Cinética; Metanol/química; Modelos Químicos; Modelos Estadísticos; Modelos Teóricos; Estereoisomerismo; Temperatura

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Flurbiprofeno / Lipasa Idioma: En Revista: Chirality Asunto de la revista: BIOLOGIA MOLECULAR / QUIMICA Año: 2007 Tipo del documento: Article Pais de publicación: Estados Unidos

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