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

Authors
Type
Published Article
Journal
Chirality
0899-0042
Publisher
Wiley Blackwell (John Wiley & Sons)
Publication Date
Volume
19
Issue
4
Pages
245–249
Identifiers
PMID: 17094073
Source
Medline

Abstract

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.

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