title: R-stereopreference analysis of lipase Novozym 435 in kinetic resolution of flurbiprofen.
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.
authors.affiliation: Department of Chemical and Biomolecular Engineering, National University of Singapore, Singapore 117576.
authors.forename: Hua Yun
authors.initials: HY
authors.lastname: Zhang
authors.forename: Xin
authors.initials: X
authors.lastname: Wang
authors.forename: Chi Bun
authors.initials: CB
authors.lastname: Ching
mesh_terms: D002175:Candida / Q000201:enzymology; D002257:Carbonic Anhydrase Inhibitors / Q000737:chemistry; D004305:Dose-Response Relationship, Drug; D004800:Enzymes, Immobilized / Q000737:chemistry; D004951:Esterification; D005480:Flurbiprofen / Q000737:chemistry*; D005656:Fungal Proteins; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D008956:Models, Chemical; D015233:Models, Statistical; D008962:Models, Theoretical; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D002257:Carbonic Anhydrase Inhibitors; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D005480:Flurbiprofen; C093667:Novozyme 435; D008049:Lipase; D000432:Methanol