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A kinetic and thermodynamic study of the lipase-catalyzed remote resolution of a chiral tertiary alcohol

Paper ID Volume ID Publish Year Pages File Format Full-Text
3568 175 2012 6 PDF Available
Title
A kinetic and thermodynamic study of the lipase-catalyzed remote resolution of a chiral tertiary alcohol
Abstract

The kinetics and thermodynamics of Candida antarctica lipase B-catalyzed remote asymmetric alcoholysis of the citalopram intermediate 3-[(acetyloxy)methyl]-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-benzonitrile (diol monoacetate) have been studied. A kinetic model based on the reversible ping-pong bi-bi mechanism with competitive enantiomer substrates was proposed. The product inhibition by each diol enantiomer and the substrate inhibition by isobutyl alcohol were also considered. The diffusion limitation was proven to be negligible. By reducing the degree of freedom in parameter estimation by model discrimination and Haldane equations, 14 free parameters were successfully identified. The model parameters were simulated by the Matlab program using time–concentration curves of different diol monoacetate concentrations; the simulated values fit the experimental values well, with an average relative error of 9.6%. The reaction activity and enantioselectivity of C. antarctica lipase B toward the tertiary alcohol were investigated by kinetic and thermodynamic analysis using simulated kinetic parameters.

► Novozym 435 catalyzed remote asymmetric alcoholysis of a tertiary alcohol. ► The chiral discrimination was achieved four bonds away from the center. ► A kinetic model based on the reversible ping-pong bi-bi mechanism was proposed. ► The product inhibition and substrate inhibition were also considered. ► The kinetic and thermodynamic analysis were investigated using kinetic parameters.

Keywords
Dynamic modeling; Kinetic parameters; Lipase; Immobilized enzymes; Tertiary alcohol; Asymmetric alcoholysis
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A kinetic and thermodynamic study of the lipase-catalyzed remote resolution of a chiral tertiary alcohol
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Publisher
Database: Elsevier - ScienceDirect
Journal: Biochemical Engineering Journal - Volume 65, 15 June 2012, Pages 57–62
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us