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Asymmetric hydrolysis of dimethyl-3-phenylglutarate in sequential batch reactor operation catalyzed by immobilized Geobacillus thermocatenulatus lipase

Paper ID Volume ID Publish Year Pages File Format Full-Text
53762 46983 2015 6 PDF Available
Title
Asymmetric hydrolysis of dimethyl-3-phenylglutarate in sequential batch reactor operation catalyzed by immobilized Geobacillus thermocatenulatus lipase
Abstract

•BTL2 lipase was immobilized on silica and Sepharose with different chemical surfaces;.•Activity, stability and selectivity of BTL2 lipase depend of the support used.•Heterofunctional Sepharose allowed to obtaining the most active and selective biocatalyst.•(S)-monomethyl ester can be synthesized in batch with high enantiomeric excesses.

The main goal of this work was to study the stereoselective behavior of immobilized Geobacillus thermocatenulatus lipase (BTL2) in a sequential batch reactor using the partial and asymmetric hydrolysis of dimethyl-3 phenylglutarate (DMFG) as a model reaction. To reach this goal, BTL2 lipase was immobilized on Sepharose and silica supports with cyanogen bromide and octyl groups (monofunctional supports) and undecanol-glyoxyl and octyl-epoxides groups (heterofunctional supports), to determine the effect of the enzyme orientation during the immobilization process on their catalytic properties. In the hydrolysis of DMFG, the biocatalyst obtained with undecanol-glyoxyl Sepharose proved to be the most stereolective with an enantiomeric excess (e.e.) value of 90% in aqueous media. This behavior can be attributed to differences in the orientation of the lipase on the support. In sequential batch reactor operation, the e.e. remained constant in the first two batches; however, from the third batch on the e.e. decreased slightly maybe due to a change in the conformation of the enzyme at the reaction conditions. Finally, the high purity S-methyl-3-phenyl glutarate produced in sequential batch reactor operation shows that the biocatalyst can be reused at least twice without losing stereoselectivity, favoring a reduction in the process cost.

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Keywords
Asymmetric hydrolysis; Dimethyl-3-phenylglutarate; Stereoselectivity; Silica supports; Sequential batch reactor
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Asymmetric hydrolysis of dimethyl-3-phenylglutarate in sequential batch reactor operation catalyzed by immobilized Geobacillus thermocatenulatus lipase
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Today - Volume 255, 15 October 2015, Pages 21–26
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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