Sporopollenin as an efficient green support for covalent immobilization of a lipase

de Souza, Stefânia P.; Bassut, Jonathan; Marquez, Heiddy V.; Junior, Ivaldo I.; Miranda, Leandro S. M.; Huang, Youkui; Mackenzie, Grahame; Boa, Andrew N.; de Souza, Rodrigo O. M. A.

Abstract

Sporopollenin exine capsules (SECs), derived from the spores of Lycopodium clavatum, have been functionalised with 1,n-diamines and the resulting aminoalkyl microcapsules used to immobilize Candida antarctica lipase B (Cal B) via a glutaradehyde-based diimine covalent linker. The supported enzyme efficiently catalyzes the esterification of oleic acid with ethanol. Initial rates using the SEC-CalBs were comparable to the commercial enzyme Novozym 435, but displayed up to 20-fold higher specific activity. The supported enzymes could also be recycled and after four cycles displayed only a modest decrease in conversions. In a kinetic resolution the SEC-CalBs efficiently acetylated rac-1-phenylethanol, with conversions up to 37% after 5 hours and product enantiomeric excesses of >99%. Related to this, the dynamic resolution of rac-1-phenylethylamine, in the presence of Pd-BaSO₄ and ammonium formate, led to the acetylated amine with a 94% conversion and >99% ee.

Citation

de Souza, S. P., Bassut, J., Marquez, H. V., Junior, I. I., Miranda, L. S. M., Huang, Y., Mackenzie, G., Boa, A. N., & de Souza, R. O. M. A. (2015). Sporopollenin as an efficient green support for covalent immobilization of a lipase. Catalysis science & technology, 5(6), 3130-3136. https://doi.org/10.1039/c4cy01682c

• Journal Article Type: Article
• Acceptance Date: Jan 17, 2015
• Online Publication Date: Jan 26, 2015
• Publication Date: 2015
• Deposit Date: Mar 15, 2016
• Publicly Available Date: Nov 23, 2017
• Journal: Catalysis Science and Technology
• Print ISSN: 2044-4753
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 5
• Issue: 6
• Pages: 3130-3136
• DOI: https://doi.org/10.1039/c4cy01682c
• Keywords: Catalysis
• Public URL: https://hull-repository.worktribe.com/output/474141
• Publisher URL: http://pubs.rsc.org/en/content/articlelanding/2015/cy/c4cy01682c#!divAbstract
• Additional Information: Author's accepted manuscript of article published in: Catalysis science & technology, 2015, v.5, issue 6
• Contract Date: Nov 23, 2017