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Conflict of Interest: In relation to this article, we declare that there is no conflict of interest.

Publication history: Received August 21, 2008
Accepted November 27, 2008

This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/bync/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Molecular modeling and experimental verification of lipase-catalyzed enantioselective esterification of racemic naproxen in supercritical carbon dioxide

Cheong Hoon Kwon Jeong Yeong Jeong Jeong Won Kang^†

Department of Chemical and Biological Engineering, Korea University, 5 ga Anam-dong, Sungbuk-gu, Seoul 136-701, Korea

jwkang@korea.ac.kr

Korean Journal of Chemical Engineering, January 2009, 26(1), 214-219(6), 10.1007/s11814-009-0035-8

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Abstract

Experimental and simulation analyses were performed on the lipase-catalyzed esterification reaction of racemic naproxen by CALB (candida antarctica lipase B) enzyme in supercritical carbon dioxide. The reaction pathways were investigated by quantum mechanical analysis, and the enantioselectivity of the products was predicted by molecular dynamics simulation analysis. Calculated results from molecular modeling in supercritical carbon dioxide were qualitatively compared with experimental data by using racemic naproxen as a substrate. All molecular modeling results and experimental data were acquired and compared with those in ambient and supercritical condition. Moreover, to verify the stability of enzymatic reaction in each solvent condition, reaction pathways were investigated in several solvent conditions (vacuum, water, hexane and supercritical carbon dioxide), and the stability of enzymatic reaction in supercritical carbon dioxide was compared with other solvent conditions.

Keywords

Racemic Naproxen Candida antarctica Lipase B Enantioselectivity Supercritical Carbon Dioxide Quantum Mechanical Analysis Molecular Dynamics Simulation

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