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

Korean Journal of Chemical Engineering, Vol.26, No.1, 214-219, January, 2009

DOI10.1007/s11814-009-0035-8 Export Citation

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

Cheong Hoon Kwon, Jeong Yeong Jeong, and Jeong Won Kang^†

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

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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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[1] Kazlauskas RJ, Curr. Opin. Chem. Biol., 4, 81 (2000)

[2] Dybala-Defratyka A, Rostkowski M, Paneth P, Arch. Biochem. Biophys., 474, 274 (2008)

[3] Cui YM, Wei DZ, Yu JT, Biotechnol. Lett., 19, 86 (1997)

[4] Wu JY, Liu SW, Enzyme Microb. Technol., 26(2-4), 124 (2000)

[5] Kwon CH, Shin DY, Lee JH, Kim SW, Kang JW, J. Microbiol. Biotechnol., 17, 1098 (2007)

[6] Chi YM, Nakamura K, Yano T, Agric. Biol. Chem., 52, 1541 (1988)

[7] Junco S, Casimiro T, Ribeiro N, Ponte MD, Marques HM, J. Incl. Phenom. Macrocycl. Chem., 44, 69 (2002)

[8] Lee EG, Won HS, Chung BH, Process Biochem., 37, 293 (2001)

[9] Yasmin T, Jiang T, Han B, Zhang J, Ma X, J. Mol. Catal. BEnzym., 41, 27 (2006)

[10] Lee EG, Chung BH, Biotechnol. Bioeng., 15, 415 (2000)

[11] Giordano C, Castaldi G, Tetrahedron, 45, 243 (1990)

[12] Cui YM, Wei DZ, Yu JT, Biotechnol. Lett., 19(9), 865 (1997)

[13] Habulin M, Knez Z, J. Chem. Technol. Biotechnol., 76(12), 1260 (2001)

[14] Sakaki K, Giorno L, Drioli E, J. Membr. Sci., 184(1), 27 (2001)

[15] Stewart JJP, J. Comput. Chem., 10, 209 (1989)

[16] Discovery Studio Modeling version 2.0, Accelrys Inc. (2008)

[17] Brooks BR, Bruccoleri S, Olafson BD, States DJ, Swaminathan S, Karplus M, J. Comp. Chem., 4, 187 (1983)

[18] Monecke P, Friedemann R, Naumann S, Csuk R, J. Mol. Model., 4, 395 (1998)

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