Enantioselective esterification of (R,S)-2-methylalkanoic acid with Carica papaya lipase in organic solvents
作者： Chun-Sheng Chang , Ssu-Ching Ho
DOI: 10.1007/S10529-011-0692-7
关键词: Enantioselective synthesis 、 Carica 、 Chemistry 、 Reaction temperature 、 Organic chemistry 、 Water activity 、 Lipase 、 Catalysis
摘要: Isooctane was the best reaction medium for enantioselective esterification of (R,S)-2-methylalkanoic acid with n-butanol using Carica papaya lipase as catalyst. Increasing linear alkyl-chain length racemic 2-methylalkanoic acids from ethyl to hexyl increased enantioselectivity (E) 2.1 98.2 at 35°C. Decreasing temperature 40 20°C 14 33 2-methylhexanoic n-butanol. We obtained a maximum enantioselectivity, E = 24.3, in isooctane water activity 0.33, and
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Yanis Caro, Michel Pina, Fabrice Turon, Stephane Guilbert, Estelle Mougeot, David V. Fetsch, Philip Attwool, Jean Graille, Plant lipases: Biocatalyst aqueous environment in relation to optimal catalytic activity in lipase‐catalyzed synthesis reactions Biotechnology and Bioengineering. ,vol. 77, pp. 693- 703 ,(2002) , 10.1002/BIT.10155
Karl-Heinz Engel, Lipase-catalyzed enantioselective esterification of 2-methylalkanoic acids Tetrahedron-asymmetry. ,vol. 2, pp. 165- 168 ,(1991) , 10.1016/S0957-4166(00)82349-6
Per Berglund, Mats Holmquist, Erik Hedenström, Karl Hult, Hans-Erik Högberg, 2-Methylalkanoic acids resolved by esterification catalysed by lipase from Candida rugosa: Alcohol chain length and enantioselectivity Tetrahedron-asymmetry. ,vol. 4, pp. 1869- 1878 ,(1993) , 10.1016/S0957-4166(00)80427-9
Paul A. Fitzpatrick, Alexander M. Klibanov, How can the solvent affect enzyme enantioselectivity Journal of the American Chemical Society. ,vol. 113, pp. 3166- 3171 ,(1991) , 10.1021/JA00008A054
Chun-Chi Chen, Shau-Wei Tsai, Carica papaya lipase: a novel biocatalyst for the enantioselective hydrolysis of (R,S)-naproxen 2,2,2-trifluoroethyl ester Enzyme and Microbial Technology. ,vol. 36, pp. 127- 132 ,(2005) , 10.1016/J.ENZMICTEC.2004.07.004
Pierre Villeneuve, Plant lipases and their applications in oils and fats modification European Journal of Lipid Science and Technology. ,vol. 105, pp. 308- 317 ,(2003) , 10.1002/EJLT.200390061
Per Berglund, Mats Holmquist, Karl Hult, Hans-Erik H�gberg, Alcohols as enantioselective inhibitors in a lipase catalysed esterification of a chiral acyl donor Biotechnology Letters. ,vol. 17, pp. 55- 60 ,(1995) , 10.1007/BF00134196
Hans-Erik Högberg, Helen Edlund, Per Berglund, Erik Hedenström, Water activity influences enantioselectivity in a lipase-catalysed resolution by esterification in an organic solvent Tetrahedron: Asymmetry. ,vol. 4, pp. 2123- 2126 ,(1993) , 10.1016/S0957-4166(00)80055-5
N.W.J.T. Heinsman, M.C.R. Franssen, A. van der Padt, R.M. Boom, K. van't Riet, Ae. de Groot, Lipase-mediated resolution of branched chain fatty acids Biocatalysis and Biotransformation. ,vol. 20, pp. 297- 309 ,(2002) , 10.1080/10242420290025511
Maria L. Maciel, Thomsen J. Hansen, Scott B. Aldinger, John N. Labows, Flavor chemistry of cashew apple juice Journal of Agricultural and Food Chemistry. ,vol. 34, pp. 923- 927 ,(1986) , 10.1021/JF00071A039