The kinetic resolution of 2-(4-chlorophenoxy) propionic acid using Candida rugosa lipase
作者： Zanariah Ujang , Widya Huzana Husain , Mak Choo Seng , Ahmad Hazri Abdul Rashid
DOI: 10.1016/S0032-9592(03)00039-6
关键词:
摘要: Abstract The effect of solvent, operating temperature, enzyme concentration and immobilization on activity enantioselectivity a Candida rugosa lipase for the kinetic resolution ±2-(4-chlorophenoxy) propionic acid with 1-butanol in organic solvents was studied. crude powder gave more than 50% conversion an enantiomeric excess (ee) 100% remaining S-acid at 40 °C carbon tetrachloride as solvent. Higher enantioselectivities were obtained when reactions performed temperatures between 30 lower water activities, aw. Immobilization onto various types support results loss selectivity. best preparation immobilized silica gel. This 33% overall ee 46% S-acid. Continuous process via packed bed reactor resulted around 50 S enantiomer.
elsevier.com
sci-hub.se 参考文章(15)
Annikka Mustranta, Use of lipases in the resolution of racemic ibuprofen. Applied Microbiology and Biotechnology. ,vol. 38, pp. 61- 66 ,(1992) , 10.1007/BF00169420
Pierre Pepin, Robert Lortie, Influence of water activity on the enantioselective esterification of (R,S)‐ibuprofen by Candida antarctica lipase B in solventless media Biotechnology and Bioengineering. ,vol. 63, pp. 502- 505 ,(1999) , 10.1002/(SICI)1097-0290(19990520)63:4<502::AID-BIT14>3.0.CO;2-O
Eva M. Sánchez, J. Felipe Bello, Manuel G. Roig, Francisco J. Burguillo, JoséM. Moreno, JoséV. Sinisterra, Kinetic and enantioselective behavior of the lipase from Candida cylindracea : A comparative study between the soluble enzyme and the enzyme immobilized on agarose and silica gels Enzyme and Microbial Technology. ,vol. 18, pp. 468- 476 ,(1996) , 10.1016/0141-0229(95)00133-6
Shi-Hao Pan, Takuo Kawamoto, Toshiaki Fukui, Kenji Sonomoto, Atsuo Tanaka, Stereoselective esterification of halogen-containing carboxylic acids by lipase in organic solvent: effects of alcohol chain length Applied Microbiology and Biotechnology. ,vol. 34, pp. 47- 51 ,(1990) , 10.1007/BF00170922
Amélie Ducret, Michael Trani, Robert Lortie, Lipase-catalyzed enantioselective esterification of ibuprofen in organic solvents under controlled water activity Enzyme and Microbial Technology. ,vol. 22, pp. 212- 216 ,(1998) , 10.1016/S0141-0229(97)00180-4
Michael J. Barton, John P. Hamman, Kenneth C. Fichter, Gary J. Calton, Enzymatic resolution of (R,S)-2-(4-hydroxyphenoxy) propionic acid Enzyme and Microbial Technology. ,vol. 12, pp. 577- 583 ,(1990) , 10.1016/0141-0229(90)90130-I
Krista Frings, Martin Koch, Winfried Hartmeier, Kinetic resolution of 1-phenyl ethanol with high enantioselectivity with native and immobilized lipase in organic solvents Enzyme and Microbial Technology. ,vol. 25, pp. 303- 309 ,(1999) , 10.1016/S0141-0229(99)00044-7
Toshiaki Fukui, Takuo Kawamoto, Kenji Sonomoto, Atsuo Tanaka, Construction of a non-support bioreactor: optical resolution of 2-(4-chlorophenoxy)propanoic acid in an organic solvent system Applied Microbiology and Biotechnology. ,vol. 35, pp. 563- 567 ,(1991) , 10.1007/BF00169616
Uwe Bornscheuer, Andrea Herar, Lars Kreye, Volker Wendel, Andreas Capewell, Hartmut H. Meyer, Thomas Scheper, Fragiskos N. Kolisis, Factors affecting the lipase catalyzed transesterification reactions of 3-hydroxy esters in organic solvents. Tetrahedron-asymmetry. ,vol. 4, pp. 1007- 1016 ,(1993) , 10.1016/S0957-4166(00)80145-7
S. Ueji, R. Fujino, N. Ōkubo, T. Miyazawa, S. Kurita, M. Kitadani, A. Muromatsu, Solvent-induced inversion of enantiosflectivity in lipase-catalyzed esterification of 2-phenoxypropionic acids Biotechnology Letters. ,vol. 14, pp. 163- 168 ,(1992) , 10.1007/BF01023352