Enantioselective resolution of racemic ibuprofen esters using different lipases immobilized on octyl sepharose

Journal of Molecular Catalysis B: Enzymatic

Volumn 104, Issue , 2014, Pages 87-94

  Yousefi, Maryam ^a   Mohammadi, Mehdi ^b   Habibi, Zohreh ^c  

^a AVICENNA RESEARCH INSTITUTE   (Iran)

^b NATIONAL INSTITUTE OF GENETIC ENGINEERING AND BIOTECHNOLOGY   (Iran)

^c SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

(R,S) ibuprofen; Candida rugosa lipase; Immobilization; Kinetic resolution; Rhizopus oryzae lipase

Indexed keywords

CANDIDA; ENZYME IMMOBILIZATION; ESTERIFICATION; ESTERS; HEXANE; HYDROLYSIS; LIPASES; ORGANIC SOLVENTS; PARAFFINS; POLYOLS; RADIOACTIVE WASTE VITRIFICATION;

(R,S)-IBUPROFEN; CANDIDA RUGOSA LIPASE; CRITICAL REACTION PARAMETERS; ENANTIOSELECTIVE HYDROLYSIS; KINETIC RESOLUTION; PHYSICAL ADSORPTION; RACEMIC IBUPROFEN ESTERS; RHIZOPUS ORYZAE LIPASE;

ENANTIOSELECTIVITY;

CANDIDA RUGOSA LIPASE; ESTER; HEXANE; IBUPROFEN; IONIC LIQUID; RHIZOPUS ORYZAE LIPASE; SEPHAROSE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ADSORPTION; ARTICLE; CANDIDA RUGOSA; CONTROLLED STUDY; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVATION; ENZYME CHEMISTRY; ENZYME IMMOBILIZATION; HYDROLYSIS; RHIZOPUS ORYZAE; TEMPERATURE;

EID: 84898652877     PISSN: 13811177     EISSN: 18733158     Source Type: Journal    
DOI: 10.1016/j.molcatb.2014.03.005     Document Type: Article

References (60)

1. A. Sánchez, F. Valero, J. Lafuente, and C. Solà Enzyme Microb. Technol. 27 2000 157 166
2. F. Hasan, A.A. Shah, and A. Hameed Enzyme Microb. Technol. 39 2006 235 251
3. J.Y. Xin, S.B. Li, Y. Xu, and L.L. Wang Biotechnol. Bioeng. 68 2000 78 83
4. T. Siódmiak, M. Ziegler-Borowska, and M.P. Marszałł J. Mol. Catal. B: Enzym. 94 2013 7 14
5. Y. Liu, F. Wang, and T. Tan J. Mol. Catal. B: Enzym. 56 2009 126 130
6. D. Chávez-Flores, and J.M. Salvador Biotechnol. J. 4 2009 1222 1224
7. C. Mateo, J.M. Palomo, G. Fernandez-Lorente, J.M. Guisan, and R. Fernandez-Lafuente Enzyme Microb. Technol. 40 2007 1451 1463
8. O. Barbosa, R. Torres, C. Ortiz, Á. Berenguer-Murcia, R.C. Rodrigues, and R. Fernandez-Lafuente Biomacromolecules 14 2013 2433 2462
9. R.C. Rodrigues, C. Ortiz, Á. Berenguer-Murcia, R. Torres, and R. Fernández-Lafuente Chem. Soc. Rev. 42 2013 6290 6307
10. M.L. Verma, C.J. Barrow, and M. Puri Appl. Microbiol. Biotechnol. 97 2013 23 39
11. E.T. Hwang, and M.B. Gu Eng. Life Sci. 13 2013 49 61
12. C. Garcia-Galan, Á. Berenguer-Murcia, R. Fernandez-Lafuente, and R.C. Rodrigues Adv. Synth. Catal. 353 2011 2885 2904
13. K. Hernandez, and R. Fernandez-Lafuente Enzyme Microb. Technol. 48 2011 107 122
14. R.A. Sheldon Adv. Synth. Catal. 349 2007 1289 1307
15. P.V. Iyer, and L. Ananthanarayan Process Biochem. 43 2008 1019 1032
16. R. Fernandez-Lafuente Enzyme Microb. Technol. 45 2009 405 418
17. R.C. Rodrigues, Á. Berenguer-Murcia, and R. Fernandez-Lafuente Adv. Synth. Catal. 353 2011 2216 2238
18. A.G. Cunha, G. Fernández-Lorente, M.L. Gutarra, J.V. Bevilaqua, R.V. Almeida, L.M. Paiva, R. Fernández-Lafuente, J.M. Guisán, and D.M. Freire Appl. Biochem. Biotechnol. 156 2009 133 145
19. A. Bastida, P. Sabuquillo, P. Armisen, R. Fernández-Lafuente, J. Huguet, and J.M. Guisan Biotechnol. Bioeng. 58 1998 486 493
20. L. Sarda, and P. Desnuelle Biochim. Biophys. Acta 30 1958 513 521
21. U. Bornscheuer, O.-W. Reif, R. Lausch, R. Freitag, T. Scheper, F.N. Kolisis, and U. Menge Biochim. Biophys. Acta: Gen. Subjects 1201 1994 55 60
22. L. Brady, A.M. Brzozowski, Z.S. Derewenda, E. Dodson, G. Dodson, S. Tolley, J.P. Turkenburg, L. Christiansen, B. Huge-Jensen, and L. Norskov Nature 1990 767 770
23. A. Brzozowski, U. Derewenda, Z. Derewenda, G. Dodson, D. Lawson, J. Turkenburg, F. Bjorkling, B. Huge-Jensen, S. Patkar, and L. Thim Nature 351 1991 491 494
24. Z.S. Derewenda, U. Derewenda, and G.G. Dodson J. Mol. Biol. 227 1992 818 839
25. Z.S. Derewenda Nat. Struct. Biol. 2 1995 347
26. P. Grochulski, Y. Li, J. Schrag, F. Bouthillier, P. Smith, D. Harrison, B. Rubin, and M. Cygler J. Biol. Chem. 268 1993 12843 12847
27. A. Louwrier, G.J. Drtina, and A.M. Klibanov Biotechnol. Bioeng. 50 1996 1 5
28. M. Noble, A. Cleasby, L. Johnson, M. Egmond, and L. Frenken FEBS Lett. 331 1993 123 128
29. F. Winkler, A. d'Arcy, and W. Hunziker Nature 343 1990 771 774
30. G. Fernández-Lorente, L. Betancor, A.V. Carrascosa, and J.M. Guisán J. Am. Oil Chem. Soc. 88 2011 1173 1178
31. R.D. Schmid, and R. Verger Angew. Chem. Int. Ed. 37 1998 1608 1633
32. R. Fernandez-Lafuente, P. Armisén, P. Sabuquillo, G. Fernández-Lorente, and J.M. Guisán Chem. Phys. Lipids 93 1998 185 197
33. P. Domínguez de María, J.M. Sánchez-Montero, J.V. Sinisterra, and A.R. Alcántara Biotechnol. Adv. 24 2006 180 196
34. K.P. Dhake, D.D. Thakare, and B.M. Bhanage Flav. Frag. J. 28 2013 71 83
35. H. Gustafsson, E.M. Johansson, A. Barrabino, M. Odén, and K. Holmberg Colloids Surf. B: Biointerfaces 100 2012 22 30
36. A.R. Alcántara, I.E. de Fuentes, and J.V. Sinisterra Chem. Phys. Lipids 93 1998 169 184
37. R.C. Rodrigues, and R. Fernandez-Lafuente J. Mol. Catal. B: Enzym. 64 2010 1 22
38. X.-W. Yu, C. Sha, Y.-L. Guo, R. Xiao, and Y. Xu Biotechnol. Biofuels 6 2013 29
39. Z. Habibi, M. Mohammadi, and M. Yousefi Process Biochem. 48 2013 669 676
40. M.B. Lakin, T.H. Shockley, E.G. Zey, US Patents 5,300,301 (1994).
41. A. Ghanem, M.N. Aboul-Enein, A. El-Azzouny, and M.F. El-Behairy J. Chromatogr. A 1217 2010 1063 1074
42. C.S. Chen, S.H. Wu, G. Girdaukas, and C.J. Sih J. Am. Chem. Soc. 109 1987 2812 2817
43. I. Nieto, S. Rocchietti, D. Ubiali, G. Speranza, C.F. Morelli, I.E. Fuentes, A.R. Alcantara, and M. Terreni Enzyme Microb. Technol. 37 2005 514 520
44. G. Fernandez-Lafuente, Z. Cabrera, C. Godoy, R. Fernandez-Lafuente, J.M. Palomo, and J.M. Guisan Process Biochem. 43 2008 1061 1067
45. J.L. Kaar, A.M. Jesionowski, J.A. Berberich, R. Moulton, and A.J. Russell J. Am. Chem. Soc. 125 2003 4125 4131
46. T. Itoh, E. Akasaki, K. Kudo, and S. Shirakami Chem. Lett. 30 2001 262 263
47. S. Park, and R.J. Kazlauskas Curr. Opin. Biotechnol. 14 2003 432 437
48. R. Madeira Lau, F. Van Rantwijk, K. Seddon, and R. Sheldon Org. Lett. 2 2000 4189 4191
49. S.J. Nara, J.R. Harjani, and M.M. Salunkhe Tetrahedron Lett. 43 2002 2979 2982
50. R.A. Sheldon, R.M. Lau, M.J. Sorgedrager, F. van Rantwijk, and K.R. Seddon Green Chem. 4 2002 147 151
51. S. Ransac, E. Rogalska, Y. Gargouri, A. Deveer, F. Paltauf, G. De Haas, and R. Verger J. Biol. Chem. 265 1990 20263 20270
52. E. Rogalska, S. Ransac, and R. Verger J. Biol. Chem. 268 1993 792 794
53. A. Ghanem Tetrahedron 63 2007 1721 1754
54. G. Caron, and R.J. Kazlauskas Tetrahedron: Asym. 4 1993 1995 2000
55. C. Laane, S. Boeren, K. Vos, and C. Veeger Biotechnol. Bioeng. 30 1987 81 87
56. W.S. Long, P.C. Kow, A.H. Kamaruddin, and S. Bhatia Process Biochem. 40 2005 2417 2425
57. J. Moreno, and J. Sinisterra J. Mol. Catal. A: Chem. 98 1995 171 184
58. F. Monot, E. Paccard, F. Borzeix, M. Bardin, and J.-P. Vandecasteele Appl. Microbiol. Biotechnol. 39 1993 483 486
59. W.S. Long, A. Kamaruddin, and S. Bhatia J. Membr. Sci. 247 2005 185 200
60. E. Drioli, and L. Giorno Biocatalytic Membrane Reactors: Applications in Biotechnology and the Pharmaceutical Industry 1999 CRC Press London