Enzymatic hydrolysis of racemic ibuprofen esters using Rhizomucor miehei lipase immobilized on different supports

Process Biochemistry

Volumn 48, Issue 4, 2013, Pages 669-676

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

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

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

^c AVICENNA RESEARCH INSTITUTE   (Iran)

Author keywords

Enantioselectivity; Ibuprofen; Immobilization; Kinetic resolution; Rhizomucor miehei lipase

Indexed keywords

CATALYTIC BEHAVIOR; COVALENT ATTACHMENT; HYDROLYSIS REACTION; IBUPROFEN; INCREASING TEMPERATURES; KINETIC RESOLUTION; RACEMIC IBUPROFEN ESTERS; RHIZOMUCOR MIEHEI LIPASE;

ENANTIOSELECTIVITY; ENZYMATIC HYDROLYSIS; ESTERIFICATION; IONIC LIQUIDS; ISOMERS; RADIOACTIVE WASTE VITRIFICATION;

ESTERS;

RHIZOMUCOR; RHIZOMUCOR MIEHEI;

EID: 84878020174     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2013.02.020     Document Type: Article

References (56)

1. M.V. Madhav, and C.B. Ching Study on the enzymatic hydrolysis of racemic methyl ibuprofen ester J Chem Technol Biotechnol 76 2001 941 948
2. S. Adams, P. Bresloff, and C. Mason Pharmacological differences between the optical isomers of ibuprofen: evidence for metabolic inversion of the (-)-isomer J Pharm Pharmacol 28 1976 256 257
3. C. Reichel, H. Bang, K. Brune, G. Geisslinger, and S. Menzel 2-Arylpropionyl-CoA epimerase: partial peptide sequences and tissue localization Biochem Pharmacol 50 1995 1803 1806
4. Y. Liu, F. Wang, and T. Tan Cyclic resolution of racemic ibuprofen via coupled efficient lipase and acid-base catalysis Chirality 21 2009 349 353
5. K. Williams, R. Day, R. Knihinicki, and A. Duffield The stereoselective uptake of ibuprofen enantiomers into adipose tissue Biochem Pharmacol 35 1986 3403
6. D.R. Palleros Experimental organic chemistry 2000 John Wiley & Sons New York
7. J.Y. Xin, S.B. Li, Y. Xu, and L.L. Wang Enzymatic resolution of (S)-(+)-naproxen in a trapped aqueous-organic solvent biphase continuous reactor Biotechnol Bioeng 68 2000 78 83
8. T. Nishigaki, Y. Yasufuku, S. Murakami, Y. Ebara, and S. Ueji A great improvement of the enantioselectivity of lipase-catalyzed hydrolysis and esterification using co-solvents as an additive Bull Chem Soc Jpn 81 2008 617 622
9. R.C. Rodrigues, and R. Fernandez-Lafuente Lipase from Rhizomucor miehei as a biocatalyst in fats and oils modification J Mol Catal B: Enzym 66 2010 15 32
10. R.C. Rodrigues, C.A. Godoy, G. Volpato, M.A.Z. Ayub, R. Fernandez-Lafuente, and J.M. Guisan Immobilization-stabilization of the lipase from Thermomyces lanuginosus: critical role of chemical amination Process Biochem 44 2009 963 968
11. R.C. Rodrigues, and R. Fernandez-Lafuente Lipase from Rhizomucor miehei as an industrial biocatalyst in chemical process J Mol Catal B: Enzym 64 2010 1 22
12. K. Nagaoka, and Y. Yamada Purification of Mucor lipases and their properties Agric Biol Chem 37 1973 2791 2796
13. C. Garcia-Galan, A. Berenguer-Murcia, R. Fernandez-Lafuente, and R.C. Rodrigues Potential of different enzyme immobilization strategies to improve enzyme performance Adv Synth Catal 353 2011 2885 2904
14. R.C. Rodrigues, C. Ortiz, Á. Berenguer-Murcia, R. Torres, and R. Fernández-Lafuente Modifying enzyme activity and selectivity by immobilization Chem Soc Rev 2013 doi:10.1039/C 2C S35231A
15. P. Villeneuve, J.M. Muderhwa, J. Graille, and M.J. Haas Customizing lipases for biocatalysis: a survey of chemical, physical and molecular biological approaches J Mol Catal B: Enzym 9 2000 113 148
16. E. Katchalski-Katzir Immobilized enzymes-learning from past successes and failures Trends Biotechnol 11 1993 471 478
17. C. Mateo, J.M. Palomo, G. Fernandez-Lorente, J.M. Guisan, and R. Fernandez-Lafuente Improvement of enzyme activity, stability and selectivity via immobilization techniques Enzyme Microb Technol 40 2007 1451 1463
18. J. Porath, and R. Axén Immobilization of enzymes to agar, agarose, and sephadex support Methods Enzymol 44 1976 19 45
19. N. D'Antona, P. Lombardi, G. Nicolosi, and G. Salvo Large scale preparation of enantiopure S-ketoprofen by biocatalysed kinetic resolution Process Biochem 38 2002 373 377
20. R. De la Casa, J. Guisán, J. Sánchez-Montero, and J. Sinisterra Modification of the activities of two different lipases from Candida rugosa with dextrans Enzyme Microb Technol 30 2002 30 40
21. Y. Hongwei, W. Jinchuan, and C. Chi Bun Kinetic resolution of ibuprofen catalyzed by Candida rugosa lipase in ionic liquids Chirality 17 2005 16 21
22. A. Sánchez, F. Valero, J. Lafuente, and C. Solà Highly enantioselective esterification of racemic ibuprofen in a packed bed reactor using immobilised Rhizomucor miehei lipase Enzyme Microb Technol 27 2000 157 166
23. P.O. Carvalho, F.J. Contesini, R. Bizaco, S.A. Calafatti, and G.A. Macedo Optimization of enantioselective resolution of racemic ibuprofen by native lipase from Aspergillus niger J Ind Microbiol Biotechnol 33 2006 713 718
24. C.S. Chang, and C.S. Hsu Lipase-catalyzed enantioselective esterification of (S)-naproxen hydroxyalkyl ester in organic media Biotechnol Lett 25 2003 413 416
25. E. Henke, S. Schuster, H. Yang, and U.T. Bornscheuer Lipase-catalyzed resolution of ibuprofen Monatsh Chem Chem Mon 131 2000 633 638
26. A. Sánchez, P. Ferrer, A. Serrano, F. Valero, C. Solà, M. Pernas, M. Rúa, R. Fernández-Lafuente, J. Guisán, and R. De la Casa A controlled fed-batch cultivation for the production of new crude lipases from Candida rugosa with improved properties in fine chemistry J Biotechnol 69 1999 169 182
27. W.S. Long, P.C. Kow, A.H. Kamaruddin, and S. Bhatia Comparison of kinetic resolution between two racemic ibuprofen esters in an enzymic membrane reactor Process Biochem 40 2005 2417 2425
28. H. Fazlena, A. Kamaruddin, and M. Zulkali Dynamic kinetic resolution: alternative approach in optimizing S-ibuprofen production Bioprocess Biosyst Eng 28 2006 227 233
29. P. Overbeeke, J. Jongejan, and J. Heijnen Solvent effect on lipase enantioselectivity. Evidence for the presence of two thermodynamic states Biotechnol Bioeng 70 2000 278 290
30. C. Elend, C. Schmeisser, H. Hoebenreich, H. Steele, and W. Streit Isolation and characterization of a metagenome-derived and cold-active lipase with high stereospecificity for (R)-ibuprofen esters J Biotechnol 130 2007 370 377
31. A. Bastida, P. Sabuquillo, P. Armisen, R. Fernández-Lafuente, J. Huguet, and J.M. Guisan A single step purification, immobilization, and hyperactivation of lipases via interfacial adsorption on strongly hydrophobic supports Biotechnol Bioeng 58 2000 486 493
32. I. Nieto, S. Rocchietti, D. Ubiali, G. Speranza, C.F. Morelli, I.E. Fuentes, A.R. Alcantara, and M. Terreni Immobilization of different protein fractions from Rhizomucor miehei lipase crude extract: enzymatic resolution of (R,S)-2-tetralol Enzyme Microb Technol 37 2005 514 520
33. M.M. Bradford A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal Biochem 72 1976 248 254
34. N. Nakajima, and Y. Ikada Mechanism of amide formation by carbodiimide for bioconjugation in aqueous media Bioconjugate Chem 6 1995 123 130
35. J. Schnapp, and Y. Shalitin Immobilization of enzymes by covalent binding to amine supports via cyanogen bromide activation Biochem Biophys Res Commun 70 1976 8 14
36. G. Fernandez-Lorente, C.A. Godoy, A.A. Mendes, F. Lopez-Gallego, V. Grazu, B. de las Rivas, J.M. Palomo, J. Hermoso, R. Fernandez-Lafuente, and J.M. Guisan Solid-phase chemical amination of a lipase from Bacillus thermocatenulatus to improve its stabilization via covalent immobilization on highly activated glyoxyl-agarose Biomacromolecules 9 2008 2553 2561
37. J. Pedroche, M. del Mar Yust, C. Mateo, R. Fernández-Lafuente, J. Girón-Calle, M. Alaiz, J. Vioque, J.M. Guisán, and F. Millán Effect of the support and experimental conditions in the intensity of the multipoint covalent attachment of proteins on glyoxyl-agarose supports: correlation between enzyme-support linkages and thermal stability Enzyme Microb Technol 40 2007 1160 1166
38. C. Mateo, O. Abian, M. Bernedo, E. Cuenca, M. Fuentes, G. Fernandez-Lorente, J.M. Palomo, V. Grazu, B.C.C. Pessela, and C. Giacomini Some special features of glyoxyl supports to immobilize proteins Enzyme Microb Technol 37 2005 456 462
39. J.M. Bolivar, F. López-Gallego, C. Godoy, D.S. Rodrigues, R.C. Rodrigues, P. Batalla, J. Rocha-Martín, C. Mateo, R.L.C. Giordano, and J.M. Guisán The presence of thiolated compounds allows the immobilization of enzymes on glyoxyl agarose at mild pH values: new strategies of stabilization by multipoint covalent attachment Enzyme Microb Technol 45 2009 477 483
40. A. Ghanem, M.N. Aboul-Enein, A. El-Azzouny, and M.F. El-Behairy Lipase-mediated enantioselective kinetic resolution of racemic acidic drugs in non-standard organic solvents: direct chiral liquid chromatography monitoring and accurate determination of the enantiomeric excesses J Chromatogr A 1217 2010 1063 1074
41. P.O. Carvalho, F.J. Contesini, and M. Ikegaki Enzymatic resolution of (R,S)-ibuprofen and (R,S)-ketoprofen by microbial lipases from native and commercial sources Braz J Microbiol 37 2006 329 337
42. C.S. Chen, S.H. Wu, G. Girdaukas, and C.J. Sih Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systems J Am Chem Soc 109 1987 2812 2817
43. A.G. Cunha, G. Fernández-Lorente, J.V. Bevilaqua, J. Destain, L.M.C. Paiva, D.M.G. Freire, R. Fernández-Lafuente, and J.M. Guisán Immobilization of Yarrowia lipolytica lipase-a comparison of stability of physical adsorption and covalent attachment techniques Appl Biochem Biotechnol 146 2008 49 56
44. M. Erbeldinger, A.J. Mesiano, and A.J. Russell Enzymatic catalysis of formation of Z-aspartame in ionic liquid-an alternative to enzymatic catalysis in organic solvents Biotechnol Progr 16 2008 1129 1131
45. A.P. Abbott, D. Boothby, G. Capper, D.L. Davies, and R.K. Rasheed Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids J Am Chem Soc 126 2004 9142 9147
46. K.W. Kim, B. Song, M.Y. Choi, and M.J. Kim Biocatalysis in ionic liquids: markedly enhanced enantioselectivity of lipase Org Lett 3 2001 1507 1509
47. R.M. Lau, F. Van Rantwijk, K. Seddon, and R. Sheldon Lipase-catalyzed reactions in ionic liquids Org Lett 2 2000 4189 4191
48. F. van Rantwijk, and R.A. Sheldon Biocatalysis in ionic liquids Chem Rev 38 2007 2757 2785
49. J.M. Moreno, and J.V. Sinisterra A systematic analysis of the variables that control a highly stereoselective resolution of racemic non-steroidal antiinflammatory drugs using immobilized lipase from Candida cylindracea J Mol Catal A: Chem 98 1995 171 184
50. A.M. Klibanov Enzymatic catalysis in anhydrous organic solvents Trends Biochem Sci 14 1989 141 144
51. G. Fernández-Lorente, L. Betancor, A.V. Carrascosa, J.M. Palomo, and J.M. Guisan Modulation of the selectivity of immobilized lipases by chemical and physical modifications: release of omega-3 fatty acids from fish oil J Am Oil Chem Soc 89 2012 97 102
52. E. Battistel, D. Bianchi, P. Cesti, and C. Pina Enzymatic resolution of (S)-(+)-naproxen in a continuous reactor Biotechnol Bioeng 38 2004 659 664
53. C.S. Chen, and C.J. Sih General aspects and optimization of enantioselective biocatalysis in organic solvents: the use of lipases [new synthetic methods (76)] Angew Chem Int Ed English 28 2003 695 707
54. T.V. Hansen, V. Waagen, V. Partali, H.W. Anthonsen, and T. Anthonsen Co-solvent enhancement of enantioselectivity in lipase-catalysed hydrolysis of racemic esters. A process for production of homochiral C-3 building blocks using lipase B from Candida antarctica Tetrahedron: Asymmetry 6 1995 499 504
55. R.S. Phillips Temperature effects on stereochemistry of enzymatic reactions Enzyme Microb Technol 14 1992 417 419
56. F. Monot, E. Paccard, F. Borzeix, M. Bardin, and J.P. Vandecasteele Effect of lipase conditioning on its activity in organic media Appl Microbiol Biotechnol 39 1993 483 486