Evaluation of divinylsulfone activated agarose to immobilize lipases and to tune their catalytic properties

Process Biochemistry

Volumn 50, Issue 6, 2015, Pages 918-927

  Dos Santos, Jose C S ^a,b   Rueda, Nazzoly ^a,c   Torres, Rodrigo ^c   Barbosa, Oveimar ^d   Gonçalves, Luciana R B ^b   Fernandez Lafuente, Roberto ^a  

^a INSTITUTO DE CATÁLISIS Y PETROLEOQUÍMICA   (Spain)

^b FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^c UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^d UNIVERSIDAD DEL TOLIMA   (Colombia)

Author keywords

Divinylsulfone; Enzyme stabilization; Lipase from Thermomyces lanuginosus; Lipase immobilization; Lipase modulation; Multipoint covalent attachment

Indexed keywords

ENZYMES; LIPASES; PH; STABILIZATION;

DIVINYLSULFONE; ENZYME STABILIZATION; LIPASE IMMOBILIZATION; MULTIPOINT COVALENT ATTACHMENTS; THERMOMYCES LANUGINOSUS;

ENZYME IMMOBILIZATION;

EID: 84937760133     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2015.03.018     Document Type: Article

References (84)

1. R.A. Sheldon, and S. van Pelt Enzyme immobilisation in biocatalysis: why, what and how Chem Soc Rev 42 2013 6223 6235
2. R. DiCosimo, J. McAuliffe, A.J. Poulose, and G. Bohlmann Industrial use of immobilized enzymes Chem Soc Rev 42 2013 6437 6474
3. A. Liese, and L. Hilterhaus Evaluation of immobilized enzymes for industrial applications Chem Soc Rev 42 2013 6236 6249
4. S. Cantone, V. Ferrario, L. Corici, C. Ebert, D. Fattor, and P. Spizzo et al. Efficient immobilisation of industrial biocatalysts: criteria and constraints for the selection of organic polymeric carriers and immobilisation methods Chem Soc Rev 42 2013 6262 6276
5. I. Chibata, T. Tosa, and T. Sato Biocatalysis: immobilized cells and enzymes J Mol Catal 37 1986 1 24
6. W. Hartmeier Immobilized biocatalysts? From simple to complex systems Trends Biotechnol 3 1985 149 153
7. E. Katchalski-Katzir Immobilized enzymes - learning from past successes and failures Trends Biotechnol 11 1993 471 478
8. J.F. Kennedy, E.H.M. Melo, and K. Jumel Immobilized enzymes and cells Chem Eng Prog 86 1990 81 89
9. A.M. Klibanov Immobilized enzymes and cells as practical catalysts Science 219 1983 722 727
10. D. Brady, and J. Jordaan Advances in enzyme immobilisation Biotechnol Lett 31 2009 1639 1650
11. A.S. Bommarius, and M.F. Paye Stabilizing biocatalysts Chem Soc Rev 42 2013 6534 6565
12. R. Fernandez-Lafuente Stabilization of multimeric enzymes: strategies to prevent subunit dissociation Enzyme Microb Technol 45 2009 405 418
13. 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
14. K. Hernandez, and R. Fernandez-Lafuente Control of protein immobilization: coupling immobilization and site-directed mutagenesis to improve biocatalyst or biosensor performance Enzyme Microb Technol 48 2011 107 122
15. A.M. Klibanov Enzyme stabilization by immobilization Anal Biochem 93 1979 1 25
16. L. Gianfreda, and M.R. Scarfi Enzyme stabilization: state of the art Mol Cell Biochem 100 1991 97 128
17. C. Garcia-Galan, Á. 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
18. R.K. Singh, M.K. Tiwari, R. Singh, and J.K. Lee From protein engineering to immobilization: promising strategies for the upgrade of industrial enzymes Int J Mol Sci 14 2013 1232 1277
19. R.C. Rodrigues, C. Ortiz, Á. Berenguer-Murcia, R. Torres, and R. Fernández-Lafuente Modifying enzyme activity and selectivity by immobilization Chem Soc Rev 42 2013 6290 6307
20. E. Katchalski-Katzir, D.M. Kraemer, and C. Eupergit® a carrier for immobilization of enzymes of industrial potential J Mol Catal B Enzym 10 2000 157 176
21. L. Hilterhaus, B. Minow, J. Müller, M. Berheide, H. Quitmann, and M. Katzer et al. Practical application of different enzymes immobilized on sepabeads Bioprocess Biosyst Eng 31 2008 163 171
22. C. Mateo, J.M. Palomo, M. Fuentes, L. Betancor, V. Grazu, and F. López-Gallego et al. Glyoxyl agarose: a fully inert and hydrophilic support for immobilization and high stabilization of proteins Enzyme Microb Technol 39 2006 274 280
23. C. Mateo, O. Abian, M. Bernedo, E. Cuenca, M. Fuentes, and G. Fernandez-Lorente et al. Some special features of glyoxyl supports to immobilize proteins Enzyme Microb Technol 37 2005 456 462
24. O. Barbosa, C. Ortiz, Á. Berenguer-Murcia, R. Torres, R.C. Rodrigues, and R. Fernandez-Lafuente Glutaraldehyde in bio-catalysts design: a useful crosslinker and a versatile tool in enzyme immobilization RSC Adv 4 2014 1583
25. F.J. Lopez-Jaramillo, M. Ortega-Munõz, A. Megia-Fernandez, F. Hernandez-Mateo, and F. Santoyo-Gonzalez Vinyl sulfone functionalization: a feasible approach for the study of the lectin-carbohydrate interactions Bioconjug Chem 23 2012 846 855
26. P. Prikryl, J. Lenfeld, D. Horak, M. Ticha, and Z. Kucerova Magnetic bead cellulose as a suitable support for immobilization of α-chymotrypsin Appl Biochem Biotechnol 168 2012 295 305
27. M. Ortega-Muñoz, J. Morales-Sanfrutos, A. Megia-Fernandez, F.J. Lopez-Jaramillo, F. Hernandez-Mateo, and F. Santoyo-Gonzalez Vinyl sulfone functionalized silica: a ready to use pre-activated material for immobilization of biomolecules J Mater Chem 20 2010 7189
28. J.C. Begara-Morales, F.J. López-Jaramillo, B. Sánchez-Calvo, A. Carreras, M. Ortega-Muñoz, and F. Santoyo-González et al. Vinyl sulfone silica: application of an open preactivated support to the study of transnitrosylation of plant proteins by S-nitrosoglutathione BMC Plant Biol 13 2013 61
29. A.L. Medina-Castillo, J. Morales-Sanfrutos, A. Megia-Fernandez, J.F. Fernandez-Sanchez, F. Santoyo-Gonzalez, and A. Fernandez-Gutierrez Novel synthetic route for covalent coupling of biomolecules on super-paramagnetic hybrid nanoparticles J Polym Sci Part A Polym Chem 50 2012 3944 3953
30. K. Labus, A. Turek, J. Liesiene, and J. Bryjak Efficient Agaricus bisporus tyrosinase immobilization on cellulose-based carriers Biochem Eng J 56 2011 232 240
31. J. Bryjak, J. Liesiene, and B.N. Kolarz Application and properties of butyl acrylate/pentaerythrite triacrylate copolymers and cellulose-based Granocel as carriers for trypsin immobilization Colloids Surf B Biointerfaces 61 2008 66 74
32. M.D. Bale Oenick, S.J. Danielson, J.L. Daiss, M.W. Sunderberg, and R.C. Sutton Antigen-binding activity of antibodies immobilized on styrene copolymer beads Ann Biol Clin (Paris) 48 1990 651 654
33. J. Morales-Sanfrutos, J. Lopez-Jaramillo, M. Ortega-Muñoz, A. Megia-Fernandez, F. Perez-Balderas, and F. Hernandez-Mateo et al. Vinyl sulfone: a versatile function for simple bioconjugation and immobilization Org Biomol Chem 8 2010 667 675
34. J.C.S. dos Santos, N. Rueda, O. Barbosa, J.F. Fernández-Sánchez, A.L. Medina-Castillo, and T. Ramón-Márquez et al. Characterization of supports activated with divinylsulfone as a tool to immobilize and stabilize enzymes via multipoint covalent attachment RSC Adv 5 2015 20639 20649
35. E. Ilan, P.G. Morton, and T.M.S. Chang The anaerobic reaction of bovine hemoglobin with divinyl sulfone: structural changes and functional consequences Biochim Biophys Acta - Protein Struct Mol Enzymol 1163 1993 257 265
36. K.E. Jaeger, and T. Eggert Lipases for biotechnology Curr Opin Biotechnol 13 2002 390 397
37. R. Sharma, Y. Chisti, and U.C. Banerjee Production, purification, characterization, and applications of lipases Biotechnol Adv 19 2001 627 662
38. K.E. Jaeger, and M.T. Reetz Microbial lipases form versatile tools for biotechnology Trends Biotechnol 16 1998 396 403
39. R.D. Schmid, and R. Verger Lipases: interfacial enzymes with attractive applications Angew Chem Int Ed 37 1998 1608 1633
40. A. Pandey, S. Benjamin, C.R. Soccol, P. Nigam, N. Krieger, and V.T. Soccol The realm of microbial lipases in biotechnology Biotechnol Appl Biochem 29 Pt 2 1999 119 131
41. J. Zhang, H. Shi, D. Wu, Z. Xing, A. Zhang, and Y. Yang et al. Recent developments in lipase-catalyzed synthesis of polymeric materials Process Biochem 49 2014 797 806
42. C. Li, X-W. Feng, N. Wang, Y-J. Zhou, and X-Q. Yu Biocatalytic promiscuity: the first lipase-catalysed asymmetric aldol reaction Green Chem 10 2008 616
43. E. Busto, V. Gotor-Fernández, and V. Gotor Hydrolases: catalytically promiscuous enzymes for non-conventional reactions in organic synthesis Chem Soc Rev 39 2010 4504 4523
44. M. Kapoor, and M.N. Gupta Lipase promiscuity and its biochemical applications Process Biochem 47 2012 555 569
45. N.J. Turner Directed evolution drives the next generation of biocatalysts Nat Chem Biol 5 2009 567 573
46. U.T. Bornscheuer, and M. Pohl Improved biocatalysts by directed evolution and rational protein design Curr Opin Chem Biol 5 2001 137 143
47. J.M. Palomo, G. Fernandez-Lorente, C. Mateo, C. Ortiz, R. Fernandez-Lafuente, and J.M. Guisan Modulation of the enantioselectivity of lipases via controlled immobilization and medium engineering: hydrolytic resolution of mandelic acid esters Enzyme Microb Technol 31 2002 775 783
48. R.C. Rodrigues, Á. Berenguer-Murcia, and R. Fernandez-Lafuente Coupling chemical modification and immobilization to improve the catalytic performance of enzymes Adv Synth Catal 353 2011 2216 2238
49. C. Garcia-Galan, J.C.S. dos Santos, O. Barbosa, R. Torres, E.B. Pereira, and V.C. Corberan et al. Tuning of Lecitase features via solid-phase chemical modification: effect of the immobilization protocol Process Biochem 49 2014 604 616
50. J.C.S. dos Santos, C. Garcia-Galan, R.C. Rodrigues, H.B. de Sant'Ana, L.R.B. Gonçalves, and R. Fernandez-Lafuente Improving the catalytic properties of immobilized lecitase via physical coating with ionic polymers Enzyme Microb Technol 60 2014 1 8
51. O. Barbosa, R. Torres, C. Ortiz, A. Berenguer-Murcia, R.C. Rodrigues, and R. Fernandez-Lafuente Heterofunctional supports in enzyme immobilization: from traditional immobilization protocols to opportunities in tuning enzyme properties Biomacromolecules 14 2013 2433 2462
52. D.F. Izquierdo, O. Barbosa, M.I. Burguete, P. Lozano, S.V. Luis, and R. Fernandez-Lafuente et al. Tuning lipase B from Candida antarctica C-C bond promiscuous activity by immobilization on poly-styrene-divinylbenzene beads RSC Adv 4 2014 6219
53. A.M. Brzozowski, U. Derewenda, Z.S. Derewenda, G.G. Dodson, D.M. Lawson, and J.P. Turkenburg et al. A model for interfacial activation in lipases from the structure of a fungal lipase-inhibitor complex Nature 351 1991 491 494
54. K.E. Jaeger, S. Ransac, H.B. Koch, F. Ferrato, and B.W. Dijkstra Topological characterization and modeling of the 3D structure of lipase from Pseudomonas aeruginosa FEBS Lett 332 1993 143 149
55. R. Verger Interfacial activation of lipases: facts and artifacts Trends Biotechnol 15 1997 32 38
56. C. Cambillau, S. Longhi, A. Nicolas, and C. Martinez Acyl glycerol hydrolases: inhibitors, interface and catalysis Curr Opin Struct Biol 6 1996 449 455
57. R. Fernandez-Lafuente Lipase from Thermomyces lanuginosus: uses and prospects as an industrial biocatalyst J Mol Catal B Enzym 62 2010 197 212
58. 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
59. Z-F. Xie Pseudomonas fluorescens lipase in asymmetric synthesis Tetrahedron: Asymmetry 2 1991 733 750
60. D. Goswami, J.K. Basu, and S. De Lipase applications in oil hydrolysis with a case study on castor oil: a review Crit Rev Biotechnol 33 2013 81 96
61. E.M. Anderson, K.M. Larsson, and O. Kirk One biocatalyst-many applications: the use of Candida antarctica B-lipase in organic synthesis Biocatal Biotransform 16 1998 181 204
62. V. Gotor-Fernández, E. Busto, and V. Gotor Candida antarctica lipase B: an ideal biocatalyst for the preparation of nitrogenated organic compounds Adv Synth Catal 348 2006 797 812
63. L. De Maria, J. Vind, K.M. Oxenbøll, A. Svendsen, and S. Patkar Phospholipases and their industrial applications Appl Microbiol Biotechnol 74 2007 290 300
64. R. Fernandez-Lafuente, P. Armisén, P. Sabuquillo, G. Fernández-Lorente, and M.J. Guisán Immobilization of lipases by selective adsorption on hydrophobic supports Chem Phys Lipids 93 1998 185 197
65. M. Bradford Rapid sensitive method for quantification of microgram quantities of protein utilizing principle of protein-dye-binding Anal Biochem 72 1976 248 254
66. W. DeLano Pymol An open-source molecular graphics tool CCP4 Newslett Protein Crystallogr 40 2002
67. S. Ahmad, M. Gromiha, H. Fawareh, and A. Sarai ASAView: database and tool for solvent accessibility representation in proteins BMC Bioinformatics 5 2004 51
68. D. Gilis, and M. Rooman Stability changes upon mutation of solvent-accessible residues in proteins evaluated by database-derived potentials J Mol Biol 257 1996 1112 1126
69. D. Gilis, and M. Rooman Predicting protein stability changes upon mutation using database-derived potentials: solvent accessibility determines the importance of local versus non-local interactions along the sequence J Mol Biol 272 1997 276 290
70. J.M. Palomo, M. Fuentes, G. Fernández-Lorente, C. Mateo, J.M. Guisan, and R. Fernández-Lafuente General trend of lipase to self-assemble giving bimolecular aggregates greatly modifies the enzyme functionality Biomacromolecules 4 2003 1 6
71. G. Fernández-Lorente, J.M. Palomo, M. Fuentes, C. Mateo, J.M. Guisán, and R. Fernández-Lafuente Self-assembly of Pseudomonas fluorescens lipase into bimolecular aggregates dramatically affects functional properties Biotechnol Bioeng 82 2003 232 237
72. J.M. Palomo, C. Ortiz, M. Fuentes, G. Fernandez-Lorente, J.M. Guisan, and R. Fernandez-Lafuente Use of immobilized lipases for lipase purification via specific lipase-lipase interactions J Chromatogr A 1038 2004 267 273
73. J.M. Palomo, C. Ortiz, G. Fernández-Lorente, M. Fuentes, J.M. Guisán, and R. Fernández-Lafuente Lipase-lipase interactions as a new tool to immobilize and modulate the lipase properties Enzyme Microb Technol 36 2005 447 454
74. G. Fernandez-Lorente, J.M. Palomo, Z. Cabrera, R. Fernandez-Lafuente, and J.M. Guisán Improved catalytic properties of immobilized lipases by the presence of very low concentrations of detergents in the reaction medium Biotechnol Bioeng 97 2007 242 250
75. O. Barbosa, R. Torres, C. Ortiz, and R. Fernandez-Lafuente Versatility of glutaraldehyde to immobilize lipases: effect of the immobilization protocol on the properties of lipase B from Candida antarctica Process Biochem 47 2012 1220 1227
76. J.E. Mogensen, P. Sehgal, and D.E. Otzen Activation, inhibition, and destabilization of Thermomyces lanuginosus lipase by detergents Biochemistry 44 2005 1719 1730
77. J.C.S. dos Santos, C. Garcia-Galan, R.C. Rodrigues, H.B. De Sant'Ana, L.R.B. Gonçalves, and R. Fernandez-Lafuente Stabilizing hyperactivated lecitase structures through physical treatment with ionic polymers Process Biochem 49 9 2014 1511 1515
78. J. Mansfeld, and R. Ulbrich-Hofmann Site-specific and random immobilization of thermolysin-like proteases reflected in the thermal inactivation kinetics Biotechnol Appl Biochem 32 Pt 3 2000 189 195
79. J. Mansfeld, G. Vriend, B. Van Den Burg, V.G.H. Eijsink, and R. Ulbrich-Hofmann Probing the unfolding region in a thermolysin-like protease by site-specific immobilization Biochemistry 38 1999 8240 8245
80. G. Fernández-Lorente, J.M. Palomo, C. Mateo, R. Munilla, C. Ortiz, and Z. Cabrera et al. Glutaraldehyde cross-linking of lipases adsorbed on aminated supports in the presence of detergents leads to improved performance Biomacromolecules 7 2006 2610 2615
81. J.M. Palomo, G. Muñoz, G. Fernández-Lorente, C. Mateo, R. Fernández-Lafuente, and J.M. Guisán Interfacial adsorption of lipases on very hydrophobic support (octadecyl-Sepabeads): immobilization, hyperactivation and stabilization of the open form of lipases J Mol Catal B Enzym 19-20 2002 279 286
82. G.H. Peters, O.H. Olsen, A. Svendsen, and R.C. Wade Theoretical investigation of the dynamics of the active site lid in Rhizomucor miehei lipase Biophys J 71 1996 119 129
83. 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
84. N. Rueda, J.C.S. dos Santos, R. Torres, C. Ortiz, O. Barbosa, and R. Fernandez-Lafuente Improved performance of lipases immobilized on heterofunctional octyl-glyoxyl agarose beads RSC Adv 5 15 2015 11212 11222