Tuning of Lecitase features via solid-phase chemical modification: Effect of the immobilization protocol

Process Biochemistry

Volumn 49, Issue 4, 2014, Pages 604-616

  Garcia Galan, Cristina ^a   Dos Santos, José C S ^a,b   Barbosa, Oveimar ^c   Torres, Rodrigo ^c   Pereira, Ernandes B ^d   Corberan, Vicente Cortes ^a   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 FEDERAL UNIVERSITY OF ALFENAS   (Brazil)

Author keywords

2,4,6 Trinitrobenzensulfonic acid; Enzyme chemical modification; Enzyme hyperactivation; Enzyme immobilization; Enzyme stabilization; Glutaraldehyde

Indexed keywords

AMINATION; AMINES; CHEMICAL MODIFICATION; CHEMICAL STABILITY; CROSSLINKING; PH; STABILITY;

COVALENT ATTACHMENT; ENZYME STABILIZATION; GLUTARALDEHYDES; HYPERACTIVATION; IMMOBILIZATION PROTOCOLS; INTERFACIAL ACTIVATION; INTERMOLECULAR CROSSLINKING; SUBSTRATE SPECIFICITY;

ENZYME IMMOBILIZATION;

EID: 84897915516     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2014.01.028     Document Type: Article

References (62)

1. S.S. Havn, R. Ipsen, P.M. Nielsen, and H.M. Lilbæk Improving the foaming properties and heat stability of whey protein concentrates by phospholipase treatment Milchwissenschaft 61 2006 188 191
2. J.-G. Yang, Y.-H. Wang, B. Yang, G. Mainda, and Y. Guo Degumming of vegetable oil by a new microbial lipase Food Technol Biotechnol 44 2006 101 104
3. A. Na, C. Eriksson, S.-G. Eriksson, E. Österberg, and K. Holmberg Synthesis of phosphatidylcholine with (n-3) fatty acids by phospholipase A 2 in microemulsion J Am Oil Chem Soc 67 1990 766 770
4. M. Devos, L. Poisson, F. Ergan, and G. Pencreac'h Enzymatic hydrolysis of phospholipids from Isochrysis galbana for docosahexaenoic acid enrichment Enzyme Microb Technol 39 2006 548 554
5. Y. Yamamoto, M. Hosokawa, and K. Miyashita Production of phosphatidylcholine containing conjugated linoleic acid mediated by phospholipase A2 J Mol Catal B: Enzym 41 2006 92 96
6. M. Hartman, A. Lumberman, M. Florin-Christensen, and A. Tiedtke Screening for and characterization of phospholipase A1 hypersecretory mutants of Tetrahymena thermophila Appl Microbiol Biotechnol 5 2000 390 396
7. H.N. Higgs, M.H. Han, G.E. Johnson, and J.A. Glomset Cloning of a phosphatidic acid-preferring phospholipase A1 from bovine testis J Biol Chem 273 1998 5468 5477
8. S. Merino, A. Aguilar, M.M. Nogueras, M. Regue, S. Swift, and J.M. Tomas Cloning, sequencing, and role in virulence of two phospholipases (A1 and C) from mesophilic Aeromonas sp. serogroup O:34 Infect Immun 67 1999 4008 4013
9. L. De Maria, J. Vind, K.M. Oxenbøll, A. Svendsen, and S. Patkar Phospholipases and their industrial applications Appl Microb Biotechnol 74 2007 290 300
10. B. Yang, Y.-H. Wang, and J.-G. Yang Optimization of enzymatic degumming process for rapeseed oil J Am Oil Chem Soc 83 2006 653 658
11. I.-H. Kim, H.S. Garcia, and C.G. Hill Jr. Phospholipase A1-catalyzed synthesis of phospholipids enriched in n-3 polyunsaturated fatty acid residues Enzyme Microb Technol 40 2007 1130 1135
12. K.M. Gonçalves, F.K. Sutili, I.I. Júnior, M.C. Flores, E. Soter De Mariz, and L. Miranda et al. A comprehensive study on the activity and deactivation of immobilized Lecitase Ultra in esterifications of food waste streams to monoacylglycerols ChemSusChem 6 2013 872 879
13. N. Liu, M. Fu, Y. Wang, Q. Zhao, W. Sun, and M. Zhao Immobilization of Lecitase® Ultra onto a novel polystyrene DA-201 resin: characterization and biochemical properties Appl Biochem Biotechnol 168 2012 1108 1120
14. N. Liu, Y. Wang, Q. Zhao, C. Cui, M. Fu, and M. Zhao Immobilisation of Lecitase® Ultra for production of diacylglycerols by glycerolysis of soybean oil Food Chem 134 2012 301 307
15. L. Wang, Y. Wang, C. Hu, Q. Cao, X. Yang, and M. Zhao Preparation of diacylglycerol-enriched oil from free fatty acids using Lecitase Ultra-catalyzed esterification J Am Oil Chem Soc 88 2011 1557 1565
16. N. Liu, Y. Wang, Q. Zhao, Q. Zhang, and M. Zhao Fast synthesis of 1,3-DAG by Lecitase® Ultra-catalyzed esterification in solvent-free system Eur J Lipid Sci Technol 113 2011 973 979
17. M.K. Mishra, M. Harini, T. Kumaraguru, T. Lakshmi Prasanna, and N.W. Fadnavis A porous vessel bioreactor for gel entrapped biocatalysts: kinetic resolution of trans-methyl (4-methoxyphenyl)glycidate by Lecitase® Ultra in gelatin organogel (Gelozyme) J Mol Catal B: Enzym 71 2011 56 62
18. Y. Wang, M. Zhao, K. Song, L. Wang, S. Tang, and W.W. Riley Partial hydrolysis of soybean oil by phospholipase A1 (Lecitase Ultra) Food Chem 121 2010 1066 1072
19. N. Miled, F. Beisson, J. De Caro, A. De Caro, V. Arondel, and R. Verger Interfacial catalysis by lipases J Mol Catal B: Enzym 11 2001 165 171
20. U. Derewenda, L. Swenson, R. Green, Y. Wei, S. Yamaguchi, and R. Joerger et al. Current progress in crystallographic studies of new lipases from filamentous fungi Protein Eng 7 1994 551 557
21. N.J. Turner Directed evolution drives the next generation of biocatalysts Nat Chem Biol 5 2009 567 573
22. J. Kaur, and R. Sharma Directed evolution: an approach to engineer enzymes Crit Rev Biotechnol 26 2006 165 199
23. G. Fernández-Lorente, J.M. Palomo, C. Mateo, J.M. Guisan, and R. Fernandez-Lafuente Resolution of paroxetine precursor using different lipases: influence of the reaction conditions on the enantioselectivity of lipases Enzyme Microb Technol 34 2004 264 269
24. 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
25. 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
26. G. Fernandez-Lorente, M. Filice, M. Terreni, J.M. Guisan, R. Fernandez-Lafuente, and J.M. Palomo Lecitase® Ultra as regioselective biocatalyst in the hydrolysis of fully protected carbohydrates. Strong modulation by using different immobilization protocols J Mol Catal B: Enzym 51 2008 110 117
27. G. Fernandez-Lorente, J.M. Palomo, J.M. Guisan, and R. Fernandez-Lafuente Effect of the immobilization protocol in the activity, stability, and enantioslectivity of Lecitase® Ultra J Mol Catal B: Enzym 47 2007 99 104
28. Z. Cabrera, G. Fernandez-Lorente, J.M. Palomo, J.M. Guisan, and R. Fernandez-Lafuente Asymmetric hydrolysis of dimethyl 3-phenylglutarate catalyzed by Lecitase Ultra®. Effect of the immobilization protocol on its catalytic properties Enzyme Microb Technol 43 2008 531 536
29. R.C. Rodrigues, A. 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
30. O. Barbosa, M. Ruiz, C. Ortiz, M. Fernández, R. Torres, and R. Fernandez-Lafuente Modulation of the properties of immobilized CALB by chemical modification with 2,3,4-trinitrobenzenesulfonate or ethylendiamine. Advantages of using adsorbed lipases on hydrophobic supports Process Biochem 47 2012 867 876
31. R. Fernandez-Lafuente, P. Armisén, P. Sabuquillo, G. Fernández-Lorente, and J.M. Guisán Immobilization of lipases by selective adsorption on hydrophobic supports Chem Phys Lipids 93 1998 185 197
32. G. Fernández-Lorente, J.M. Palomo, Z. Cabrera, J.M. Guisán, and R. Fernández-Lafuente Specificity enhancement towards hydrophobic substrates by immobilization of lipases by interfacial activation on hydrophobic supports Enzyme Microb Technol 41 2007 565 569
33. 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
34. J. Pedroche, M. del Mar Yust, C. Mateo, R. Fernández-Lafuente, J. Girón-Calle, and M. Alaiz et al. 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
35. K.L. Carraway, and D.E. Koshland Jr. Carbodiimide modification of proteins Methods Enzymol 25 1972 616 623
36. K.L. Carraway, P. Spoerl, and D.E. Koshland Jr. Carboxyl group modification in chymotrypsin and chymotrypsinogen J Mol Biol 42 1969 133 137
37. M. Galvis, O. Barbosa, R. Torres, C. Ortiz, and R. Fernandez-Lafuente Effect of solid-phase chemical modification on the features of the lipase from Thermomyces lanuginosus Process Biochem 47 2012 460 466
38. K.L. Carraway, and D.E. Koshland Jr. Reaction of tyrosine residues in proteins with carbodiimide reagents Biochem Biphys Acta 160 1968 272 274
39. S.L. Snyder, and P.Z. Sobocinski An improved 2,4,6- trinitrobenzenesulfonic acid method for the determination of amines Anal Biochem 64 1975 284 288
40. A.A. Mendes, H.F. De Castro, S. De, D. Rodrigues, W.S. Adriano, and P.W. Tardioli et al. Multipoint covalent immobilization of lipase on chitosan hybrid hydrogels: influence of the polyelectrolyte complex type and chemical modification on the catalytic properties of the biocatalysts J Ind Microbiol Biotechnol 38 2011 1055 1066
41. S. Jagtap, and M. Rao Conformation and microenvironment of the active site of a low molecular weight 1,4-β-d-glucan glucanohydrolase from an alkalothermophilic Thermomonospora sp.: involvement of lysine and cysteine residues Biochem Biophys Res Commun 347 2006 428 432
42. S. Husain, F. Jafri, and M. Saleemuddin Effects of chemical modification on the stability of invertase before and after immobilization Enzyme Microb Technol 18 1996 275 280
43. H. Yamashita, H. Nakatani, and B. Tonomura Change of substrate specificity by chemical modification of lysine residues of porcine pancreatic α-amylase Biochim Biophys Acta 1202 1993 129 134
44. C. Dartiguenave, M.J. Bertrand, and K.C. Waldron Glutaraldehyde: behavior in aqueous solution, reaction with proteins, and application to enzyme crosslinking Biotechnology 37 2004 790 802
45. D.R. Walt, and V.I. Agayn The chemistry of enzyme and protein immobilization with glutaraldehyde Trends Anal Chem 13 1994 425 430
46. A.F.S.A. Habeeb, and R. Hiramoto Reaction of proteins with glutaraldehyde Arch Biochem Biophys 126 1968 16 26
47. O. Barbosa, C. Ortiz, A. Berenguer-Murcia, R. Rodrigo 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 1600
48. Y. Wine, N. Cohen-Hadar, A. Freeman, and F. Frolow Elucidation of the mechanism and end products of glutaraldehyde crosslinking reaction by X-ray structure analysis Biotechnol Bioeng 98 2007 711 718
49. P. Monsan Optimization of glutaraldehyde activation of a support for enzyme immobilization J Mol Catal 3 1978 371 384
50. 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
51. S.S. Wong, and L.J.C. Wong Chemical crosslinking and the stabilization of proteins and enzymes Enzyme Microb Technol 14 1992 866 874
52. 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
53. 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
54. O. Barbosa, R. Torres, C. Ortiz, and R. Fernandez-Lafuente The slow-down of the CALB immobilization rate permits to control the inter and intra molecular modification produced by glutaraldehyde Process Biochem 47 2012 766 774
55. U.K. Laemmli Cleavage of structural proteins during the assembly of the head of bacteriophage T4 Nature 227 1970 680 685
56. 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
57. 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
58. 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
59. 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
60. J.E. Mogensen, P. Sehgal, and D.E. Otzen Activation, inhibition, and destabilization of Thermomyces lanuginosus lipase by detergents Biochemistry 44 2005 1719 1730
61. J.M. Palomo, G. Muoz, 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
62. R.C. Rodrigues, C. Ortiz, A. Berenguer-Murcia, R. Torres, and R. Fernández-Lafuente Modifying enzyme activity and selectivity by immobilization Chem Soc Rev 42 2013 6290 6307