Evaluation of styrene-divinylbenzene beads as a support to immobilize lipases

Molecules

Volumn 19, Issue 6, 2014, Pages 7629-7645

  Garcia Galan, Cristina ^a   Barbosa, Oveimar ^b   Hernandez, Karel ^c   Dos Santos, Jose C S ^a,d   Rodrigues, Rafael C ^e   Fernandez Lafuente, Roberto ^a  

^a CSIC   (Spain)

^b UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^c INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

^d FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^e FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

Interfacial activation; Lipase immobilization; Modulation of lipase activity; Styrene divinylbencene matrix

Indexed keywords

IMMOBILIZED ENZYME; STYRENE; TRIACYLGLYCEROL LIPASE;

ENZYMES, IMMOBILIZED; LIPASE; STYRENE;

EID: 84903291433     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19067629     Document Type: Article

References (54)

1. Jaeger, K.E.; Eggert, T. Lipases for biotechnology. Curr. Opin. Biotechnol. 2002, 13, 390-397.
2. Sharma, R.; Chisti, Y.; Banerjee, U.C. Production, purification, characterization, and applications of lipases. Biotechnol. Adv. 2001, 19, 627-662.
3. Pandey, A.; Benjamin, S.; Soccol, C.R.; Nigam, P.; Krieger, N.; Soccol, V.T. The realm of microbial lipases in biotechnology. Biotechnol. Appl. Biochem. 1999, 29, 119-131.
4. Reetz, M .T. Lipases as practical biocatalysts. Curr. Opin. Chem. Biol. 2002, 6, 145-150.
5. Villeneuve, P.; Muderhwa, J.M.; Graille, J.; Haas, M.J. Customizing lipases for biocatalysis: A survey of chemical, physical and molecular biological approaches. J. Mol. Catal. B 2000, 9, 113-148.
6. Lozano, P.; Garcia-Verdugo, E.; Luis, S.V.; Pucheault, M.; Vaultier, M. (bio) catalytic continuous flow processes in sccO2 and/or ils: Towards sustainable (bio)catalytic synthetic platforms. Curr. Org. Syn th. 2011, 8, 810-823.
7. Lozano, P. Enzymes in neoteric solvents: From one-phase to multiphase systems. Green Chem. 2010, 12, 555-569.
8. Ghanem, A. Trends in li pase-catalyzed asymmetric access to enantiomerically pure/enriched compounds. Tetrahedron 2007, 63, 1721-1754.
9. Bornscheuer, U.T. Methods to increase enantioselectivity of lipases and esterases. Curr. Opin. Biotechnol. 2002, 13, 543-547.
10. Yahya, A.R.M.; Anderson, W.A.; Moo-Young, M. Ester synthesis in lipase-catalyzed reactions. Enzyme Microb. Technol. 1998, 23, 438-450.
11. Santaniello, E.; Ferraboschi, P.; Grisenti, P. Lipase-catalyzed transesterification in organic solvents: Applicatio ns to the preparation of enantiomerically pure compounds. Enzyme Microb. Technol. 1993, 15, 367-382.
12. Bajaj, A.; Lohan, P.; Jha, P.N.; Mehrotra, R. Biodiesel production through lipase catalyzed transesterification: An overview. J. Mol. Catal. B 2010, 62, 9-14.
13. Hari Krishna, S.; Karanth, N.G. Lipases and lipase-catalyzed esterification reactions in nonaqueous media. Catal. Rev. Sci. Eng. 2002, 44, 499-591.
14. Carboni-Oerlemans, C.; Domí nguez de María, P.; Tuin, B.; Bargeman, G.; van der Meer, A.; van Gemert, R. Hydrolase-catalysed synthesis of peroxycarboxylic acids: Biocatalytic promi scuity for practical applications. J. Biotechnol. 2006, 126, 140-151.
15. Humble M.S.Berglund P. Biocatalytic promiscuity. Eur. J. Org. Chem.2011.2011. 3391-3401.
16. Kapoor, M.; Gupta, M.N. Lipase promiscuity and its biochemical applications. Process. Biochem. 2012, 47, 555-569.
17. Mateo, C.; Palomo, J.M.; Fernandez-Lorente, G.; Guisan, J.M.; F ernandez-Lafuente, R. Improvement of enzyme activity, stability and selectivity via immobilization techniques. Enzyme Microb. Technol. 2007, 40, 1451-1463.
18. Iyer, P.V.; Ananthanarayan, L. Enzyme stability and stabilization-aqueous and non-aqueous environment. Process. Biochem. 2008, 43, 1019-1032.
19. Hernandez, K.; Fernandez-Lafuente, R. Control of protein immobilization: Coupling immobilization and site-directed mutagenesis to improve biocatalyst or biosensor performance. Enzyme Microb. Technol. 2011, 48, 107-122.
20. Rodrigues, R.C.; Ortiz, C.; Berenguer-Murcia, A.; Torres, R.; Fernandez-Lafuente, R. Modifying enzyme activity and selectivity by immobilization. Chem. Soc. Rev. 2013, 42, 6290-6307.
21. Hwang, E.T.; Gu, M.B. Enzyme stabilization by nano/microsized hybrid materials. Eng. Life Sci. 2013, 13, 49-61.
22. Verma, M.L.; Barrow, C.J.; Puri, M. Nanobiotechnol ogy as a novel paradigm for enzyme immobilisation and stabilisation with potential applications in biodiesel production. Appl. Microbiol. Biotechnol. 2013, 97, 23-39.
23. Garcia-Galan, C.; Berenguer-Murcia, A.; Fernandez-Lafuente, R.; Rodrigues, R.C., Potential of different enzyme immobilization strategies to improve enzyme performance. Adv. Synth. Catal. 2011, 353, 2885-2904.
24. Schmid, R.D.; Verger, R., Lipases: Interfacial enzymes with attractive applications. Angew. Chem. Int. Ed. 1998, 37, 1609-1633.
25. Verger, R. Interfacial activation of lipases: Facts and artifacts. Trends Biotechnol. 1997, 15, 32-38.
26. Reis, P.; Holmberg, K.; Watzke, H.; Leser, M.E.; Miller, R. Lipases at interfaces: A review. Adv. Colloid Interface Sci. 2009, 147- 148, 237-250.
27. Derewenda, Z.S.; Derewenda, U.; Dodson, G.G. The crystal and molecular structure of the rhizomucor miehei triacylglyceride lipase at 1.9 å resolution. J. Mol. Biol. 1992, 227, 818-839.
28. Uppenbe rg, J.; Patkar, S.; Bergfors, T.; Jones, T.A. Crystallization and preliminary X-ray studies of lipase b from Candida antarctica. J. Mol. Biol. 1994, 235, 790-792.
29. Carrasco-Ló pez, C.; Godoy, C.; de las Rivas, B.; Fernández-Lorente, G.; Palomo, J.M.; Guisán, J.M.; Fernández-Lafuente, R.; Martí nez-Ripoll, M.; Hermoso, J.A. Activation of bacterial thermo alkalophilic lipases is spurred by dramatic structural rearrangements. J. Biol. Chem. 2009, 284, 4365-4372.
30. Palomo, J.M.; Peñ as, M.M.; Fernández-Lorente, G.; Mateo, C.; Pisabarro, A.G.; Fernández-Lafuente, R.; Ramírez, L.; Guisá n, J.M. Solid-phase handling of hydrophobins: Immobilized hydrophobins as a new tool to study lipases. Biomacromolecules 2003, 4, 204-210.
31. Palomo, J.M.; Ortiz, C.; Fernández-Lorente, G.; Fuentes, M.; Guisán, J.M.; Fernández-Lafuen te, R. Lipase-lipase interactions as a new tool to immobilize and modulate the lipase properties. Enzyme Microb. Technol. 2005, 36, 447-454.
32. Ferná ndez-Lorente, G.; Palomo, J.M.; Fuentes, M.; Mateo, C.; Guisán, J.M.; Ferná ndez-Lafuente, R. Self-assembly of pseudomonas fluorescens lipase into bimolecular aggregates dramatically affects functional properties. Biotechnol. Bioeng. 2003, 82, 232-237.
33. Fernandez-Lafuente, R.; Armis én, P.; Sabuquillo, P.; Fernández-Lorente, G.; Guisá n, J.M. Immobilization of lipases by selective adsorption on hydrophobic supports. Chem. Phys. Lipids 1998, 93, 185-197.
34. Cabrera, Z.; Fernandez-Lorente, G.; Fernandez-Lafuente, R.; Palomo, J.M.; Guisan, J.M. Novozym 435 displays very different selectivity compared to lipase from Candida antarctica B adsorbed on other hydrophobic s upports. J. Mol. Catal. B 2009, 57, 171-176.
35. Fernandez-Lorente, G.; Cabrera, Z.; Godoy, C.; Fernandez-Lafuente, R.; Palomo, J.M.; Guisan, J.M. Interfacially activated lipases against hydro phobic supports: Effect of the support nature on the biocatalytic properties. Process. Biochem. 2008, 43, 1061-1067.
36. Hernandez K.Garcia-Galan C.Fernandez-Lafuente R. Simple and efficient immobi lization of lipase B from Candida antarctica on porous styrene-divinylbenzene beads. Enzyme Microb. Technol.2011.49.72-78.
37. Anderson, E.M.; Larsson, K.M.; Kirk, O. One biocatalyst-many applications: The use of Candida antarctica B-lipase in organic synthesis. Biocatal. Biotransform. 1998, 16, 181-204.
38. Friedrich, J.L.R.; Peñ a, F.P.; Garcia-Galan, C.; Fernandez-Lafuente, R.; Ayub, M.A.Z.; Rodrigues, R.C. Effect of immobilization protocol on optimal conditions of ethyl butyrate synthesis catalyzed by lipase B from Candida antarctica. J. Chem. Technol. Biotechnol. 2013, 88, 1089-1095.
39. Poppe, J. K.; Garcia-Galan, C.; Matte, C.R.; Fernandez-Lafuente, R.; Rodrigues, R.C.; Ayub, M.A.Z. Optimization of synthesis of fatty acid methyl esters catalyzed by lipase B from Candida antarctica immobilized in hydrophobic supports. J. M ol. Catal. B 2013, 94, 51-56.
40. Izquierdo, D.F.; Barbosa, O.; Burguete, M.I.; Lozano, P.; Luis, S.V.; Fernandez-Lafuente, R.; Garcia-Verdugo, E. Tuning lipase B from Candida antarctica c -c bond promiscuous activity by immobilization on poly-styrene-divinylbenzene beads. RSC Adv. 2014, 4, 6219-6225.
41. Graebin, N.G.; Martins, A.B.; Lorenzoni, A.S.G.; Garcia-Galan, C.; Fernandez- Lafuente, R.; Ayub, M.A.Z.; Rodrigues, R.C. Immobilization of lipase B from Candida antarctica on porous styrene-divinylbenzene beads improves butyl acetate synthesis. Biotechnol. Prog. 2012, 28, 406-412.
42. . Martins, A.B.; Friedrich, J.L.R.; Cavalheiro, J.C.; Garcia-Galan, C.; Barbosa, O.; Ayub, M.A.Z.; Fernandez-Lafuente, R.; Rodrigues, R.C. Improved production of butyl butyrate with lipase from Thermomyces lanuginosus immobilized on styrene-divinylbenzene beads. Bioresour. Technol. 2013, 134, 417-422.
43. De Abreu, L.; Fernandez-Lafuente, R.; Rodrigues, R.C.; Volpato, G.; Ayub, M.A.Z. Efficient purification-imm obilization of an organic solvent-tolerant lipase from Staphylococcus warneri EX17 on porous styrene-divinylbenzene beads. J. Mol. Catal. B 2014, 99, 51-55.
44. Fernandez-Lafuente, R. Lipase from Thermomyces lanuginosus: Uses and prospects as an industrial biocatalyst. J. Mol. Catal. B 2010, 62, 197-212.
45. Rodrigues, R.C.; Fernandez-Lafuente, R. Lipase from Rhizomucor miehei as an industrial biocatalyst in chemical process. J. Mol. Catal. B 2010, 64, 1-22.
46. Rodrigues, R.C.; Fernandez-Lafuente, R. Lipase from Rhizomucor miehei as a biocatalyst in fats and oils modification. J. Mol. Catal. B 2010, 66, 15-32.
47. De Maria, L.; Vind, J.; Oxenbøll, K.M.; Svendsen, A.; Patkar, S. Phospholipases and their industrial applications. Appl. Microbiol. Biotechnol. 2007, 74, 290-300.
48. Bastida, A.; Sabuquillo, P.; Armisen, P.; Fernández-Lafuente, R.; Huguet, J.; Guisá n, J.M. A single step purification, immobilization, and hyperactivation of lipases via interfacial adsorption on strongly hydrophobic supports. Biotechnol. Bioeng. 1998, 58, 486-493.
49. Palomo, J.M.; Ortiz, C.; Fuentes, M.; Fernandez-Lorente, G.; Guisan, J.M.; Fernandez-Lafuente, R. Use of immobilized lipases for lipa se purification via specific lipase-lipase interactions. J. Chromatogr. A 2004, 1038, 267-273.
50. Palomo, J.M.; Fuentes, M.; Fernández-Lorente, G.; Mateo, C.; Guisan, J.M.; Ferná ndez-Lafuente, R. General trend of lipase to self-assemble giving bimolecular aggregates greatly modifies the enzyme functionality. Biomacromolecules 2003, 4, 1-6.
51. Pavlidis, I.V.; Vorhaben, T.; T soufis, T.; Rudolf, P.; Bornscheuer, U.T.; Gournis, D.; Stamatis, H. Development of effective nanobiocatalytic systems through the immobilization of hydrolases on functionalized carbon-based nanomaterials. Bioresour. Technol. 201 2, 115, 164-171.
52. Mateo, C.; Abian, O.; Fern ández-Lorente, G.; Pedroche, J.; Fernández-Lafuente, R.; Guisan, J.M.; Tam, A.; Daminati, M. Epoxy sepabeads: A novel epoxy support for stabil ization of industrial enzymes via very intense multipoint covalent attachment. Biotechnol. Prog. 2002, 18, 629-634.
53. Bradford, M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein dye binding. Anal. Biochem. 1976, 72, 248-254.
54. Sé verac, E.; Galy, O.; Turon, F.; Pantel, C.A.; Condoret, J.S.; Monsan, P.; Marty, A. Selectio n of CALB immobilization method to be used in continuous oil transesterification: Analysis of the economical impact. Enzyme Microb. Technol. 2011, 48, 61-70.