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The Scientific World Journal
Volume 2014 (2014), Article ID 142123, 10 pages
http://dx.doi.org/10.1155/2014/142123
Research Article

Catalyzed Ester Synthesis Using Candida rugosa Lipase Entrapped by Poly(N-isopropylacrylamide-co-itaconic Acid) Hydrogel

1Department of Criminalistic Sciences, The Academy of Criminalistic and Police Studies, Cara Dušana 196, 11080 Belgrade, Serbia
2Department of Biochemical Engineering and Biotechnology, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia
3Department of Organic Chemical Technology, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia

Received 19 August 2013; Accepted 25 December 2013; Published 20 February 2014

Academic Editors: M. Y. Arica, P. Poltronieri, A. Tariq, and E. Van Heerden

Copyright © 2014 Nikola Milašinović et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. C. K. Sharma, G. S. Chauhan, and S. S. Kanwar, “Synthesis of medically important ethyl cinnamate ester by porcine pancreatic lipase immobilized on poly(AAc-co-HPMA-cl-EGDMA) hydrogel,” Journal of Applied Polymer Science, vol. 121, no. 5, pp. 2674–2679, 2011. View at Publisher · View at Google Scholar · View at Scopus
  2. M. Zoumpanioti, P. Parmaklis, P. D. De María, H. Stamatis, J. V. Sinisterra, and A. Xenakis, “Esterification reactions catalyzed by lipases immobilized in organogels: effect of temperature and substrate diffusion,” Biotechnology Letters, vol. 30, no. 9, pp. 1627–1631, 2008. View at Publisher · View at Google Scholar · View at Scopus
  3. V. Feddern, Z. Yang, X. Xu, E. Badiale-Furlong, and L. A. De Souza-Soares, “Synthesis of octyl dihydrocaffeate and its transesterification with tricaprylin catalyzed by Candida antarctica lipase,” Industrial and Engineering Chemistry Research, vol. 50, no. 12, pp. 7183–7190, 2011. View at Publisher · View at Google Scholar · View at Scopus
  4. D. G. Hayes, “Enzyme-catalyzed modification of oilseed materials to produce eco-friendly products,” Journal of the American Oil Chemists' Society, vol. 81, no. 12, pp. 1077–1103, 2004. View at Google Scholar · View at Scopus
  5. 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 and Microbial Technology, vol. 40, no. 6, pp. 1451–1463, 2007. View at Publisher · View at Google Scholar · View at Scopus
  6. N. Miletić, R. Rohandi, Z. Vuković, A. Nastasović, and K. Loos, “Surface modification of macroporous poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate) resins for improved Candida antarctica lipase B immobilization,” Reactive and Functional Polymers, vol. 69, no. 1, pp. 68–75, 2009. View at Publisher · View at Google Scholar · View at Scopus
  7. M. Y. Arica, H. Soydogan, and G. Bayramoglu, “Reversible immobilization of Candida rugosa lipase on fibrous polymer grafted and sulfonated p(HEMA/EGDMA) beads,” Bioprocess and Biosystems Engineering, vol. 33, no. 2, pp. 227–236, 2010. View at Publisher · View at Google Scholar · View at Scopus
  8. Z. D. Knežević, S. S. Šiler-Marinković, and V. L. Mojović, “Immobilized lipases as practical catalysts,” Acta Periodica Technologica, vol. 35, pp. 151–164, 2004. View at Publisher · View at Google Scholar
  9. S. S. Kanwar, G. S. Chauhan, S. S. Chimni, S. Chauhan, G. S. Rawat, and R. K. Kaushal, “Methacrylic acid and dodecyl methacrylate (MAc-DMA) hydrogel for enhanced catalytic activity of lipase of Bacillus coagulans MTCC-6375,” Journal of Applied Polymer Science, vol. 100, no. 2, pp. 1420–1426, 2006. View at Publisher · View at Google Scholar · View at Scopus
  10. S. S. Kanwar, H. K. Verma, R. K. Kaushal et al., “Effect of solvents and kinetic parameters on synthesis of ethyl propionate catalysed by poly (AAc-co-HPMA-cl-MBAm)-matrix-immobilized lipase of Pseudomonas aeruginosa BTS-2,” World Journal of Microbiology and Biotechnology, vol. 21, no. 6-7, pp. 1037–1044, 2005. View at Publisher · View at Google Scholar · View at Scopus
  11. L. Cao, “Immobilised enzymes: science or art?” Current Opinion in Chemical Biology, vol. 9, no. 2, pp. 217–226, 2005. View at Publisher · View at Google Scholar · View at Scopus
  12. L. Betancor, F. López-Gallego, A. Hidalgo et al., “Different mechanisms of protein immobilization on glutaraldehyde activated supports: effect of support activation and immobilization conditions,” Enzyme and Microbial Technology, vol. 39, no. 4, pp. 877–882, 2006. View at Publisher · View at Google Scholar · View at Scopus
  13. M. Nasratun, H. A. Said, A. Noraziah, and A. N. Abd Alla, “Immobilization of lipase from Candida rugosa on chitosan beads for transesterification reaction,” American Journal of Applied Sciences, vol. 6, no. 9, pp. 1653–1657, 2009. View at Publisher · View at Google Scholar · View at Scopus
  14. S. S. Betigeri and S. H. Neau, “Immobilization of lipase using hydrophilic polymers in the form of hydrogel beads,” Biomaterials, vol. 23, no. 17, pp. 3627–3636, 2002. View at Publisher · View at Google Scholar · View at Scopus
  15. R. Awang, M. R. Ghazuli, and M. Basri, “Immobilization of lipase from Candida rugosa on palm-based polyurethane foam as a support material,” The American Journal of Biochemistry and Biotechnology, vol. 3, pp. 163–166, 2007. View at Google Scholar
  16. S. Zhu, Y. Wu, and Z. Yu, “Immobilization of Candida rugosa lipase on a pH-sensitive support for enantioselective hydrolysis of ketoprofen ester,” Journal of Biotechnology, vol. 117, no. 1, pp. 397–401, 2005. View at Publisher · View at Google Scholar · View at Scopus
  17. N. Milašinović, N. Milosavljević, J. Filipović, Z. Knežević-Jugović, and M. K. Krušić, “Synthesis, characterization and application of poly(N-isopropylacrylamide-co-itaconic acid) hydrogels as supports for lipase immobilization,” Reactive and Functional Polymers, vol. 70, pp. 807–814, 2010. View at Google Scholar
  18. C. E. Orrego, N. Salgado, J. S. Valencia, G. I. Giraldo, O. H. Giraldo, and C. A. Cardona, “Novel chitosan membranes as support for lipases immobilization: characterization aspects,” Carbohydrate Polymers, vol. 79, no. 1, pp. 9–16, 2010. View at Publisher · View at Google Scholar · View at Scopus
  19. X.-J. Huang, A.-G. Yu, and Z.-K. Xu, “Covalent immobilization of lipase from Candida rugosa onto poly(acrylonitrile-co-2-hydroxyethyl methacrylate) electrospun fibrous membranes for potential bioreactor application,” Bioresource Technology, vol. 99, no. 13, pp. 5459–5465, 2008. View at Publisher · View at Google Scholar · View at Scopus
  20. D. S. Rodrigues, A. A. Mendes, W. S. Adriano, L. R. B. Gonçalves, and R. L. C. Giordano, “Multipoint covalent immobilization of microbial lipase on chitosan and agarose activated by different methods,” Journal of Molecular Catalysis B, vol. 51, no. 3-4, pp. 100–109, 2008. View at Publisher · View at Google Scholar · View at Scopus
  21. A. I. S. Brígida, A. D. T. Pinheiro, A. L. O. Ferreira, G. A. S. Pinto, and L. R. B. Gonçalves, “Immobilization of Candida antarctica lipase B by covalent attachment to green coconut fiber,” Appl Biochem Biotechnol, vol. 136, pp. 67–80, 2007. View at Google Scholar
  22. G. S. Chauhan, S. Mahajan, K. M. Sddiqui, and R. Gupta, “Immobilization of lipase on hydrogels: structural aspects of polymeric matrices as determinants of enzyme activity in different physical environments,” Journal of Applied Polymer Science, vol. 92, no. 5, pp. 3135–3143, 2004. View at Publisher · View at Google Scholar · View at Scopus
  23. I. Hirata, M. Okazaki, and H. Iwata, “Simple method for preparation of ultra-thin poly(N-isopropylacrylamide) hydrogel layers and characterization of their thermo-responsive properties,” Polymer, vol. 45, no. 16, pp. 5569–5578, 2004. View at Publisher · View at Google Scholar · View at Scopus
  24. O. H. Lowry, N. J. Rosenbrough, A. L. Farr, and R. J. Randall, “Protein measurement with the Folin phenol reagent,” The Journal of Biological Chemistry, vol. 193, no. 1, pp. 265–275, 1951. View at Google Scholar · View at Scopus
  25. N. W. Tietz and E. A. Fiereck, “A specific method for serum lipase determination,” Clinica Chimica Acta, vol. 13, no. 3, pp. 352–358, 1966. View at Google Scholar · View at Scopus
  26. H. Segel, Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady-State Enzyme Systems, John Wiley & Sons, New York, NY, USA, 1975.
  27. D. Bezbradica, D. Mijin, S. Siler-Marinkovic, and Z. Knezevic, “The Candida rugosa lipase catalyzed synthesis of amyl isobutyrate in organic solvent and solvent-free system: a kinetic study,” Journal of Molecular Catalysis B, vol. 38, no. 1, pp. 11–16, 2006. View at Publisher · View at Google Scholar · View at Scopus
  28. N. Milašinović, Z. Knežević-Jugović, Ž. Jakovljević, J. Filipović, and M. Kalagasidis Krušić, “Synthesis of n-amyl isobutyrate catalyzed by Candida rugosa lipase immobilized into poly(N-isopropylacrylamide-co-itaconic acid) hydrogels,” Chemical Engineering Journal, vol. 181-182, pp. 614–623, 2012. View at Publisher · View at Google Scholar · View at Scopus
  29. J. Mudassir and N. M. Ranjha, “Dynamic and equilibrium swelling studies: crosslinked pH sensitive methyl methacrylate-co-itaconic acid (MMA-co-IA) hydrogels,” Journal of Polymer Research, vol. 15, no. 3, pp. 195–203, 2008. View at Publisher · View at Google Scholar · View at Scopus
  30. A. Qin, M. Lu, Q. Liu, and P. Zhang, “Synthesis and characterization of thermo-sensitive poly (N-isopropylacrylamide) hydrogel with fast response rate,” Frontiers of Chemistry in China, vol. 2, no. 2, pp. 135–139, 2007. View at Publisher · View at Google Scholar · View at Scopus
  31. S. Braun, S. Rappoport, R. Zusman, D. Avnir, and M. Ottolenghi, “Biochemically active sol-gel glasses: the trapping of enzymes,” Materials Letters, vol. 10, no. 1-2, pp. 1–5, 1990. View at Google Scholar · View at Scopus
  32. M. T. Reetz, A. Zonta, V. Vijayakrishnan, and K. Schimossek, “Entrapment of lipases in hydrophobic magnetite-containing sol-gel materials: magnetic separation of heterogeneous biocatalysts,” Journal of Molecular Catalysis A, vol. 134, no. 1–3, pp. 251–258, 1998. View at Publisher · View at Google Scholar · View at Scopus
  33. S. Shtelzer, S. Rappoport, D. Avnir, M. Ottolenghi, and S. Braun, “Properties of trypsin and of acid phosphatase immobilized in sol-gel glass matrices,” Biotechnology and applied biochemistry, vol. 15, no. 3, pp. 227–235, 1992. View at Google Scholar · View at Scopus
  34. J.-P. Chen, “Production of ethyl butyrate using gel-entrapped Candida cylindracea lipase,” Journal of Fermentation and Bioengineering, vol. 82, no. 4, pp. 404–407, 1996. View at Publisher · View at Google Scholar · View at Scopus
  35. H. W. Yu, H. Chen, Y. Y. Yang, and C. B. Ching, “Effect of salts on activity, stability and enantioselectivity of Candida rugosa lipase in isooctane,” Journal of Molecular Catalysis B, vol. 35, no. 1–3, pp. 28–32, 2005. View at Publisher · View at Google Scholar · View at Scopus
  36. B. C. Páez, A. R. Medina, F. C. Rubio, P. G. Moreno, and E. M. Grima, “Modeling the effect of free water on enzyme activity in immobilized lipase-catalyzed reactions in organic solvents,” Enzyme and Microbial Technology, vol. 33, no. 6, pp. 845–853, 2003. View at Publisher · View at Google Scholar · View at Scopus
  37. M. Karra-Châabouni, I. Bouaziz, S. Boufi, A. M. Botelho do Rego, and Y. Gargouri, “Physical immobilization of Rhizopus oryzae lipase onto cellulose substrate: activity and stability studies,” Colloids and Surfaces B, vol. 66, no. 2, pp. 168–177, 2008. View at Publisher · View at Google Scholar · View at Scopus
  38. M. L. Foresti, M. Pedernera, V. Bucalá, and M. L. Ferreira, “Multiple effects of water on solvent-free enzymatic esterifications,” Enzyme and Microbial Technology, vol. 41, no. 1-2, pp. 62–70, 2007. View at Publisher · View at Google Scholar · View at Scopus
  39. P. J. Halling, “Thermodynamic predictions for biocatalysis in nonconventional media: theory, tests, and recommendations for experimental design and analysis,” Enzyme and Microbial Technology, vol. 16, no. 3, pp. 178–206, 1994. View at Publisher · View at Google Scholar · View at Scopus
  40. R. Dave and D. Madamwar, “Candida rugosa lipase immobilized in Triton-X100 microemulsion based organogels (MBGs) for ester synthesis,” Process Biochemistry, vol. 43, no. 1, pp. 70–75, 2008. View at Publisher · View at Google Scholar · View at Scopus
  41. M. B. A. Rahman, U. H. Zaidan, M. Basri, M. Z. Hussein, R. N. Z. R. A. Rahman, and A. B. Salleh, “Enzymatic synthesis of methyl adipate ester using lipase from Candida rugosa immobilised on Mg, Zn and Ni of layered double hydroxides (LDHs),” Journal of Molecular Catalysis B, vol. 50, no. 1, pp. 33–39, 2008. View at Publisher · View at Google Scholar · View at Scopus
  42. G. D. Yadav and P. S. Lathi, “Kinetics and mechanism of synthesis of butyl isobutyrate over immobilised lipases,” Biochemical Engineering Journal, vol. 16, no. 3, pp. 245–252, 2003. View at Publisher · View at Google Scholar · View at Scopus
  43. D. Bezbradica, M. Stojanović, D. Veličković et al., “Kinetic model of lipase-catalyzed conversion of ascorbic acid and oleic acid to liposoluble vitamin C ester,” Biochemical Engineering Journal, vol. 71, pp. 89–96, 2013. View at Publisher · View at Google Scholar