Table of Contents Author Guidelines Submit a Manuscript
Enzyme Research
Volume 2011 (2011), Article ID 718949, 8 pages
http://dx.doi.org/10.4061/2011/718949
Research Article

Synthesis of Isopropyl Ferulate Using Silica-Immobilized Lipase in an Organic Medium

Department of Biotechnology, Himachal Pradesh University, Summer Hill, Shimla 171 005, India

Received 11 November 2010; Revised 22 January 2011; Accepted 11 February 2011

Academic Editor: Alane Beatriz Vermelho

Copyright © 2011 Ashok Kumar and Shamsher Singh Kanwar. 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. S. S. Kanwar, R. K. Kaushal, M. L. Verma et al., “Synthesis of ethyl laurate by hydrogel immobilized lipase of Bacillus coagulans MTCC-6375,” Indian Journal of Microbiology, vol. 45, no. 3, pp. 187–193, 2005. View at Google Scholar · View at Scopus
  2. M. L. Verma and S. S. Kanwar, “Lipases,” in Wiley Encyclopedia of Industrial Biotechnology: Bioprocess, Bioseparation, and Cell Technology, vol. 5, pp. 3550–3565, 2010. View at Google Scholar
  3. H. Hirakawa, N. Kamiya, Y. Kawarabayashi, and T. Nagamune, “Log P effect of organic solvents on a thermophilic alcohol dehydrogenase,” Biochimica et Biophysica Acta, vol. 1748, no. 1, pp. 94–99, 2005. View at Publisher · View at Google Scholar
  4. S. S. Kanwar, M. Srivastava, S. S. Chimni, I. A. Ghazi, R. K. Kaushal, and G. K. Joshi, “Properties of an immobilized lipase of Bacillus coagulans BTS-1,” Acta Microbiologica et Immunologica Hungarica, vol. 51, no. 1-2, pp. 57–73, 2004. View at Google Scholar · View at Scopus
  5. D. L. Compton, “Sunscreens based on vegetable oil,” Lipid Technology, vol. 17, pp. 276–279, 2005. View at Google Scholar
  6. B. Halliwell, “Antioxidant characterization. Methodology and mechanism,” Biochemical Pharmacology, vol. 49, no. 10, pp. 1341–1348, 1995. View at Publisher · View at Google Scholar · View at Scopus
  7. J. S. Wright, E. R. Johnson, and G. A. DiLabio, “Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants,” Journal of the American Chemical Society, vol. 123, no. 6, pp. 1173–1183, 2001. View at Publisher · View at Google Scholar · View at Scopus
  8. I. Benoit, D. Navarro, N. Marnet et al., “Feruloyl esterases as a tool for the release of phenolic compounds from agro-industrial by-products,” Carbohydrate Research, vol. 341, no. 11, pp. 1820–1827, 2006. View at Publisher · View at Google Scholar · View at Scopus
  9. H. Kikuzaki, M. Hisamoto, K. Hirose, K. Akiyama, and H. Taniguchi, “The effect of trans-ferulic acid and gamma-oryzanol on ethanol-induced liver injury in C57BL mouse,” Journal of Agricultural and Food Chemistry, vol. 50, pp. 2161–2168, 2002. View at Google Scholar
  10. E. Graf, “Antioxidant potential of ferulic acid,” Free Radical Biology and Medicine, vol. 13, no. 4, pp. 435–448, 1992. View at Publisher · View at Google Scholar · View at Scopus
  11. A. F. G. Cicero and A. Gaddi, “Rice bran oil and γ-oryzanol in the treatment of hyperlipoproteinaemias and other conditions,” Phytotherapy Research, vol. 15, no. 4, pp. 277–289, 2001. View at Publisher · View at Google Scholar · View at Scopus
  12. T. Akihisa, K. Tasukawa, M. Yamaura et al., “Triterpene alcohol and sterol ferulates from rice bran and their antioxidant properties,” Journal of Agricultural and Food Chemistry, vol. 48, pp. 2313–2319, 2000. View at Google Scholar
  13. M. Reslow, P. Adlercreutz, and B. Mattiasson, “On the importance of the support material for bioorganic synthesis. Influence of water partition between solvent, enzyme and solid support in water-poor reaction media,” European Journal of Biochemistry, vol. 177, pp. 313–318, 1988. View at Google Scholar
  14. A. Zaks and A. M. Klibanov, “Enzymatic catalysis in nonaqueous solvents,” Journal of Biological Chemistry, vol. 263, no. 7, pp. 3194–3201, 1988. View at Google Scholar · View at Scopus
  15. T. Nishio, T. Chicano, and M. Kamimura, “Purification and some properties of lipase produced by Pseudomonas fragi,” Agricultural and Biological Chemistry, vol. 52, pp. 1203–1208, 1988. View at Google Scholar
  16. P. Vidinha, N. Harper, N. M. Micaelo et al., “Effect of immobilization support, water activity, and enzyme ionization state on cutinase activity and enantioselectivity in organic media,” Biotechnology and Bioengineering, vol. 85, no. 4, pp. 442–449, 2004. View at Publisher · View at Google Scholar
  17. U. K. Winkler and M. Stuckmann, “Glycogen, hyaluronate, and some other polysaccharides greatly enhance the formation of exolipase by Serratia marcescens,” Journal of Bacteriology, vol. 138, no. 3, pp. 663–670, 1979. View at Google Scholar · View at Scopus
  18. 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
  19. S. S. Kanwar, M. L. Verma, C. Maheshwari, S. Chauhan, S. S. Chimni, and G. S. Chauhan, “Properties of poly(AAc-co-HPMA-cl-EGDMA) hydrogel-bound lipase of Pseudomonas aeruginosa MTCC-4713 and its use in synthesis of methyl acrylate,” Journal of Applied Polymer Science, vol. 104, no. 1, pp. 183–191, 2007. View at Publisher · View at Google Scholar · View at Scopus
  20. M. J. Hills, I. Kiewitt, and K. D. Mukherjee, “Synthetic reactions catalyzed by immobilized lipase from oilseed rape (Brassica napus L.),” Applied Biochemistry and Biotechnology, vol. 27, no. 2, pp. 123–129, 1991. View at Publisher · View at Google Scholar · View at Scopus
  21. S. W. Park, Y. I. Kim, K. H. Chung, and S. W. Kim, “Improvement of stability of immobilized GL-7-ACA acylase through modification with glutaraldehyde,” Process Biochemistry, vol. 37, no. 2, pp. 153–163, 2001. View at Publisher · View at Google Scholar · View at Scopus
  22. J. M. Palomo, R. L. Segura, G. Fernandez-Lorente, R. Fernandez-Lafuente, and J. M. Guisán, “Glutaraldehyde modification of lipases adsorbed on aminated supports: a simple way to improve their behaviour as enantioselective biocatalyst,” Enzyme and Microbial Technology, vol. 40, no. 4, pp. 704–707, 2007. View at Publisher · View at Google Scholar · View at Scopus
  23. H. J. Chae, M. J. In, and E. Y. Kim, “Optimization of protease immobilization by covalent binding using glutaraldehyde,” Applied Biochemistry and Biotechnology. Part A, vol. 73, no. 2-3, pp. 195–204, 1998. View at Google Scholar · View at Scopus
  24. A. Kumar and S. S. Kanwar, “Synthesis of ethyl ferulate in organic medium using celite-immobilized lipase,” Bioresource Technology, vol. 102, no. 3, pp. 2162–2167, 2011. View at Publisher · View at Google Scholar
  25. R. G. Jensen, D. R. Galluzzo, and V. J. Bush, “Selectivity is an important characteristic of lipases (acylglycerol hydrolases),” Biocatalysis, vol. 3, pp. 307–317, 1990. View at Google Scholar
  26. U. T. Bornscheuer, “Lipase-catalyzed syntheses of monoacylglycerols,” Enzyme and Microbial Technology, vol. 17, no. 7, pp. 578–586, 1995. View at Publisher · View at Google Scholar · View at Scopus
  27. R. R. Klein, G. King, R. A. Moreau, G. P. McNeill, P. Villeneuve, and M. J. Haas, “Additive effects of acyl-binding site mutations on the fatty acid selectivity of Rhizopus delemar lipase,” Journal of the American Oil Chemists' Society, vol. 74, no. 11, pp. 1401–1407, 1997. View at Google Scholar · View at Scopus
  28. J. S. Rhee and S. J. Kwon, “Water activity control in lipase-catalyzed reaction system,” Journal of Microbiology and Biotechnology, vol. 8, no. 3, pp. 191–196, 1998. View at Google Scholar · View at Scopus
  29. C. H. Lee and K. L. Parkin, “Effect of water activity and immobilization on fatty acid selectivity for esterification reactions mediated by lipases,” Biotechnology and Bioengineering, vol. 75, no. 2, pp. 219–227, 2001. View at Publisher · View at Google Scholar · View at Scopus
  30. V. Dandavate, J. Jinjala, H. Keharia, and D. Madamwar, “Production, partial purification and characterization of organic solvent tolerant lipase from Burkholderia multivorans V2 and its application for ester synthesis,” Bioresource Technology, vol. 100, no. 13, pp. 3374–3381, 2009. View at Publisher · View at Google Scholar
  31. H. Konthanen, M. Tenkanen, R. Fagerstrom, and T. Reinikainen, “Characterization of steryl esterase activities in commercial lipase preprations,” Journal of Biotechnology, vol. 108, pp. 51–59, 2004. View at Google Scholar
  32. M. Tsuchiyama, T. Sakamoto, T. Fujita, S. Murata, and H. Kawasaki, “Esterification of ferulic acid with polyols using a ferulic acid esterase from Aspergillus niger,” Biochimica et Biophysica Acta, vol. 1760, no. 7, pp. 1071–1079, 2006. View at Publisher · View at Google Scholar · View at Scopus
  33. H. Kontkanen, M. Tenkanen, R. Fagerström, and T. Reinikainen, “Characterisation of steryl esterase activities in commercial lipase preparations,” Journal of Biotechnology, vol. 108, no. 1, pp. 51–59, 2004. View at Publisher · View at Google Scholar · View at Scopus
  34. M. L. Verma, G. S. Chauhan, and S. S. Kanwar, “Enzymatic synthesis of isopropyl myristate using immobilized lipase from Bacillus cereus MTCC 8372,” Acta Microbiologica et Immunologica Hungarica, vol. 55, no. 3, pp. 327–342, 2008. View at Publisher · View at Google Scholar · View at Scopus
  35. P. J. Halling, “Effects of water on equilibria catalysed by hydrolytic enzymes in biphasic reaction systems,” Enzyme and Microbial Technology, vol. 6, no. 11, pp. 513–516, 1984. View at Google Scholar · View at Scopus
  36. 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
  37. F. Chamouleau, D. Coulon, M. Girardin, and M. Ghoul, “Influence of water activity and water content on sugar esters lipase-catalyzed synthesis in organic media,” Journal of Molecular Catalysis B, vol. 11, no. 4–6, pp. 949–954, 2001. View at Publisher · View at Google Scholar · View at Scopus
  38. R. D. Sonwalkar, C. C. Chen, and LU. K. Ju, “Roles of silica gel in polycondensation of lactic acid in organic solvent,” Bioresource Technology, vol. 87, no. 1, pp. 69–73, 2003. View at Publisher · View at Google Scholar · View at Scopus
  39. R. N. Z. R. A. Rahman, S. N. Baharum, A. B. Salleh, and M. Basri, “S5 lipase: an organic solvent tolerant enzyme,” Journal of Microbiology, vol. 44, no. 6, pp. 583–590, 2006. View at Google Scholar · View at Scopus
  40. J. P. Glusker, A. K. Katz, and C. W. Bock, “Metal ions in biological systems,” The Rigaku Journal, vol. 16, pp. 8–16, 1999. View at Google Scholar