LIPASE-CATALYZED SYNTHESIS OF STRUCTURED LIPIDS IN POLAR SOLVENTS (original) (raw)

Abstract

The effect of acetone on structured lipid synthesis by Lipozyme IM60 in n-hexane was studied. Transesterification of tristearin with capric, lauric, myristic, palmitic and oleic acids was performed individually and in combinations at equal mole ratios. Higher incorporation of oleic acid was observed with the addition of acetone when compared to other fatty acids. Incorporation of capric acid decreased with increase in acetone concentration. The overall activity of enzyme decreased in acetone compared to n-hexane.

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References (18)

  1. ARROYO, M., MORENO, M.J. and SINISTERRA, J.V. 1995. Alteration of the activity and selectivity of immobilized lipases by the effect of the amount of water in the organic medium. J. Mol. Catal. A-Chem. 97, 195-201.
  2. BELLOT, J.C., CHOISNARD, L., CASTILLO, E. and MARTY, A. 2001. Combining solvent engineering and thermodynamic modeling to enhance selectivity during monoglyceride synthesis by lipase-catalyzed esterification. Enzyme Microb. Technol. 28. 362-369.
  3. DOSSAT, V., COMBES, D. and MARTY, A. 1999. Continuous enzymatic transesterification of high oleic sunflower oil in a packed bed reactor: influence of the glycerol production. Enzyme Microb. Technol. 25, 194-200.
  4. F E W E R , P., GUEGAN, P., YVERGNAUX, F., CALLEGARI, J.P., DUFOSSE, L. and BINET, A. 2001. Evaluation of regioselectivity of lipases based on synthesis reaction conducted with propyl alcohol, isopropyl alcohol and propylene glycol. J. Mol. Catal. B-Enzym. 11, 445-453.
  5. FOMUSO, L.B. and AKOH, C.C. 1998. Structured lipids: Lipase-catalyzed interesterification oftricaproin and trilinolein. J. Am. Oil Chem. SOC. 75,405-410.
  6. GAO, X.G., CAO, S.G. and ZHANG, K.C. 1997. The influence of different physicochemical parameters of the solvent on the activity and selectivity of lipase. Acta. Biochim. Biophys. Sinica (Chinese) 29, 337-342.
  7. HARALDSSON, G.G., KRISTINSSON, B., SIGURDARDOTTIR. R., GUDMUNDSSON, G.G. and BREIVIK, H. 1997. The preparation of concentrates of eicosapentaenoic acid and docosahexaenoic acid by lipase-catalyzed transesterification of fish oil with ethanol. J. Am. Oil Chem. SOC. 74, 1419-1424.
  8. JAASKELAINEN, S., VERMA, C.S., HUBBARD, R.E. and CAVES, L.S.D. 1999. Identifying key electrostatic interactions in Rhizomucor miehei lipase: the influence of solvent dielectric. Theor. Chem. Acc. 101, 175-179.
  9. LEE, K.T. and AKOH, C.C. 1998. Structured lipids: Synthesis and applications. Food Rev. Intern. 14, 17-34.
  10. MACKENZIE, A.D. and STEVENSON, D.E. 1995. Modification of the nutritional properties of fats using lipase-catalyzed directed interesterification. Biotechnol. Lett. 17. 383-388.
  11. MURALIDHAR, R.V., MARCHANT, R. and NIGAM, P. 2001. Lipases in racemic resolutions. J. Chem. Technol. Biotechnol. 7, 3-8.
  12. NAGAO, T., SHIMADA, Y., SUGIHARA, A., MURATA, A., KOMEMUSHI, S. and TOMINAGA, Y. 2001. Use of thermostable Fusarium heterosporum lipase for production of structured lipid containing oleic and palmitic acids in organic solvent- free system. J. Am. Oil Chem. SOC. 78, 167-1 72.
  13. RAHMATULLA, M.S.K., SHUKLA, V.K.S. and MUKHERJEE, K.D. 1994. Enrichment of y-linolenic acid from evening primrose oil and borage oil via lipase- catalyzed hydrolysis. J. Am. Oil Chem. SOC. 71, 569-573.
  14. REIMANN, A., ROBB, D.A. and HALLING, P.J. 1994. Solvation of cbz-amino acid nitrophenyl eaters in organic media and the kinetics of their transesterification by subtilisin. Biotechnol. Bioeng. 43, 1081-1086. 1993. Marked dependence of enzyme prochiral selectivity on the solvent. J. Am. Chem. SOC. 115,390-396.
  15. UEJI, S., FUJINO, R., OKUBO, N., MIYAZAWA, T., KURITA, S., KITADANI, M. and MUROMATSU, A. 1992. Solvent-induced inversion of enantioselectivity in lipase-catalyzed esterification of 2-phenoxypropionic acids. Biotechnol. Lett. 14, WATANABE, Y., MIYAWAKI, Y., ADACHI, S., NAKANISHI, K. and MATSUNO, R. 2000. Synthesis of lauroyl saccharides through lipase-catalyzed condensation in microaqueous water-miscible solvents. J. Mol. Catal. B-Enzym. 10, 241 -247.
  16. WEHTJE, E., COSTES, D. and ADLERCREUTZ, P. 1997. Enantioselectivity of lipases: effects of water activity. J. Mol. Catal. B-Enzym. 3, 221-230.
  17. WESCOIT, C.R. and KLIBANOV, A.M. 1993. Solvent variation inverts substrate- specificity of an enzyme. J. Am. Chem. SOC. I IS, 1629-1631.
  18. TERRADAS, F., TESTON-HENRY, M., FITZPATRICK, P.A. and KLIBANOV, A.M. 163-168.