Enzymic synthesis of fatty esters by hydrophobic lipase derivatives immobilized on organic polymer beads

Abstract

Lipase fromCandida rugosa was modified with several hydrophobic modifiers before being adsorbed onto organic polymer beads. The effects of different enzyme modifiers, supports, solvents, reaction temperatures, fatty acids, and alcohols on the activity of the immobilized enzyme were investigated. The immobilized lipases were good biocatalysts for esterification reactions in organic solvents. They exhibited high activities in all solvents tested, including polar solvents. The activity seemed to depend on the type of support rather than on the modifier of the enzyme. The medium polar support, XAD7, appeared to be the best for the modified lipases. The immobilized lipase favored the medium-chain fatty acids rather than the long-chain fatty acids as acyl donors. The alcohol selectivity of the enzyme was unchanged upon immobilization. The native and immobilized lipases favored the short-chain and terpene alcohols as nucleophiles.

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References

  1. 1.

    Choo, S., and J.S. Rhee,Biotechnol. Bioengin. 41:204 (1993).

    Article  Google Scholar 

  2. 2.

    Ruckenstein, E., and X. Wang, Ibid.:821 (1993).

    Article  CAS  Google Scholar 

  3. 3.

    Basri, M., K. Ampon, W.M.Z. Wan Yunus, C.N.A. Razak and A.B. Salleh,J. Chem. Technol. Biotechnol. 59:37 (1994).

    Article  CAS  Google Scholar 

  4. 4.

    Basri, M., A.B. Salleh, K. Ampon, W.M.Z. Wan Yunus and C.N.A. Razak,Biocatalysis 4:313 (1991).

    CAS  Google Scholar 

  5. 5.

    Ampon, K., A.B. Salleh, F. Salam, W.M.Z. Wan Yunus, C.N.A. Razak and M. Basri,Enzyme Microb. Technol. 13:597 (1991).

    Article  CAS  Google Scholar 

  6. 6.

    Basri, M., K. Ampon, W.M.Z. Wan Yunus, C.N.A. Razak and A.B. Salleh,J. Am. Oil Chem. Soc. 69:579 (1992).

    CAS  Google Scholar 

  7. 7.

    Wofsy, M., and S.J. Singer,Biochem. 21:104 (1963).

    Google Scholar 

  8. 8.

    Hazra, A.K., S.P. Chock and R.W. Albers,Analyt. Biochem. 137:437 (1985).

    Article  Google Scholar 

  9. 9.

    Fields, R.,Biochem. J. 124:581 (1972).

    Google Scholar 

  10. 10.

    Malcata, F.X., H.R. Reyes, H.S. Garcia, C.J.G. Hill and C.H. Amundson,J. Am. Oil Chem. Soc. 67:890 (1990).

    Article  CAS  Google Scholar 

  11. 11.

    Laane, C., S. Boeren, K. Vos and C. Veeger,Biotechnol. Bioengin. 30:81 (1986).

    Article  Google Scholar 

  12. 12.

    Basri, M., K. Ampon, W.M.Z. Wan Yunus, C.N.A. Razak and A.B. Salleh,Appl. Biochem. Biotechnol. 48:158 (1994).

    Google Scholar 

  13. 13.

    Gorman, L.A., and J.S. Dordick,Biotechnol. Bioengin. 39:392 (1992).

    Article  CAS  Google Scholar 

  14. 14.

    Bar-Eli, A., and E. Katchalski,J. Biol. Chem. 238:1690 (1963).

    CAS  Google Scholar 

  15. 15.

    Glassmeyer, C.K., and J.D. Ogle,Biochem. 10:786 (1971).

    Article  CAS  Google Scholar 

  16. 16.

    Koshiro, S., K. Sonomoto, A. Tanaka and S. Fukui,J. Biotechnol. 2:47 (1985).

    Article  CAS  Google Scholar 

  17. 17.

    Kawamoto, T., K. Sonomoto and A. Tanaka,Biocatalysis I:137 (1987).

    Google Scholar 

  18. 18.

    Cabezas, M.J., C. Del Campo, E. Llama and J.V. Sinisterra,J. Molec. Catalysis 71:261 (1992).

    Article  CAS  Google Scholar 

  19. 19.

    Hills, M., I. Kiewitt and K. Mukherjee,J. Am. Oil Chem. Soc. 67:561 (1990).

    Article  CAS  Google Scholar 

  20. 20.

    Pan, S., T. Kawamoto, T. Fukui, K. Sonomoto and A. Tanaka,Appl. Microbiol. Biotechnol. 34:47 (1990)

    Article  CAS  Google Scholar 

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Correspondence to M. Basri.

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Basri, M., Ampon, K., Wan Yunus, W.M.Z. et al. Enzymic synthesis of fatty esters by hydrophobic lipase derivatives immobilized on organic polymer beads. J Am Oil Chem Soc 72, 407–411 (1995). https://doi.org/10.1007/BF02636079

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Key words

  • Esterification
  • hydrophobic
  • immobilization
  • immobilized enzyme
  • lipase modification
  • selectivity
  • supports