Solvent-Free Biotransformations of Lipids

  • Tsuneo Yamane
Part of the Methods in Biotechnology book series (MIBT, volume 15)


Although it has not been explicitly recognized in the literature, biotransformations in organic media can be classified as either solvent-based or solvent-free reactions. In the former systems, one or more substrates are dissolved in an inert organic solvent that does not participate in the reaction in any respect, but to provide an environment for the enzyme to exert its action on the dissolved substrate(s). In a solvent-free system, no other compounds but substrate(s) and enzyme are present in a reactor. In principle, one substrate can be used in a large excess over another and, if so, it may also act as a solvent for other reactants. Examples of such “neat” biotransformations can be found even in the early literature (1-3).


Caprylic Acid Saturated Salt Solution Molar Yield Partial Glyceride Miehei Lipase 
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  1. 1.
    Zaks, A. and Klibanov, A. M. (1984) Enzymatic catalysis in organic media at 100υC. Science 224, 1249–1251.CrossRefGoogle Scholar
  2. 2.
    Yamane, T., Hoq, M. M., Itoh, S., and Shimizu, S. (1986) Glycerolysis of fat by lipase. J. Jpn. Oil Chem. Soc. 35, 625–631.Google Scholar
  3. 3.
    Hirata, H., Higuchi, K., and Yamashina, T. (1989) Enzyme reaction in organic solvent. III. Effect of water content and inhibition of alcohol for the lipase catalyzed transesterification in tributyrin and 1-octanol. J. Jpn. Oil Chem. Soc. 38, 48–52.Google Scholar
  4. 4.
    McNeill, G. P., Shimizu, S., and Yamane, T. (1990) Solid phase enzymatic glycerolysis of beef tallow resulting in a high yield of monoglycerides. J. Am. Oil Chem. Soc. 67, 779–783.CrossRefGoogle Scholar
  5. 5.
    McNeill, G. P., Shimizu, S., and Yamane, T. (1991) High yield enzymatic glycerolysis of fats and oils. J. Am. Oil Chem. Soc. 68, 1–5.CrossRefGoogle Scholar
  6. 6.
    McNeill, G. P. and Yamane, T. (1991) Further improvements in the yield of monoglycerides during enzymatic glycerolysis of fats and oils. J. Am. Oil Chem. Soc. 68, 6–10.CrossRefGoogle Scholar
  7. 7.
    Yamane, T., Kang, S.-T., Kawahara, K., and Koizumi, Y. (1994) High-yield diacylglycerol formation by solid-phase enzymatic glycerolysis of hydrogenated beef tallow. J. Am. Oil Chem. Soc. 71, 339–342.CrossRefGoogle Scholar
  8. 8.
    Bornsheuer, U. T. and Yamane, T. (1994) Activity and stability of lipase in the solid-phase glycerolysis of triolein. Enzyme Microb. Technol. 16, 864–869.CrossRefGoogle Scholar
  9. 9.
    Rosu, R., Uozaki, Y., Iwasaki, Y., and Yamane, T. (1997) Repeated use of immobilized lipase for monoacylglycerol production by solid phase glycerolysis of olive oil. J. Am. Oil Chem. Soc. 74, 445–450.CrossRefGoogle Scholar
  10. 10.
    Yamane, T., Suzuki, T., Sahashi, Y., Vikersveen, L., and Hoshino, T. (1992) of polyunsaturated fatty acid enriched fish oil by lipase-catalyzed acidolysis without solvent. J. Am. Oil Chem. Soc. 69, 1104–1107.CrossRefGoogle Scholar
  11. 11.
    Yamane, T., Suzuki, T., and Hoshino, T. (1993) Increasing n-3 polyunsaturated fatty acid content offish oil by temperature control of lipase-catalyzed acidolysis. J. Am. Oil Chem. Soc. 70, 1285–1287.CrossRefGoogle Scholar
  12. 12.
    Vulfson, E. N., Gill, I., and Sarney, D. B. (1996) Productivity of enzymatic catalysis in non-aqueous media: New concepts. Section 9.2. Enzymatic solvent-free synthesis, in Enzymatic Reactions in Organic Media (Koskinen, A. M. P. and Klibanov, A. M., eds.), Blackie Academic & Professional, Glasgow, pp. 245–254.Google Scholar
  13. 13.
    Lee, K.-T. and Akoh, C. C. (1998) Solvent-free enzymatic synthesis of structured lipids from peanut oil and caprylic acid in a stirred tank batch reactor. J. Am. Oil Chem. Soc. 75, 1533–1537.CrossRefGoogle Scholar
  14. 14.
    Iwasaki, Y., Han, J.-J., Narita, M., Rosu, R., and Yamane, T. (1999) Enzymatic synthesis of structured lipids from single cell oil of high docosahexaenoic acid content. J. Am. Oil Chem. Soc. 76, 563–569.CrossRefGoogle Scholar
  15. 15.
    Christensen, M. S., Høy, C.-E., Becker, C. C., and Redgrave, T. G. (1995) Intestinal absorption and lymphatic transport of eicosapentaenoic (EPA), docosahexaenoic (DHA), and decanoic acids: dependence on intramolecular triacylglycerol structure. Am. J. Clin. Nutr. 61, 56–61.Google Scholar
  16. 16.
    Adelhorst, K., Björkling, F., Godtfredsen, S. E., and Kirk, O. (1990) Enzymecatalyzed preparation of 6-O-acylglucopyrasides. Synthesis 112–115.Google Scholar
  17. 17.
    Fregapane, G., Sarney, D. B., and Vulfson, E. N. (1991) Enzymatic solvent-free synthesis of sugar acetal fatty acid esters. Enzyme Microb. Technol. 13, 796–800.CrossRefGoogle Scholar
  18. 18.
    Fregapane, G., Sarney, D. B., Greenberg, S. G., Knight, D. J., and Vulfson, E. N. (1994) Enzymatic synthesis of mono sac charide fatty acid esters and their comparison with conventional products. J. Am. Oil Chem. Soc. 71, 87–91.CrossRefGoogle Scholar
  19. 19.
    Fregapane, G., Sarney, D. B., and Vulfson, E. N. (1994) Facile chemo-enzymatic synthesis of monosaccharide fatty acid esters. Biocatalysis 11, 9–18.CrossRefGoogle Scholar
  20. 20.
    Sarney, D. B., Kapeller, H., Fregapane, G., and Vulfson, E. N. (1994) Chemo-enzymatic synthesis of disaccharide fatty acid esters. J. Am. Oil Chem. Soc. 71, 711–714.CrossRefGoogle Scholar
  21. 21.
    Yamane, T. (1987) Enzyme technology for the lipids industry: an engineering overview. J. Am. Oil Chem. Soc. 64, 1657–1662.CrossRefGoogle Scholar
  22. 22.
    Yamane, T., Kozima, Y., Ichiryu, T., and Shimizu, S. (1988) Biocatalysis in microaqueous organic solvent. Ann. NYAcad. Sci. 542, 282–293.CrossRefGoogle Scholar
  23. 23.
    Yamane, T. (1988) Importance of moisture content control for enzymatic reactions in organic solvents: a novel concept of “microaqueous.” Biocatalysis 2, 1–9.CrossRefGoogle Scholar
  24. 24.
    Bornscheuer, U. T. and Yamane, T. (1995) Fatty acid vinylesters as acylating agents: a new method for the enzymatic synthesis of monoacylglycerols. J. Am. Oil Chem. Soc. 72, 193–197.CrossRefGoogle Scholar
  25. 25.
    Han, J.-J., Iwasaki, Y., and Yamane, T. (1999) monitoring of lipase-catalyzed transesterification between eicosapentaenoic acid ethyl ester and tricaprylin by silver ion high-performance liquid chromatography and high-temperature gas chromatography. J. Am. Oil Chem. Soc. 76, 31–39.CrossRefGoogle Scholar
  26. 26.
    Rosu, R., Yasui, M., Iwasaki, Y., and Yamane, T. (1999) Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solventfree system. J. Am. Oil Chem. Soc. 76, 839–844.CrossRefGoogle Scholar
  27. 27.
    Tatara, T., Fujii, T., Kawase, T., and Minagawa, M. (1983) Quantitative determination of tri-,di-, monooleins and free oleic acid by the thin layer chromatography/flame ionization detector system using internal standards and boric acid impregnated chromarod. Lipids 18, 732–736.CrossRefGoogle Scholar

Copyright information

© Humana Press Inc. 2001

Authors and Affiliations

  • Tsuneo Yamane
    • 1
  1. 1.Laboratory of Molecular Biotechnology, Graduate School of Bio- and Agro-SciencesNagoya UniversityNagoyaJapan

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