Skip to main content

Solvent-Free Biotransformations of Lipids

  • Protocol
Enzymes in Nonaqueous Solvents

Part of the book series: Methods in Biotechnology ((MIBT,volume 15))

Abstract

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).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Protocol
USD 49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Zaks, A. and Klibanov, A. M. (1984) Enzymatic catalysis in organic media at 100υC. Science 224, 1249–1251.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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. 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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  16. Adelhorst, K., Björkling, F., Godtfredsen, S. E., and Kirk, O. (1990) Enzymecatalyzed preparation of 6-O-acylglucopyrasides. Synthesis 112–115.

    Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  19. Fregapane, G., Sarney, D. B., and Vulfson, E. N. (1994) Facile chemo-enzymatic synthesis of monosaccharide fatty acid esters. Biocatalysis 11, 9–18.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  21. Yamane, T. (1987) Enzyme technology for the lipids industry: an engineering overview. J. Am. Oil Chem. Soc. 64, 1657–1662.

    Article  CAS  Google Scholar 

  22. Yamane, T., Kozima, Y., Ichiryu, T., and Shimizu, S. (1988) Biocatalysis in microaqueous organic solvent. Ann. NYAcad. Sci. 542, 282–293.

    Article  CAS  Google Scholar 

  23. Yamane, T. (1988) Importance of moisture content control for enzymatic reactions in organic solvents: a novel concept of “microaqueous.” Biocatalysis 2, 1–9.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2001 Humana Press Inc.

About this protocol

Cite this protocol

Yamane, T. (2001). Solvent-Free Biotransformations of Lipids. In: Vulfson, E.N., Halling, P.J., Holland, H.L. (eds) Enzymes in Nonaqueous Solvents. Methods in Biotechnology, vol 15. Humana Press. https://doi.org/10.1385/1-59259-112-4:509

Download citation

  • DOI: https://doi.org/10.1385/1-59259-112-4:509

  • Publisher Name: Humana Press

  • Print ISBN: 978-0-89603-929-2

  • Online ISBN: 978-1-59259-112-1

  • eBook Packages: Springer Protocols

Publish with us

Policies and ethics