Advertisement

Chemoselective Amidification of Amino-Polyols Catalyzed with Lipases in Organic Solvents

  • Thierry Maugard
  • Magali Remaud-Simeon
  • Pierre Monsan
Part of the Methods in Biotechnology book series (MIBT, volume 15)

Abstract

Glycamide surfactants are nonionic surfactants in which the hydrophilic moiety (an amino-alditol derivative) and the hydrophobic moiety (a fatty acid) are linked via an amide bond (1). Such sugar fatty amide surfactants can be obtained by chemical synthesis, using the Schotten-Baumann reaction between an amino-alditol and a fatty acid chloride in aqueous alkaline medium. An important drawback of this approach is the formation of salts by neutralization.

Keywords

Fatty Acid Methyl Ester Ester Synthesis Ethyl Lactate Differential Refractometer Candida Antarctica Lipase 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Hildreth, J. (1982) N-D-Gluco-N-methylalkanamide compounds, a new class of non-ionic detergents for membrane biochemistry. Biochem. J. 207, 363–366.Google Scholar
  2. 2.
    Matos, J. R., Blair West, J., and Wong, C. H. (1987) Lipase catalysed synthesis of peptides: preparation of a Penicillin G precursor and other peptides. Biotechnol. Lett., 9, 233–236.CrossRefGoogle Scholar
  3. 3.
    Inada, Y., Nishimura, H., Takahashi, K., Yoshimoto, T., Ranjan Saha, A., and Saito, Y. (1984) Ester synthesis catalysed by polyethylene glycol modified lipase in benzene. Biochem. Biophys. Res. Commun. 122, 845–850.CrossRefGoogle Scholar
  4. 4.
    Zacks, A. and Klibanov, A. M. (1985) Enzyme catalysed processes in organic solvents. Proc. Natl. Acad. Sci. USA 82, 3192–3196.CrossRefGoogle Scholar
  5. 5.
    Margolin, A. L. and Klibanov, A. M. (1987) Peptide synthesis catalysed by lipases in anhydrous organic solvents. J. Am. Chem. Soc. 109, 3802–3804.CrossRefGoogle Scholar
  6. 6.
    West, J. B. and Wong, C. H. (1987) Use of nonproteases in peptide synthesis. Tetrahedron Lett. 28, 1629–1632.CrossRefGoogle Scholar
  7. 7.
    Montet, D., Pina, M., Graille, J., Renard, G., and Grimaud, J. (1989) Synthesis of-lauryloleyl-amide by the Mucor miehei lipase in an organic medium. Fatty Sci. Technol. 1, 14–18.Google Scholar
  8. 8.
    Bistline, G., Bilik, A., and Fearheller, S. H. (1991) Lipase catalysed formation of fatty amides. J. Am. Oil Chem. Soc. 68, 95–98.CrossRefGoogle Scholar
  9. 9.
    Tuccio, B. and Comeau, L. (1991) Lipase-catalysed synthesis of N-octyl-alkylamides in organic media. Tetrahedron Lett. 32, 2763–2764.CrossRefGoogle Scholar
  10. 10.
    Montet, D., Servat, F., Graille, J., Pina, M., Grimaud, J., Galzy, P., et al. (1990) Enzymatic synthesis of N-epsilon-acyllysines. J. Am. Oil Chem. Soc. 67, 771–774.CrossRefGoogle Scholar
  11. 11.
    Godtfredsen, S. and Björkling, F. (1990) An enzyme catalysed process forpreparing N-acyl amino acids and N-acyl amino acid amides. International Patent Application No WO 90/14429.Google Scholar
  12. 12.
    Montet, D., Graille, J., Servat, F., Renard, G., and Marcou, I. (1989) Study of the acylation of aminopropanols catalysed by acyltransferases. Rev. Fr. Corps Gras 2, 79–83.Google Scholar
  13. 13.
    Goldberg, M., Thomas, D., and Legoy, M. D. (1990) Water activity as a key parameter of synthesis reactions: the example of lipase in biphasic (liquid/solid) media. Enzyme Microb. Technol. 12, 976–981.CrossRefGoogle Scholar
  14. 14.
    Valivety, R. H., Halling, P., and Macrae, A. (1993) Water as a competitive inhibitor of lipase catalysed esterification in organic media. Biotechnol. Lett. 15, 1133–1138.CrossRefGoogle Scholar
  15. 15.
    Svensson, I., Wehtje, E., Adlercreutz, P., and Mattiasson, B. (1994) Effect of water activity on reaction rates and aquilibrium positions in enzymatic esterifications. Biotechnol. Bioeng. 44, 549–556.CrossRefGoogle Scholar
  16. 16.
    Halling, P. (1984) Effects of water on equilibria catalysed by hydrolytic enzymes in biphasic reaction systems. Enzyme Microb. Technol. 6, 513–516.CrossRefGoogle Scholar
  17. 17.
    Halling, P. (1994) Thermodynamic predictions for biocatalysis in nonconventional media: theory, tests and recommendations for experimental design and analysis. Enzyme Microb. Technol. 16, 178–205.CrossRefGoogle Scholar
  18. 18.
    Dordick, J. (1989) Enzymatic catalysis in monophasic organic solvents. Enzyme Microb. Technol. 11, 194–211.CrossRefGoogle Scholar
  19. 19.
    Valivety, R. H., Rakels, J. L. L., Blanco, R. M., Johnston, G. A., Brown, L., Suckling, C. J., et al. (1990) Measurement of pH changes in an inaccessible aqueous phase during biocatalysis in organic media. Biotechnol. Lett. 12, 475–480.CrossRefGoogle Scholar
  20. 20.
    Maugard, T., Remaud-Simeon, M., Petre, D., and Monsan, P. (1997) Lipase-catalysed chemoselective N-acylation of amino-sugar derivatives in hydrophobic solvent: acid-amine ion-pair effects. Tetrahedron 53, 7587–7594.CrossRefGoogle Scholar
  21. 21.
    Maugard, T., Remaud-Simeon, M., Petre, D., and Monsan, P. (1997) Enzymatic synthesis of glycamide surfactants by amidification reaction. Tetrahedron 53, 5185–5194.CrossRefGoogle Scholar
  22. 22.
    Maugard, T., Remaud-Simeon, M., and Monsan, P. (1998) Kinetic study of chemoselective acylation of amino-alditol by immobilised lipase in organic solvent: effect of substrate ionisation. Biochim. Biophys. Acta 1387, 177–183.CrossRefGoogle Scholar
  23. 23.
    Maugard, T., Remaud-Simeon, M., Petre, D., and Monsan, P. (1997) Lipase-catalysed synthesis of biosurfactants by transacylation of N-methyl-glucamine and fatty-acid methyl esters. Tetrahedron 53, 7629–7634.CrossRefGoogle Scholar

Copyright information

© Humana Press Inc. 2001

Authors and Affiliations

  • Thierry Maugard
    • 1
  • Magali Remaud-Simeon
    • 1
  • Pierre Monsan
    • 1
  1. 1.Centre de Bioingenierie Gilbert Durand, Departément de Genie Biochimique et AlimentaireComplexe Scientifique de RangueilToulouse CedexFrance

Personalised recommendations