Novel chemo-enzymatic access to amphiphilic cyclodextrins

  • Audrey Favrelle
  • Véronique Bonnet
  • Catherine Sarazin
  • Florence Djedaïni-Pilard
Original Article

Abstract

A new class of mono-substituted amphiphilic cyclodextrins was synthesized in a one-step lipase catalysed amidification. Microbial and animal lipases were able to catalyse this reaction. Depending on the acyl donors, various hydrophobic moieties have been grafted on methylated β-cyclodextrin. Azoninyl-methylated-β-cyclodextrin derivatives were also obtained by reaction of acetaldehyde and modified cyclodextrins in presence of dedicated lipase.

Keywords

Amidification Amphiphilic Cyclodextrin Fatty acids Lipase Solvent free medium Vinyl esters 

References

  1. 1.
    Perly, B., Moutard, S., Djedaini-Pilard, F.: Amphiphilic cyclodextrins: from a general concept to properties and applications. Pharma Chem. 4, 4–9 (2005)Google Scholar
  2. 2.
    Moutard, S., Djedaini-Pilard, F., Meudal, S., Luijten, W., Perly, B., Pilard, S.: Structural identification of new glycolipid based on cyclodextrin using high-resolution positive and negative electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 17, 2535–2540 (2003)CrossRefGoogle Scholar
  3. 3.
    Moutard, S., Perly, B., Gode, P., Demailly, G., Djedaini-Pilard, F.: Novel glycolipids based on cyclodextrins. J. Inclusion Phenom. Macrocycl. Chem. 44, 317–322 (2002)CrossRefGoogle Scholar
  4. 4.
    Virto, C., Adlercreutz, P.: Lysophosphatidylcholine synthesis with Candida antarctica lipase B (Novozym 435). Enz. Microb. Technol. 26, 630–635 (2000)CrossRefGoogle Scholar
  5. 5.
    Virto, C., Svensson, I., Adlercreutz, P.: Enzymatic synthesis of lysophosphatidic acid and phosphatidic acid. Enz. Microb. Technol. 24, 651–658 (1999)CrossRefGoogle Scholar
  6. 6.
    Garcia-Junceda, E., Garcia-Garcia, J.F., Bastida, A., Fernandez-Mayoralas, A.: Enzymes in the synthesis of bioactive compounds: the prodigious decades. Bioorg. Med. Chem. 12, 1817–1834 (2004)CrossRefGoogle Scholar
  7. 7.
    Faber, K.: Biotransformations of non-natural compounds: state of the art and future development. Pure Appl. Chem. 69, 1613–1632 (1997)Google Scholar
  8. 8.
    Klibanov, A.M.: Enzymes that work in organic solvents. Chemtech. 16, 354–359 (1986)Google Scholar
  9. 9.
    Maugard, T., Remaud-Simeon, M., Petre, D., Monsan, P.: Enzymatic synthesis of glycamide surfactants by amidification reaction. Tetrahedron 53, 5185–5194 (1997)CrossRefGoogle Scholar
  10. 10.
    Pedersen, N.R., Kristensen, J.B., Bauw, G., Ravoo, B.J., Darcy, R., Larsen, K.L., Pedersen, L.H.: Thermolysin catalyses the synthesis of cyclodextrin esters in DMSO. Tetrahedron Asymmetry 16, 615–622 (2005)CrossRefGoogle Scholar
  11. 11.
    Defaye, J., Crouzy, S., Evrard, N., Law, H.: Procédé de préparation régiosélectif de dérivés monosulfonylés en C6 des CDs. French Patent WO 9961483. (1999)Google Scholar
  12. 12.
    Djedaini Pilard, F., Azaroual Bellanger, N., Gosnat, M., Vernet, D., Perly, B.: Potential formation of intramolecular inclusion complexes in peptido-cyclodextrins as evidenced by NMR spectroscopy. J. Chem. Soc. Perkin Trans. 2, 723–730 (1995)Google Scholar
  13. 13.
    Djedaïni-Pilard, F., Désalos, J., Perly, B.: Synthesis of a new molecular carrier: N-(Leu-enkephalin)yl 6-amido-6-deoxycyclomaltoheptaose. Tetrahedron Lett. 34, 2457–2460 (1993)CrossRefGoogle Scholar
  14. 14.
    Hanessian, S., Benalil, A., Laferrière, C.: The synthesis of functionalized cyclodextrins as scaffolds and templates for molecular diversity, catalysis, and inclusion phenomena. J. Org. Chem. 60, 4786–4797 (1995)CrossRefGoogle Scholar
  15. 15.
    Melton, L.D., Slessor, K.N.: Synthesis of monosubstituted cyclohexaamyloses. Carbohydr. Res. 18, 29–37 (1971)CrossRefGoogle Scholar
  16. 16.
    Decagny, B., Jan, S., Vuillemard, J.C., Sarazin, C., Séguin, J.P., Gosselin, C., Barbotin, J.N., Ergan, J.N.: Synthesis of wax ester through triolein alcoholysis: choice of the lipase and study of the mechanism. Enz. Microb. Technol. 22, 578–582 (1998)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • Audrey Favrelle
    • 1
    • 2
  • Véronique Bonnet
    • 1
  • Catherine Sarazin
    • 2
  • Florence Djedaïni-Pilard
    • 1
  1. 1.Laboratoire de GlucidesUMR 6219, Université de Picardie Jules VerneAmiens CedexFrance
  2. 2.Génie Enzymatique et Cellulaire, UMR 6022Université de Picardie Jules VerneAmiensFrance

Personalised recommendations