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Solvent-free chemo-enzymatic synthesis of fatty acyl-β-cyclodextrin

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Abstract

Lipase-catalyzed transesterifications were carried out without solvent and in mild conditions on permethylated β-cyclodextrins derivatives to obtain lipidyl-cyclodextrin, a new class of amphiphilic compounds with expected auto-assembly properties. Good conversion rate, of 6I-(N-hydroxyethylsuccinamido)-6I-deoxy-2I, 3I-di-O-methyl-hexakis (2II–VII,3II–VII,6II–VII-tri-O-methyl) cyclomaltoheptaose were obtained by using lipozyme as catalyst. Critical Aggregation Concentrations of these new derivatives of amphiphilic cyclodextrins (5.10−3 and 5.10−4 M) are in favor of an auto-association behavior. Finally, NMR experiments were carried out to evaluate the self-assembly of the compounds in water. The resulting supramolecular aggregates have potential to be used as nano-carriers for drug.

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Acknowledgments

This work was supported by le Conseil Régional de Picardie under the scientific “IBFBio” program.

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Authors and Affiliations

  1. Laboratoire des Glucides, FRE 3517 CNRS Université de Picardie Jules Verne, 80039, Amiens, France

    Véronique Bonnet, Audrey Favrelle, Frédéric Aubry & Florence Djedaïni-Pilard

  2. Génie Enzymatique et Cellulaire, UMR 6022 CNRS, Université de Picardie Jules Verne, 80039, Amiens, France

    Audrey Favrelle & Catherine Sarazin

Authors
  1. Véronique Bonnet
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  2. Audrey Favrelle
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  3. Frédéric Aubry
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  4. Catherine Sarazin
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  5. Florence Djedaïni-Pilard
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Correspondence to Véronique Bonnet.

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Dedicated in memory of Frederic Aubry.

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Bonnet, V., Favrelle, A., Aubry, F. et al. Solvent-free chemo-enzymatic synthesis of fatty acyl-β-cyclodextrin. J Incl Phenom Macrocycl Chem 77, 155–161 (2013). https://doi.org/10.1007/s10847-012-0229-2

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  • DOI: https://doi.org/10.1007/s10847-012-0229-2

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