Synthesis of lipophosphoramidyl-cyclodextrins and their supramolecular properties.

The synthesis of lipophosphoramidyl-β-CD was obtained by an Atherton-Todd (AT) reaction that involved dioleylphosphite and either functionalized permethylated or native β-cyclodextrin. This AT reaction that produced dioleylphosphoramide by making use of the amino group grafted on cyclodextrin, was optimized for these cyclic oligosaccharides. These new amphiphilic compounds were fully characterized, and their self-assembling properties were investigated: the mean size diameter and polydispersity measured by Dynamic Light Scattering (DLS) were affected by the nature of the aqueous media and the temperature of storage.

Molecular dynamics studies of native and substituted cyclodextrins in different media: 1. Charge derivation and force field performances.

Molecular dynamics simulations describing the solvation process of native and modified cyclodextrins (per-substituted α-, β-, and γ-cyclodextrins, as well as an amino-acid derived β-cyclodextrin) have been performed. A homogeneous force field, namely "q4md-CD", has been built from the development of a new force field topology database and from a combination of the GLYCAM04 and Amber99SB force fields to correctly describe the geometrical, structural, dynamical and hydrogen bonding aspects of heterogeneous cyclodextrin based systems. These include native, organo- and peptidic-linked cyclodextrins.