99552-37-1

Three fluorinated β-cyclodextrin derivatives, namely 5, 9 and 12, were prepared with the hope that the fluorine reporter group may assist in direct evaluation of the complexation properties of these potential drug carriers. Two of the synthesized derivatives, the previously reported monofluoro-β-cyclodextrin 9 and the novel trifluoroethylthio-β-cyclodextrin 12, displayed reasonable aqueous solubility and thus were suitable for drug-cyclodextrin complexation studies. Preliminary NMR results (1H and 19F) on the host-guest complex formation of both of these cyclodextrin derivatives with amantidine, a therapeutic agent employed in the treatment of Influenza A infections, are also presented.

Hydrolysis of 6-deoxyamylose and mono-6-deoxy-6-fluorocyclomaltoheptaose by porcine-pancreatic alpha amylase produces low-molecular-weight modified products, which have been analyzed by chemical and chromatographic techniques. Results for both substrates show that modified D-glucose and two isomers of modified maltoses are produced in the enzyme reaction. In addition, the formation of maltoses modified in the nonreducing residue is more favored than the formation of maltoses modified in the reducing residue. These results indicate that productive binding of 6-fluoro- and 6-deoxy-D-glucose residues is permitted at subsites 1 through 4 of the amylase-active site but that binding of these modified residues may be less favorable at subsite 3, the subsite at which catalytic attack occurs.