Mono（2-phenylseleno-2-deoxy）-β-cyclodextrin（2） and mono[2-（p-methoxyphenylseleno）-2-deoxy]-β-cyclodextrin（4）, were newly synthesized and characterized by combustion analyses, IR, 1H NMR and 13 C NMR. Spectrofluorometric titrations have been performed in aqueous phosphate buffer solution（pH 7.20, 0.1 mol/L） at 25 ℃ to give the complex K S and -ΔG° for the stoichiometric 1∶1 inclusion complexation of mono（6-phenylseleno-6-deoxy）-β-cyclodextrin（1）, mono[6-（p-methoxyphenylseleno）-6-deoxy]-β-cyclodextrin（3） and the novel cyclodextrin derivatives 2 and 4 with L- and D-tryptophan. The molecular binding ability and selectivity for L- and D-tryptophan of modified β-cyclodextrins（14） are discussed from the size/shape-fit and geometrical complement relationships between the host cavity and the guest molecule. The results obtained indicate that van der Waals force and hydrophobic interactions dominate the complexation of 1—4 and the aromatic substituents introduced extend the original hydrophobicity of cavity and the molecular binding ability, but reduce the enantioselectivity for L/D-tryptophan guests.
