Synthesis of L-cystine bridged bis(p-cyclodextrin) and its cooperative binding toward guest molecule

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A novel p-cyclodextrin derivative, L-cystine bridged bis(β-cyclodextrin) 1 has been synthesized and characterized by 1H NMR, 13C NMR, IR, Raman and combustion analyses. Spectrofluorometric titrations have been performed in aqueous phosphate buffer solution (pH=7.20) at 25℃ to give the complex stability constants (Ks) and Gibbs free energy changes (-△G°) for the stoichiometric 1 : 1 inclusion complexation of 1 with four dyes. The binding abilities and molecular selectivities are discussed from the viewpoint of size/shape-fit and electrostatic interactions between hosts and guests. 2D ROESY investigation for the complexation between host and guest further confirms the cooperative binding of bridged cyclodextrin 1 with guest. A novel p-cyclodextrin derivative, L-cystine bridged bis (β-cyclodextrin) 1 has been synthesized and characterized by 1H NMR, 13C NMR, IR, Raman and combustion analyzes. Spectrofluorometric titrations have been performed in aqueous phosphate buffer solution (pH = 7.20) at 25 ° C give the complex stability constants (Ks) and Gibbs free energy changes (- ΔG °) for the stoichiometric 1: 1 inclusion complex of 1 with four dyes. The binding abilities and molecular selectivities are discussed from a viewpoint of size / shape-fit and electrostatic interactions between hosts and guests. 2D ROESY investigation for the complexation between host and guest further confirms the cooperative binding of bridged cyclodextrin 1 with guest.
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