Formation of inclusion complexes between dimers of (R)-3-hydroxybutanoic acid and β-cyclodextrin: thermodynamic study of the complexation and conformational analysis of the complexed dimers

Jun Li, K. Toh
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引用次数: 4

Abstract

The formation of inclusion complexes of di[(R)-3-hydroxybutanoate] (Dimer 1) and the methyl ester of di[(R)-3-hydroxybutanoate] (Dimer 2) with β-cyclodextrin (β-CD) was studied by NMR spectroscopy. The stoichiometry of the complexation was 1 ∶ 1 (host ∶ guest). Thermodynamic analysis revealed that the complex formation is enthalpically favorable, but entropically unfavorable. Dimer 1 forms hydrogen bonds with β-CD more frequently than Dimer 2 because 1 has two hydroxy groups. Conformational analysis of the 3HB (3-hydroxybutanoate) dimers in the complexes indicates that they have extended (trans) forms. In contrast, in solution without β-CD, the end of both Dimers 1 and 2 takes a sickle (gauche) shape due to formation of intermolecular hydrogen bonds.
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(R)-3-羟基丁酸二聚体与β-环糊精包合物的形成:络合的热力学研究及络合二聚体的构象分析
采用核磁共振波谱法研究了二[(R)-3-羟基丁酸酯](二聚体1)和二[(R)-3-羟基丁酸酯](二聚体2)与β-环糊精(β-CD)的包合物的形成。络合物的化学计量为1∶1(主∶客体)。热力学分析表明,该络合物的形成在焓上是有利的,但在熵上是不利的。二聚体1比二聚体2更容易与β-CD形成氢键,因为二聚体1有两个羟基。对配合物中3HB(3-羟基丁酸酯)二聚体的构象分析表明它们具有扩展(反式)形式。相反,在没有β-CD的溶液中,由于分子间氢键的形成,二聚体1和2的末端呈镰刀状(间扭式)形状。
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