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A Modular Phosphorylated Glycoluril-Derived Molecular Tweezer for Potent Binding of Aliphatic Diamines

机译:用于脂族二胺的有效结合的模块化磷酸化糖型甘油衍生的分子镊子

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摘要

A molecular tweezer based on a glycoluril-derived framework bearing four phosphate groups was synthesized and shown to be capable of binding organic amines in aqueous solution. This work reports the K_a values for 30 complexes of this molecular tweezer and amine guests, determined by means of ~1H NMR titrations. Both the hydrophobic cavity and the phosphate groups contribute to the binding. Bulkier molecules and molecules bearing negatively charged groups like carboxylates in amino acids bind less tightly due to a steric clash and coulombic repulsion. The narrow cavity and the strong ionic interactions of the phosphate groups with ammonium guests favor binding of aliphatic diamines. These binding properties clearly distinguish this system from structurally related molecular clips and tweezers.
机译:合成基于含有四个磷酸盐基团的糖精衍生骨架的分子镊子并显示能够在水溶液中结合有机胺。 这项工作报告了这款分子镊子和胺类客人的30个复合物的K_A值,通过〜1H NMR滴定决定。 疏水性腔和磷酸盐基团都有助于结合。 由于空间冲突和库仑排斥,抗膨胀的分子和含有带负电荷的基团,如氨基酸中的羧酸盐的紧密紧密结合。 氨基酸盐基团的窄腔和磷酸基团的强离子相互作用有利于脂族二胺的结合。 这些结合性质清楚地将该系统与结构相关的分子夹和镊子区分开来。

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