A Preorganized Hydrogen-Bonding Motif for the Molecular Recognition of Carbohydrates.,ChemPhysChem

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A Preorganized Hydrogen-Bonding Motif for the Molecular Recognition of Carbohydrates.
ChemPhysChem ( IF 2.3 ) Pub Date : 2020-01-09 , DOI: 10.1002/cphc.201900907
Oscar Francesconi ₁ , Federico Cicero ₁ , Cristina Nativi ₁ , Stefano Roelens ₁

Affiliation

The choice between adaptive and preorganized architectures, or of the most effective hydrogen bonding groups to be selected, are dilemmas that supramolecular chemists must address in designing synthetic receptors for such a challenging guest as carbohydrates. In this paper, structurally related architectures featuring two alternative hydrogen bonding motifs were compared to ascertain the structural and functional origin of their binding differences and the advantages that can be expected in monosaccharide recognition. A set of structurally related macrocyclic receptors were prepared, and their binding properties were measured by NMR and ITC techniques in chloroform vs a common saccharidic target, namely, the β‐octyl glycoside of D‐glucose. Results showed that the diaminocarbazolic motif, recently reported as the constituting unit of highly effective receptors for saccharides in water, is a superior hydrogen bonding motif compared to the previously described diaminopyrrolic motif, which was successfully employed in molecular recognition of carbohydrates in polar organic solvents, due to intrinsic structural and functional factors, rather than to hydrophobic contributions. In addition, the occurrence of a rare example of a thermodynamic template effect exerted by the beta‐glucoside has been ascertained, enhancing the synthesis outcome of the otherwise low yielding preparation of the described macrocyclic receptors.

中文翻译：

用于碳水化合物分子识别的预组装氢键基序。

适应性结构和预组织结构之间的选择，或要选择的最有效的氢键基团，是超分子化学家在设计诸如碳水化合物之类的具有挑战性的客体的合成受体时必须解决的难题。在本文中，比较了具有两个氢键替代基序的结构相关结构，以确定它们结合差异的结构和功能来源，以及在单糖识别中可以预期的优势。制备了一组结构相关的大环受体，并通过NMR和ITC技术在氯仿与糖精的常见靶标（即D-葡萄糖的β-辛基糖苷）之间测定了它们的结合特性。结果表明，二氨基咔唑基序最近被报道为水中糖类高效受体的组成单元，与先前描述的二氨基吡咯基序相比，它是一种优越的氢键基序，由于固有的结构和功能因素，该基元已成功用于极性有机溶剂中碳水化合物的分子识别，而不是疏水作用。另外，已经确定了由β-葡萄糖苷发挥热力学模板作用的罕见例子的发生，从而增强了所描述的大环受体原本产量低的制备方法的合成结果。由于内在的结构和功能因素，而不是由于疏水作用，该技术已成功用于极性有机溶剂中碳水化合物的分子识别。此外，已经确定了由β-葡萄糖苷产生的热力学模板效应的罕见例子的发生，从而增强了所描述的大环受体原本产量低的制备方法的合成结果。由于内在的结构和功能因素，而不是由于疏水作用，该技术已成功用于极性有机溶剂中碳水化合物的分子识别。此外，已经确定了由β-葡萄糖苷产生的热力学模板效应的罕见例子的发生，从而增强了所描述的大环受体原本产量低的制备方法的合成结果。

更新日期：2020-01-09

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