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首页> 外文期刊>Chemistry: A European journal >Chiral diaminopyrrolic receptors for selective recognition of mannosides, Part 2: A 3D view of the recognition modes by X-ray, NMR spectroscopy, and molecular modeling
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Chiral diaminopyrrolic receptors for selective recognition of mannosides, Part 2: A 3D view of the recognition modes by X-ray, NMR spectroscopy, and molecular modeling

机译：手性二氨基吡咯类受体，用于甘露糖苷的选择性识别，第2部分：通过X射线，NMR光谱和分子建模的识别模式的3D视图

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摘要

The structural features of a representative set of five complexes of octyl α- and β-mannosides with some members of a new generation of chiral tripodal diaminopyrrolic receptors, namely, (R)-5 and (S)- and (R)-7, have been investigated in solution and in the solid state by a combined X-ray, NMR spectroscopy, and molecular modeling approach. In the solid state, the binding arms of the free receptors 7 delimit a cleft in which two solvent molecules are hydrogen bonded to the pyrrolic groups and to the benzenic scaffold. In a polar solvent (CD_3CN), chemical shift and intermolecular NOE data, assisted by molecular modeling calculations, ascertained the binding modes of the interaction between the receptor and the glycoside for these complexes. Although a single binding mode was found to adequately describe the complex of the acyclic receptor 5 with the α-mannoside, for the complexes of the cyclic receptors 7 two different binding modes were required to simultaneously fit all the experimental data. In all cases, extensive binding through hydrogen bonding and CH-π interactions is responsible for the affinities measured in the same solvent. Furthermore, the binding modes closely account for the recognition preferences observed toward the anomeric glycosides and for the peculiar enantiodiscrimination properties exhibited by the chiral receptors. Binding modes: The binding modes of the interaction between α- and β-mannosides and chiral diaminopyrrolic tripodal receptors, elucidated by combined X-ray, NMR spectroscopy, and molecular modeling calculations, account for the affinities and the enantioselectivity features measured in a polar solvent. Extensive hydrogen bonding and CH-π interactions are the driving force for recognition, in which docking of the mannosyl into the cleft of the receptor occurs with the β face anchored on the benzenic scaffold through the H-4 proton (see graphic).
机译：具有代表性的五种辛基α-和β-甘露糖苷配合物与新一代手性三脚架二氨基二吡咯受体的一些配合物（即（R）-5和（S）-和（R）-7）的结构特征已通过组合X射线，NMR光谱和分子建模方法对溶液和固态进行了研究。在固态下，自由受体7的结合臂界定了裂口，其中两个溶剂分子氢键合至吡咯基团和苯并支架上。在极性溶剂（CD_3CN）中，化学位移和分子间NOE数据在分子模型计算的辅助下确定了这些复合物在受体和糖苷之间相互作用的结合方式。尽管发现单一结合模式足以描述无环受体5与α-甘露糖苷的复合物，但对于环状受体7的复合物，需要两种不同的结合模式以同时拟合所有实验数据。在所有情况下，通过氢键和CH-π相互作用的广泛键合是在同一溶剂中测得的亲和力的原因。此外，结合模式紧密地解释了观察到的对异头糖苷的识别偏好和手性受体所表现出的独特的对映异构特性。结合模式：结合X射线，NMR光谱和分子模型计算阐明了α-和β-甘露糖苷与手性二氨基吡咯三脚架受体之间相互作用的结合模式，说明了在极性溶剂中测得的亲和力和对映选择性。广泛的氢键和CH-π相互作用是识别的驱动力，其中甘露糖基对接到受体的缝隙中，β面通过H-4质子锚定在苯甲酸支架上（见图）。

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