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首页> 外文期刊>Chemistry: A European journal >Highly Effective Recognition of Carbohydrates by Phenanthroline-Based Receptors: a- versus b-Anomer Binding Preference
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Highly Effective Recognition of Carbohydrates by Phenanthroline-Based Receptors: a- versus b-Anomer Binding Preference

机译：基于菲咯啉的受体对碳水化合物的高效识别：a-和b-异构体结合偏好

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摘要

1H NMR spectroscopic titrations in competitive and non-competitive media, as well as binding studies in two-phase systems, such as phase transfer of sugars from aqueous into organic solvents and dissolution of solid carbohydrates in apolar media revealed both highly effective recognition of neutral carbohydrates and interesting binding preferences of an acyclic phenanthroline- based receptor 1. Compared to the previously described acyclic receptors, compound 1 displays significantly higher binding affinities, the rare capability to extract sugars from water into non-polar organic solutions and aversus b-anomer binding preference in the recognition of glycosides, which differs from those observed for other receptor systems. X-ray crystallographic investigations revealed the presence of water molecules in the binding pocket of 1 that are engaged in the formation of hydrogen-bonding motifs similar to those suggested by molecular modelling for the sugar OH groups in the receptor– sugar complexes. The molecular modelling calculations, synthesis, crystal structure and binding properties of 1 are described and compared with those of the previously described receptors.
机译：在竞争性和非竞争性介质中的1H NMR光谱滴定，以及在两相系统中的结合研究，例如糖从水性相转移到有机溶剂中以及固体碳水化合物在非极性介质中的溶解，都显示出对中性碳水化合物的高效识别和非环菲咯啉基受体1的有趣的结合偏好。与先前描述的非环受体相比，化合物1的结合亲和力明显更高，从水中将糖提取到非极性有机溶液中的罕见能力以及b-异头异构体的结合偏好在识别糖苷方面，与其他受体系统所观察到的不同。 X射线晶体学研究表明，在1的结合口袋中存在水分子，这些水分子参与氢键基序的形成，类似于分子模拟受体-糖复合物中糖基OH所暗示的那些。描述了1的分子建模计算，合成，晶体结构和结合特性，并将其与先前描述的受体进行了比较。

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