Molecular Recognition of N-Acetylneuraminic Acid by Acyclic Pyridinium- and Quinolinium-Based Receptors in Aqueous Media: Recognition through Combination of Cationic and Neutral Recognition Sites
Molecular Recognition of N-Acetylneuraminic Acid by Acyclic Pyridinium- and Quinolinium-Based Receptors in Aqueous Media: Recognition through Combination of Cationic and Neutral Recognition Sites
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DOI：
10.1021/jo301966z
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发表时间：
2013-01-18
影响因子：
3.6
通讯作者：
Mazik, Monika
中科院分区：
文献类型：
--
作者：
Geffert, Christoph;Kuschel, Matthias;Mazik, Monika
化合物5b-8b、10b和11b含有一个被中性和阳离子识别位点取代的三乙苯支架，在竞争激烈的溶剂中被证明是最常见的唾液酸N-乙酰神经氨酸(NeuAc)的有效受体。在水介质中，这些化合物被证实是比对称的基于吡啶和喹啉的化合物9b和12b更强大的NeuAc受体。与天然蛋白质-唾液酸络合物一样，中性/电荷增强的氢键、离子对、CH-pi和van der Waals相互作用的组合似乎是这种自然广泛存在的阴离子碳水化合物在水介质中有效结合的原因。
Compounds 5b-8b and 10b, and 11b, containing a triethylbenzene scaffold substituted with both neutral and cationic recognition sites, were shown to be effective receptors for N-acetylneuraminic acid (NeuAc), the most common occurring sialic acid, in highly competitive solvents. These compounds were established to be more powerful receptors for NeuAc than the symmetrical pyridinium- and quinolinium-based compounds 9b and 12b in aqueous media. As in natural protein-sialic acid complexes, the combination of neutral/charge-reinforced hydrogen bonds, ion pairs, CH-pi, and van der Waals interactions seems to be responsible for the effective binding of this naturally widespread anionic carbohydrate in aqueous media.