Mazik Monika, Kuschel Matthias
Institut für Organische Chemie der Technischen Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
Chemistry. 2008;14(8):2405-19. doi: 10.1002/chem.200701269.
Neutral imidazole/aminopyridine- and indole/aminopyridine-based receptors, 1 and 2, have been established as highly effective and selective carbohydrate receptors. These receptors effectively recognise neutral carbohydrates through multiple interactions, including neutral hydrogen bonds and CH...pi interactions between the sugar CH groups and the aromatic rings of the receptors. The design of these receptors was inspired by the binding motifs observed in the crystal structures of protein-carbohydrate complexes. The formation of very strong complexes with beta-glucopyranoside 5, beta-maltoside 8, and alpha-maltoside 9 in organic media has been characterised by 1H NMR spectroscopy and confirmed by a second, independent technique, namely fluorescence spectroscopy. The syntheses, molecular-modelling studies, binding properties of the receptors 1 and 2 toward selected mono- and disaccharides as well as comparative binding studies with receptors 3 and 4 are described.
基于中性咪唑/氨基吡啶和吲哚/氨基吡啶的受体1和2已被确立为高效且选择性的碳水化合物受体。这些受体通过多种相互作用有效地识别中性碳水化合物，包括中性氢键以及糖的CH基团与受体芳香环之间的CH…π相互作用。这些受体的设计灵感来源于在蛋白质 - 碳水化合物复合物晶体结构中观察到的结合基序。通过1H NMR光谱对其在有机介质中与β - 吡喃葡萄糖苷5、β - 麦芽糖苷8和α - 麦芽糖苷9形成的非常强的复合物进行了表征，并通过第二种独立技术即荧光光谱进行了确认。本文描述了受体1和2的合成、分子建模研究、对选定单糖和二糖的结合特性以及与受体3和4的比较结合研究。
