Highly effective acyclic carbohydrate receptors consisting of aminopyridine, imidazole, and indole recognition units |
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Authors: | Mazik Monika Kuschel Matthias |
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Institution: | Institut für Organische Chemie der Technischen Universit?t Braunschweig, Hagenring 30, 38106 Braunschweig, Germany, Fax: (+49)?5313‐9181‐85 |
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Abstract: | 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. |
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Keywords: | carbohydrates hydrogen bonds molecular recognition receptors supramolecular chemistry |
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