Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 7, Pages 2057-2061Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409124
Keywords
carbohydrates; dendrimers; molecular recognition; receptors; supramolecular chemistry
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Funding
- Engineering and Physical Sciences Research Council [EP/I028501/1]
- Bristol Chemical Synthesis Doctoral Training Centre [EP/G036764/1]
- EPSRC [EP/I028501/1, EP/K03927X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/I028501/1, 1114107, EP/K03927X/1] Funding Source: researchfish
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Dendritic side chains have been used to modify the binding environment in anthracene-based synthetic carbohydrate receptors. Control of length, charge, and branching enabled the positioning of side-chain carboxylate groups in such a way that they assisted in binding substrates rather than blocking the cavity. Conformational degeneracy in the dendrimers resulted in effective preorganization despite the flexibility of the system. Strong binding was observed to glucosammonium ions in water, with K-a values up to 7000M(1). Affinities for uncharged substrates (glucose and N-acetylglucosamine) were also enhanced, despite competition from solvent and the absence of electrostatic interactions.
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