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Affinity Enhancement by Dendritic Side Chains in Synthetic Carbohydrate Receptors
Author(s) -
Destecroix Harry,
Renney Charles M.,
Mooibroek Tiddo J.,
Carter Tom S.,
Stewart Patrick F. N.,
Crump Matthew P.,
Davis Anthony P.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201409124
Subject(s) - side chain , chemistry , affinities , dendrimer , branching (polymer chemistry) , receptor , carboxylate , binding affinities , stereochemistry , carbohydrate , biophysics , biochemistry , organic chemistry , polymer , biology
Abstract 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 7000 M −1 . Affinities for uncharged substrates (glucose and N ‐acetylglucosamine) were also enhanced, despite competition from solvent and the absence of electrostatic interactions.