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Platform Synthetic Lectins for Divalent Carbohydrate Recognition in Water
Author(s) -
Carter Tom S.,
Mooibroek Tiddo J.,
Stewart Patrick F. N.,
Crump Matthew P.,
Galan M. Carmen,
Davis Anthony P.
Publication year - 2016
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.201603082
Subject(s) - chemistry , divalent , molecular recognition , pyrene , aqueous solution , carbohydrate , receptor , combinatorial chemistry , stereochemistry , biochemistry , molecule , organic chemistry
Abstract Biomimetic carbohydrate receptors (“synthetic lectins”) have potential as agents for biological research and medicine. However, although effective strategies are available for “all‐equatorial” carbohydrates (glucose, etc.), the recognition of other types of saccharide under natural (aqueous) conditions is less well developed. Herein we report a new approach based on a pyrene platform with polar arches extending from aryl substituents. The receptors are compatible with axially substituted carbohydrates, and also feature two identical binding sites, thus mimicking the multivalency observed for natural lectins. A variant with negative charges forms 1:2 host/guest complexes with aminosugars, with K 1 >3000 m −1 for axially substituted mannosamine, whereas a positively charged version binds the important α‐sialyl unit with K 1 ≈1300 m −1 .