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Sulfate‐Selective Recognition by Using Neutral Dipeptide Anion Receptors in Aqueous Solution
Author(s) -
Elmes Robert B. P.,
K. Y. Yuen Karen,
Jolliffe Katrina A.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201400292
Subject(s) - squaramide , chemistry , dipeptide , hydrogen bond , thiourea , aqueous solution , selectivity , amide , molecular recognition , receptor , peptide , combinatorial chemistry , stereochemistry , molecule , organic chemistry , biochemistry , organocatalysis , enantioselective synthesis , catalysis
The synthesis of six small peptide anion receptors based on thiourea and squaramide recognition moieties is described. These new receptors bind to tetrahedral sulfate anions with remarkable affinity and selectivity in aqueous solution as shown by NMR spectroscopy. Molecular modelling suggests that selectivity is mediated by a hydrogen bond network incorporating the amide backbone protons in a manner similar to that found in the sulfate‐binding protein.