Enantioselective binding of amino acids and amino alcohols by self-assembled chiral basket-shaped receptors
until further notice
Number of pages
SourceTetrahedron, 60, 2, (2004), pp. 291-300
Article / Letter to editor
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Synthetic Organic Chemistry
Physical Organic Chemistry
Physical Organic and Supramolecular Chemistry
SubjectMolecular Materials; Physical Organic Chemistry
Amino acid appended diphenylglycoluril-based chiral molecular receptors 2 and 3 have been prepared and their aggregation has been studied in water at various pH's and in chloroform. The binding of several biologically relevant guests with aromatic moieties to these aggregates has been studied with UV-Vis spectroscopy in competition experiments with 4-(4-nitrophenylazo)resorcinol (Magneson) and 2-(4-hydroxyphenylazo)benzoic acid (HABA) as probes. Aggregates of chiral host 2b showed binding of catecholamines and aromatic amino acids in an aqueous environment, as well as discrimination between amino acid enantiomers, and can be considered a mimic for adrenergic receptors. (C) 2003 Elsevier Ltd. All rights reserved.
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