Journal
TETRAHEDRON
Volume 60, Issue 2, Pages 291-300Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2003.11.019
Keywords
supramolecular chemistry; receptors; enantioselectivity; amino acids
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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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