Enantioselective binding of amino acids and amino alcohols by self-assembled chiral basket-shaped receptors

Amino acid appended diphenylglycoluril-based chiral molecular receptors and have been prepared and their aggregation has been studied in water at various pHʹs 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 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.