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Synthesis and NMR characterization of β‐alanine‐bridged hemispherodextrin, a very efficient chiral selector in EKC
Author(s) -
Cucinotta Vincenzo,
Giuffrida Alessandro,
Maccarrone Giuseppe,
Messina Marianna,
Puglisi Antonino,
Vecchio Graziella
Publication year - 2007
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.200600813
Subject(s) - moiety , enantiomer , chemistry , alanine , molecule , nuclear magnetic resonance spectroscopy , amino acid , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry
A capped derivative of β‐CD (THALAH) was synthesized and characterized by NMR spectroscopy at different pH values. A trehalose moiety, bonded through β‐alanine bridges to the CD cavity, is included in the capping unit, giving peculiar properties to this molecule. The hemispherodextrin thus obtained was tested as a chiral selector in EKC. At neutral pH, the monocationic species of THALAH behaves as a very efficient selector separating successfully all the 11 tested enantiomeric pairs of dansyl‐derivatives of amino acids, some of them even at concentrations as low as 0.15 mM. The differences observed in the migration order among the different systems give suggestions about the mechanism of molecular recognition between the selector and the analytes.