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Histamine‐modified β‐cyclodextrins for the enantiomeric separation of dansyl‐amino acids in capillary electrophoresis
Author(s) -
Galaverna Gianni,
Corradini Roberto,
Dossena Arnaldo,
Marchelli Rosangela,
Vecchio Graziella
Publication year - 1997
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.1150180609
Subject(s) - capillary electrophoresis , chemistry , moiety , enantiomer , deprotonation , amino acid , imidazole , chromatography , electrophoresis , stereochemistry , medicinal chemistry , organic chemistry , ion , biochemistry
Abstract Two novel monosubstituted β‐cyclodextrins (CD) bearing the histamine moiety linked to the upper CD rim, either through the amino group or the imidazole nitrogen 1 N, CD‐hm and CD‐mh, were successfully used as chiral selectors in capillary electrophoresis for the enantiomeric discrimination of dansyl (Dns)‐amino acids. Good results were obtained by using low concentrations of the selectors (1–3 m M ). The effect of pH on the chiral discrimination was studied in order to modulate the number and the position of the positive charges. By increasing the pH from 5 to 7.5, chiral discrimination decreased along with the deprotonation of the imidazolyl moiety. Inversion of the migration order was observed with the two CDs, depending on the relative position of the charged moieties on the upper rim. Ion pair interaction coupled to inclusion complexation seems to account for the discrimination process. The effects of the temperature, CD concentration and capillary length on chiral resolution were also examined.