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Separation of enantiomers of ephedrine by capillary electrophoresis using cyclodextrins as chiral selectors: Comparative CE, NMR and high resolution MS studies
Author(s) -
Vega Elena D.,
Lomsadze Ketevan,
Chankvetadze Lali,
Salgado Antonio,
Scriba Gerhard K. E.,
Calvo Enrique,
López Juan A.,
Crego Antonio L.,
Marina Maria L.,
Chankvetadze Bezhan
Publication year - 2011
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.201100015
Subject(s) - ephedrine , chemistry , enantiomer , capillary electrophoresis , cationic polymerization , analyte , chirality (physics) , chromatography , electrophoresis , circular dichroism , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , neuroscience , biology , quark
The enantiomer migration order (EMO) of ephedrine was investigated in the presence of various CDs in CE. The molecular mechanisms of chiral recognition were followed for the ephedrine complexes with native α‐ and β‐CD and heptakis(2,3‐di‐ O ‐acetyl‐6‐ O ‐sulfo)‐β‐CD (HDAS‐β‐CD) by CE, NMR spectroscopy and high‐resolution MS. Minor structural differences were observed between the complexes of ephedrine with α‐ and β‐CD although the migration order of enantiomers was opposite when these two CDs were applied as chiral selectors in CE. The EMO was also opposite between β‐CD and HDAS‐β‐CD. Significant structural differences were observed between ephedrine complexes with the native CDs and HDAS‐β‐CD. The latter CD was advantageous as chiral CE selector not only due to its opposite electrophoretic mobility compared with that of the cationic chiral analyte, but also primarily due to its enhanced chiral recognition ability towards the enantiomers of ephedrine.