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Separation of enantiomers of norephedrine by capillary electrophoresis using cyclodextrins as chiral selectors: Comparative CE and NMR studies
Author(s) -
Lomsadze Ketevan,
Vega Elena Domínguez,
Salgado Antonio,
Crego Antonio L.,
Scriba Gerhard K.E.,
Marina Maria Luisa,
Chankvetadze Bezhan
Publication year - 2012
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.201200062
Subject(s) - chemistry , enantiomer , capillary electrophoresis , chirality (physics) , cyclodextrin , proton nmr , chromatography , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
In this study, the enantiomer migration order ( EMO ) of norephedrine ( NEP ) in the presence of various CD s was investigated by CE . NMR and CE techniques were used to analyze the mechanism of the chiral recognition between NEP enantiomers and four CD s, i.e., native α‐ CD , β‐ CD , heptakis(2,3‐di‐O‐acetyl‐6‐O‐sulfo)‐β‐ CD ( HDAS ‐β‐ CD ), and heptakis(2,3‐di‐O‐methyl‐6‐O‐sulfo)‐β‐ CD (HDMS‐β‐ CD ). EMO was reversed in the presence of α‐ CD and β‐ CD , although only minor differences in the structures of the complexes formed between NEP and these CD s could be derived from rotating frame nuclear Overhauser experiments ( ROESY ). The complexes between the enantiomers of NEP and the sulfated CD s, HDMS‐β‐ CD , and HDAS ‐β‐ CD , were substantially different. However, EMO of NEP was identical in the presence of these CD s. HDAS ‐β‐ CD proved to be the most suitable chiral selector for the CE enantioseparation of NEP .