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Mechanistic study on the opposite migration order of clenbuterol enantiomers in capillary electrophoresis with β‐cyclodextrin and single‐isomer heptakis(2,3‐diacetyl‐6‐sulfo)‐β‐cyclodextrin
Author(s) -
Chankvetadze Bezhan,
Lomsadze Ketevan,
Bergenthal Dieter,
Breitkreutz Jörg,
Bergander Klaus,
Blaschke Gottfried
Publication year - 2001
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/1522-2683(200109)22:15<3178::aid-elps3178>3.0.co;2-f
Subject(s) - chemistry , enantiomer , cyclodextrin , capillary electrophoresis , beta cyclodextrins , diacetyl , chromatography , beta (programming language) , clenbuterol , electrophoresis , mass spectrometry , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , computer science , programming language
Opposite migration order was observed for the enantiomers of the chiral β 2 ‐adrenergic drug clenbuterol (CL) in capillary electrophoresis (CE) when resolved with native β‐cyclodextrin (β‐CD) and heptakis (2,3‐diacetyl‐6‐sulfo)‐β‐CD (HDAS‐β‐CD). The possible mechanisms of the affinity reversal of the CL enantiomers depending on the structure of the CD were studied using 1 H‐nuclear magnetic resonance ( 1 H‐NMR) spectrometry and one‐dimensional rotating frame nuclear Overhauser and exchange spectrometry (1‐D ROESY). Significant differences were observed between the structure of the (±)‐CL complexes with β‐CD and HDAS‐β‐CD.