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Comparative enantioseparations with native β‐cyclodextrin, randomly acetylated β‐cyclodextrin and heptakis‐(2,3‐di‐ O ‐acetyl)‐β‐cyclodextrin in capillary electrophoresis
Author(s) -
Chankvetadze Bezhan,
Lomsadze Ketevan,
Burjanadze Naira,
Breitkreutz Joerg,
Pintore Giorgio,
Chessa Mario,
Bergander Klaus,
Blaschke Gottfried
Publication year - 2003
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.200390126
Subject(s) - capillary electrophoresis , enantiomer , cyclodextrin , chemistry , beta cyclodextrins , acetylation , beta (programming language) , chromatography , stereochemistry , biochemistry , computer science , programming language , gene
Comparative enantioseparations were performed with three neutral cyclodextrins (CDs) in capillary electrophoresis (CE). In particular, native β‐CD was compared with single component heptakis(2,3‐di‐ O ‐acetyl)‐β‐CD (HDA‐β‐CD) and randomly acetylated β‐CD (Ac‐β‐CD) with the emphasis on the enantiomer migration order. The opposite affinity of the enantiomers of several chiral analytes was observed towards native β‐CD and its acetylated derivatives. The enantiomer affinity pattern of some chiral analytes was also opposite towards the two acetylated derivatives of β‐CD. In the case of the chiral drug clenbuterol (CL) an attempt was made to evaluate the possible structural reasons of the affinity reversal using one‐ and two‐dimensional as well as transverse rotating frame nuclear Overhauser effect spectroscopy (ROESY). Significant differences were observed between the structure of the CL complexes with β‐CD and HDA‐β‐CD.