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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

Chankvetadze, Bezhan and Lomsadze, Ketevan and Burjanadze, Naira and Breitkreutz, Jörg and Pintore, Giorgio Antonio Mario and Chessa, Mario and Bergander, Klaus and Blaschke, Gottfried (2003) Comparative enantioseparations with native β-cyclodextrin, randomly acetylated β-cyclodextrin and heptakis-(2,3-di-O-acetyl)-β-cyclodextrin in capillary electrophoresis. Electrophoresis, Vol. 24 (6), p. 1083-1091. eISSN 1522-2683. Article.

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DOI: 10.1002/elps.200390126

Abstract

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.

Item Type:Article
ID Code:4458
Status:Published
Refereed:Yes
Uncontrolled Keywords:Capillary electrophoresis, cyclodextrin, enantioseparation, enantiomer migration order, otating frame nuclear overhauser effect spectroscopy
Subjects:Area 05 - Scienze biologiche > BIO/15 Biologia farmaceutica
Divisions:001 Università di Sassari > 01 Dipartimenti > Farmaco, chimico, tossicologico
Publisher:Wiley
eISSN:1522-2683
Copyright Holders:© 2003 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Publisher Policy:2003, 24, 1083–1091
Deposited On:01 Sep 2010 15:39

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