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Capillary electrophoresis, nuclear magnetic resonance and mass spectrometry studies of opposite chiral recognition of chlorpheniramine enantiomers with various cyclodextrins

Chankvetadze, Bezhan and Burjanadze, Naira and Bergenthal, Dieter and Strickmann, Dirk and Blaschke, Gottfried and Pintore, Giorgio Antonio Mario and Cerri, Riccardo (1998) Capillary electrophoresis, nuclear magnetic resonance and mass spectrometry studies of opposite chiral recognition of chlorpheniramine enantiomers with various cyclodextrins. Electrophoresis, Vol. 19 (12), p. 2101-2108. eISSN 1522-2683. Article.

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DOI: 10.1002/elps.1150191210

Abstract

Markedly different chiral separation abilities were observed for native β-cyclodextrin (β-CD), carboxymethyl- β-CD (CM- β-CD) and heptakis (2,3,6-tri-O-methyl)- β-CD (TM-β-CD) towards the enantiomers of (±)-chlorpheniramine ((±)-CHL) in capillary electrophoresis (CE). Native β-CD afforded almost baseline enantioseparation at a concentration of 18 mg/mL, whereas only 1 mg/mL solution of CM- β-CD was required for adequate enantioseparation. TM- β-CD allowed the nearly baseline enantioseparation only at a concentration as high as 80 mg/mL. Moreover, the migration order of (±)-CHL in the presence of TM-β-CD was opposite to that with β-CD and CM- β-CD. 1H and 13C-NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS) have been used in order to obtain preliminary information about the stoichiometry and the binding constants in the intermolecular diastereomeric complexes of (±)-CHL with these CDs.

Item Type:Article
ID Code:4450
Status:Published
Refereed:Yes
Uncontrolled Keywords:Opposite migration order of enantiomers, enantioseparation in capillary electrophoresis, chiral recognition in nuclear magnetic resonance spectroscopy, electrospray ionization mass spectrometry of cyclodextrin complexes, cyclodextrins, (±)-chlorpheniramine
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:© 1998 Wiley-VCH Verlag GmbH
Deposited On:06 Sep 2010 19:23

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