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

Authors
  • Chankvetadze, B
  • Pintore, G
  • Burjanadze, N
  • Bergenthal, D
  • Strickmann, D
  • Cerri, R
  • Blaschke, G
Type
Published Article
Journal
Electrophoresis
Publication Date
Sep 01, 1998
Volume
19
Issue
12
Pages
2101–2108
Identifiers
PMID: 9761188
Source
Medline
License
Unknown

Abstract

Markedly different chiral separation abilities were observed for native beta-cyclodextrin (beta-CD), carboxymethyl-beta-CD (CM-beta-CD) and heptakis (2,3,6-tri-O-methyl)-beta-CD (TM-beta-CD) towards the enantiomers of (+/-)-chlorpheniramine ((+/-)-CHL) in capillary electrophoresis (CE). Native beta-CD afforded almost baseline enantioseparation at a concentration of 18 mg/mL, whereas only 1 mg/mL solution of CM-beta-CD was required for adequate enantioseparation. TM-beta-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-beta-CD was opposite to that with beta-CD and CM-beta-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.

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