ISSN:
0173-0835
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
;
Chemistry
;
Biochemistry and Biotechnology
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Biology
,
Chemistry and Pharmacology
Notes:
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.
Additional Material:
10 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/elps.1150191210
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