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Enantioseparation of aminoglutethimide with cyclodextrins in capillary electrophoresis and studies of selector-selectand interactions using NMR spectroscopy and electrospray ionization mass spectrometry.
Chankvetadze, Bezhan; Fillet, Marianne; Burjanadze, N. et al.
2000In Enantiomer, 5 (3-4), p. 313-22
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Keywords :
Aminoglutethimide/chemistry/isolation & purification; Cyclodextrins/chemistry; Electrophoresis, Capillary; Magnetic Resonance Spectroscopy/methods; Molecular Structure; Spectrometry, Mass, Electrospray Ionization/methods; Stereoisomerism
Abstract :
[en] The enantiomers of aminoglutethimide [2-(p-aminophenyl)-2-ethylglutarimide, AGT] can be resolved in CE using all of three most commonly used native cyclodextrins (CD): alpha-, beta-, and gamma-CDs. The migration order of the enantiomers was opposite using beta-CD compared to alpha- and gamma-CDs as chiral selectors. In order to examine some underlying mechanisms of the chiral recognition the interaction of AGT with the chiral selectors was studied with one- and two-dimensional NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS). The Job's and Scott's plots constructed based on the complexation-induced chemical shifts (CICS) observed in NMR spectra provided some preliminary information on the stoichiometry of the intermolecular complexes but did not seem to be absolutely reliable perhaps because the self-association of the analyte molecules and the formation of multiple type selectand-selector complexes. Therefore, an attempt was made to characterize the complexes using ESI-MS. This technique provided information on the stoichiometry and relative affinity constants of selector-selectand complexes. The information on the structure of complexes in the solution was obtained using one-dimensional rotating frame nuclear Overhauser enhancement (1D-ROESY) NMR spectroscopic studies. Significant differences were observed between the structures of the AGT complexes with beta- and gamma-CD.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Chankvetadze, Bezhan;  University of Munster > Germany
Fillet, Marianne ;  Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments
Burjanadze, N.;  University of Munster, Germany
Bergenthal, D.;  University of Munster, Germany
Bergander, C.;  University of Munster, Germany
Luftmann, H.;  University of Munster, Germany
Crommen, Jacques ;  Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments
Blaschke, G.;  University of Munster, Germany
Language :
English
Title :
Enantioseparation of aminoglutethimide with cyclodextrins in capillary electrophoresis and studies of selector-selectand interactions using NMR spectroscopy and electrospray ionization mass spectrometry.
Publication date :
2000
Journal title :
Enantiomer
ISSN :
1024-2430
Publisher :
Taylor & Francis, Philadelphia, United States - Pennsylvania
Volume :
5
Issue :
3-4
Pages :
313-22
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
Available on ORBi :
since 10 August 2009

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