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Separation of brompheniramine enantiomers by capillary electrophoresis and study of chiral recognition mechanisms of cyclodextrins using NMR-spectroscopy, UV spectrometry, electrospray ionization mass spectrometry and X-ray crystallography

Chankvetadze, Bezhan and Burjanadze, Naira and Pintore, Giorgio Antonio Mario and Bergenthal, Dieter and Bergander, Klaus and Mühlenbrock, Christoph and Breitkreuz, Jörg and Blaschke, Gottfried (2000) Separation of brompheniramine enantiomers by capillary electrophoresis and study of chiral recognition mechanisms of cyclodextrins using NMR-spectroscopy, UV spectrometry, electrospray ionization mass spectrometry and X-ray crystallography. Journal of Chromatography A, Vol. 875 (1-2), p. 471-484. ISSN 0021-9673. Article.

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DOI: 10.1016/S0021-9673(00)00153-9

Abstract

Opposite migration order was observed for the enantiomers of brompheniramine {N-[3-(4-bromphenyl)-3-(2-pyridyl)propyl]-N,N-dimethylamine} (BrPh) in capillary electrophoresis (CE) when native β-cyclodextrin (β-CD) and heptakis(2,3,6-tri-O-methyl)-β-CD (TM-β-CD) were used as chiral selectors. NMR spectrometry was applied in order to obtain information about the stoichiometry, binding constants and structure of the selector–selectand complexes in solution. The data were further confirmed by UV spectrometry and electrospray ionization mass spectrometry. The structure of the complexes in the solid state was determined using X-ray crystallography performed on the co-crystals precipitated from the 1:1 aqueous solution of selector and selectand. This multiple approach allowed an elucidation of the most likely structural reason for a different affinity (binding strength) of BrPh enantiomers towards β-CD and TM-β-CD. However, the question about a force responsible for the opposite affinity pattern of BrPh enantiomers towards these CDs could not be answered definitely.

Item Type:Article
ID Code:4468
Status:Published
Refereed:Yes
Uncontrolled Keywords:Enantiomer separation, chiral selectors, pharmaceutical analysis, brompheniramine, cyclodextrins
Subjects:Area 05 - Scienze biologiche > BIO/15 Biologia farmaceutica
Divisions:001 Università di Sassari > 01 Dipartimenti > Farmaco, chimico, tossicologico
Publisher:Elsevier Science
ISSN:0021-9673
Deposited On:02 Sep 2010 12:41

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