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.

摘要: 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 beta-cyclodextrin (beta-CD) and heptakis(2,3,6-tri-O-methyl)-beta-CD (TM-beta-CD) were used as chiral selectors. NMR spectrometry applied to obtain information about stoichiometry, binding constants structure selector-selectand complexes solution. The data further confirmed by UV electrospray ionization mass spectrometry. solid state determined using X-ray crystallography performed on co-crystals precipitated from 1:1 aqueous solution selector selectand. This multiple approach allowed an elucidation most likely structural reason a different affinity (binding strength) BrPh towards beta-CD TM-beta-CD. However, question force responsible opposite pattern these CDs could not be answered definitely.