Chiral separation of highly negatively charged enantiomers by capillary electrophoresis

Abstract

The separation of two highly negatively charged enantiomeric organic disulfates containing two chiral centers was investigated by capillary electrophoresis using cyclodextrin based chiral selectors added to the run buffer. The optimum separation for the enantiomers was achieved in less than 3 min at 25 °C with a run buffer of 10 mM glycine pH 2.4 and 5 mM QA-β-CD, which is a positively charged quaternary ammonium β-cyclodextrin derivative. The method resulted in baseline resolution, excellent linearity, and highly reproducible migration times allowing facile evaluation of the enantiomeric purity of the individual isomers. Detection limits for the enantiomeric pair were determined to be 0.3 ng/μl (S/N=3). The nature of the selector–enantiomer interaction and a quantitative measurement of the apparent stability constants that governed chiral discrimination of the enantiomers with QA-β-CD were also investigated by UV-Vis spectroscopy and electrospray ionization mass spectrometry.