Determination of the enantiomeric purity of 2-(2′-carboxy-3′-phenylcyclopropyl)glycines by chiral capillary electrophoresis

Abstract

A fast and practical chiral capillary electrophoretic method has been developed for determination of the enantiomeric purity of 2-(2′-carboxy-3′-phenylcyclopropyl)glycine (PCCG) compounds. In particular, the isomer PCCG-13, a potent selective and competitive antagonist at phospholipaseD-coupled metabotropic glutamate receptors (mGluRs), was completely resolved from its enantiomer PCCG-15 by use of dimethyl-β-cyclodextrin (DMCD) as chiral selector. pH 9.0 running buffer containing 2-amino-2-methyl-1,3-propanediol (AMPD; 100mM) was a suitable medium enabling resolution of the enantiomers in a short (32.5 cm total length) poly(vinyl alcohol) (PVA)-coated capillary. Because of the suppression of the electroosmotic flow and the good peak shape, baseline resolution of the enantiomers was obtained by use of the optimum concentration of chiral selector. For quantitative purposes at impurity levels, high sample loading was required and adequate separation was obtained in the presence of 80 mM DMCD.