Evaluation of quantitative structure property relationships necessary for enantioresolution with lambda- and sulfobutylether lambda-carrageenan in capillary electrophoresis

Lambda-carrageenan, a linear, high molecular weight sulfated polysaccharide , was successfully employed in both its native and sulfobutyl derivatized f orm as a chiral selector in capillary electrophoresis for the separation of enantiomers of basic pharmaceutical compounds. In order to characterize th e chiral selectivity properties of this chiral selector, various structural ly related racemic compounds were analyzed for enantiomeric interactions us ing capillary electrophoresis. The results of these studies were then ratio nalized and analyzed utilizing a general quantitative structure-property re lationship (QSPR) evaluation in order to predict critical analyte structura l requirements for successful enantiomeric separation. Important structural components of the analytes were found to include the aromatic content, the type of substitution on the aromatic ring, presence of a primary or second ary protonated amine, and an overall positive charge to the molecule. Chira lity 12:688-696, 2000. (C) 2000 Wiley-Liss, Inc.