Evaluation of quantitative structure property relationships necessary for enantioresolution with lambda- and sulfobutylether lambda-carrageenan in capillary electrophoresis
Gm. Beck et al., Evaluation of quantitative structure property relationships necessary for enantioresolution with lambda- and sulfobutylether lambda-carrageenan in capillary electrophoresis, CHIRALITY, 12(9), 2000, pp. 688-696
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.