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Evaluation of quantitative structure property relationships necessary for enantioresolution with lambda‐ and sulfobutylether lambda‐carrageenan in capillary electrophoresis
Author(s) -
Beck Gregory M.,
Neau Steven H.,
Holder Andrew J.,
Hemenway Jeffrey N.
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/1520-636x(2000)12:9<688::aid-chir8>3.0.co;2-9
Subject(s) - chemistry , capillary electrophoresis , enantiomer , analyte , amine gas treating , chirality (physics) , molecule , chromatography , selectivity , protonation , combinatorial chemistry , stereochemistry , organic chemistry , ion , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , catalysis
Lambda‐carrageenan, a linear, high molecular weight sulfated polysaccharide, was successfully employed in both its native and sulfobutyl derivatized form as a chiral selector in capillary electrophoresis for the separation of enantiomers of basic pharmaceutical compounds. In order to characterize the chiral selectivity properties of this chiral selector, various structurally related racemic compounds were analyzed for enantiomeric interactions using capillary electrophoresis. The results of these studies were then rationalized and analyzed utilizing a general quantitative structure‐property relationship (QSPR) evaluation in order to predict critical analyte structural 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 secondary protonated amine, and an overall positive charge to the molecule. Chirality 12:688–696, 2000. © 2000 Wiley‐Liss, Inc.