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Increments to chiral recognition facilitating enantiomer separations of chiral acids, bases, and ampholytes using Cinchona-based zwitterion exchanger chiral stationary phases.
MedLine Citation:
PMID:  22761133     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
The intramolecular distances of anion and cation exchanger sites of zwitterionic chiral stationary phases represent potential tuning sites for enantiomer selectivity. In this contribution, we investigate the influence of alkanesulfonic acid chain length and flexibility on enantiomer separations of chiral acids, bases, and amphoteric molecules for six Cinchona alkaloid-based chiral stationary phases in comparison with structurally related anion and cation exchangers. Employing polar-organic elution conditions, we observed an intramolecular counterion effect for acidic analytes which led to reduced retention times but did not impair enantiomer selectivities. Retention of amphoteric analytes is based on simultaneous double ion pairing of their charged functional groups with the acidic and basic sites of the zwitterionic selectors. A chiral center in the vicinity of the strong cation exchanger site is vital for chiral separations of bases. Sterically demanding side chains are beneficial for separations of free amino acids. Enantioseparations of free (un-derivatized) peptides were particularly successful in stationary phases with straight-chain alkanesulfonic acid sites, pointing to a beneficial influence of more flexible moieties. In addition, we observed pseudo-enantiomeric behavior of quinine and quinidine-derived chiral stationary phases facilitating reversal of elution orders for all analytes.
Authors:
Stefanie Wernisch; Reinhard Pell; Wolfgang Lindner
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of separation science     Volume:  35     ISSN:  1615-9314     ISO Abbreviation:  J Sep Sci     Publication Date:  2012 Jul 
Date Detail:
Created Date:  2012-07-04     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101088554     Medline TA:  J Sep Sci     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  1560-72     Citation Subset:  IM    
Copyright Information:
© 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Institute for Analytical Chemistry, University of Vienna, Vienna, Austria.
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