Document Detail

Synergistic effects on enantioselectivity of zwitterionic chiral stationary phases for separations of chiral acids, bases, and amino acids by HPLC.
MedLine Citation:
PMID:  18855417     Owner:  NLM     Status:  MEDLINE    
In an attempt to overcome the limited applicability scope of earlier proposed Cinchona alkaloid-based chiral weak anion exchangers (WAX) and recently reported aminosulfonic acid-based chiral strong cation exchangers (SCX), which are conceptionally restricted to oppositely charged solutes, their individual chiral selector (SO) subunits have been fused in a combinatorial synthesis approach into single, now zwitterionic, chiral SO motifs. The corresponding zwitterionic ion-exchange-type chiral stationary phases (CSPs) in fact combined the applicability spectra of the parent chiral ion exchangers allowing for enantioseparations of chiral acids and amine-type solutes in liquid chromatography using polar organic mode with largely rivaling separation factors as compared to the parent WAX and SCX CSPs. Furthermore, the application spectrum could be remarkably expanded to various zwitterionic analytes such as alpha- and beta-amino acids and peptides. A set of structurally related yet different CSPs consisting of either a quinine or quinidine alkaloid moiety as anion-exchange subunit and various chiral or achiral amino acids as cation-exchange subunits enabled us to derive structure-enantioselectivity relationships, which clearly provided strong unequivocal evidence for synergistic effects of the two oppositely charged ion-exchange subunits being involved in molecular recognition of zwitterionic analytes by zwitterionic SOs driven by double ionic coordination.
Christian V Hoffmann; Reinhard Pell; Michael Lämmerhofer; Wolfgang Lindner
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-10-15
Journal Detail:
Title:  Analytical chemistry     Volume:  80     ISSN:  1520-6882     ISO Abbreviation:  Anal. Chem.     Publication Date:  2008 Nov 
Date Detail:
Created Date:  2008-11-14     Completed Date:  2009-02-02     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0370536     Medline TA:  Anal Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8780-9     Citation Subset:  IM    
Christian Doppler Laboratory for Molecular Recognition Materials, Department of Analytical Chemistry & Food Chemistry, University of Vienna, Währinger Strasse 38, A-1090 Vienna, Austria.
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MeSH Terms
Alkaloids / chemistry
Amines / chemistry*,  isolation & purification*
Amino Acids / chemistry*,  isolation & purification*
Chromatography, High Pressure Liquid
Dipeptides / chemistry,  isolation & purification
Substrate Specificity
Sulfonic Acids / chemistry
Reg. No./Substance:
0/Alkaloids; 0/Amines; 0/Amino Acids; 0/Dipeptides; 0/Sulfonic Acids

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