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Molecules 2015, 20(1), 70-87; doi:10.3390/molecules20010070

Comparison of the Separation Performances of Cinchona Alkaloid-Based Zwitterionic Stationary Phases in the Enantioseparation of β2- and β3-Amino Acids

1
Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary
2
Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary
3
Department of Chemistry, University of Warsaw, Pasteura str. 1, 02-093 Warsaw, Poland
4
Department of Analytical Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria
*
Author to whom correspondence should be addressed.
Academic Editor: Stig Allenmark
Received: 10 November 2014 / Accepted: 15 December 2014 / Published: 23 December 2014
(This article belongs to the Special Issue Dynamic Stereochemistry)
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Abstract

The enantiomers of twelve unusual β2- and β3-homoamino acids containing the same side-chains were separated on chiral stationary phases containing a quinine- or quinidine-based zwitterionic ion-exchanger as chiral selector. The effects of the mobile phase composition, the nature and concentration of the acid and base additives and temperature on the separations were investigated. The changes in standard enthalpy, ∆(∆H°), entropy, ∆(∆S°), and free energy, ∆(∆G°), were calculated from the linear van’t Hoff plots derived from the ln α vs. 1/T curves in the studied temperature range (10–50 °C). The values of the thermodynamic parameters depended on the nature of the selectors, the structures of the analytes, and the positions of the substituents on the analytes. A comparison of the zwitterionic stationary phases revealed that the quinidine-based ZWIX(−)™ column exhibited much better selectivity for both β2- and β3-amino acids than the quinine-based ZWIX(+)™ column, and the separation performances of both the ZWIX(+)™ and ZWIX(−)™ columns were better for β2-amino acids. The elution sequence was determined in some cases and was observed to be R < S and S < R on the ZWIX(+)™ and ZWIX(−)™ columns, respectively. View Full-Text
Keywords: column liquid chromatography; β2-amino acids; β3-amino acids; Cinchona alkaloid-based chiral stationary phases column liquid chromatography; β2-amino acids; β3-amino acids; Cinchona alkaloid-based chiral stationary phases
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Ilisz, I.; Grecsó, N.; Misicka, A.; Tymecka, D.; Lázár, L.; Lindner, W.; Péter, A. Comparison of the Separation Performances of Cinchona Alkaloid-Based Zwitterionic Stationary Phases in the Enantioseparation of β2- and β3-Amino Acids. Molecules 2015, 20, 70-87.

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