High-performance liquid chromatographic separation of unusual β3-amino acid enantiomers in different chromatographic modes on Cinchona alkaloid-based zwitterionic chiral stationary phases

被引:0
作者
István Ilisz
Nóra Grecsó
Roman Papoušek
Zoltán Pataj
Petr Barták
László Lázár
Ferenc Fülöp
Wolfgang Lindner
Antal Péter
机构
[1] University of Szeged,Department of Inorganic and Analytical Chemistry
[2] University of Szeged,Institute of Pharmaceutical Chemistry
[3] Palacký University,Department of Analytical Chemistry, Faculty of Science, Regional Centre of Advanced Technologies and Materials
[4] University of Vienna,Department of Analytical Chemistry
来源
Amino Acids | 2015年 / 47卷
关键词
Enantiomer separation; HPLC; β; -Amino acids; alkaloid-based zwitterionic columns;
D O I
暂无
中图分类号
学科分类号
摘要
Polar-ionic and hydro-organic mobile phase mode of high-performance liquid chromatographic separations of 23 sterically constrained primary β3-amino acid enantiomers containing, alkyl, aryl or heteroaryl side-chains were carried out by using newly developed Cinchona alkaloid-based zwitterionic chiral selectors and the stationary phases Chiralpak ZWIX(+)™ and ZWIX(−)™. In the polar-ionic mode, the effects of the composition of the bulk solvent and the natures of the co- and counter-ions, while in the hydro-organic mode, the effects of the pH, the counter-ion concentration and the structures of the analytes were investigated. The separations of the enantiomers of these 23 primary β3-amino acids, which can be classified as a series of quasi- (pseudo-) homologs, were optimized in both chromatographic modes. The elution sequence was determined in most cases and a reversal of elution order on ZWIX(+)™ and ZWIX(−)™ column was observed. On the basis of this intermolecular recognition model between the selectors and the given enantiomers an indirect assignment of the resolved enantiomer via chromatography is proposed.
引用
收藏
页码:2279 / 2291
页数:12
相关论文
共 202 条
  • [1] Adlof R(2004)Analysis of triglyceride isomers by silver-ion high-performance liquid chromatography: effect of column temperature on retention time J Chromatogr A 46 109-113
  • [2] List G(2009)High-performance liquid chromatographic enantioseparation of 2-aminomono- and dihydroxycyclopentanecarboxylic and 2-aminodihydroxycyclohexanecarboxylic acids on macrocyclic glycopeptide-based phases J Chromatogr A 1216 927-932
  • [3] Berkecz R(2000)A study of the thermodynamics and influence of temperature on chiral high-performance liquid chromatographic separations using cellulosetris (3,5-dimethylphenylcarbamate) coated zirconia stationary phases Chromatographia 52 535-542
  • [4] Ilisz I(2003)Effect of phase ratio on van’t Hoff analysis in reversed-phase liquid chromatography, and phase-ratio-independent estimation of transfer enthalpy J Chromatogr A 1003 101-111
  • [5] Benedek G(1976)IUPAC Nomenclature of organic chemistry, section F, stereochemistry Pure Appl Chem 45 11-30
  • [6] Fülöp F(2000)Application of a new chiral stationary phase containing the glycopeptide antibiotic A-40,926 in the direct chromatographic resolution of β-amino acids Tetrahedron Asymmetry 11 2375-2385
  • [7] Armstrong DW(1998)A closer study of chiral retention mechanisms Chirality 10 375-381
  • [8] Péter A(2012)Peptidic foldamers: ramping up diversity Chem Soc Rev 41 687-702
  • [9] Castells CB(1977)Asymmetric syntheses of β-amino acids by the addition of chiral amines to C=C double bonds Chem Pharm Bull 25 1319-1325
  • [10] Carr RW(2013)High-performance liquid chromatographic enantioseparation of isoxazoline-fused 2-aminocyclopentanecarboxylic acids on a chiral ligand-exchange stationary phase J Sep Sci 36 1335-1342