Liquid and subcritical fluid chromatographic enantioseparation of Nα-Fmoc proteinogenic amino acids on Quinidine-based zwitterionic and anion-exchanger type chiral stationary phases. A comparative study

Gyula Lajkó, Nóra Grecsó, Gábor Tóth, Ferenc Fülöp, Wolfgang Lindner, István Ilisz, Antal Péter

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Stereoselective high-performance liquid chromatographic and subcritical fluid chromatographic separations of 19 Nα-Fmoc proteinogenic amino acid enantiomers were carried out by using Quinidine-based zwitterionic and anion-exchanger-type chiral stationary phases Chiralpak ZWIX(−) and QD-AX. For optimization of retention and enantioselectivity, the ratio of bulk solvent components (MeOH/MeCN, H2O/MeOH, or CO2/MeOH) and the nature and concentration of the acid and base additives (counter- and co-ions) were systematically varied. The effect of column temperature on the enantioseparation was investigated and thermodynamic parameters were calculated from the van't Hoff plots ln α vs. 1/T. The thermodynamic parameters revealed that the enantioseparations were enthalpy-driven. The elution sequence was determined in all cases and with the exception of Fmoc-Cys(Trt)-OH, it was identical on both chiral stationary phases whereby the L-enantiomers eluted before the D-enantiomers.

Original languageEnglish
Pages (from-to)225-238
Number of pages14
JournalChirality
Volume29
Issue number6
DOIs
Publication statusPublished - 2017

Keywords

  • HPLC
  • N-Fmoc protein amino acids
  • SFC
  • enantiomer separation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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