Liquid and subcritical fluid chromatographic enantioseparation of N α -Fmoc proteinogenic amino acids on Quinidine -based zwitterionic and anion-exchanger type chiral stationary phases. A comparative study
| Autor: | Gyula Lajkó, István Ilisz, Antal Péter, Ferenc Fülöp, Nóra Grecsó, Wolfgang Lindner, Gábor Tóth |
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| Rok vydání: | 2017 |
| Předmět: |
Pharmacology
Proteinogenic amino acid chemistry.chemical_classification Chromatography 010405 organic chemistry Elution 010401 analytical chemistry Organic Chemistry 01 natural sciences High-performance liquid chromatography Catalysis 0104 chemical sciences Analytical Chemistry Amino acid Solvent chemistry Drug Discovery Organic chemistry Stereoselectivity Acid–base reaction Enantiomer Spectroscopy |
| Zdroj: | Chirality. 29:225-238 |
| ISSN: | 0899-0042 |
| DOI: | 10.1002/chir.22700 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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