High-performance liquid chromatographic enantioseparation of cyclic β-aminohydroxamic acids on zwitterionic chiral stationary phases based on Cinchona alkaloids
| Autor: | Beáta Fekete, Antal Péter, Ferenc Fülöp, Tímea Orosz, Gyula Lajkó, Márta Palkó, Wolfgang Lindner, Nóra Grecsó, István Ilisz |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Cinchona Alkaloids
Cinchona Hydroxamic Acids 01 natural sciences Biochemistry High-performance liquid chromatography Analytical Chemistry Phase (matter) Environmental Chemistry Organic chemistry Solvent composition Chromatography High Pressure Liquid Spectroscopy Amination Chromatography biology 010405 organic chemistry Chemistry Elution 010401 analytical chemistry Temperature Stereoisomerism biology.organism_classification 0104 chemical sciences Cyclization Thermodynamics Acid–base reaction Enantiomer |
| Zdroj: | Analytica Chimica Acta. 921:84-94 |
| ISSN: | 0003-2670 |
| DOI: | 10.1016/j.aca.2016.03.044 |
| Popis: | Cyclic β-aminohydroxamic acid enantiomer pairs were stereoselectively separated by high-performance liquid chromatography on the recently developed Cinchona alkaloid-based zwitterionic chiral stationary phases Chiralpak ZWIX(+)™, ZWIX(−)™, ZWIX(+A) and ZWIX(−A). The results of variation of the applied chromatographic conditions, such as the bulk solvent composition, the concentrations and ratio of the acid and base additives, the presence of water as mobile phase additive and the counter-ion concentration furnished a better understanding of the retention mechanism. A thermodynamic study in the temperature range 5–50 °C revealed enthalpy-controlled enantiodiscrimination in all cases. The structure–selectivity relationships clearly indicated the importance of the strereochemistry of the functional groups. From an enantiorecognition aspect, the diexo position of the functional groups always proved more favorable than the diendo position. The elution sequence was determined in all cases and was found to reversed when ZWIX(+)™ was changed to ZWIX(−)™ or ZWIX(+A) to ZWIX(−A). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect