Mechanistic considerations of enantiorecognition on novel Cinchona alkaloid-based zwitterionic chiral stationary phases from the aspect of the separation of trans-paroxetine enantiomers as model compounds
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
26955754
DOI
10.1016/j.jpba.2016.02.043
PII: S0731-7085(16)30105-4
Knihovny.cz E-resources
- Keywords
- Enantiomer separation, High-performance liquid chromatography (HPLC), Molecular dynamic simulations, Zwitterionic chiral stationary phases, trans-Paroxetine enantiomers,
- MeSH
- Models, Chemical * MeSH
- Cinchona Alkaloids chemistry MeSH
- Paroxetine chemistry MeSH
- Stereoisomerism MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Cinchona Alkaloids MeSH
- Paroxetine MeSH
The enantiomers of trans-paroxetine were separated on four chiral stationary phases (CSPs) based on chiral zwitterionic Cinchona alkaloids fused with (R,R)- or (S,S)-trans-2-aminocyclohexanesulfonic acid. The enantioseparations were carried out in polar-ionic or in hydro-organic mobile phases with MeOH/THF, MeCN/THF, MeCN/THF/H2O and MeOH/MeCN/THF containing organic acid and base additives, in the temperature range 0-50°C. The effects of the mobile phase composition, the natures and concentrations of the additives and temperature on the separations were investigated. Thermodynamic parameters were calculated from plots of ln α vs 1/T. Δ(ΔH°) ranged between -3.0 and +1.5 kJ mol(-1), and Δ(ΔS°) between -8.8 and +5.9 J mol(-1)K(-1). The enantioseparation was generally enthalpically controlled, the retention factor and separation factor decreasing with increasing temperature, but entropically controlled separation was also observed. The elution sequences of the paroxetine enantiomers on the two pairs of pseudo-enantiomeric CSPs were investigated, and an attempt was made to explain the observed anomalies in silico in order to gain an insight into the underlying molecular recognition events between the four chiral selectors and the analyte enantiomers.
Department of Analytical Chemistry University of Vienna Währingerstrasse 38 1090 Vienna Austria
Department of Pharmaceutical Sciences University of Perugia Via Fabretti 48 06123 Perugia Italy
Institute of Pharmaceutical Chemistry University of Szeged H 6720 Szeged Eötvös u 6 Hungary
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