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
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F16%3A43902790" target="_blank" >RIV/60461373:22310/16:43902790 - isvavai.cz</a>
Výsledek na webu
<a href="http://dx.doi.org/10.1016/j.jpba.2016.02.043" target="_blank" >http://dx.doi.org/10.1016/j.jpba.2016.02.043</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jpba.2016.02.043" target="_blank" >10.1016/j.jpba.2016.02.043</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
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
Popis výsledku v původním jazyce
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, Meal/THF, Meal/THF/H2O and MeOH/MeCN/THF containing organic acid and base additives, in the temperature range 0-50 degrees 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 In alpha vs 1/T. Delta(Delta H degrees) ranged between -3.0 and +1.5 kJ mol(-1), and Delta(Delta S degrees) 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 pseudoenantiomeric 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.
Název v anglickém jazyce
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
Popis výsledku anglicky
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, Meal/THF, Meal/THF/H2O and MeOH/MeCN/THF containing organic acid and base additives, in the temperature range 0-50 degrees 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 In alpha vs 1/T. Delta(Delta H degrees) ranged between -3.0 and +1.5 kJ mol(-1), and Delta(Delta S degrees) 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 pseudoenantiomeric 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.
Klasifikace
Druh
J<sub>x</sub> - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)
CEP obor
CB - Analytická chemie, separace
OECD FORD obor
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Návaznosti výsledku
Projekt
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Návaznosti
N - Vyzkumna aktivita podporovana z neverejnych zdroju
Ostatní
Rok uplatnění
2016
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Journal of Pharmaceutical and Biomedical Analysis
ISSN
0731-7085
e-ISSN
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Svazek periodika
124
Číslo periodika v rámci svazku
květen
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
10
Strana od-do
164-173
Kód UT WoS článku
000374202000019
EID výsledku v databázi Scopus
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