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

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>

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CB - Analytická chemie, separace

OECD FORD obor

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Projekt

—

Návaznosti

N - Vyzkumna aktivita podporovana z neverejnych zdroju

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Pharmaceutical and Biomedical Analysis

ISSN

0731-7085

e-ISSN

—

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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