Study of different chiral columns for the enantiomeric separation of azoles using supercritical fluid chromatography

Producción CientíficaThe enantiomeric separation of antifungal compounds is an arduous task in pharmaceutical and biomedical fields due to the different properties that each diastereoisomer presents. The enantioseparation of a group of fungicides (sulconazole, bifonazole, triadimefon and triadimenol) using supercritical fluid chromatography was achieved in this work. For this goal, four different chiral columns based on polysaccharide derivatives, as well as the effect of different chromatographic parameters such as temperature, type and percentage of organic modifier (methanol, ethanol and isopropanol), were thoroughly investigated. The inversion of the elution order of enantiomers as a result of a change in the stationary phase or organic modifier was also evaluated by employing a circular dichroism detector. The best separation conditions, in terms of the enantioresolution and analysis time, were obtained with the Lux® Cellulose-2 column using isopropanol as the organic modifier

Separación enantiomérica de azoles quirales por cromatografía de fluidos supercríticos con columnas derivadas de polisacáridos

En este trabajo se ha estudiado la separación enantiomérica de cuatro fungicidas quirales: sulconazol, bifonazol, triadimefon y triadimenol, utilizando la Cromatografía de Fluidos Supercríticos (SFC). Para ello, se ha investigado la influencia de la fase estacionaria, el tipo y porcentaje de modificador orgánico y la temperatura. Los tres modificadores orgánicos empleados fueron metanol, etanol y 2-propanol. Con la columna Chiralcel OD no se logró la separación enantioselectiva de ninguno de ellos. Por el contrario, con la columna Lux Cellulose2 se consiguieron muy buenas separaciones, obteniéndose enantiorresoluciones hasta línea de base para todos los fungicidas, con diferentes modificadores orgánicos en diferentes condiciones de temperatura. Finalmente, se seleccionaron las mejores condiciones para llevar a cabo la separación enantiomérica de cada uno de los compuestos.The enantiomeric separation of four chiral fungicides (sulconazole, bifonazole, triadimefon and triadimenol) using Supercritical Fluid Chromatography has been studied in this work. For this purpose, the effect of stationary phase, type and percentage of organic modifier (methanol, ethanol and 2-propanol) and temperature was investigated. The Chiralcel OD column did not provide good enantioresolutions for any of the compounds studied. On the other hand, using the LuxCellulose2 column, baseline separations were successfully achieved for all the compounds, with different organic modifiers and temperatures conditions. Finally, the best conditions for enantiomeric separation were established.Grado en Químic