Multimilligram enantioresolution of sulfoxide proton pump inhibitors by liquid chromatography on polysaccharide-based chiral stationary phase.
The enantiomers of sulfoxide proton pump inhibitors--omeprazole, lansoprazole, rabeprazole and Ro 18-5364--were enantiomerically separated by liquid chromatography at multimilligram scale on a polysaccharide-based chiral stationary phase using normal and polar organic conditions as mobile phase. The values of the recovery and production rate were significant for each enantiomer; better results were achieved using a solid-phase injection system. However, this system was applied just for the enantiomeric separation of omeprazole to demonstrate the applicability of this injection mode at milligram scale. The chiroptical characterization of the compounds was performed using a polarimeter and a circular dichroism detector. The higher enantiomeric purity obtained for the isolated enantiomers suggests that the methods here described should be considered as a simple and rapid way to obtain enantiomeric pure standards for analytical purpose.
Belaz
Kátia Roberta Anacleto
KR
Departamento de Química, Universidade Federal de São Carlos, Cx Postal 676, São Carlos 13560-905, SP, Brazil.
Coimbra
Mariana
M
Barreiro
Juliana Cristina
JC
Montanari
Carlos A
CA
Cass
Quezia Bezerra
QB
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D011134:Polysaccharides / Q000737:chemistry*; D054328:Proton Pump Inhibitors / Q000737:chemistry*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
D011134:Polysaccharides; D054328:Proton Pump Inhibitors; D013454:Sulfoxides