Enantioseparation of ondansetron by countercurrent chromatography using sulfobutyl ether-β-cyclodextrin as chiral selector.

Abstract

Ondansetron, a highly selective 5-hydroxytryptamine 3 receptor antagonist, was successfully enantioseparated by recycling countercurrent chromatography using sulfobutyl ether-β-cyclodextrin as chiral selector. Important factors for the enantioseparation were optimized, including different organic solvent, type of substituted β-cyclodextrin, pH of aqueous phase, concentration of chiral selector, and separation temperature. A biphasic solvent system composed of n-hexane: n-butyl acetate: 0.1mol/L phosphate buffer solution pH 9.2 with 50mmol/L of sulfobutyl ether-β-cyclodextrin (2.5:7.5:10, v/v/v) was selected. Under optimized separation conditions, 5mg of ondansetron was enantioseparated using recycling countercurrent chromatography, yielding 1.2 and 1.5mg of ondansetron enantiomers with 97.5 and 95.8% purity and the recovery reached 48-60%.