Novel chiral stationary phases (CSP) for enantioseparation processes

Abstract

Chiral stationary phases based on mono-(6-azido-6-deoxy)-perfunctionalized b-cyclodextrins, heptakis-(6-azido-6-deoxy-2,3-di-O-perfunctionalized)-b-cyclodextrins, and partial-6-(5-pent-1-enylated)-perfunctionalized-b-cyclodextrin were prepared and immobilized onto silica gel via mono, multiple urethane Linkages and ether covalent bonded respectively. A preparative scale column based on mono-(6-azido-6-deoxy)-perphenylcarbamoylated-b-cyclodextrin immobilized on silica gel was also synthesized. The enantioseparation abilities of these CSPs were evalued toward a wide variety of racemes. The results showed that they possessed excellent enantioresolution ability under both normal and reversed phases condition over amines, b-blockers, tropines, pyrimidine and simple organic compounds. Collection of pure isomers of several drugs on preparative scale was also successfully accomplished.The possible mechanism of enantioseparation was elucidated, chromatographic properties, such as thermodynamic studies, the effects of solvent, organic modifier, substituted groups of CSPs, immobilization methods and the influence of silica gel were inspected. The results showed that these immobilized CSPs exhibited excellent enantioseparation abilities under wide pH value from 2A?C to 40A?C.