Synthesis and chromatographic properties of a novel chiral stationary phase derived from heptakis(6-azido-6-deoxy-2,3-di-O-phenylcarbamoylated)-β-cyclodextrin immobilized onto amino-functionalized silica gel via multiple urea linkages

A novel chiral stationary phase (PPHCDN7) was prepared by immobilization of heptakis(6-azido-6-deoxy-2,3-di-O-phenylcarbamoylated)-beta-cyclodextrin (PPHCD) onto the surface of amino-functionalized silica gel via multiple urea linkages derived from an extended application of the Staudinger reaction. A wide range of structurally divergent racemic drugs and other compounds were successfully separated into their enantiomers under both normal and reversed-phase conditions. beta-Adrenergic blockers and racemic tertiary, secondary and primary amines were readily separated using a mixture of methanol and aqueous triethylammonium acetate buffer. The optimal pH value for the separation falls in the range of 4.65 to 6.30. With atropine and isoproterenol, good enantioseparations with separation factors of alpha>5 were easily attainable. (C) 2002 Published by Elsevier Science B.V.