The evaluation and consideration of the enantioselectivity of three newly developed host-guest interaction type HPLC chiral stationary phases are summarized in this paper. It was found that the novel chiral stationary phase containing a sugar chain between β-cyclodextrin and silica gel support (SUMICHIRAL® OA-7000) has different enantioselectivity from conventional cyclodextrin-type stationary phases. Furthermore, it was shown that the β-cyclodextrin stationary phase with acetylated hydroxyl groups (OA-7700) has excellent enantiomeric separation ability for many aromatic amines. These factors were considered from the viewpoint of the separation mechanism. We also designed the chiral stationary phase in which a pseudo-18-crown-6-ether derivative was immobilized on silica gel with an amide bond (OA-8000) and evaluated its enantioselectivity. In the separation of chiral primary amines, we found that OA-7700 and OA-8000 have complementary enantioselectivity to the difference in substituents of guest compounds and considered this factor. The developed stationary phases can
perform chiral separation using a reverse phase mobile phase and is expected to be effectively used for analysis of chiral drugs.