Reversed-phase liquid chromatographic enantioseparation by cycloalkylcarboxylates of cellulose and amylose

Three novel cycloalkylcarboxylates, cyclopentyl, cyclobexyl, and 1-adamantylcarboxylates of cellulose and amylose were prepared and their chiral recognition abilities as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) were evaluated using a methanol-water mobile phase. Among these esters, cellulose tris(cyclohexylcarboxylate) showed a relatively high chiral recognition ability. The 1-adamantylcarboxylates of cellulose and amylose showed dissimilar chiral recognition abilities from the other two, probably due to the low degree of substitution and the high hydrophobicity of this group. (C) 2004 Wiley-Liss, Inc.