Development of New Chiral Packing Material for HPLC Based on the Structure Control of Polysaccharide Derivatives and Their Immobilization onto Silica Gel

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Phenylcarbamate derivatives of cellulose and amylose are known to show high chiral recognition as chiral stationary phases (CSPs) in HPLC. However, the solvents such as chloroform and tetrahydrofuran, which dissolve or swell the polysacoharide derivatives, cannot be used as main mobile phases for the CSPs. In order to overcome this defect, the cellulose 3,5-dimethylphenylcarbamate derivative having a regioselective vinyl group was immobilized to silica gel via the radical copolymerization with vinyl monomer under various immobilization conditions.・When the content of the vinyl monomer was low, the chiral recognition abilities of the obtained CSPs were similar to those of the coated CSP.・The immobilization was attained more effectively by using silica gel having a vinyl group.・Cellulose derivative having a random vinyl group at the 2-, 3-, and 6-positions were prepared by the one-pot process to avoid the complicated synthetic process. The obtained derivative was quantitatively immobilized on silica gel as well as the cellulose derivatives having the regioselective vinyl group.・When the cellulose derivative having a vinyl group was copolymerized with 2,3-dimethylbutadiene, the chiral recognition ability of the immobilized CSP was close to those of the coated CSP.This immobilization method was effective for other phenylcarbamate derivatives of cellulose and amylose, indicating that it must be valuable for the preparation of the polysaccharide-based packing materials for the next generation.