Development of Efficient Chiral Packing and Their Recognition Mechanism

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Phenylcarbamate derivatives of polysaccharides such as cellulose and amylose show high chiral recognition abilities as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) and can resolve a broad range of enantiomers. In this study, the chiral recognition mechanism of the phenylcarbamate derivatives was mainly investigated.1. We found that amylose tris (3, 5-dimethylphenylcarbamate) (ADMPC) with low degree of polymerization is soluble in chloroform. This enabled us to study the chiral recognition mechanism of ADMPC by NMR spectroscopy. ADMPC exhibited chiral discrimination for many enantiomers in NMR as well as in HPLC.A good agreement was observed on the results of HPLC and NMR studies when chloroform was employed as a common solvent. Moreover, the structure of ADMPC in solution was investigated by NMR using 2D NOESY technique coupled with a computer modeling and left-handed 4.3 helical structure was obtained as the most probable one for ADMPC.2. The calculations of interaction energies between cellulose tris (phenylcarbamate) or cellulose tris (3,5-dimethylphenylcarbamate) and some racemates were performed by various methods to gain insight into the mechanism for the chiral recognition on phenylcarbamates of cellulose. The results of the calculations were good agreement with the results in the chromatographic resolution.3. Water-soluble amylose and some disaccharides were used as chiral selectors in capillary electrophoresis and they could resolve some racemates including several chiral drugs.