Abstract:

Five new amylose derivatives, namely amylose 2-benzoate-3-(4-chlorophenylcarbamate)-6-(3,5-dimethylphenylcarbamate), amylose 2-benzoate-3-(4-chlorophenylcarbamate)-6-(3,5-dichlorophenylcarbamate), amylose 2-benzoate-3,6-bis(4-chlorophenylcarbamate), amylose 2-(4-chlorobenzoate)-3,6-bis(4-chlorophenylcarbamate) and amylose 2-(4-chlorobenzoate)-3,6-biscyclohexylcarbamate, were synthesized by a series of regioselective process. These derivatives were then coated on the surface of aminopropyl silica gels, and used as chiral stationary phases (CSPs) for high performance liquid chromatography (HPLC). These derivatives were characterized by ¹H-nuclear magnetic resonance (¹H-NMR) and Fourier transform infrared (FT-IR) spectroscopies, and their chiral recognition abilities were evaluated using nine racemates by HPLC. Compared with other amylose derivatives, some racemates were better resolved on the new CSPs. The obtained results indicate that the property and position of substituents at 2-, 3- and 6-positions of glucose unit have great influence on the chiral recognition abilities of the amylose derivatives.

Key words: amylose, benzoates, chiral recognition, chiral stationary phases (CSPs), enantioseparation, high performance liquid chromatography (HPLC), phenylcarbamates