Synthesis and chiral recognition of novel amylose derivatives containing regioselectively benzoate and phenylcarbamate groups |
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Authors: | Jun Shen Tomoyuki Ikai Yoshio Okamoto |
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Affiliation: | 1. School of Material Science and Chemical Engineering, Harbin Engineering University, Harbin, China;2. EcoTopia Science Institute, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan |
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Abstract: | A new class of regioselectively substituted amylose derivatives bearing three different substituents at 2-, 3- and 6-positions, and two different substituents at 2-position and 3-, 6-positions were synthesized by a sequential process based on the esterification of 2-position of a glucose unit. Their chiral recognition abilities were evaluated as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). Each derivative had its own characteristic recognition ability depending on the arrangement of side chains at the three positions. Among the derivatives, amylose 2-(4-t-butylbenzoate) and amylose 2-(4-chlorobenzoate) series exhibited high chiral recognition. Some racemates can be efficiently separated on these derivatives as well as on the amylose tris-3,5-dimethylphenylcarbamate, which is commercially available as Chiralpak AD and one of the most powerful CSPs. The structures of the amylose derivatives were also investigated by circular dichroism spectroscopy. |
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Keywords: | Regioselective substitution Polysaccharide Chiral stationary phase CSP High-performance liquid chromatography HPLC Enantioseparation |
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