Controlled synthesis and chiral recognition of immobilized cellulose and amylose tris(cyclohexylcarbamate)s/3-(triethoxysilyl)propylcarbamates as chiral packing materials for high-performance liquid chromatography

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• 作者：Jun Shen^a ; Shuangyan Liu^a ; Pengfei Li^a ; Xiande Shen^a ; Yoshio Okamoto^a ; ^b ; ^{okamoto@apchem.nagoya-u.ac.jp}
• 关键词：Cyclohexylcarbamate ; Polysaccharide ; Immobilization ; Chiral packing material (CPM) ; Chiral stationary phase ; High-performance liquid chromatography (HPLC) ; Thin-layer chromatography (TLC)
• 刊名：Journal of Chromatography A
• 出版年：2012
• 期刊代码：47_00219673
• 类别：ch
• 出版时间：13 July, 2012
• 卷：1246
• 期：Complete
• 页码：137-144
• 文件大小：693 K

摘要

The cyclohexylcarbamates of cellulose and amylose bearing a controlled amount of 3-(triethoxysilyl)propyl residue were synthesized by a one-pot process and efficiently immobilized onto silica gel through the intermolecular polycondensation of triethoxysilyl group. Their chiral recognition abilities were evaluated as chiral packing materials (CPMs) for high-performance liquid chromatography (HPLC). The immobilized CPMs exhibited comparable or higher recognition abilities than the conventional coated-type CPMs. The universal solvent compatibility of the immobilized CPMs clearly contributes to the improvement of chiral recognition for most racemates used in the present study. Interestingly, a significantly improved resolution for racemic trans-stilbene oxide (伪 = 2.23) could be attained on the immobilized CPM using the eluent containing 30 vol.%chloroform in hexane, which cannot be used for the conventional coated-type CPMs. On the CPMs, almost no resolution of trans-stilbene oxide was attained by a typical eluent, hexane-2-propanol mixture (90/10, v/v). The novel immobilized CPM can also be used in thin-layer chromatography (TLC) due to the absence of an aromatic group.