Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, PR China.
Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China.
Carbohydr Polym. 2017 Sep 15;172:223-229. doi: 10.1016/j.carbpol.2017.05.049. Epub 2017 May 18.
Traditional cellulose-based chiral stationary phases (CSPs) are prepared by physically coating cellulose derivatives onto substrates and only compatible with a very limited range of solvents as the mobile phase. Therefore, chemical immobilization of cellulose derivatives onto silica gel has been efficiently applied to improve the solvent compatibility of cellulose-based CSPs. Here we developed a novel approach to homogeneously modifying cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC). A series of carboxylic acid functionalized CDMPCs (CC-Xs) with controlled amounts and randomly distributed carboxylic acid groups was synthesized. CC-Xs were effectively immobilized onto amine-modified silica gel to afford immobilized CSPs. Compared to coated-type CSPs, immobilized CSPs significantly improved the solvent compatibility while maintaining similar chiral recognition abilities, but the introduction of excessive functional groups led to a deteriorated performance for columns. Moreover, a commercial drug, atenolol, was also sufficiently separated on the immobilized CSPs.
传统的基于纤维素的手性固定相（CSP）是通过将纤维素衍生物物理涂覆在基质上制备的，并且仅与非常有限范围的溶剂作为流动相兼容。因此，纤维素衍生物的化学固定化已有效地应用于改善基于纤维素的 CSP 的溶剂兼容性。在这里，我们开发了一种均匀修饰纤维素三（3,5-二甲基苯基氨基甲酸酯）（CDMPC）的新方法。合成了一系列具有受控数量和随机分布羧酸基团的羧酸功能化 CDMPC（CC-Xs）。CC-Xs 有效地固定在胺改性硅胶上，得到固定化 CSP。与涂层型 CSP 相比，固定化 CSP 显著提高了溶剂兼容性，同时保持了相似的手性识别能力，但过多的官能团的引入导致柱性能恶化。此外，商业药物阿替洛尔也可以在固定化 CSP 上充分分离。
