Controlled synthesis, immobilization and chiral recognition of carboxylic acid functionalized cellulose tris(3,5-dimethylphenylcarbamate)

Miaomiao Han; Xiaosa Jin; Han Yang; Xiao Liu; Yadong Liu; Shengxiang Ji

doi:10.1016/j.carbpol.2017.05.049

Controlled synthesis, immobilization and chiral recognition of carboxylic acid functionalized cellulose tris(3,5-dimethylphenylcarbamate)

Carbohydr Polym. 2017 Sep 15:172:223-229. doi: 10.1016/j.carbpol.2017.05.049. Epub 2017 May 18.

Authors

Miaomiao Han¹, Xiaosa Jin², Han Yang¹, Xiao Liu³, Yadong Liu¹, Shengxiang Ji⁴

Affiliations

¹ Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, PR China.
² 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.
³ Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, PR China; University of Science and Technology of China, Hefei 230026, Anhui, PR China.
⁴ Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, PR China. Electronic address: sji@ciac.ac.cn.

PMID: 28606529
DOI: 10.1016/j.carbpol.2017.05.049

Abstract

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.

Keywords: Chiral separation; Chiral stationary phase; HPLC; Immobilization; Polysaccharide derivative.