High performance chiral separation materials based on chitosan bis(3,5-dimethylphenylcarbamate)-(alkyl urea)s

Jing Wang; Jiang-Bo Xi; Wei Chen; Shao-Hua Huang; Zheng-Wu Bai

doi:10.1016/j.carbpol.2016.09.047

High performance chiral separation materials based on chitosan bis(3,5-dimethylphenylcarbamate)-(alkyl urea)s

Carbohydr Polym. 2017 Jan 20:156:481-489. doi: 10.1016/j.carbpol.2016.09.047. Epub 2016 Sep 15.

Authors

Jing Wang¹, Jiang-Bo Xi¹, Wei Chen¹, Shao-Hua Huang², Zheng-Wu Bai³

Affiliations

¹ School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China.
² Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China.
³ School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430073, China. Electronic address: zwbai@wit.edu.cn.

PMID: 27842849
DOI: 10.1016/j.carbpol.2016.09.047

Abstract

Enantioseparation plays an important role for many fields and for pharmaceutical industry in particular. Chiral stationary phase (CSP) is the core of chiral liquid chromatography that effectively implements enantioseparation. In order to develop coated type CSPs with excellent enantioseparation capability and high tolerance against mobile phases, in this work, a series of chitosan bis(3,5-dimethylphenylcarbamate)-(alkyl urea)s were synthesized, which were coated on 3-aminopropyl silica gel to afford new CSPs. Owing to strong hydrogen bonds formed among the synthesized derivatives, the supra-structure of the derivatives should be highly ordered. Hence, these CSPs could provide excellent separation capability and could tolerate common organic solvents that are usually prohibited for coated type CSPs of cellulose and amylose derivatives. Therefore the newly prepared CSPs exhibited promising prospects for enantioseparation of chiral compounds.

Keywords: Chiral stationary phase; Chitosan; Derivatization; Enantioseparation; High performance liquid chromatography.