Preparation and Chiral Recognition of Chiral Stationary Phases Derived from Benzoylated Chitosan

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	Preparation and Chiral Recognition of Chiral Stationary Phases Derived from Benzoylated Chitosan
	Luo, Ying-bin 1; Wang, Xiao-chen 1; Chen, Wei 1; Huang, Shao-hua 2; Bai, Zheng-wu 1
	2014-08-20
发表期刊	ACTA POLYMERICA SINICA
期号	8 页码:1103-1109
摘要	In order to develop novel chiral stationary phases ( CSPs ), chitosan was modified by benzoyl chlorides with various substituents, successively using methylsulfonic acid and N, N-dimethylacetamide as the solvents. In this way, new derivatives of chitosan bis ( benzoate )-( benzamide ), chitosan bis ( 4-methylbenzoate )- ( 4-methylbenzamide ), chitosan bis ( 3, 5-dimethylbenzoate )- ( 3, 5-dimethylbnzamide ) and chitosan bis ( 4-chlorobenzoate )-( 4-chlorobenzamide ) were synthesized. The corresponding CSPs were prepared by coating the chitosan derivatives on porous 3-aminopropyl silica gel employing N, N-dimethylforamide as the solvent. The chiral recognition capability of the CSPs was evaluated towards structurally various chiral compounds in normal phase conditions, and the results showed that these CSPs possessed satisfactory enantioselectivity. The CSP prepared from chitosan bis ( 4-methylbenzoate ) - ( 4-methylbenzamide ) with a coating ratio of 16% exhibited better chiral recognition capability than that prepared from the same derivative with a coating ratio of 20%. The CSP based on chitosan bis ( 3,5-dimethylbenzoate ) - ( 3,5-dimethylbenzamide ) showed stronger chiral recognition capability than the CSPs based on the other derivatives. Meanwhile, the CSP derived from chitosan bis( 4-methylbenzoate ) - ( 4-methylbenzamide ) separated the chiral compounds with highest resolutions. This feature is similar to that of the CSP derived from cellulose tris( 4-methylbenzoate ), and different from that of the CSP prepared from amylose tris( 4-methylbenozate ) that bear poor chiral recognition capability. The reason may be related to the similarity of chitosan and cellulose in which the repeating units are all connected by beta-1, 4-glycosidic bond, other than alpha-1,4-glycosidic bond in amylose. In addition, the CSPs generally demonstrated better resolutions in the mobile phases simultaneously containing ethanol and methanol.
文章类型	Article
关键词	Chitosan Benzoylation Coating Chiral Stationary Phase Chiral Recognition
WOS标题词	Science & Technology ; Physical Sciences
关键词[WOS]	POLYSACCHARIDE DERIVATIVES ; SILICA-GEL ; CHROMATOGRAPHIC RESOLUTION ; ENANTIOMERS ; SEPARATION ; DISCRIMINATION ; IMMOBILIZATION ; CHITIN ; COLUMN ; NMR
收录类别	SCI
语种	英语
WOS研究方向	Polymer Science
WOS类目	Polymer Science
WOS记录号	WOS:000340351000011
引用统计
文献类型	期刊论文
条目标识符	http://ir.qibebt.ac.cn/handle/337004/6316
专题	公共实验室
作者单位	1.Wuhan Inst Technol, Sch Chem & Environm Engn, Wuhan 430073, Peoples R China 2.Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, Qingdao 266101, Peoples R China
推荐引用方式 GB/T 7714	Luo, Ying-bin,Wang, Xiao-chen,Chen, Wei,et al. Preparation and Chiral Recognition of Chiral Stationary Phases Derived from Benzoylated Chitosan[J]. ACTA POLYMERICA SINICA,2014(8):1103-1109.
APA	Luo, Ying-bin,Wang, Xiao-chen,Chen, Wei,Huang, Shao-hua,&Bai, Zheng-wu.(2014).Preparation and Chiral Recognition of Chiral Stationary Phases Derived from Benzoylated Chitosan.ACTA POLYMERICA SINICA(8),1103-1109.
MLA	Luo, Ying-bin,et al."Preparation and Chiral Recognition of Chiral Stationary Phases Derived from Benzoylated Chitosan".ACTA POLYMERICA SINICA .8(2014):1103-1109.