A high-performance chiral selector derived from chitosan (p-methylbenzylurea) for efficient enantiomer separation

doi:10.1016/j.talanta.2018.03.048

QIBEBT-IR

	A high-performance chiral selector derived from chitosan (p-methylbenzylurea) for efficient enantiomer separation
	Tang, Sheng 1; Mei, Xiaomeng 1; Chen, Wei 1; Huang, Shao-Hua 2; Bai, Zheng-Wu 1
	2018-08-01
发表期刊	TALANTA
ISSN	0039-9140
卷号	185 页码:42-52
摘要	N-Methoxycarbonyl chitosan was prepared by selectively modifying the amino group at the 2-position of chitosan with methyl chloroformate, which was further functionalized with p-methylbenzylamine to produce chitosan (p-methylbenzylurea). Then, the hydroxyl groups at the 3- and 6-positions of the glucose skeleton were modified with various phenyl isocyanates, affording a series of chitosan 3,6-bis(arylcarbamate)-2-(p-methylbenzylurea)s, which were characterized and proposed as chiral selectors for enantiomer separation. Nineteen racemates, most of which are drugs or intermediates for drugs, were selected as the model analytes to evaluate the enantioseparation performance. The structure-performance relationship of the chiral selectors was investigated in detail. It was found that the methyl-substituted chiral selectors possessed more preferable enantioseparation performance compared with the chloro-substituted ones, and the chiral selectors containing a methyl substituent at the 4-position of the benzene ring showed the best chiral recognition and separation ability with 17 racemates being recognized and 13 racemates being baseline separated. The prepared chiral separation materials derived from these chiral selectors exhibited favorable solvent tolerance towards ethyl acetate, acetone, chloroform and a low proportion of tetrahydrofuran in normal phase. To sum up, this work provided a useful reference for the design and preparation of high-performance chiral separation materials for efficient enantiomer separation.
文章类型	Article
关键词	Chitin Chitosan Polysaccharide Chiral Stationary Phase Enantiomer Separation
WOS标题词	Science & Technology ; Physical Sciences
DOI	10.1016/j.talanta.2018.03.048
关键词[WOS]	LIQUID-CHROMATOGRAPHIC ENANTIOSEPARATION ; PHASE MICROEXTRACTION TECHNIQUES ; STATIONARY PHASES ; CARBAMATE DERIVATIVES ; AUTOMATION ; AMYLOSE ; SILICA ; UREA)S ; HPLC
收录类别	SCI
语种	英语
WOS研究方向	Chemistry
项目资助者	National Natural Science Foundation of China(51373127) ; Natural Science Foundation of Hubei Province(2017CFB220)
WOS类目	Chemistry, Analytical
WOS记录号	WOS:000433656200007
出版者	ELSEVIER SCIENCE BV
引用统计
文献类型	期刊论文
条目标识符	http://ir.qibebt.ac.cn/handle/337004/11454
专题	中国科学院青岛生物能源与过程研究所
通讯作者	Bai, Zheng-Wu
作者单位	1.Wuhan Inst Technol, Sch Chem & Environm Engn, Wuhan 430205, Hubei, Peoples R China 2.Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, Key Lab Biobased Mat, Qingdao 266101, Peoples R China
推荐引用方式 GB/T 7714	Tang, Sheng,Mei, Xiaomeng,Chen, Wei,et al. A high-performance chiral selector derived from chitosan (p-methylbenzylurea) for efficient enantiomer separation[J]. TALANTA,2018,185:42-52.
APA	Tang, Sheng,Mei, Xiaomeng,Chen, Wei,Huang, Shao-Hua,&Bai, Zheng-Wu.(2018).A high-performance chiral selector derived from chitosan (p-methylbenzylurea) for efficient enantiomer separation.TALANTA,185,42-52.
MLA	Tang, Sheng,et al."A high-performance chiral selector derived from chitosan (p-methylbenzylurea) for efficient enantiomer separation".TALANTA 185(2018):42-52.