Performance comparison of chiral separation materials derived from N-cyclohexylcarbonyl and N-hexanoyl chitosans

doi:10.1016/j.chroma.2017.11.067

CORC > 青岛生物能源与过程研究所 > 中国科学院青岛生物能源与过程研究所 > 条件保障部公共实验室

	Performance comparison of chiral separation materials derived from N-cyclohexylcarbonyl and N-hexanoyl chitosans
	Tang, Sheng 1; Liu, Jian-De 1; Chen, Wei 1; Huang, Shao-Hua 2; Zhang, Juan 1; Bai, Zheng-Wu 1
刊名	JOURNAL OF CHROMATOGRAPHY A
	2018-01-12
卷号	1532 页码:112-123
关键词	Polysaccharides Chitin Chitosan Chiral Stationary Phase High-performance Liquid Chromatography
ISSN号	0021-9673
DOI	10.1016/j.chroma.2017.11.067
文献子类	Article
英文摘要	Chitosan bis(phenylcarbamate)-(N-cyclohexylformamide)s and chitosan bis(phenylcarbamate)-(N-hexanamide)s were synthesized as chiral selectors for enantiomeric separation. Since two types of substituents with different structures were, respectively, introduced onto the 2-position and the 3-/6-positions of the glucose skeleton in the chitosans through a "heterogeneous" modification pathway, the enantioseparation performances of the chiral selectors could be improved. Influence of the type and position of the substituents on chiral recognition and enantioseparation abilities was studied in detail, and the structural dependence on enantioseparation performance was particularly demonstrated. It was found that methyl- and chloro-substituted chitosan bis(phenylcarbamate)(N-hexanamide)s possessed comparable enantioseparation performances, whereas chloro-substituted chitosan bis(phenylcarbamate)-(N-cyclohexylformamide)s exhibited much more powerful chiral recognition and enantioseparation abilities than the methyl-substituted ones. Among all the prepared chiral selectors, those with the combination of the cyclohexyl group at the 2-position of the glucose skeleton in the chitosan derivatives and the chlorophenyl group at the 3-/6-positions seemed to be more preferable for enantiomeric separation. As a result, the chitosan bis(3,4-dichlorophenylcarbamate)-(N-cyclohexylformamide) possessed the best enantioseparation performance. The solvent tolerability of the prepared chiral selectors was also investigated in the present study. Compared with the classical coated type chiral separation materials derived from cellulose/amylose derivatives, the N-cyclohexylcarbonyl and N-hexanoyl chitosans based chiral stationary phases were observed to possess more favorable solvent tolerability, thus possibly widening their applications for various practical enantioseparations. (C) 2017 Elsevier B.V. All rights reserved.
WOS关键词	LIQUID-CHROMATOGRAPHIC ENANTIOSEPARATION ; STATIONARY PHASES ; PACKING MATERIALS ; ENANTIOMERS ; DERIVATIVES ; AMYLOSE ; RESOLUTION ; CELLULOSE ; SELECTORS ; SILICA
WOS研究方向	Biochemistry & Molecular Biology ; Chemistry
语种	英语
出版者	ELSEVIER SCIENCE BV
WOS记录号	WOS:000423894500013
资助机构	National Natural Science Foundation of China(51373127 ; Natural Science Foundation of Hubei Province(2017CFB220) ; 81503036)
内容类型	期刊论文
源URL	[http://ir.qibebt.ac.cn/handle/337004/10589]
专题	青岛生物能源与过程研究所_条件保障部公共实验室
通讯作者	Huang, Shao-Hua; 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,Liu, Jian-De,Chen, Wei,et al. Performance comparison of chiral separation materials derived from N-cyclohexylcarbonyl and N-hexanoyl chitosans[J]. JOURNAL OF CHROMATOGRAPHY A,2018,1532:112-123.
APA	Tang, Sheng,Liu, Jian-De,Chen, Wei,Huang, Shao-Hua,Zhang, Juan,&Bai, Zheng-Wu.(2018).Performance comparison of chiral separation materials derived from N-cyclohexylcarbonyl and N-hexanoyl chitosans.JOURNAL OF CHROMATOGRAPHY A,1532,112-123.
MLA	Tang, Sheng,et al."Performance comparison of chiral separation materials derived from N-cyclohexylcarbonyl and N-hexanoyl chitosans".JOURNAL OF CHROMATOGRAPHY A 1532(2018):112-123.