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Performance comparison of chiral separation materials derived from N-cyclohexylcarbonyl and N-hexanoyl chitosans
Tang, Sheng1; Liu, Jian-De1; Chen, Wei1; Huang, Shao-Hua2; Zhang, Juan1; Bai, Zheng-Wu1
2018-01-12
发表期刊JOURNAL OF CHROMATOGRAPHY A
ISSN0021-9673
卷号1532页码:112-123
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.
文章类型Article
关键词Polysaccharides Chitin Chitosan Chiral Stationary Phase High-performance Liquid Chromatography
WOS标题词Science & Technology ; Life Sciences & Biomedicine ; Physical Sciences
DOI10.1016/j.chroma.2017.11.067
关键词[WOS]LIQUID-CHROMATOGRAPHIC ENANTIOSEPARATION ; STATIONARY PHASES ; PACKING MATERIALS ; ENANTIOMERS ; DERIVATIVES ; AMYLOSE ; RESOLUTION ; CELLULOSE ; SELECTORS ; SILICA
收录类别SCI
语种英语
WOS研究方向Biochemistry & Molecular Biology ; Chemistry
项目资助者National Natural Science Foundation of China(51373127 ; Natural Science Foundation of Hubei Province(2017CFB220) ; 81503036)
WOS类目Biochemical Research Methods ; Chemistry, Analytical
WOS记录号WOS:000423894500013
出版者ELSEVIER SCIENCE BV
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文献类型期刊论文
条目标识符http://ir.qibebt.ac.cn/handle/337004/10590
专题公共实验室
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
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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.
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