| 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
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| 2018-01-12 | |
| Source Publication | JOURNAL OF CHROMATOGRAPHY A
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| ISSN | 0021-9673 |
| Volume | 1532Pages:112-123 |
| Abstract | 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. |
| Subtype | Article |
| Keyword | Polysaccharides Chitin Chitosan Chiral Stationary Phase High-performance Liquid Chromatography |
| WOS Headings | Science & Technology ; Life Sciences & Biomedicine ; Physical Sciences |
| DOI | 10.1016/j.chroma.2017.11.067 |
| WOS Keyword | LIQUID-CHROMATOGRAPHIC ENANTIOSEPARATION ; STATIONARY PHASES ; PACKING MATERIALS ; ENANTIOMERS ; DERIVATIVES ; AMYLOSE ; RESOLUTION ; CELLULOSE ; SELECTORS ; SILICA |
| Indexed By | SCI |
| Language | 英语 |
| WOS Research Area | Biochemistry & Molecular Biology ; Chemistry |
| Funding Organization | National Natural Science Foundation of China(51373127 ; Natural Science Foundation of Hubei Province(2017CFB220) ; 81503036) |
| WOS Subject | Biochemical Research Methods ; Chemistry, Analytical |
| WOS ID | WOS:000423894500013 |
| Publisher | ELSEVIER SCIENCE BV |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.qibebt.ac.cn/handle/337004/10590 |
| Collection | 公共实验室 |
| Corresponding Author | Huang, Shao-Hua; Bai, Zheng-Wu |
| Affiliation | 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 |
| Recommended Citation 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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