The synthesis of the locating substitution derivatives of chitosan by click reaction at the 6-position of chitin

Yu Chen; Yanchun Ye; Yanyan Jing; Yuanyuan Gao; Yanwen Guo; Huimin Tan

doi:10.1155/2015/419506

The synthesis of the locating substitution derivatives of chitosan by click reaction at the 6-position of chitin

Yu Chen^*
, Yanchun Ye
, Yanyan Jing
, Yuanyuan Gao
, Yanwen Guo
, Huimin Tan

^*Corresponding author for this work

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

A novel method to prepare the macrocyclic compound locating substitution derivatives of chitosan was investigated, by using cyclodextrin as the model of macrocyclic compound. The method combines the advantages of activated 6-OH of chitin and high efficiency of click reaction. Chitin C₆-OH p-toluenesulfonate (CTN-6-OTs) was generated and subsequently transferred to chitin C₆-N₃ via nucleophilic substitution. Afterwards, β-cyclodextrin was immobilized at 6-OH of chitin via click reaction to afford CTN-6-CD. Ultimately, CTS-6-CD was obtained by removing the acetyl group of chitin unit. The structures and properties of these products were characterized by FTIR, TG, and XRD, respectively. It was found that CTN-6-CD synthesized at the optimum conditions has an immobilized loading of 1.6126 × 10-4 mol/g and that of the corresponding CTS-6-CD, generated by removal of the acetyl group, was 1.6891 × 10-4 mol/g.

Original language	English
Article number	419506
Journal	International Journal of Polymer Science
Volume	2015
DOIs	https://doi.org/10.1155/2015/419506
Publication status	Published - 2015

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@article{eff0ec9c750142779b6b0d0e9b9e71f6,

title = "The synthesis of the locating substitution derivatives of chitosan by click reaction at the 6-position of chitin",

abstract = "A novel method to prepare the macrocyclic compound locating substitution derivatives of chitosan was investigated, by using cyclodextrin as the model of macrocyclic compound. The method combines the advantages of activated 6-OH of chitin and high efficiency of click reaction. Chitin C6-OH p-toluenesulfonate (CTN-6-OTs) was generated and subsequently transferred to chitin C6-N3 via nucleophilic substitution. Afterwards, β-cyclodextrin was immobilized at 6-OH of chitin via click reaction to afford CTN-6-CD. Ultimately, CTS-6-CD was obtained by removing the acetyl group of chitin unit. The structures and properties of these products were characterized by FTIR, TG, and XRD, respectively. It was found that CTN-6-CD synthesized at the optimum conditions has an immobilized loading of 1.6126 {\texttimes} 10-4 mol/g and that of the corresponding CTS-6-CD, generated by removal of the acetyl group, was 1.6891 {\texttimes} 10-4 mol/g.",

author = "Yu Chen and Yanchun Ye and Yanyan Jing and Yuanyuan Gao and Yanwen Guo and Huimin Tan",

note = "Publisher Copyright: {\textcopyright} 2015 Yu Chen et al.",

year = "2015",

doi = "10.1155/2015/419506",

language = "English",

volume = "2015",

journal = "International Journal of Polymer Science",

issn = "1687-9422",

publisher = "John Wiley and Sons Ltd",

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TY - JOUR

T1 - The synthesis of the locating substitution derivatives of chitosan by click reaction at the 6-position of chitin

AU - Chen, Yu

AU - Ye, Yanchun

AU - Jing, Yanyan

AU - Gao, Yuanyuan

AU - Guo, Yanwen

AU - Tan, Huimin

PY - 2015

Y1 - 2015

N2 - A novel method to prepare the macrocyclic compound locating substitution derivatives of chitosan was investigated, by using cyclodextrin as the model of macrocyclic compound. The method combines the advantages of activated 6-OH of chitin and high efficiency of click reaction. Chitin C6-OH p-toluenesulfonate (CTN-6-OTs) was generated and subsequently transferred to chitin C6-N3 via nucleophilic substitution. Afterwards, β-cyclodextrin was immobilized at 6-OH of chitin via click reaction to afford CTN-6-CD. Ultimately, CTS-6-CD was obtained by removing the acetyl group of chitin unit. The structures and properties of these products were characterized by FTIR, TG, and XRD, respectively. It was found that CTN-6-CD synthesized at the optimum conditions has an immobilized loading of 1.6126 × 10-4 mol/g and that of the corresponding CTS-6-CD, generated by removal of the acetyl group, was 1.6891 × 10-4 mol/g.

AB - A novel method to prepare the macrocyclic compound locating substitution derivatives of chitosan was investigated, by using cyclodextrin as the model of macrocyclic compound. The method combines the advantages of activated 6-OH of chitin and high efficiency of click reaction. Chitin C6-OH p-toluenesulfonate (CTN-6-OTs) was generated and subsequently transferred to chitin C6-N3 via nucleophilic substitution. Afterwards, β-cyclodextrin was immobilized at 6-OH of chitin via click reaction to afford CTN-6-CD. Ultimately, CTS-6-CD was obtained by removing the acetyl group of chitin unit. The structures and properties of these products were characterized by FTIR, TG, and XRD, respectively. It was found that CTN-6-CD synthesized at the optimum conditions has an immobilized loading of 1.6126 × 10-4 mol/g and that of the corresponding CTS-6-CD, generated by removal of the acetyl group, was 1.6891 × 10-4 mol/g.

UR - https://www.scopus.com/pages/publications/84928157526

U2 - 10.1155/2015/419506

DO - 10.1155/2015/419506

M3 - Article

AN - SCOPUS:84928157526

SN - 1687-9422

VL - 2015

JO - International Journal of Polymer Science

JF - International Journal of Polymer Science

M1 - 419506

ER -

The synthesis of the locating substitution derivatives of chitosan by click reaction at the 6-position of chitin

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