Efficient Side-chain Modification of Dextran via Base-catalyzed Epoxide Ring-opening and Thiol-ene Click Chemistry in Aqueous Media

Ming-qiang Li; Zhao-hui Tang; Chao Wang; Yu Zhang; Hai-tao Cui; Xue-si Chen

doi:10.1007/s10118-014-1489-7

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Efficient Side-chain Modification of Dextran via Base-catalyzed Epoxide Ring-opening and Thiol-ene Click Chemistry in Aqueous Media

Rapid Communication | Updated：2021-06-21

- Efficient Side-chain Modification of Dextran via Base-catalyzed Epoxide Ring-opening and Thiol-ene Click Chemistry in Aqueous Media
- Efficient Side-chain Modification of Dextran via Base-catalyzed Epoxide Ring-opening and Thiol-ene Click Chemistry in Aqueous Media
- Chinese Journal of Polymer Science 2014年32卷第8期页码：969-974
- Affiliations：
  
  a.Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
  b.School of Science, Changchun institute of technology, Changchun 130012, China
  c.University of Chinese Academy of Sciences, Beijing 100049, China
- Author bio：
  
  **Xue-si Chen (陈学思), E-mail: xschen@ciac.ac.cn
- Funds：
  
  National Natural Science Foundation of China(51373168;51390484;51233004;51321062)
- DOI：10.1007/s10118-014-1489-7
  中图分类号：
- 收稿：2014-04-10，
  
  修回：2014-05-16，
  
  录用：2014-05-20，
  
  纸质出版：2014-08
- Accepted：
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Ming-qiang Li, Zhao-hui Tang, Chao Wang, 等. Efficient Side-chain Modification of Dextran via Base-catalyzed Epoxide Ring-opening and Thiol-ene Click Chemistry in Aqueous Media[J]. Chinese Journal of Polymer Science, 2014,32(8):969-974.

Ming-qiang Li, Zhao-hui Tang, Chao Wang, et al. Efficient Side-chain Modification of Dextran via Base-catalyzed Epoxide Ring-opening and Thiol-ene Click Chemistry in Aqueous Media[J]. Chinese Journal of Polymer Science, 2014, 32(8): 969-974. DOI: 10.1007/s10118-014-1489-7.
Ming-qiang Li, Zhao-hui Tang, Chao Wang, 等. Efficient Side-chain Modification of Dextran via Base-catalyzed Epoxide Ring-opening and Thiol-ene Click Chemistry in Aqueous Media[J]. Chinese Journal of Polymer Science, 2014,32(8):969-974. DOI： 10.1007/s10118-014-1489-7.

Ming-qiang Li, Zhao-hui Tang, Chao Wang, et al. Efficient Side-chain Modification of Dextran via Base-catalyzed Epoxide Ring-opening and Thiol-ene Click Chemistry in Aqueous Media[J]. Chinese Journal of Polymer Science, 2014, 32(8): 969-974. DOI: 10.1007/s10118-014-1489-7. DOI：

摘要

Abstract

In this study

a novel approach by combining base-catalyzed epoxide ring-opening and thiol-ene click chemistry is presented for the side-chain modification of dextran. The vinyl-modified dextran is prepared by a basic epoxide ring opening reaction of allyl glycidyl ether in 0.1 mol/L NaOH

followed by thiol-addition click reaction of three model sulfhydryl compounds using water-soluble Irgacure 2959 as the photoinitiator

leading to side-chain functionalized dextran modified with carboxyl

bidentate dicarboxyl or amino groups. This is the first example of combining epoxide ring-opening and thiolene click chemistry for side-chain modification of dextran in aqueous media. Importantly

it may also be extended as a convenient and efficient method for the side-chain modification of other polysaccharides.

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