Citation: Ming-qiang Li, Zhao-hui Tang, Chao Wang, Yu Zhang, Hai-tao Cui, Xue-si Chen. 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 shu

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

Ming-qiang Li ^1,2,3 ,
Zhao-hui Tang ⁴ ,
Chao Wang ^1,5,3 ,
Yu Zhang ^1,2,3 ,
Hai-tao Cui ^1,2,3 ,
Xue-si Chen ⁴

1.
1. Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
2.
2. University of Chinese Academy of Sciences, Beijing 100049, China
3.
4.
Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
5.
2. School of Science, Changchun institute of technology, Changchun 130012, China

Received Date: 10 April 2014
Revised Date: 16 May 2014

Fund Project: This work was financially supported by the National Natural Science Foundation of China (Nos. 51373168, 51390484, 51233004 and 51321062).

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 thiol-ene 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.
- Functionalization,
- Thiol-ene click chemistry,
- Dextran,
- Sulphur compounds,
- Green chemistry
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