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

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

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

摘要: 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.

关键词:

English

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

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
Available Online: 05 August 2014
Fund Project:
This work was financially supported by the National Natural Science Foundation of China (Nos. 51373168, 51390484, 51233004 and 51321062).

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 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.

Key words:

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

English

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

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

English

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

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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