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

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...

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Bibliographic Details
Published in:Chinese journal of polymer science 2014-08, Vol.32 (8), p.969-969
Main Authors: Li, Ming-qiang, Tang, Zhao-hui, Wang, Chao, Zhang, Yu, Cui, Hai-tao, Chen, Xue-si
Format: Article
Language:English
Subjects:
Characterization and Evaluation of Materials
Chemical reactions
Chemistry
Chemistry and Materials Science
Condensed Matter Physics
Dextrans
Ethers
Industrial Chemistry/Chemical Engineering
Media
Photoinitiators
Polymer Sciences
Polysaccharides
Rapid Communication
Ring opening
Synthesis (chemistry)
侧链
化学
水介质
环和
环氧化物
硫醇
碱催化
葡聚糖
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Summary: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.
ISSN:0256-7679
1439-6203
DOI:10.1007/s10118-014-1489-7