Chemical Fucosylation of a Polysaccharide: A Semisynthetic Access to Fucosylated Chondroitin Sulfate

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• 作者：Antonio Laezza ; Alfonso Iadonisi ; Cristina De Castro ; Mario De Rosa ; Chiara Schiraldi ; Michelangelo Parrilli ; Emiliano Bedini
• 刊名：Biomacromolecules
• 出版年：2015
• 出版时间：July 13, 2015
• 年：2015
• 卷：16
• 期：7
• 页码：2237-2245
• 全文大小：445K
• ISSN：1526-4602

文摘

Chemical O-glycosylation of polysaccharides is an almost unexplored reaction. This is mainly due to the difficulties in derivatizing such complex biomacromolecules in a quantitative manner and with a fine control of the obtained structural parameters. In this work, chondroitin raw material from a microbial source was chemo- and regioselectively protected to give two polysaccharide intermediates, that acted in turn as glycosyl acceptors in fucosylation reactions. Further manipulations on the fucosylated polysaccharides, including multiple de-O-benzylation and sulfation, furnished for the first time nonanimal sourced fucosylated chondroitin sulfates (fCSs)鈥損olysaccharides obtained so far exclusively from sea cucumbers (Echinoidea, Holothuroidea) and showing several very interesting biological activities. A semisynthetic fCS was characterized from a structural point of view by means of 2D-NMR techniques, and preliminarily assayed in an anticoagulant test.