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

Antonio Laezza, Alfonso Iadonisi, Cristina De Castro, Mario De Rosa, Chiara Schiraldi, Michelangelo Parrilli, Emiliano Bedini

Biomacromolecules 2015 Jul 13

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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)-polysaccharides 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.

Citation

Antonio Laezza, Alfonso Iadonisi, Cristina De Castro, Mario De Rosa, Chiara Schiraldi, Michelangelo Parrilli, Emiliano Bedini. Chemical Fucosylation of a Polysaccharide: A Semisynthetic Access to Fucosylated Chondroitin Sulfate. Biomacromolecules. 2015 Jul 13;16(7):2237-45