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.

Chemical Fucosylation of a Polysaccharide: A Semisynthetic Access to Fucosylated Chondroitin Sulfate / Laezza, Antonio; Iadonisi, Alfonso; DE CASTRO, Cristina; Mario De, Rosa; Chiara, Schiraldi; Parrilli, Michelangelo; Bedini, Emiliano. - In: BIOMACROMOLECULES. - ISSN 1525-7797. - 16:(2015), pp. 2237-2245. [10.1021/acs.biomac.5b00640]

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

LAEZZA, ANTONIO;IADONISI, ALFONSO;DE CASTRO, CRISTINA;PARRILLI, MICHELANGELO;BEDINI, EMILIANO
2015

Abstract

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.
2015
Chemical Fucosylation of a Polysaccharide: A Semisynthetic Access to Fucosylated Chondroitin Sulfate / Laezza, Antonio; Iadonisi, Alfonso; DE CASTRO, Cristina; Mario De, Rosa; Chiara, Schiraldi; Parrilli, Michelangelo; Bedini, Emiliano. - In: BIOMACROMOLECULES. - ISSN 1525-7797. - 16:(2015), pp. 2237-2245. [10.1021/acs.biomac.5b00640]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/611288
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