title: Chemical Fucosylation of a Polysaccharide: A Semisynthetic Access to Fucosylated Chondroitin Sulfate.
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.
authors.affiliation: †Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, via Cintia 4, I-80126 Napoli, Italy.
authors.forename: Antonio
authors.initials: A
authors.lastname: Laezza
authors.affiliation: †Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, via Cintia 4, I-80126 Napoli, Italy.
authors.forename: Alfonso
authors.initials: A
authors.lastname: Iadonisi
authors.affiliation: ‡Department of Soil, Plant, Environmental, and Animal Production Sciences, University of Naples Federico II, via Università 100, I-80055 Portici, Italy.
authors.forename: Cristina De
authors.initials: CD
authors.lastname: Castro
authors.affiliation: §Department of Experimental Medicine, Second University of Naples, via de Crecchio 7, I-80138 Napoli, Italy.
authors.forename: Mario
authors.initials: M
authors.lastname: De Rosa
authors.affiliation: §Department of Experimental Medicine, Second University of Naples, via de Crecchio 7, I-80138 Napoli, Italy.
authors.forename: Chiara
authors.initials: C
authors.lastname: Schiraldi
authors.affiliation: ∥Department of Biology, University of Naples Federico II, Complesso Universitario Monte S.Angelo, via Cintia 4, I-80126 Napoli, Italy.
authors.forename: Michelangelo
authors.initials: M
authors.lastname: Parrilli
authors.affiliation: †Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, via Cintia 4, I-80126 Napoli, Italy.
authors.forename: Emiliano
authors.initials: E
authors.lastname: Bedini
mesh_terms: D000818:Animals; D000925:Anticoagulants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002809:Chondroitin Sulfates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008279:Magnetic Resonance Imaging; D015394:Molecular Structure
chemical_list: D000925:Anticoagulants; C517150:fucosylated chondroitin sulfate; D002809:Chondroitin Sulfates