Synthesis, NMR and Conformational Studies of Fucoidan Fragments, 8: Convergent Synthesis of Branched and Linear Oligosaccharides

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Abstract
The brown seaweed polysaccharides fucoidans inhibit microbial adhesion, angiogenesis, P- and l-selectin-mediated inflammation, and blood coagulation. In this communication we report on the efficient highly stereoselective blockwise synthesis of linear and branched fucoidan chains related oligosaccharides α-l-Fucp-(1→3)-[α-l-Fucp-(1→3)]n-α-l-Fucp-OPr (n = 2, 4, 6), α-l-Fucp-(1→4)-[α-l-Fucp-(1→3)-α-l-Fucp-(1→4)]n-α-l-Fucp-OPr (n = 1, 2), α-l-Fucp-(1→3)-α-l-Fucp-(1→3)-[α-l-Fucp-(1→2)]-α-l-Fucp-OPr and their derivatives bearing sulfonato groups at O2 or at O4 of fucose residues. [2+2], [2+4], and [4+4] Carbohydrate skeleton assembling strategies were applied for the synthesis of tetra-, hexa-, and octasaccharides, respectively. The target oligosaccharides are regarded as model compounds to assess the structure of fucoidan fragments responsible for their biological activity.