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Synthesis 2006(23): 4017-4031  
DOI: 10.1055/s-2006-950333
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© Georg Thieme Verlag Stuttgart · New York

Synthesis, NMR and Conformational Studies of Fucoidan Fragments, 8: [1] Convergent Synthesis of Branched and Linear Oligosaccharides

Nadezhda Ustyuzhaninaa, Vadim Krylovb, Alexey Gracheva, Alexey Gerbsta, Nikolay Nifantiev*a
a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow B-334, Russian Federation
Fax: +7(495)1358784; e-Mail: nen@ioc.ac.ru;
b Higher Chemical College, Russian Academy of Sciences, Miusskaya sq. 9, 125047 Moscow, Russian Federation
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Publication History

Received 31 May 2006
Publication Date:
20 October 2006 (online)

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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.

Key words

carbohydrates - fucoidan - glycosylation - α-fucosylation - stereoselectivity