Abstract
An efficient method for the regioselective 3-O-silylation of beta-thiofucopyranoside was disclosed. Based on this discovery, we described a high-yielding strategy for the synthesis of the natural core structure of L-fucan and its fully sulfated derivative. The bioassay suggested that octyl 2,3,4-tri-O-sulfo-alpha-L-fucopyranosyl-(1-->3)-2,4-di-O-sulfo-alpha-L-fucopyranosyl-(1-->3)-2,4-di-O-sulfo-alpha-L-fucopyranosyl-(1-->3)-2,4-di-O-sulfo-beta-L-fucopyranoside presented better antitumor activities than that of the free tetramer based on Sarcoma 180 cells and Lewis lung carcinoma model studies.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Carbohydrate Sequence
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Cell Line, Tumor
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Glycosides / chemical synthesis*
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Glycosides / chemistry
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Glycosides / pharmacology*
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Mice
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Molecular Sequence Data
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Oligosaccharides / chemical synthesis*
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Oligosaccharides / chemistry
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Oligosaccharides / pharmacology*
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Sulfuric Acid Esters / chemical synthesis*
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Sulfuric Acid Esters / chemistry
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Sulfuric Acid Esters / pharmacology*
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Xenograft Model Antitumor Assays
Substances
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Antineoplastic Agents
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Glycosides
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Oligosaccharides
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Sulfuric Acid Esters
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octyl 2,3,4-tri-O-sulfofucopyranosyl-1-3-2,4-di-O-sulfofucopyranosyl-1-3-2,4-di-O-sulfofucopyranosyl-1-3-2,4-di-O-sulfofucopyranoside