Abstract
Octyl 2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1-->3)-2-O-sulfo-alpha-L-fucopyranosyl-(1-->4)-2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1-->3)-2-O-sulfo-alpha-L-fucopyranosyl-(1-->4)-2,3-di-O-sulfo-beta-L-fucopyranoside, a fucosyl pentasaccharide with a regular structure resembling the repeating unit of a natural sulfated fucan, was chemically synthesized using a convergent '2+3' strategy. Regioselective 3-O-silylation of beta-thiofucopyranoside and AgOTf-catalyzed glycosylation of the protected glycosyl trichloroacetimidate facilitated a one-pot trisaccharide synthesis. The synthesized target compound showed good antitumor activity in vivo, and promising anticoagulant activity in vitro.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Anticoagulants / chemical synthesis*
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Anticoagulants / chemistry
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Anticoagulants / pharmacology*
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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 Conformation
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Carbohydrate Sequence
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Cell Line, Tumor
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Cell Survival / drug effects
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Drug Screening Assays, Antitumor
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Humans
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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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Stereoisomerism
Substances
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Anticoagulants
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Antineoplastic Agents
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Oligosaccharides
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octyl-2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1-3)-2-O-sulfo-alpha-L-fucopyranosyl-(1-4)-2,3-di-O-sulfo-alpha-L-fucopyranosyl-(1-3)-2-O-sulfo-alpha-L-fucopyranosyl-(1-4)-2,3-di-O-sulfo-beta-L-fucopyranoside