Abstract
Nitrogen-in-the-ring analogues of l-fucose and l-rhamnose were prepared, which feature a spirocyclopropyl moiety in place of the methyl group of the natural sugar. The synthetic route involved a titanium-mediated aminocyclopropanation of a glycononitrile as the key step. Four new spirocyclopropyl iminosugar analogues were generated, which displayed some activity towards l-fucosidase and l-rhamnosidase.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclopropanes / chemical synthesis*
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Cyclopropanes / chemistry
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Cyclopropanes / pharmacology
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Fucose / analogs & derivatives*
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Fucose / chemical synthesis
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Fucose / chemistry
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Fucose / pharmacology
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Glycoside Hydrolases / antagonists & inhibitors
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Glycoside Hydrolases / metabolism
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Kinetics
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Magnetic Resonance Spectroscopy
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Optical Rotation
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Rhamnose / analogs & derivatives*
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Rhamnose / chemical synthesis
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Rhamnose / chemistry
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Rhamnose / pharmacology
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Spectrometry, Mass, Electrospray Ionization
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry
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Spiro Compounds / pharmacology
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alpha-L-Fucosidase / antagonists & inhibitors
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alpha-L-Fucosidase / metabolism
Substances
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Cyclopropanes
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Enzyme Inhibitors
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Spiro Compounds
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Fucose
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Glycoside Hydrolases
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alpha-L-rhamnosidase
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alpha-L-Fucosidase
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Rhamnose