Abstract
The first synthesis of 1,2-trans-homoiminosugars devised as mimics of β-D-GlcNAc and α-D-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a β-amino alcohol skeletal rearrangement applied to a polyhydroxylated azepane. The β-D-GlcNAc derivative has been coupled to serine to deliver an iminosugar C-amino acid. The two homoiminosugars demonstrate moderate glycosidase inhibition.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amino Alcohols / chemical synthesis*
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Amino Alcohols / chemistry
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Enzyme Inhibitors / chemistry*
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Galactosamine / analogs & derivatives
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Galactosamine / chemical synthesis*
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Galactosamine / chemistry
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Glucosamine / analogs & derivatives
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Glucosamine / chemical synthesis*
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Glucosamine / chemistry
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Glycoside Hydrolases / antagonists & inhibitors*
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Glycoside Hydrolases / chemistry*
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Heterocyclic Compounds / chemistry*
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Magnetic Resonance Spectroscopy
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Molecular Structure
Substances
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Amino Alcohols
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Enzyme Inhibitors
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Heterocyclic Compounds
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Galactosamine
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Glycoside Hydrolases
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Glucosamine