Abstract
Valienol-derived allylic C-1 bromides have been used as carbaglycosyl donors for α-xylo configured valienamine pseudodisaccharide synthesis. We synthesised valienamine analogues of the Glc(α1→3)Glc and Glc(α1→3)Man disaccharides representing the linkages cleaved by α-Glucosidase II in N-glycan biosynthesis. These (N1→3)-linked pseudodisaccharides were found to have some α-Glucosidase II inhibitory activity, while two other (N1→6)-linked valienamine pseudodisaccharides failed to inhibit the enzyme.
Copyright © 2011 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Biocatalysis
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Chemistry Techniques, Synthetic
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Cyclohexenes / chemical synthesis
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Cyclohexenes / chemistry
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Cyclohexenes / 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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Glycoside Hydrolase Inhibitors*
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Hexosamines / chemical synthesis
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Hexosamines / chemistry
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Hexosamines / pharmacology*
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Molecular Conformation
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Polysaccharides / biosynthesis*
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Polysaccharides / chemistry
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Stereoisomerism
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Structure-Activity Relationship
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alpha-Glucosidases / metabolism
Substances
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Cyclohexenes
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Enzyme Inhibitors
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Glycoside Hydrolase Inhibitors
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Hexosamines
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Polysaccharides
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valienamine
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alpha-Glucosidases