Abstract
A series of fluorine and non-fluorine-substituted C-glucosylidenes (exo-glucals) has been synthesized via a modified Julia olefination. The deprotected exo-glucals were prepared in five steps from commercially available d-gluconolactone. The evaluation of this original family of compounds against a panel of glycosidases showed a highly specific in vitro activity towards mammalian β-glucosidase depending on the double bond substituents.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkenes / chemistry*
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Dose-Response Relationship, Drug
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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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Glycosides
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Molecular Structure
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Monosaccharides / chemical synthesis
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Monosaccharides / chemistry
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Monosaccharides / pharmacology*
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Saccharomyces cerevisiae / enzymology
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Structure-Activity Relationship
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beta-Glucosidase / antagonists & inhibitors*
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beta-Glucosidase / metabolism
Substances
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Alkenes
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C-glycoside
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Enzyme Inhibitors
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Glycosides
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Monosaccharides
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beta-Glucosidase