Abstract
A series of 13 aminocyclitol derivatives belonging to two different families is described. Their configuration is governed by the regio- and stereocontrolled epoxide opening of a suitably protected conduritol-B epoxide. Studies on several glycosyl processing enzymes indicate that some of them are good inhibitors of glucosylceramide hydrolase. A rationale to account for preliminary structure-activity relationships is provided.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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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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Glucosidases / antagonists & inhibitors
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Glucosidases / metabolism
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Glucosylceramides / metabolism*
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Hexosamines / chemical synthesis*
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Hexosamines / chemistry
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Hexosamines / pharmacology
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Inositol / analogs & derivatives*
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Inositol / chemical synthesis
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Inositol / chemistry
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Inositol / pharmacology
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Kinetics
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Magnetic Resonance Spectroscopy
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Models, Molecular
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Optical Rotation
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Spectrometry, Mass, Electrospray Ionization
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Structure-Activity Relationship
Substances
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Enzyme Inhibitors
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Glucosylceramides
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Hexosamines
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Inositol
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Glucosidases
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conduritol epoxide