Abstract
Synthesis of a panel of iso(thio)urea-type ring-modified castanospermine analogues bearing a freely mutarotating pseudoanomeric hydroxyl group results in tight-binding beta-glucosidase inhibitors with unusual binding signatures; the presence of an N-octyl substituent imparts a remarkable anomeric selectivity, promoting strong binding of the appropriate beta-anomer by the beta-glucosidase.
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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Indolizines / chemical synthesis
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Indolizines / chemistry*
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Indolizines / pharmacology*
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Models, Molecular
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Molecular Conformation
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Stereoisomerism
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Structure-Activity Relationship
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Thermodynamics
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Thiourea / analogs & derivatives
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Thiourea / chemistry
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beta-Glucosidase / antagonists & inhibitors*
Substances
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Enzyme Inhibitors
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Indolizines
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beta-Glucosidase
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Thiourea
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castanospermine