Abstract
The 1D and 1L enantiomers of 1,2-anhydro-myo-inositol (conduritol B epoxide) were synthesised from 1D-pinitol and 1L-quebrachitol, respectively, and their activities were compared in selected glycosidase inhibition assays. The 1D enantiomer was found to be the active isomer, functioning as an irreversible inhibitor of sweet almond beta-D-glucosidase. Neither isomer was active against the alpha-D-glucosidase from Bacillus stearothermophilus or the beta-D-galactosidase from Aspergillus oryzae.
Publication types
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Comparative Study
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Research Support, Non-U.S. Gov't
MeSH terms
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Aspergillus oryzae / enzymology
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Bacterial Proteins / antagonists & inhibitors
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Carbohydrate Conformation
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / pharmacology
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Fungal Proteins / antagonists & inhibitors
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Geobacillus stearothermophilus / enzymology
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Glycoside Hydrolase Inhibitors
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Glycoside Hydrolases / antagonists & inhibitors*
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Indolizines / 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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Magnetic Resonance Spectroscopy
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Plant Proteins / antagonists & inhibitors
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Stereoisomerism
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Structure-Activity Relationship
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Substrate Specificity
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beta-Galactosidase / antagonists & inhibitors
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beta-Glucosidase / antagonists & inhibitors
Substances
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Bacterial Proteins
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Enzyme Inhibitors
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Fungal Proteins
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Glycoside Hydrolase Inhibitors
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Indolizines
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Plant Proteins
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pinitol
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Inositol
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quebrachitol
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Glycoside Hydrolases
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beta-Glucosidase
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beta-Galactosidase
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conduritol epoxide
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castanospermine