Abstract
The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)-3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAc)(3). The N-substituted derivatives 4 and ent-4 so-obtained have been tested against two alpha-glucosidases, two amyloglucosidases, two beta-glucosidases and one beta-xylosidase for their inhibitory activities. Although (-)-3 and (+)-3 do not inhibit any of these enzymes at 1mM concentration, N-benzylated derivatives of (-)-conduramine B-1 are selective and competitive inhibitors of beta-glucosidases with K(i) in low micromolecular range.
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 niger / enzymology
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Bacteria, Anaerobic / enzymology
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Bridged Bicyclo Compounds / chemical synthesis*
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Bridged Bicyclo Compounds / pharmacology
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Cellulases / antagonists & inhibitors*
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Cyclohexenes
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Enzyme Inhibitors / chemical synthesis*
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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 Structure
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Prunus / enzymology
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Saccharomyces cerevisiae / enzymology
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Stereoisomerism
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Structure-Activity Relationship
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Xylosidases / antagonists & inhibitors*
Substances
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Bridged Bicyclo Compounds
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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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valienamine
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Cellulases
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Xylosidases
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exo-1,4-beta-D-xylosidase