Abstract
In order to investigate the hypothesis that the glycosidase inhibitor isofagomine was bound to alpha- or beta-glucosidase in a 1,4B conformation, a number of bicyclic aziridines that adopt the 1,4B or B1,4 conformations were synthesised and investigated. (1R)-2-endo,3-exo-2,3-Dihydroxy-4-endo-4-hydroxymethyl-6- azabicyclo[3.1.0]hexane (5) and its N-methyl and N-benzyl analogues and (1S)-2-exo-3-endo-2,3-dihydroxy-4- endo-4-hydroxymethyl-6-azabicyclo-[3.1.0]hexane (6) were synthesised. The aziridines 5 and 6 were found to be weak or not inhibitors of alpha-glucosidase, beta-glucosidase and alpha-fucosidase.
MeSH terms
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Animals
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Aziridines / chemistry*
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Aziridines / metabolism*
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Aziridines / pharmacology
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Cattle
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Enzyme Inhibitors / chemistry*
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Enzyme Inhibitors / metabolism*
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Enzyme Inhibitors / pharmacology
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Glycoside Hydrolase Inhibitors*
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Imino Pyranoses
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Molecular Conformation
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Piperidines / pharmacology
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Prunus / enzymology
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Yeasts / enzymology
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alpha-Glucosidases / metabolism
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alpha-L-Fucosidase / antagonists & inhibitors
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alpha-L-Fucosidase / metabolism
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beta-Glucosidase / antagonists & inhibitors*
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beta-Glucosidase / metabolism
Substances
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Aziridines
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Enzyme Inhibitors
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Glycoside Hydrolase Inhibitors
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Imino Pyranoses
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Piperidines
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isofagomine
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alpha-Glucosidases
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beta-Glucosidase
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alpha-L-Fucosidase