Aziridines as a structural motif to conformational restriction of azasugars |
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Authors: | Lopez Lopez Oscar Fernández-Bolaños José G Lillelund Vinni H Bols Mikael |
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Institution: | Department of Chemistry, University of Aarhus, Langelandsgade 140, DK-8000 Aarhus, Denmark. |
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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- azabicyclo3.1.0]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. |
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