Aziridines as a structural motif to conformational restriction of azasugars

Literature Information

Publication Date 2003-01-13
DOI 10.1039/B210038J
Impact Factor 3.876
Authors

José G. Fernández-Bolaños, Vinni H. Lillelund, Mikael Bols


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Abstract

In order to investigate the hypothesis that the glycosidase inhibitor isofagomine was bound to α-or β-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 α-glucosidase, β-glucosidase and α-fucosidase.

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Organic & Biomolecular Chemistry
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