Bicyclic 1-Azafagomine Derivatives: Synthesis and Glycosidase Inhibitory Testing

Abstract

The synthesis of a series of 1-azafagomine derivatives that are tethered with five- and six-membered 1,2-annulated ring systems is described. These compounds were used in order to explore whether a hydrogen-bond acceptor group on the carbon atom corresponding to the glycosidic oxygen is able to interact with the catalytic acidic residue of β-glucosidase. The hydrogen-bond acceptor group was installed at various positions on the annulated ring system making it possible to study the effect of altering the position of this group.

Key words

iminosugars - glycosidases - glycosidase inhibitor - hydrogen bond - hydrogen bond acceptor - catalytic acidic residue

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