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Synthesis 2019; 51(21): 4066-4077
DOI: 10.1055/s-0039-1690019
DOI: 10.1055/s-0039-1690019
paper
Bicyclic 1-Azafagomine Derivatives: Synthesis and Glycosidase Inhibitory Testing
Spanish MICINN (CTQ2016-78703-P), the Junta de Andalucía (FQM134), the European Regional Development Fund (FEDER) (501100008530), and the University of Stavanger.Further Information
Publication History
Received: 02 June 2019
Accepted after revision: 12 July 2019
Publication Date:
14 August 2019 (online)
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 residueSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690019.
- Supporting Information
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