Issue 10, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis and evaluation of sulfonium analogues of isofucofagomine as glycosidase inhibitors

Víctor Ulgar,ab   José G. Fernández-Bolañosb  and  Mikael Bols*a  

* Corresponding authors

a Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark
E-mail: mb@chem.au.dk
Fax: +45 86196199
Tel: +45 89423963

b Department of Organic Chemistry, Faculty of Chemistry, University of Seville, PO Box 553, 41071 Seville, Spain
E-mail: bolanos@us.es
Fax: +34 954624960
Tel: +34 954557150

Abstract

A series of L-fucopyranose analogues having a sulfur substituent at the anomeric position were synthesised. A sulfide, a methylsulfonium ion, a sulfoxide and a sulfone analogue were made. The synthesised compounds were tested for inhibition of two α-fucosidases. The methylsulfonium ion was found to be a moderately strong competitive inhibitor, and 700 times more potent than the corresponding sulfide.

Graphical abstract: Synthesis and evaluation of sulfonium analogues of isofucofagomine as glycosidase inhibitors

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Article information

DOI
https://doi.org/10.1039/B202021C
Article type
Paper
Submitted
26 Feb 2002
Accepted
28 Mar 2002
First published
17 Apr 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1242-1246

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Synthesis and evaluation of sulfonium analogues of isofucofagomine as glycosidase inhibitors

V. Ulgar, J. G. Fernández-Bolaños and M. Bols, J. Chem. Soc., Perkin Trans. 1, 2002, 1242 DOI: 10.1039/B202021C

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