Issue 24, 2011
From the journal:

Organic & Biomolecular Chemistry

Synthesis of 1,2,3-triazole linked galactopyranosides and evaluation of cholera toxin inhibition†

David J. Leaver,a   Raymond M. Dawson,c   Jonathan M. White,d   Anastasios Polyzos*b  and  Andrew B. Hughes*a  

* Corresponding authors

a Department of Chemistry, La Trobe University, Victoria, Australia
E-mail: tahughes@optusnet.com.au
Fax: +613 9479 1226
Tel: +613 9479 1353

b CSIRO Materials Science and Engineering, Clayton South, Victoria, Australia
E-mail: tash.polyzos@csiro.au
Fax: +613 9545 2446
Tel: +613 9545 8172

c Human Protection and Performance Division, DSTO Melbourne, 506 Lorimer Street, Fishermans Bend, Victoria, Australia

d Bio21 Institute, School of Chemistry, University of Melbourne, Parkville, Victoria, Australia

Abstract

We report the synthesis of a series of bivalent 1,2,3-triazole linked galactopyranosides as potential inhibitors of cholera toxin (CT). The inhibitory activity of the bivalent series was examined (ELISA) and the series showed low inhibitory activity (millimolar IC50s). Conversely, the monomeric galactotriazole analogues were strong inhibitors of cholera toxin (IC50 = 71–75 μM).

Graphical abstract: Synthesis of 1,2,3-triazole linked galactopyranosides and evaluation of cholera toxin inhibition

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Article information

DOI
https://doi.org/10.1039/C1OB06317K
Article type
Paper
Submitted
03 Aug 2011
Accepted
22 Sep 2011
First published
03 Nov 2011

Org. Biomol. Chem., 2011,9, 8465-8474

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Synthesis of 1,2,3-triazole linked galactopyranosides and evaluation of cholera toxin inhibition

D. J. Leaver, R. M. Dawson, J. M. White, A. Polyzos and A. B. Hughes, Org. Biomol. Chem., 2011, 9, 8465 DOI: 10.1039/C1OB06317K

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