Modelling, synthesis and biological evaluation of novel glucoronide-based probes of Vibrio cholerae sialidase

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Title Modelling, synthesis and biological evaluation of novel glucoronide-based probes of Vibrio cholerae sialidase
Author Mann, Maretta; Thomson, Robin Joy; Dyason, Jeffrey Clifford; McAtamney, Sarah; von Itzstein, Mark
Journal Name Bioorganic & Medicinal Chemistry
Year Published 2006
Place of publication Oxford, UK
Publisher Pergamon
Abstract The development of sialidase inhibitors is an area of continuing interest due to their potential use as therapeutic agents to combat viral and bacterial infections. Herein, we report our studies involving the sialidase from the pathogen Vibrio cholerae, through the modelling, synthesis and biological evaluation of mimetics of 5-acetamido-2,6-anhydro-3,5-dideoxy-d-glycero-d-galacto-non-2-enonic acid (Neu5Ac2en, 1), a naturally occurring sialidase inhibitor. These mimetics are O- and S-glycosides of N-acetyl-d-glucosaminuronic acid in which the aglycone portion effectively replaces the C-6 glycerol side chain of Neu5Ac2en (1). The choice of aglycones was aided by use of the X-ray crystal structure of V. cholerae sialidase complexed with Neu5Ac2en (1). All Neu5Ac2en mimetics tested were found to inhibit V. cholerae sialidase as determined using a standard fluorometric assay.
Peer Reviewed Yes
Published Yes
Publisher URI http://www.elsevier.com/wps/find/journaldescription.cws_home/129/description#description
Alternative URI http://dx.doi.org/10.1016/j.bmc.2005.10.004
Volume 14
Page from 1518
Page to 1537
ISSN 0968-0896
Date Accessioned 2007-02-23
Language en_AU
Research Centre Institute for Glycomics
Faculty Institute for Glycomics
Subject PRE2009-Biological and Medical Chemistry; PRE2009-Organic Chemical Synthesis
URI http://hdl.handle.net/10072/13717
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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