An efficient approach to N-acetyl-D-glucosaminuronic acid-based sialylmimetics as potential sialidase inhibitors

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Title An efficient approach to N-acetyl-D-glucosaminuronic acid-based sialylmimetics as potential sialidase inhibitors
Author Mann, Maretta; Thomson, Robin Joy; von Itzstein, Mark
Journal Name Biorganic & Medicinal Chemistry Letters
Editor Dr D L Boger
Year Published 2004
Place of publication UK
Publisher Pergamon
Abstract A novel approach to the synthesis of β-glycosides of N-acetyl-D-glucosaminuronic acid, in six steps and good overall yield from N-acetyl-D-glucosamine, has been developed. The key synthetic step was the Lewis acid mediated O-glycosidation of methyl 1,3,4-tri-O-pivaloyl-N-acetyl-D-glucosaminuronate (11). Elaboration of glucosaminuronides 15 and 18 provided novel sialylmimetics 21 and 22, which showed inhibition of Vibrio cholerae sialidase.
Peer Reviewed Yes
Published Yes
Publisher URI http://www.elsevier.com/wps/find/journaldescription.cws_home/972/description#description
Alternative URI http://dx.doi.org/10.1016/j.bmcl.2004.08.064
Volume 14
Page from 5555
Page to 5558
ISSN 0960-894X
Date Accessioned 2005-03-22
Language en_AU
Research Centre Institute for Glycomics
Faculty Institute for Glycomics
Subject PRE2009-Biological and Medical Chemistry
URI http://hdl.handle.net/10072/5049
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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