Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid

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Title Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid
Author Pearson, Andrew; Kiefel, Milton; Ferro, Vito; von Itzstein, Mark
Journal Name Carbohydrate Research
Year Published 2005
Place of publication Oxford, England
Publisher Elsevier Ltd
Abstract This work describes our preliminary efforts towards the development of aryl glucuronides as potential probes for heparanase. During the course of these initial investigations, attempted glycosidation of methyl 2,3,4-tri-O-acetyl-α-d-glucopyranosyluronate trichloroacetimidate with 4-hydroxycinnamic acid gave a complex mixture of four different components. These were identified as the 1-cinnamyl glucuronate ester 13, the cinnamyl linked disaccharide 14, the glucuronate trichloroacetamide 15, and the glucuronyl α-fluoride 16. This paper rationalises the formation of each of these products, and reports our efforts in trying to optimise the formation of the α-fluoride 16.
Peer Reviewed Yes
Published Yes
Publisher URI http://www.elsevier.com/wps/find/journaldescription.cws_home/424829/description#description
Alternative URI http://dx.doi.org/10.1016/j.carres.2005.06.029
Volume 340
Issue Number 13
Page from 2077
Page to 2085
ISSN 0008-6215
Date Accessioned 2006-03-09
Date Available 2009-10-19T05:25:04Z
Language en_AU
Research Centre Institute for Glycomics
Faculty Institute for Glycomics
Subject PRE2009-Organic Chemical Synthesis
URI http://hdl.handle.net/10072/4188
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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