Journal
CARBOHYDRATE RESEARCH
Volume 340, Issue 13, Pages 2077-2085Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2005.06.029
Keywords
heparan sulfate; D-glucuronic acid; glycosyl fluoride; glycoside formation; heparanase
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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-alpha-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 alpha-fluoride 16. This paper rationalises the formation of each of these products, and reports our efforts in trying to optimise the formation of the alpha-fluoride 16. (C) 2005 Elsevier Ltd. All rights reserved.
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