Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1391063 | Carbohydrate Research | 2005 | 9 Pages |
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.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide