title: Towards the synthesis of aryl glucuronides as potential heparanase probes. An interesting outcome in the glycosidation of glucuronic acid with 4-hydroxycinnamic acid.
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-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.
authors.affiliation: Institute for Glycomics, Griffith University (Gold Coast Campus), PMB 50, Gold Coast Mail Centre, Australia.
authors.forename: Andrew G
authors.initials: AG
authors.lastname: Pearson
authors.forename: Milton J
authors.initials: MJ
authors.lastname: Kiefel
authors.forename: Vito
authors.initials: V
authors.lastname: Ferro
authors.forename: Mark
authors.initials: M
authors.lastname: von Itzstein
mesh_terms: D003373:Coumaric Acids / Q000737:chemistry*; D020723:Glucuronic Acid / Q000737:chemistry*; D005966:Glucuronidase / Q000378:metabolism; D020719:Glucuronides / Q000138:chemical synthesis*; D006031:Glycosylation; D015335:Molecular Probes / Q000138:chemical synthesis; D011422:Propionates; D000099175:Heparanase
chemical_list: D003373:Coumaric Acids; D020723:Glucuronic Acid; D005966:Glucuronidase; D020719:Glucuronides; D015335:Molecular Probes; D011422:Propionates; D000099175:Heparanase; C495469:p-coumaric acid