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