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

Carbohydr Res. 2005 Sep 26;340(13):2077-85. doi: 10.1016/j.carres.2005.06.029.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coumaric Acids / chemistry*
  • Glucuronic Acid / chemistry*
  • Glucuronidase / metabolism
  • Glucuronides / chemical synthesis*
  • Glycosylation
  • Molecular Probes / chemical synthesis
  • Propionates


  • Coumaric Acids
  • Glucuronides
  • Molecular Probes
  • Propionates
  • Glucuronic Acid
  • heparanase
  • Glucuronidase
  • p-coumaric acid