Synthesis of disaccharide fragments of the AT-III binding domain of heparin and their sulfonatomethyl analogues

Carbohydr Res. 2011 Sep 27;346(13):1827-36. doi: 10.1016/j.carres.2011.06.021. Epub 2011 Jun 24.

Abstract

d-Glucuronate and l-iduronate-containing disaccharides related to the antithrombin-binding domain of heparin were prepared. The carboxylic function of the uronic acid unit was formed on a disaccharide level in the case of the glucuronate, while on a monosaccharide level in the case of the iduronate derivatives. Synthesis of their sulfonic acid analogues was carried out analoguosly applying sulfonatomethyl-containing acceptors in the form of either salts or methyl esters. Significant difference could be observed in the methyl ether formation reactions of the sulfonatomethyl-containing uronate disaccharides and the non-sulfonic acid uronates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antithrombin III / chemistry*
  • Carbohydrate Sequence
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry*
  • Heparin / chemistry*
  • Iduronic Acid / chemistry

Substances

  • Disaccharides
  • Iduronic Acid
  • Antithrombin III
  • Heparin