Synthesis of iduronic acid building blocks for the modular assembly of glycosaminoglycans

J Org Chem. 2003 Sep 19;68(19):7559-61. doi: 10.1021/jo0340760.

Abstract

The modular synthesis of glycosaminoglycans requires straightforward methods for the production of large quantities of protected uronic acid building blocks. In particular, the preparation of fully differentiated iduronic acids has proven particularly challenging. An efficient route to methyl 3-O-benzyl-1,2-O-isopropylidene-alpha-l-idopyranosiduronate 6 from diacetone glucose in nine steps and 36% overall yield is described. Idopyranosiduronate 6 is useful as a glycosyl acceptor and as an intermediate that may be further elaborated into iduronic acid trichloroacetimidate glycosyl donors for the assembly of glycosaminoglycan structures as illustrated here.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Combinatorial Chemistry Techniques
  • Glycosaminoglycans / chemical synthesis*
  • Glycosylation
  • Iduronic Acid / chemistry

Substances

  • Glycosaminoglycans
  • Iduronic Acid