A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides

Org Biomol Chem. 2015 Dec 14;13(46):11208-19. doi: 10.1039/c5ob01706h. Epub 2015 Sep 18.

Abstract

d-Glucosamine derivatives bearing latent O4 functionality provide modified H/HS-type disaccharide donors for a final stage capping approach enabling introduction of conjugation-suitable, non-reducing terminal functionality to biologically important glycosaminoglycan oligosaccharides. Application to the synthesis of the first O4-terminus modified synthetic LMWH decasaccharide and an HS-like dodecasaccharide is reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Anticoagulants / chemical synthesis
  • Anticoagulants / chemistry*
  • Crystallography, X-Ray
  • Disaccharides / chemical synthesis
  • Disaccharides / chemistry*
  • Glucosamine / analogs & derivatives*
  • Glucosamine / chemical synthesis
  • Glycosaminoglycans / chemical synthesis
  • Glycosaminoglycans / chemistry*
  • Heparin / analogs & derivatives*
  • Heparin / chemical synthesis
  • Heparin, Low-Molecular-Weight / analogs & derivatives*
  • Heparin, Low-Molecular-Weight / chemical synthesis
  • Models, Molecular
  • Oligosaccharides / chemical synthesis
  • Oligosaccharides / chemistry*

Substances

  • Anticoagulants
  • Disaccharides
  • Glycosaminoglycans
  • Heparin, Low-Molecular-Weight
  • Oligosaccharides
  • Heparin
  • Glucosamine