Get access

First Synthesis of Heparan Sulfate Tetrasaccharides Containing both N-Acetylated and N-Unsubstituted Glucosamine—Search for Putative 10E4 Epitopes

Authors

  • Daniel Hamza Dr.,

    1. Laboratoire de Chimie Organique Multifonctionnelle, Equipe de Glycochimie Moléculaire et Macromoléculaire, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR CNRS-UPS 8182, Université Paris Sud 11, Bât. 420, 91405 Orsay Cedex, France, Fax: (+33) 169-164-715
    Search for more papers by this author
  • Ricardo Lucas Dr.,

    1. Laboratoire de Chimie Organique Multifonctionnelle, Equipe de Glycochimie Moléculaire et Macromoléculaire, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR CNRS-UPS 8182, Université Paris Sud 11, Bât. 420, 91405 Orsay Cedex, France, Fax: (+33) 169-164-715
    Search for more papers by this author
  • Ten Feizi Prof.,

    1. Glycosciences Laboratory, Imperial College Faculty of Medicine, Northwick Park & St Mark's Campus, Harrow, Middlesex HA1 3UJ, UK
    Search for more papers by this author
  • Wengang Chai Dr.,

    1. Glycosciences Laboratory, Imperial College Faculty of Medicine, Northwick Park & St Mark's Campus, Harrow, Middlesex HA1 3UJ, UK
    Search for more papers by this author
  • David Bonnaffé Prof.,

    1. Laboratoire de Chimie Organique Multifonctionnelle, Equipe de Glycochimie Moléculaire et Macromoléculaire, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR CNRS-UPS 8182, Université Paris Sud 11, Bât. 420, 91405 Orsay Cedex, France, Fax: (+33) 169-164-715
    Search for more papers by this author
  • André Lubineau Prof.

    1. Laboratoire de Chimie Organique Multifonctionnelle, Equipe de Glycochimie Moléculaire et Macromoléculaire, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR CNRS-UPS 8182, Université Paris Sud 11, Bât. 420, 91405 Orsay Cedex, France, Fax: (+33) 169-164-715
    Search for more papers by this author

Abstract

original image

A methodology allowing the differentiation of azido groups in protected oligosaccharides was optimized. It allowed the first synthesis of tetrasaccharides 1 and 2 containing both N-acetylated and N-unsubstituted glucosamine, as well as glucuronic and/or iduronic acid residues. These tetrasaccharides were then examined for their ability to interact with 10E4, an antibody recognizing early lesions in the brain of scrapie prion-infected mice.

Ancillary