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First Synthesis of Heparan Sulfate Tetrasaccharides Containing both N ‐Acetylated and N ‐Unsubstituted Glucosamine—Search for Putative 10E4 Epitopes
Author(s) -
Hamza Daniel,
Lucas Ricardo,
Feizi Ten,
Chai Wengang,
Bonnaffé David,
Lubineau André
Publication year - 2006
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200600356
Subject(s) - acetylation , heparan sulfate , glucosamine , chemistry , glucuronic acid , tetrasaccharide , epitope , biochemistry , glycobiology , stereochemistry , glycosaminoglycan , glycan , antibody , glycoprotein , biology , gene , immunology , polysaccharide
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.