Synthesis of glycosaminoglycan oligosaccharides. Part 5: Synthesis of a putative heparan sulfate tetrasaccharide antigen involved in prion diseases

The synthesis of the putative prion-associated heparan sulfate tetrasaccharide containing two d-glucuronic acid units is reported. Key to the synthesis were the differentiation of the N-acetylated and N-unsubstituted glucosamine units, the high-yielding glucosylation at O-4 of an N-acetyl- d-glucosa...

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Bibliographic Details
Published in:Tetrahedron 2010-10, Vol.66 (40), p.8036-8046
Main Authors: Daragics, Katalin, Fügedi, Péter
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Glycosylation
Heparan sulfate
N-Acetyl- d-glucosamine
Oligosaccharide synthesis
Organic chemistry
Preparations and properties
Prion diseases
Thioglycosides
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Summary:The synthesis of the putative prion-associated heparan sulfate tetrasaccharide containing two d-glucuronic acid units is reported. Key to the synthesis were the differentiation of the N-acetylated and N-unsubstituted glucosamine units, the high-yielding glucosylation at O-4 of an N-acetyl- d-glucosamine derivative and the α-selective glycosylation of the 4′-OH group of a β- d-Glc pA-(1→4)- d-Glc pNAc disaccharide building block with a disaccharide thioglycoside donor. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.08.004