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

被引：15

作者：

Daragics, Katalin ^{[1
]}

Fuegedi, Peter ^{[1
]}

机构：

[1] Hungarian Acad Sci, Chem Res Ctr, Dept Carbohydrate Chem, H-1025 Budapest, Hungary

来源：

TETRAHEDRON | 2010年 / 66卷 / 40期

关键词：

Heparan sulfate; Prion diseases; Oligosaccharide synthesis; N-Acetyl-D-glucosamine; Glycosylation; Thioglycosides; N-ACETYLGLUCOSAMINE; EFFICIENT SYNTHESIS; ALZHEIMERS-DISEASE; MODULAR SYNTHESIS; THIOGLYCOSIDES; GLYCOSYLATION; PROTEOGLYCANS; PROTEIN; TRISACCHARIDE; GLUCOSAMINE;

D O I：

10.1016/j.tet.2010.08.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-o-glucosamine derivative and the alpha-selective glycosylation of the 4'-OH group of a beta-D-GlcpA-(1 -> 4)-D-GlcpNAc disaccharide building block with a disaccharide thioglycoside donor. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：8036 / 8046

页数：11

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