De novo synthesis of uronic acid building blocks for assembly of heparin oligosaccharides

被引：59

作者：

Adibekian, Alexander ^{[1
]}

Bindschadler, Pascal ^{[1
]}

Timmer, Mattie S. M. ^{[1
]}

Noti, Christian ^{[1
]}

Schutzenmeister, Nina ^{[1
]}

Seeberger, Peter H. ^{[1
]}

机构：

[1] ETH, Organ Chem Lab, Swiss Fed Inst Technol, CH-8093 Zurich, Switzerland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2007年 / 13卷 / 16期

关键词：

carbohydrates; de novo synthesis; heparin; oligosaccharides; uronic acids;

D O I：

10.1002/chem.200700141

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient de novo synthesis of uronic acid building blocks is described. The synthetic strategy relies on the stereoselective elongation of thioacetal protected dialdehydes 12a and 17. The dialdehydes are prepared from D-xylose, a cheap and commercially available source. A highly stereoselective MgBr2 center dot OEt2-mediated Mukaiyama aldol addition to C4-aldehyde 12 a is performed to obtain D-glucuronic acid building block 16, whereas L-iduronic acid building block 22 is prepared by MgBr2 center dot OEt2-mediated cyanation of C5-aldehyde 17. Synthesis of a heparin disaccharide demonstrates the utility of the de novo strategy for the assembly of glycosaminoglycan oligosaccharides.

引用

页码：4510 / 4522

页数：13

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