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分枝杆菌中的阿拉伯呋喃糖苷:一种高度分支的六糖及含β-阿拉伯呋喃糖基残基的相关片段的合成

Arabinofuranosides from mycobacteria: synthesis of a highly branched hexasaccharide and related fragments containing beta-arabinofuranosyl residues.

作者信息

Yin Haifeng, D'Souza Francis W, Lowary Todd L

机构信息

Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.

出版信息

J Org Chem. 2002 Feb 8;67(3):892-903. doi: 10.1021/jo010910e.

Abstract

The synthesis of 11 oligosaccharides (4-14) containing beta-arabinofuranosyl residues is reported. The glycans are all fragments of two polysaccharides, arabinogalactan and lipoarabinomannan, which are found in the cell wall complex of mycobacteria. In the preparation of the targets, the key step was a low-temperature glycosylation reaction that installed the beta-arabinofuranosyl residues with good to excellent stereocontrol.

摘要

报道了11种含有β-阿拉伯呋喃糖基残基的寡糖(4-14)的合成。这些聚糖都是两种多糖——阿拉伯半乳聚糖和脂阿拉伯甘露聚糖的片段,它们存在于分枝杆菌的细胞壁复合物中。在制备目标化合物时,关键步骤是低温糖基化反应,该反应以良好至优异的立体控制引入了β-阿拉伯呋喃糖基残基。

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