Synthesis of N-linked glycan derived from Gram-negative bacterium, Campylobacter jejuni
Synthesis of N-linked glycan derived from Gram-negative bacterium, Campylobacter jejuni
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DOI：
10.1016/j.tet.2007.05.126
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发表时间：
2007-08-20
期刊：
影响因子：
2.1
通讯作者：
Ito, Yukishige
中科院分区：
文献类型：
--
作者：
Amin, Mohammed Nurul;Ishiwata, Akihiro;Ito, Yukishige
最近的研究表明，在某些原核生物中存在天冬酰胺(Asn)-连接（n -连接）糖蛋白。在本文中，我们描述了从空肠弯曲杆菌中提取的一种新型n-聚糖的化学合成，这是一种由Asn-linked bacillosamine (Bac)，重复GalNAc和分支Glc组成的七糖，即GalNAc- α (1,4)-GalNAc- α (1,4)-[Glc- β (1,3)-] GalNAc- α (1,4)-GalNAc- α (1,4)-GalNAc- α (1,3)-Bac。该合成从一个bac受体开始，与4- o -五氟丙酰（PFP）保护供体连续糖基化，得到七糖。叠氮化物基团还原后，再进行去苄基化，完成目标低聚糖的合成。(c) 2007 Elsevier Ltd.版权所有。
Recent research has revealed the presence of asparagine (Asn)-linked (N-linked) glycoproteins in certain prokaryotes. In this paper, we describe the chemical synthesis of a novel N-glycan derived from Campylobacter jejuni, a heptasaccharide composed of Asn-linked bacillosamine (Bac), repeating GalNAc, and branching Glc, namely GalNAc-alpha(1,4)-GalNAc-alpha(1,4)-[Glc-beta(1,3)-] GalNAc-alpha(1,4)-GalNAc-alpha(1,4)-GalNAc-alpha(1,3)-Bac. The synthesis started from a Bac-acceptor, which was consecutively glycosylated with 4-O-pentafluoropropionyl (PFP) protected donors to give heptasaccharide. Reduction of azide groups was followed by debenzylation to complete the synthesis of the target oligosaccharide. (c) 2007 Elsevier Ltd. All rights reserved.