Total Synthesis of the Escherichia coli O111 O-Specific Polysaccharide Repeating Unit
Total Synthesis of the Escherichia coli O111 O-Specific Polysaccharide Repeating Unit
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DOI：
10.1002/chem.201204394
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发表时间：
2013-03-01
影响因子：
4.3
通讯作者：
Seeberger, Peter H.
中科院分区：
文献类型：
--
作者：
Calin, Oliviana;Eller, Steffen;Seeberger, Peter H.
首次从革兰氏阴性菌大肠杆菌O111中合成了o抗原五糖重复单元，从四个单糖构建块开始。合成方法的关键是二糖基化反应，将三糖10和粘胶糖5结合。大肠杆菌构建块(5)是从非碳水化合物前体中重新获得的。五糖在还原端配备了一个氨基间隔，为随后的免疫研究中与载体蛋白的结合提供了一个手柄。
The first total synthesis of the O-antigen pentasaccharide repeating unit from Gram-negative bacteria Escherichia coli O111 was achieved starting from four monosaccharide building blocks. Key to the synthetic approach was a bis-glycosylation reaction to combine trisaccharide 10 and colitose 5. The colitose building block (5) was obtained de novo from non-carbohydrate precursors. The pentasaccharide was equipped at the reducing end with an amino spacer to provide a handle for subsequent conjugation to a carrier protein in anticipation of immunological studies.