Saccharide-linked ethynylpyridine oligomers: Primary structures encode chiral helices
Saccharide-linked ethynylpyridine oligomers: Primary structures encode chiral helices
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DOI：
10.1021/ma801470r
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发表时间：
2008-10-14
期刊：
影响因子：
5.5
通讯作者：
Inouye, Masahiko
中科院分区：
文献类型：
--
作者：
Abe, Hajime;Murayama, Daisuke;Inouye, Masahiko
合成了一系列糖苷连接的2，6-吡啶亚乙炔基（间乙炔基吡啶）低聚化合物，并研究了它们的分子内手性诱导。低聚物的一级结构，如乙炔基吡啶部分和接头的长度以及端基和连接糖苷的类型是不同的。从圆二色谱（CD）和H-1 NMR分析，它被发现，糖苷和乙炔基吡啶部分之间的分子内氢键诱导形成的高阶，手性螺旋的低聚物。螺旋的CD信号的符号和强度被发现强烈依赖于乙炔基吡啶的长度和末端基团和糖苷的类型。这些结果表明，低聚物在其一级结构中编码其高级结构。
A series of glycoside-linked oligomeric 2,6-pyridylene-ethynylene (m-ethynylpyridine) compounds were prepared and studied for their intramolecular chiral induction. The primary structure of the oligomers, such as the lengths of ethynylpyridine moieties and linkers and the types of terminal groups and linked glycosides, was varied. From circular dichroism (CD) and H-1 NMR analyses, it was found that the intramolecular hydrogen bonds between the glycoside and ethynylpyridine moieties induced the formation of higher-order, chiral helices of the oligomers. The sign and strength of CD signals for the helices were found to depend strongly on the length of ethynylpyridines and the types of terminal groups and glycosides. These results showed that the oligomers encode their higher-order structures in their primary structures.