Stabilization of Chiral Helices for Saccharide-Linked Ethynylpyridine Oligomers Possessing a Conformationally Well-Defined Linkage
Stabilization of Chiral Helices for Saccharide-Linked Ethynylpyridine Oligomers Possessing a Conformationally Well-Defined Linkage
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DOI：
10.1002/ejoc.201201376
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发表时间：
2013-03
影响因子：
2.8
通讯作者：
Fumihiro Kayamori;H. Abe;M. Inouye
中科院分区：
文献类型：
--
作者：
Fumihiro Kayamori;H. Abe;M. Inouye
以β-D-吡喃葡萄糖苷为模板，通过邻苯连接基合成了四聚和八聚2，6-吡啶亚乙炔基低聚物，并对其高级结构进行了研究。这些低聚物通过乙炔基吡啶部分和葡萄糖苷模板之间的分子内氢键形成手性螺旋结构。邻亚苯基接头的刚性稳定螺旋结构，以改善其CD活性和对质子环境的抗性。此外，通过添加Cu（OTf）2和Zn（NO3）2盐来增强螺旋稳定化。
Tetrameric and octameric 2,6-pyridylene ethynylene oligomers linked to a β-D-glucopyranoside template through an o-phenylene linker were prepared and studied for their higher-order structure. These oligomers formed chiral helical structures through intramolecular hydrogen bonding between the ethynylpyridine moiety and the glucoside template. The rigidity of the o-phenylene linker stabilizes the helical structure to improve its CD activity and resistance against protic surroundings. Furthermore, the helical stabilization was enhanced by the addition of Cu(OTf)2 and Zn(NO3)2 salts.