Saccharide Recognition by Oligo(meta-ethynylpyridine)s in Protic Media

作     者：Masahiko Inouye 

作者机构：Faculty of Pharmaceutical Sciences Toyama Medical and Pharmaceutical University Toyama 930-0194 Japan 

出 版 物：《复旦学报（自然科学版）》 (Journal of Fudan University：Natural Science)

年 卷 期：2005年第44卷第5期

页      面：734-735页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

主　　题：糖类 分子识别 氢结合 多糖 大环 缩合物 

摘      要：Previously, we have reported tris(ethynylpyridine) macrocycles as synthetic receptors for ribofuranosides, deoxyribofuranosides, and glucopyranosides[1]. The hydrogen-bonding skeletons of the macrocycles consisted of meta-tethered ethynylpyridine trimers. If the ethynylpyridine unit is polymerized, the resulting oligo- and poly(meta-ethynylpyridine) s would adopt unfolded, somewhat zigzag conformations because each pyridine nitrogen is mainly located on opposite sides of the ethynediyl bonds to cancel the dipoles. When the polymer meets with a saccharide, its pseudolinear conformation may be guided to a well-ordered helical structure in order that the nitrogen atoms of the pyridine rings inwardly interact with peripheral saccharide-OH groups in a manner similar to those of the macrocycles (Fig. 1). Thus, the chirality of saccharides added can be transferred to the helical sense of the polymer, depending on the stereochemistry of the saccharides.