Saccharide-dependent induction of chiral helicity in achiral synthetic hydrogen-bonding oligomers
Saccharide-dependent induction of chiral helicity in achiral synthetic hydrogen-bonding oligomers
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DOI：
10.1021/ja039371g
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发表时间：
2004-02-25
影响因子：
15
通讯作者：
Abe, H
中科院分区：
文献类型：
--
作者：
Inouye, M;Waki, M;Abe, H
众所周知，生物聚合物的构象转变受到与小分子的非共价相互作用的影响。我们发现，合成的聚合物，聚和低聚（间乙炔基吡啶）的，引导螺旋结构的不带电的氢键相互作用与封闭在聚合物的内球的natural。圆二色谱（CD）研究表明，糖的手性转移到聚合物的螺旋意义。在天然重要的己糖的正辛基吡喃糖苷中，β-葡糖苷最有效地诱导CD。尺寸调节的18聚体和更长的低聚物也显示出与聚合物类似的诱导CD。此外，天然单糖被提取到极性较低的有机溶剂的聚合物的帮助下，诱导类似的CD信号。
Conformational transitions of biopolymers are well-known to be affected by noncovalent interactions with small molecules. We found that synthetic polymers, poly- and oligo(meta-ethynylpyridine)s, are guided to helical structures by uncharged hydrogen-bonding interactions with saccharides enclosed in the inner sphere of the polymers. Circular dichroism (CD) studies revealed that chirality of saccharide was transferred to the helical sense of the polymers. Among the n-octyl pyranosides of naturally important hexoses, beta-glucoside induced CDs most effectively. Size-regulated 18-mer and longer oligomers also showed the induced CDs similar to those for the polymers. Furthermore, native monosaccharides were extracted into less polar organic solvent with the help of the polymers, inducing similar CD signals.