Intramolecular Versus Intermolecular Induction of Helical Handedness in Pyridinedicarboxamide Oligomers
Intramolecular Versus Intermolecular Induction of Helical Handedness in Pyridinedicarboxamide Oligomers
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DOI：
10.1002/ejoc.200400641
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发表时间：
2005-04
影响因子：
2.8
通讯作者：
V. Maurizot;C. Dolain;I. Huc
中科院分区：
文献类型：
--
作者：
V. Maurizot;C. Dolain;I. Huc
本文提出了一种新的合成2，6-二氨基吡啶和4-癸氧基-2，6-吡啶二甲酸低聚酰胺的合成路线。这些化合物在溶液中采用稳定的单螺旋构象。NMR和圆二色性研究表明，分子内和分子间手性诱导在这些螺旋是可能的。分子内诱导通过将单个手性基团连接到低聚物的末端来实现。分子间诱导是由手性羧酸或磺酸与低聚酰胺末端残基之间的各种非共价相互作用引起的。分子内诱导似乎比分子间诱导更有效。当两种效应竞争时，分子内诱导占优势。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2005）
A new convergent synthetic scheme has been developed to prepare oligoamides of 2,6-diaminopyridine and 4-decyloxy-2,6-pyridinedicarboxylic acid. These compounds adopt stable single helical conformations in solution. NMR and circular dichroism studies show that intramolecular and intermolecular chiral induction of handedness in these helices is possible. Intramolecular induction is effected by attaching a single chiral group to the end of an oligomer. Intermolecular induction results from various noncovalent interactions between chiral carboxylic or sulfonic acids and the terminal residues of the oligoamides. Intramolecular induction appears to be more efficient than intermolecular induction. When both effects compete, intramolecular induction prevails. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)