Acid-induced molecular-structural transformation of N-methyl aromatic oligoamides bearing pyridine-2-carboxamide

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• 作者：Ryu Yamasaki ; Saori Fujikake ; Ai Ito ; Kentaro Migita ; Nobuyoshi Morita ; Osamu Tamura ; Iwao Okamoto ; ^{iokamoto@ac.shoyaku.ac.jp" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Pyridine-2-carboxamide ; Foldamer ; Acid-induced conformational alteration ; Amide oligomer ; Stepwise elongation
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：6 January 2016
• 年：2016
• 卷：57
• 期：1
• 页码：56-59
• 全文大小：1184 K

文摘

Amide oligomers composed of pyridine-2-carboxamide as the repeating unit were synthesized in a stepwise manner and their structures were examined by means of ¹H NMR, NOE measurements, and DFT calculations. All the synthesized oligomers adopted a folded conformation, but became partially unfolded at the C-terminal upon addition of acid. A characteristic long-range hydrogen bond, which stabilizes local folding, was present in oligomers with a long main chain.