Moriuchi Toshiyuki, Nagai Takayoshi, Hirao Toshikazu
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka 565-0871, Japan.
Org Lett. 2005 Nov 10;7(23):5265-8. doi: 10.1021/ol052134t.
[structures: see text] The symmetrical introduction of two dipeptide chains of heterochiral sequence (-L-Ala-D-Pro-NHPy) into the ferrocene scaffold as a central reverse-turn unit was demonstrated to induce both antiparallel beta-sheet-like and type II beta-turn-like structures simultaneously, affording the chirality-organized structure. The ferrocene bearing only one dipeptide chain (-L-Ala-D-Pro-NHPy) exhibited a left-handed helically ordered molecular assembly through a network of intermolecular hydrogen bonds instead of intramolecular hydrogen bonds.
[结构:见正文] 作为中心反向转角单元,将两条异手性序列(-L-丙氨酸-D-脯氨酸-NHPy)的二肽链对称引入二茂铁支架中,结果表明可同时诱导反平行β-折叠样结构和II型β-转角样结构,从而形成手性有序结构。仅带有一条二肽链(-L-丙氨酸-D-脯氨酸-NHPy)的二茂铁通过分子间氢键网络而非分子内氢键表现出左手螺旋有序分子组装。