Altering the folding patterns of naphthyl trimers

Altering the folding patterns of naphthyl trimers
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DOI:
10.1021/ja046722y
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发表时间:
2005-03-02
影响因子:
15
通讯作者:
Iverson, BL
Iverson, BL
中科院分区:
化学1区
文献类型:
--
作者:
Gabriel, GJ;Sorey, S;Iverson, BL

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蛋白质可以采用螺旋和片状二级结构,这取决于它们的氨基酸的一级序列,已经开发了非天然折叠体来模拟这些蛋白质结构以及研究各种类型的非共价相互作用。在这里,我们报告了一个战略,以获得两个不同的折叠拓扑结构在水溶液中使用固有的识别性能的芳香供体/受体相互作用。这些低聚物由富电子的1,5-二烷氧基萘(Dan)和缺电子的1,4,5,8-萘四羧酸二酰亚胺(Ndi)单元构成。序列Dan-Ndi-Dan的三聚体在溶液中显示出采用褶状折叠,而其结构异构体Dan-Dan-Ndi采用插入式或转弯式折叠。紫外-可见光谱和NOESY光谱分析与两种不同的构象一致。这项研究说明了折叠萘基低聚物的可设计性,并鼓励使用定向芳族相互作用,在水中构建更大,更复杂的组件。
Proteins can adopt helical and sheet-type secondary structures that depend on their primary sequence of amino acids, Nonnatural foldamers have been developed to emulate these protein structures as well as investigate various types of noncovalent interactions. Here we report a strategy to access two distinct folding topologies in aqueous solutions using the inherent recognition properties of aromatic donor/acceptor interactions. These oligomers are constructed of electron-rich 1,5-dialkoxynaphthalene (Dan) and electron-deficient 1,4,5,8-naphthalenetetracarboxylic diimide (Ndi) units. A trimer of the sequence Dan-Ndi-Dan was shown to adopt a pleated fold in solution, while its constitutional isomer, Dan-Dan-Ndi, adopted an intercalative or turn-type fold. UV-vis and NOESY spectroscopy analyses were consistent with the two different conformations. This study illustrates the designability of folding naphthyl oligomers and encourages the use of directed aromatic interactions to construct larger and more complex assemblies in water.