Role of Achiral Nucleobases in Multicomponent Chiral Self‐Assembly: Purine‐Triggered Helix and Chirality Transfer,Angewandte Chemie International Edition

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Role of Achiral Nucleobases in Multicomponent Chiral Self‐Assembly: Purine‐Triggered Helix and Chirality Transfer
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2016-11-03 , DOI: 10.1002/anie.201608638
Ming Deng _{1,

2} , Li Zhang ₁ , Yuqian Jiang ₃ , Minghua Liu _{1,

2,

3,

4}

Affiliation

Chiral self‐assembly is a basic process in biological systems, where many chiral biomolecules such as amino acids and sugars play important roles. Achiral nucleobases usually covalently bond to saccharides and play a significant role in the formation of the double helix structure. However, it remains unclear how the achiral nucleobases can function in chiral self‐assembly without the sugar modification. Herein, we have clarified that purine nucleobases could trigger N‐(9‐fluorenylmethox‐ycarbonyl) (Fmoc)‐protected glutamic acid to self‐assemble into helical nanostructures. Moreover, the helical nanostructure could serve as a matrix and transfer the chirality to an achiral fluorescence probe, thioflavin T (ThT). Upon chirality transfer, the ThT showed not only supramolecular chirality but also circular polarized fluorescence (CPL). Without the nucleobase, the self‐assembly processes cannot happen, thus providing an example where achiral molecules played an essential role in the expression and transfer of the chirality.

中文翻译：

非手性核糖核酸酶在多组分手性自组装中的作用：嘌呤触发的螺旋和手性转移

手性自组装是生物系统中的基本过程，其中许多手性生物分子（例如氨基酸和糖）起着重要作用。非手性核碱基通常与糖共价键合，并在双螺旋结构的形成中起重要作用。然而，尚不清楚在不进行糖修饰的情况下，非手性核苷如何在手性自组装中发挥功能。在本文中，我们已经阐明嘌呤核苷碱基可以触发N-（9-芴基甲氧羰基羰基）（Fmoc）保护的谷氨酸自组装成螺旋纳米结构。此外，螺旋纳米结构可以用作基质，并将手性传递给非手性荧光探针硫黄素T（ThT）。在手性转移时，ThT不仅显示超分子手性，还显示圆偏振荧光（CPL）。没有核碱基，自组装过程就不会发生，因此提供了一个示例，其中非手性分子在手性的表达和转移中起着至关重要的作用。

更新日期：2016-11-03

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