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π-Stacking Driven Aggregation and Folding of Squaramides.
The Journal of Physical Chemistry A ( IF 2.7 ) Pub Date : 2020-06-12 , DOI: 10.1021/acs.jpca.0c03120
Saumik Sen 1 , Arkaprabha Basu 1 , Tirthendu Sen 1 , G Naresh Patwari 1
Affiliation  

Competing noncovalent interactions play a pivotal role in the folding and assembly of three-dimensional structures, especially in flexible molecules. Calculations using density functional theory reveal that two squaramide rings aggregate to form a slipped antiparallel π-stacked dimer with high propensity. This π–π stacking interaction is used to design foldamers in which the squaramides are tethered by a simple methylene bridge, and consequently, the structure folds on to itself incorporating a “turn” element. The variation in relative energy with respect to change in dihedral angle for these foldamers show that for all the structures two rings are displaced in space and the folding potential is asymmetric, starting from seemingly symmetric molecules. The addition of successive squaramide rings connected with simple methylene bridges leads to the formation of higher-order structures with a “Turn-Stack-Turn” structural motif. The “Turn-Stack-Turn” motif can be used in designing new synthetic foldamers which could potentially mimic closely related biological systems. Further, it was found that the aggregation of the folded structures was energetically favored over the unfolded structures. The present set of calculations are important in light of the fact that these simple methylene bridged squaramide rings present synthetic challenges.

中文翻译:

π堆积驱动的方括号的聚集和折叠。

竞争性非共价相互作用在三维结构的折叠和组装中起着关键作用,尤其是在柔性分子中。使用密度泛函理论的计算表明,两个方胺环聚集形成具有高倾向性的滑动反平行π堆积二聚体。这种π-π堆积相互作用被用于设计折叠剂,其中的方酰胺通过一个简单的亚甲基桥进行束缚,因此,该结构折叠起来并带有“转弯”元素。这些折叠器相对于二面角变化的相对能量变化表明,对于所有结构,两个环在空间上都是移位的,并且从看似对称的​​分子开始,折叠势是不对称的。与简单的亚甲基桥连接的连续的方酰胺环的添加导致形成具有“ Turn-Stack-Turn”结构基序的高阶结构。“ Turn-Stack-Turn”主题可用于设计新的合成折叠剂,这些折叠剂可能会模仿紧密相关的生物系统。此外,发现折叠结构的聚集在能量上比未折叠结构更有利。鉴于这些简单的亚甲基桥连的方酰胺环存在合成难题,因此,本组计算非常重要。发现折叠结构的聚集在能量上比未折叠结构更有利。鉴于这些简单的亚甲基桥连的方酰胺环存在合成难题,因此,本组计算非常重要。发现折叠结构的聚集在能量上优于未折叠结构。鉴于这些简单的亚甲基桥连的方酰胺环存在合成难题,因此这一组计算非常重要。
更新日期:2020-07-16
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