Chiral crystallization of aromatic helical foldamers via complementarities in shape and end functionalities

Biomolecules such as α-helices are exclusively right-handed without contamination by their left-handed counterparts. Within the abiotic world, chiral or external perturbations have to be applied to the abiotic helical foldamers or polymers to control and bias their helical screw sense. Otherwise, it...

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Bibliographic Details
Main Authors: Li, Sam F. Y., Zhao, Huaiqing, Ong, Wei Qiang, Zhou, Feng, Fang, Xiao, Chen, Xueyuan, Su, Haibin, Cho, Nam-Joon, Zeng, Huaqiang
Other Authors: School of Materials Science & Engineering
Format: Article
Language:English
Published: 2013
Online Access:https://hdl.handle.net/10356/101461
http://hdl.handle.net/10220/11105
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Institution: Nanyang Technological University
Language: English
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Summary:Biomolecules such as α-helices are exclusively right-handed without contamination by their left-handed counterparts. Within the abiotic world, chiral or external perturbations have to be applied to the abiotic helical foldamers or polymers to control and bias their helical screw sense. Otherwise, it is not possible to separate racemic helical foldamers composed of achiral building blocks. By designing two complementary “sticky” groups, incorporating them into the ends of helical pentamers and taking advantage of the energetically more favored full overlap, which involves helical backbones, we succeeded in demonstrating, for the first time, a spontaneous resolution of racemic helices into their enantiopure single-handed helical forms via chiral crystallization without the use of chiral auxiliary or external stimuli.