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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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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spelling sg-ntu-dr.10356-1014612020-06-01T10:01:40Z Chiral crystallization of aromatic helical foldamers via complementarities in shape and end functionalities Li, Sam F. Y. Zhao, Huaiqing Ong, Wei Qiang Zhou, Feng Fang, Xiao Chen, Xueyuan Su, Haibin Cho, Nam-Joon Zeng, Huaqiang School of Materials Science & Engineering 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. 2013-07-10T06:12:15Z 2019-12-06T20:38:58Z 2013-07-10T06:12:15Z 2019-12-06T20:38:58Z 2012 2012 Journal Article Zhao, H., Ong, W. Q., Zhou, F., Fang, X., Chen, X., Li, S. F. Y., et al. (2012). Chiral crystallization of aromatic helical foldamers via complementarities in shape and end functionalities. Chemical Science, 3(6), 2042-2046. https://hdl.handle.net/10356/101461 http://hdl.handle.net/10220/11105 10.1039/c2sc20219k en Chemical science © 2012 The Royal Society of Chemistry.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
description 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.
author2 School of Materials Science & Engineering
author_facet School of Materials Science & Engineering
Li, Sam F. Y.
Zhao, Huaiqing
Ong, Wei Qiang
Zhou, Feng
Fang, Xiao
Chen, Xueyuan
Su, Haibin
Cho, Nam-Joon
Zeng, Huaqiang
format Article
author Li, Sam F. Y.
Zhao, Huaiqing
Ong, Wei Qiang
Zhou, Feng
Fang, Xiao
Chen, Xueyuan
Su, Haibin
Cho, Nam-Joon
Zeng, Huaqiang
spellingShingle Li, Sam F. Y.
Zhao, Huaiqing
Ong, Wei Qiang
Zhou, Feng
Fang, Xiao
Chen, Xueyuan
Su, Haibin
Cho, Nam-Joon
Zeng, Huaqiang
Chiral crystallization of aromatic helical foldamers via complementarities in shape and end functionalities
author_sort Li, Sam F. Y.
title Chiral crystallization of aromatic helical foldamers via complementarities in shape and end functionalities
title_short Chiral crystallization of aromatic helical foldamers via complementarities in shape and end functionalities
title_full Chiral crystallization of aromatic helical foldamers via complementarities in shape and end functionalities
title_fullStr Chiral crystallization of aromatic helical foldamers via complementarities in shape and end functionalities
title_full_unstemmed Chiral crystallization of aromatic helical foldamers via complementarities in shape and end functionalities
title_sort chiral crystallization of aromatic helical foldamers via complementarities in shape and end functionalities
publishDate 2013
url https://hdl.handle.net/10356/101461
http://hdl.handle.net/10220/11105
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