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Chiral recognition and enantiomer excess determination based on emission wavelength change of AIEgen rotor

Chiral recognition, such as enantioselective interactions of enzyme with chiral agents, is one of the most important issues in the natural world. But artificial chiral receptors are much less efficient than natural ones. For tackling the chiral recognition and enantiomer excess (ee) analysis, up unt...

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Autores principales: Hu, Ming, Yuan, Ying-Xue, Wang, Weizhou, Li, Dong-Mi, Zhang, Hong-Chao, Wu, Bai-Xing, Liu, Minghua, Zheng, Yan-Song
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6952378/
https://www.ncbi.nlm.nih.gov/pubmed/31919426
http://dx.doi.org/10.1038/s41467-019-13955-z
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author Hu, Ming
Yuan, Ying-Xue
Wang, Weizhou
Li, Dong-Mi
Zhang, Hong-Chao
Wu, Bai-Xing
Liu, Minghua
Zheng, Yan-Song
author_facet Hu, Ming
Yuan, Ying-Xue
Wang, Weizhou
Li, Dong-Mi
Zhang, Hong-Chao
Wu, Bai-Xing
Liu, Minghua
Zheng, Yan-Song
author_sort Hu, Ming
collection PubMed
description Chiral recognition, such as enantioselective interactions of enzyme with chiral agents, is one of the most important issues in the natural world. But artificial chiral receptors are much less efficient than natural ones. For tackling the chiral recognition and enantiomer excess (ee) analysis, up until now all the fluorescent receptors have been developed based on fluorescence intensity changes. Here we report that the chiral recognition of a large number of chiral carboxylic acids, including chiral agrochemicals 2,4-D, is carried out based on fluorescent colour changes rather than intensity changes of AIEgen rotors. Moreover, the fluorescence wavelength of the AIEgen rotor linearly changes with ee of the carboxylic acid, enabling the ee to be accurately measured with average absolute errors (AAE) of less than 2.8%. Theoretical calculation demonstrates that the wavelength change is ascribed to the rotation of the AIEgen rotor upon interaction with different enantiomers.
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spelling pubmed-69523782020-01-13 Chiral recognition and enantiomer excess determination based on emission wavelength change of AIEgen rotor Hu, Ming Yuan, Ying-Xue Wang, Weizhou Li, Dong-Mi Zhang, Hong-Chao Wu, Bai-Xing Liu, Minghua Zheng, Yan-Song Nat Commun Article Chiral recognition, such as enantioselective interactions of enzyme with chiral agents, is one of the most important issues in the natural world. But artificial chiral receptors are much less efficient than natural ones. For tackling the chiral recognition and enantiomer excess (ee) analysis, up until now all the fluorescent receptors have been developed based on fluorescence intensity changes. Here we report that the chiral recognition of a large number of chiral carboxylic acids, including chiral agrochemicals 2,4-D, is carried out based on fluorescent colour changes rather than intensity changes of AIEgen rotors. Moreover, the fluorescence wavelength of the AIEgen rotor linearly changes with ee of the carboxylic acid, enabling the ee to be accurately measured with average absolute errors (AAE) of less than 2.8%. Theoretical calculation demonstrates that the wavelength change is ascribed to the rotation of the AIEgen rotor upon interaction with different enantiomers. Nature Publishing Group UK 2020-01-09 /pmc/articles/PMC6952378/ /pubmed/31919426 http://dx.doi.org/10.1038/s41467-019-13955-z Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Hu, Ming
Yuan, Ying-Xue
Wang, Weizhou
Li, Dong-Mi
Zhang, Hong-Chao
Wu, Bai-Xing
Liu, Minghua
Zheng, Yan-Song
Chiral recognition and enantiomer excess determination based on emission wavelength change of AIEgen rotor
title Chiral recognition and enantiomer excess determination based on emission wavelength change of AIEgen rotor
title_full Chiral recognition and enantiomer excess determination based on emission wavelength change of AIEgen rotor
title_fullStr Chiral recognition and enantiomer excess determination based on emission wavelength change of AIEgen rotor
title_full_unstemmed Chiral recognition and enantiomer excess determination based on emission wavelength change of AIEgen rotor
title_short Chiral recognition and enantiomer excess determination based on emission wavelength change of AIEgen rotor
title_sort chiral recognition and enantiomer excess determination based on emission wavelength change of aiegen rotor
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6952378/
https://www.ncbi.nlm.nih.gov/pubmed/31919426
http://dx.doi.org/10.1038/s41467-019-13955-z
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