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Chirality Sensing of N-Heterocycles via (19)F NMR
[Image: see text] Methods to rapidly detect and differentiate chiral N-heterocyclic compounds become increasingly important owing to the widespread application of N-heterocycles in drug discovery and materials science. We herein report a (19)F NMR-based chemosensing approach for the prompt enantioan...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10206601/ https://www.ncbi.nlm.nih.gov/pubmed/37234104 http://dx.doi.org/10.1021/jacsau.2c00661 |
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author | Gu, Guangxing Xu, Zhenchuang Wen, Lixian Liang, Jinhua Wang, Chenyang Wan, Xiaolong Zhao, Yanchuan |
author_facet | Gu, Guangxing Xu, Zhenchuang Wen, Lixian Liang, Jinhua Wang, Chenyang Wan, Xiaolong Zhao, Yanchuan |
author_sort | Gu, Guangxing |
collection | PubMed |
description | [Image: see text] Methods to rapidly detect and differentiate chiral N-heterocyclic compounds become increasingly important owing to the widespread application of N-heterocycles in drug discovery and materials science. We herein report a (19)F NMR-based chemosensing approach for the prompt enantioanalysis of various N-heterocycles, where the dynamic binding between the analytes and a chiral (19)F-labeled palladium probe create characteristic (19)F NMR signals assignable to each enantiomer. The open binding site of the probe allows the effective recognition of bulky analytes that are otherwise difficult to detect. The chirality center distal to the binding site is found sufficient for the probe to discriminate the stereoconfiguration of the analyte. The utility of the method in the screening of reaction conditions for the asymmetric synthesis of lansoprazole is demonstrated. |
format | Online Article Text |
id | pubmed-10206601 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-102066012023-05-25 Chirality Sensing of N-Heterocycles via (19)F NMR Gu, Guangxing Xu, Zhenchuang Wen, Lixian Liang, Jinhua Wang, Chenyang Wan, Xiaolong Zhao, Yanchuan JACS Au [Image: see text] Methods to rapidly detect and differentiate chiral N-heterocyclic compounds become increasingly important owing to the widespread application of N-heterocycles in drug discovery and materials science. We herein report a (19)F NMR-based chemosensing approach for the prompt enantioanalysis of various N-heterocycles, where the dynamic binding between the analytes and a chiral (19)F-labeled palladium probe create characteristic (19)F NMR signals assignable to each enantiomer. The open binding site of the probe allows the effective recognition of bulky analytes that are otherwise difficult to detect. The chirality center distal to the binding site is found sufficient for the probe to discriminate the stereoconfiguration of the analyte. The utility of the method in the screening of reaction conditions for the asymmetric synthesis of lansoprazole is demonstrated. American Chemical Society 2023-05-02 /pmc/articles/PMC10206601/ /pubmed/37234104 http://dx.doi.org/10.1021/jacsau.2c00661 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Gu, Guangxing Xu, Zhenchuang Wen, Lixian Liang, Jinhua Wang, Chenyang Wan, Xiaolong Zhao, Yanchuan Chirality Sensing of N-Heterocycles via (19)F NMR |
title | Chirality Sensing
of N-Heterocycles via (19)F NMR |
title_full | Chirality Sensing
of N-Heterocycles via (19)F NMR |
title_fullStr | Chirality Sensing
of N-Heterocycles via (19)F NMR |
title_full_unstemmed | Chirality Sensing
of N-Heterocycles via (19)F NMR |
title_short | Chirality Sensing
of N-Heterocycles via (19)F NMR |
title_sort | chirality sensing
of n-heterocycles via (19)f nmr |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10206601/ https://www.ncbi.nlm.nih.gov/pubmed/37234104 http://dx.doi.org/10.1021/jacsau.2c00661 |
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