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Hydrophobic chirality amplification in confined water cages
The manipulation of the transition states of a chemical process is essential to achieve the desired selectivity. In particular, transition states of chemical reactions can be significantly modified in a confined environment. We report a catalytic reaction with remarkable amplification of stereochemi...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6382825/ https://www.ncbi.nlm.nih.gov/pubmed/30787285 http://dx.doi.org/10.1038/s41467-019-08792-z |
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author | Song, Choong Eui Park, Si Joon Hwang, In-Soo Jung, Min Jung Shim, So Young Bae, Han Yong Jung, Ji Yoon |
author_facet | Song, Choong Eui Park, Si Joon Hwang, In-Soo Jung, Min Jung Shim, So Young Bae, Han Yong Jung, Ji Yoon |
author_sort | Song, Choong Eui |
collection | PubMed |
description | The manipulation of the transition states of a chemical process is essential to achieve the desired selectivity. In particular, transition states of chemical reactions can be significantly modified in a confined environment. We report a catalytic reaction with remarkable amplification of stereochemical information in a confined water cage. Surprisingly, this amplification is significantly dependent on droplet size. This water-induced chirality amplification stems from the hydrophobic hydration effects, which ensures high proximity of the catalyst and substrates presumably at the transition state, leading to higher enantioselectivity. Flow and batch reactors were evaluated to confirm the generality of this water-induced chirality amplification. Our observation on efficient chiral induction in confined water cages might lead to an understanding of the chirality amplification in the prebiotic era, which is a key feature for the chemical evolution of homochirality. |
format | Online Article Text |
id | pubmed-6382825 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-63828252019-02-22 Hydrophobic chirality amplification in confined water cages Song, Choong Eui Park, Si Joon Hwang, In-Soo Jung, Min Jung Shim, So Young Bae, Han Yong Jung, Ji Yoon Nat Commun Article The manipulation of the transition states of a chemical process is essential to achieve the desired selectivity. In particular, transition states of chemical reactions can be significantly modified in a confined environment. We report a catalytic reaction with remarkable amplification of stereochemical information in a confined water cage. Surprisingly, this amplification is significantly dependent on droplet size. This water-induced chirality amplification stems from the hydrophobic hydration effects, which ensures high proximity of the catalyst and substrates presumably at the transition state, leading to higher enantioselectivity. Flow and batch reactors were evaluated to confirm the generality of this water-induced chirality amplification. Our observation on efficient chiral induction in confined water cages might lead to an understanding of the chirality amplification in the prebiotic era, which is a key feature for the chemical evolution of homochirality. Nature Publishing Group UK 2019-02-20 /pmc/articles/PMC6382825/ /pubmed/30787285 http://dx.doi.org/10.1038/s41467-019-08792-z Text en © The Author(s) 2019 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 Song, Choong Eui Park, Si Joon Hwang, In-Soo Jung, Min Jung Shim, So Young Bae, Han Yong Jung, Ji Yoon Hydrophobic chirality amplification in confined water cages |
title | Hydrophobic chirality amplification in confined water cages |
title_full | Hydrophobic chirality amplification in confined water cages |
title_fullStr | Hydrophobic chirality amplification in confined water cages |
title_full_unstemmed | Hydrophobic chirality amplification in confined water cages |
title_short | Hydrophobic chirality amplification in confined water cages |
title_sort | hydrophobic chirality amplification in confined water cages |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6382825/ https://www.ncbi.nlm.nih.gov/pubmed/30787285 http://dx.doi.org/10.1038/s41467-019-08792-z |
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