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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...

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Autores principales: Song, Choong Eui, Park, Si Joon, Hwang, In-Soo, Jung, Min Jung, Shim, So Young, Bae, Han Yong, Jung, Ji Yoon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
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.
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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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