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Emergence of single-molecular chirality from achiral reactants

The synthesis of enantiopure molecules from achiral precursors without the need for pre-existing chirality is a major challenge associated with the origin of life. We here show that an enantiopure product can be obtained from achiral starting materials in a single organic reaction. An essential char...

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Autores principales: Steendam, René R. E., Verkade, Jorge M. M., van Benthem, Tim J. B., Meekes, Hugo, van Enckevort, Willem J. P., Raap, Jan, Rutjes, Floris P. J. T., Vlieg, Elias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Pub. Group 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4263183/
https://www.ncbi.nlm.nih.gov/pubmed/25412651
http://dx.doi.org/10.1038/ncomms6543
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author Steendam, René R. E.
Verkade, Jorge M. M.
van Benthem, Tim J. B.
Meekes, Hugo
van Enckevort, Willem J. P.
Raap, Jan
Rutjes, Floris P. J. T.
Vlieg, Elias
author_facet Steendam, René R. E.
Verkade, Jorge M. M.
van Benthem, Tim J. B.
Meekes, Hugo
van Enckevort, Willem J. P.
Raap, Jan
Rutjes, Floris P. J. T.
Vlieg, Elias
author_sort Steendam, René R. E.
collection PubMed
description The synthesis of enantiopure molecules from achiral precursors without the need for pre-existing chirality is a major challenge associated with the origin of life. We here show that an enantiopure product can be obtained from achiral starting materials in a single organic reaction. An essential characteristic of this reaction is that the chiral product precipitates from the solution, introducing a crystal–solution interface which functions as an asymmetric autocatalytic system that provides sufficient chiral amplification to reach an enantiopure end state. This approach not only provides more insight into the origin of life but also offers a pathway to acquire enantiopure compounds for industrial applications.
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spelling pubmed-42631832014-12-16 Emergence of single-molecular chirality from achiral reactants Steendam, René R. E. Verkade, Jorge M. M. van Benthem, Tim J. B. Meekes, Hugo van Enckevort, Willem J. P. Raap, Jan Rutjes, Floris P. J. T. Vlieg, Elias Nat Commun Article The synthesis of enantiopure molecules from achiral precursors without the need for pre-existing chirality is a major challenge associated with the origin of life. We here show that an enantiopure product can be obtained from achiral starting materials in a single organic reaction. An essential characteristic of this reaction is that the chiral product precipitates from the solution, introducing a crystal–solution interface which functions as an asymmetric autocatalytic system that provides sufficient chiral amplification to reach an enantiopure end state. This approach not only provides more insight into the origin of life but also offers a pathway to acquire enantiopure compounds for industrial applications. Nature Pub. Group 2014-11-21 /pmc/articles/PMC4263183/ /pubmed/25412651 http://dx.doi.org/10.1038/ncomms6543 Text en Copyright © 2014, Nature Publishing Group, a division of Macmillan Publishers Limited. All Rights Reserved. http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Steendam, René R. E.
Verkade, Jorge M. M.
van Benthem, Tim J. B.
Meekes, Hugo
van Enckevort, Willem J. P.
Raap, Jan
Rutjes, Floris P. J. T.
Vlieg, Elias
Emergence of single-molecular chirality from achiral reactants
title Emergence of single-molecular chirality from achiral reactants
title_full Emergence of single-molecular chirality from achiral reactants
title_fullStr Emergence of single-molecular chirality from achiral reactants
title_full_unstemmed Emergence of single-molecular chirality from achiral reactants
title_short Emergence of single-molecular chirality from achiral reactants
title_sort emergence of single-molecular chirality from achiral reactants
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4263183/
https://www.ncbi.nlm.nih.gov/pubmed/25412651
http://dx.doi.org/10.1038/ncomms6543
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