The Chirality Chain in Valine: How the Configuration at the C(α) Position through the O(cis)C′C(α)N Torsional System Leads to Distortion of the Planar Group C(α)C′(O(cis))O(trans) to a Flat Tetrahedron

Solid‐state structures, based on a Cambridge Structural Database (CSD) search, show that there is a C(α)N/C′O(cis) attraction in the torsional system O(cis)C′C(α)N of valine, causing a chirality chain. The C(α) configuration controls the chirality of the rotation around the C′−C(α) bond, which in tu...

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Detalles Bibliográficos
Autores principales: Brunner, Henri, Tsuno, Takashi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6120350/
https://www.ncbi.nlm.nih.gov/pubmed/30186736
http://dx.doi.org/10.1002/open.201800137
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author Brunner, Henri
Tsuno, Takashi
author_facet Brunner, Henri
Tsuno, Takashi
author_sort Brunner, Henri
collection PubMed
description Solid‐state structures, based on a Cambridge Structural Database (CSD) search, show that there is a C(α)N/C′O(cis) attraction in the torsional system O(cis)C′C(α)N of valine, causing a chirality chain. The C(α) configuration controls the chirality of the rotation around the C′−C(α) bond, which in turn induces a distortion of the planar unit C(α)C′(O)O to a flat asymmetric tetrahedron. Conformational “reactions” take place in an energy profile with respect to clockwise and counterclockwise rotation around the C′−C(α) bond as well as stretching and flattening of the tetrahedron. The molecular property C(α)N/C′O(cis) attraction of valine is maintained in its di‐ and tripeptides.
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spelling pubmed-61203502018-09-05 The Chirality Chain in Valine: How the Configuration at the C(α) Position through the O(cis)C′C(α)N Torsional System Leads to Distortion of the Planar Group C(α)C′(O(cis))O(trans) to a Flat Tetrahedron Brunner, Henri Tsuno, Takashi ChemistryOpen Communications Solid‐state structures, based on a Cambridge Structural Database (CSD) search, show that there is a C(α)N/C′O(cis) attraction in the torsional system O(cis)C′C(α)N of valine, causing a chirality chain. The C(α) configuration controls the chirality of the rotation around the C′−C(α) bond, which in turn induces a distortion of the planar unit C(α)C′(O)O to a flat asymmetric tetrahedron. Conformational “reactions” take place in an energy profile with respect to clockwise and counterclockwise rotation around the C′−C(α) bond as well as stretching and flattening of the tetrahedron. The molecular property C(α)N/C′O(cis) attraction of valine is maintained in its di‐ and tripeptides. John Wiley and Sons Inc. 2018-09-03 /pmc/articles/PMC6120350/ /pubmed/30186736 http://dx.doi.org/10.1002/open.201800137 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Brunner, Henri
Tsuno, Takashi
The Chirality Chain in Valine: How the Configuration at the C(α) Position through the O(cis)C′C(α)N Torsional System Leads to Distortion of the Planar Group C(α)C′(O(cis))O(trans) to a Flat Tetrahedron
title The Chirality Chain in Valine: How the Configuration at the C(α) Position through the O(cis)C′C(α)N Torsional System Leads to Distortion of the Planar Group C(α)C′(O(cis))O(trans) to a Flat Tetrahedron
title_full The Chirality Chain in Valine: How the Configuration at the C(α) Position through the O(cis)C′C(α)N Torsional System Leads to Distortion of the Planar Group C(α)C′(O(cis))O(trans) to a Flat Tetrahedron
title_fullStr The Chirality Chain in Valine: How the Configuration at the C(α) Position through the O(cis)C′C(α)N Torsional System Leads to Distortion of the Planar Group C(α)C′(O(cis))O(trans) to a Flat Tetrahedron
title_full_unstemmed The Chirality Chain in Valine: How the Configuration at the C(α) Position through the O(cis)C′C(α)N Torsional System Leads to Distortion of the Planar Group C(α)C′(O(cis))O(trans) to a Flat Tetrahedron
title_short The Chirality Chain in Valine: How the Configuration at the C(α) Position through the O(cis)C′C(α)N Torsional System Leads to Distortion of the Planar Group C(α)C′(O(cis))O(trans) to a Flat Tetrahedron
title_sort chirality chain in valine: how the configuration at the c(α) position through the o(cis)c′c(α)n torsional system leads to distortion of the planar group c(α)c′(o(cis))o(trans) to a flat tetrahedron
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6120350/
https://www.ncbi.nlm.nih.gov/pubmed/30186736
http://dx.doi.org/10.1002/open.201800137
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