A hemicryptophane with a triple-stranded helical structure

A hemicryptophane cage bearing amine and amide functions in its three linkers was synthesized in five steps. The X-ray molecular structure of the cage shows a triple-stranded helical arrangement of the linkers stabilized by intramolecular hydrogen bonds between amide and amine groups. The chirality...

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Autores principales: Long, Augustin, Perraud, Olivier, Jeanneau, Erwann, Aronica, Christophe, Dutasta, Jean-Pierre, Martinez, Alexandre
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6071729/
https://www.ncbi.nlm.nih.gov/pubmed/30112093
http://dx.doi.org/10.3762/bjoc.14.162
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author Long, Augustin
Perraud, Olivier
Jeanneau, Erwann
Aronica, Christophe
Dutasta, Jean-Pierre
Martinez, Alexandre
author_facet Long, Augustin
Perraud, Olivier
Jeanneau, Erwann
Aronica, Christophe
Dutasta, Jean-Pierre
Martinez, Alexandre
author_sort Long, Augustin
collection PubMed
description A hemicryptophane cage bearing amine and amide functions in its three linkers was synthesized in five steps. The X-ray molecular structure of the cage shows a triple-stranded helical arrangement of the linkers stabilized by intramolecular hydrogen bonds between amide and amine groups. The chirality of the cyclotriveratrylene unit controls the propeller arrangement of the three aromatic rings in the opposite part of the cage. (1)H NMR studies suggest that this structure is retained in solution.
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spelling pubmed-60717292018-08-15 A hemicryptophane with a triple-stranded helical structure Long, Augustin Perraud, Olivier Jeanneau, Erwann Aronica, Christophe Dutasta, Jean-Pierre Martinez, Alexandre Beilstein J Org Chem Full Research Paper A hemicryptophane cage bearing amine and amide functions in its three linkers was synthesized in five steps. The X-ray molecular structure of the cage shows a triple-stranded helical arrangement of the linkers stabilized by intramolecular hydrogen bonds between amide and amine groups. The chirality of the cyclotriveratrylene unit controls the propeller arrangement of the three aromatic rings in the opposite part of the cage. (1)H NMR studies suggest that this structure is retained in solution. Beilstein-Institut 2018-07-24 /pmc/articles/PMC6071729/ /pubmed/30112093 http://dx.doi.org/10.3762/bjoc.14.162 Text en Copyright © 2018, Long et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Long, Augustin
Perraud, Olivier
Jeanneau, Erwann
Aronica, Christophe
Dutasta, Jean-Pierre
Martinez, Alexandre
A hemicryptophane with a triple-stranded helical structure
title A hemicryptophane with a triple-stranded helical structure
title_full A hemicryptophane with a triple-stranded helical structure
title_fullStr A hemicryptophane with a triple-stranded helical structure
title_full_unstemmed A hemicryptophane with a triple-stranded helical structure
title_short A hemicryptophane with a triple-stranded helical structure
title_sort hemicryptophane with a triple-stranded helical structure
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6071729/
https://www.ncbi.nlm.nih.gov/pubmed/30112093
http://dx.doi.org/10.3762/bjoc.14.162
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