Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand

[Image: see text] We report a chiral deep cavitand receptor based on calix[5]arene stabilized by a cooperative network of hydrogen bonds and having a highly flexible structure. The cavitand displays enantioselective molecular recognition with a series of chiral quaternary ammonium salts, providing u...

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Autores principales: Álvarez-Yebra, Rubén, López-Coll, Ricard, Galán-Masferrer, Pere, Lledó, Agustí
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10186369/
https://www.ncbi.nlm.nih.gov/pubmed/37038894
http://dx.doi.org/10.1021/acs.orglett.3c00463
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author Álvarez-Yebra, Rubén
López-Coll, Ricard
Galán-Masferrer, Pere
Lledó, Agustí
author_facet Álvarez-Yebra, Rubén
López-Coll, Ricard
Galán-Masferrer, Pere
Lledó, Agustí
author_sort Álvarez-Yebra, Rubén
collection PubMed
description [Image: see text] We report a chiral deep cavitand receptor based on calix[5]arene stabilized by a cooperative network of hydrogen bonds and having a highly flexible structure. The cavitand displays enantioselective molecular recognition with a series of chiral quaternary ammonium salts, providing unprecedented stability ratios between the corresponding diastereomeric host–guest complexes. Molecular dynamics simulations corroborate the higher flexibility of the new host and the emergence of superior induced-fit behavior with regards to resorcin[4]arene derived self-folding cavitands.
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spelling pubmed-101863692023-05-17 Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand Álvarez-Yebra, Rubén López-Coll, Ricard Galán-Masferrer, Pere Lledó, Agustí Org Lett [Image: see text] We report a chiral deep cavitand receptor based on calix[5]arene stabilized by a cooperative network of hydrogen bonds and having a highly flexible structure. The cavitand displays enantioselective molecular recognition with a series of chiral quaternary ammonium salts, providing unprecedented stability ratios between the corresponding diastereomeric host–guest complexes. Molecular dynamics simulations corroborate the higher flexibility of the new host and the emergence of superior induced-fit behavior with regards to resorcin[4]arene derived self-folding cavitands. American Chemical Society 2023-04-11 /pmc/articles/PMC10186369/ /pubmed/37038894 http://dx.doi.org/10.1021/acs.orglett.3c00463 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Álvarez-Yebra, Rubén
López-Coll, Ricard
Galán-Masferrer, Pere
Lledó, Agustí
Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand
title Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand
title_full Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand
title_fullStr Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand
title_full_unstemmed Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand
title_short Enantioselective Molecular Recognition in a Flexible Self-Folding Cavitand
title_sort enantioselective molecular recognition in a flexible self-folding cavitand
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10186369/
https://www.ncbi.nlm.nih.gov/pubmed/37038894
http://dx.doi.org/10.1021/acs.orglett.3c00463
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