The Impact of Solvent and the Receptor Structure on Chiral Recognition Using Model Acyclic Bisamides Decorated with Glucosamine Pendant Arms

[Image: see text] We investigated the influence of various factors (including solvent mixtures) on chiral recognition of chiral carboxylates, using the titration method under (1)H NMR control. We found that strong binding carboxylates (geometrical matching) is not enough for the satisfactory differe...

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Autores principales: Wasiłek, Sylwia, Jurczak, Janusz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7506935/
https://www.ncbi.nlm.nih.gov/pubmed/32812751
http://dx.doi.org/10.1021/acs.joc.0c01693
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author Wasiłek, Sylwia
Jurczak, Janusz
author_facet Wasiłek, Sylwia
Jurczak, Janusz
author_sort Wasiłek, Sylwia
collection PubMed
description [Image: see text] We investigated the influence of various factors (including solvent mixtures) on chiral recognition of chiral carboxylates, using the titration method under (1)H NMR control. We found that strong binding carboxylates (geometrical matching) is not enough for the satisfactory differentiation of enantiomers. Moreover, solvent mixture studies indicate a significant influence of environment on the formation of diastereomeric complexes and variations among them. Our findings offer insights into the complementarity of chiral recognition processes.
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spelling pubmed-75069352020-09-22 The Impact of Solvent and the Receptor Structure on Chiral Recognition Using Model Acyclic Bisamides Decorated with Glucosamine Pendant Arms Wasiłek, Sylwia Jurczak, Janusz J Org Chem [Image: see text] We investigated the influence of various factors (including solvent mixtures) on chiral recognition of chiral carboxylates, using the titration method under (1)H NMR control. We found that strong binding carboxylates (geometrical matching) is not enough for the satisfactory differentiation of enantiomers. Moreover, solvent mixture studies indicate a significant influence of environment on the formation of diastereomeric complexes and variations among them. Our findings offer insights into the complementarity of chiral recognition processes. American Chemical Society 2020-08-19 2020-09-18 /pmc/articles/PMC7506935/ /pubmed/32812751 http://dx.doi.org/10.1021/acs.joc.0c01693 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Wasiłek, Sylwia
Jurczak, Janusz
The Impact of Solvent and the Receptor Structure on Chiral Recognition Using Model Acyclic Bisamides Decorated with Glucosamine Pendant Arms
title The Impact of Solvent and the Receptor Structure on Chiral Recognition Using Model Acyclic Bisamides Decorated with Glucosamine Pendant Arms
title_full The Impact of Solvent and the Receptor Structure on Chiral Recognition Using Model Acyclic Bisamides Decorated with Glucosamine Pendant Arms
title_fullStr The Impact of Solvent and the Receptor Structure on Chiral Recognition Using Model Acyclic Bisamides Decorated with Glucosamine Pendant Arms
title_full_unstemmed The Impact of Solvent and the Receptor Structure on Chiral Recognition Using Model Acyclic Bisamides Decorated with Glucosamine Pendant Arms
title_short The Impact of Solvent and the Receptor Structure on Chiral Recognition Using Model Acyclic Bisamides Decorated with Glucosamine Pendant Arms
title_sort impact of solvent and the receptor structure on chiral recognition using model acyclic bisamides decorated with glucosamine pendant arms
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7506935/
https://www.ncbi.nlm.nih.gov/pubmed/32812751
http://dx.doi.org/10.1021/acs.joc.0c01693
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