Cargando…
Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors
Anion binding studies of 1,10-phenanthroline- and 2-pyridyl-substituted urea-based receptors reveal that guest-dependent conformations exist in structural variants related to a previously investigated bipyridyl-based receptor. Dynamic conformational switching persists in a monofunctional pyridyl-ure...
Autores principales: | , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2014
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4068745/ https://www.ncbi.nlm.nih.gov/pubmed/24976946 http://dx.doi.org/10.1039/c4sc00950a |
_version_ | 1782322447400304640 |
---|---|
author | Gavette, Jesse V. Evoniuk, Christopher J. Zakharov, Lev N. Carnes, Matthew E. Haley, Michael M. Johnson, Darren W. |
author_facet | Gavette, Jesse V. Evoniuk, Christopher J. Zakharov, Lev N. Carnes, Matthew E. Haley, Michael M. Johnson, Darren W. |
author_sort | Gavette, Jesse V. |
collection | PubMed |
description | Anion binding studies of 1,10-phenanthroline- and 2-pyridyl-substituted urea-based receptors reveal that guest-dependent conformations exist in structural variants related to a previously investigated bipyridyl-based receptor. Dynamic conformational switching persists in a monofunctional pyridyl-urea receptor, and the preorganization provided by a phenanthroline-based analogue promotes convergence of anion coordinating groups to a single guest. Despite this predisposition for anion coordination, the conformational flexibility of the bipyridyl-based receptor provides the most selective motif for H(2)PO(4) (–) coordination. Furthermore, the two new phenanthrolyl- and pyridyl-receptors serve as models of the bipyridyl-based receptor, elucidating accurate stepwise association constants for 1 : 2 host/guest binding by this receptor, and suggest that oxoanions prefer the embrace of a “U” conformation in 1 : 1 complexes. |
format | Online Article Text |
id | pubmed-4068745 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-40687452015-01-07 Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors Gavette, Jesse V. Evoniuk, Christopher J. Zakharov, Lev N. Carnes, Matthew E. Haley, Michael M. Johnson, Darren W. Chem Sci Chemistry Anion binding studies of 1,10-phenanthroline- and 2-pyridyl-substituted urea-based receptors reveal that guest-dependent conformations exist in structural variants related to a previously investigated bipyridyl-based receptor. Dynamic conformational switching persists in a monofunctional pyridyl-urea receptor, and the preorganization provided by a phenanthroline-based analogue promotes convergence of anion coordinating groups to a single guest. Despite this predisposition for anion coordination, the conformational flexibility of the bipyridyl-based receptor provides the most selective motif for H(2)PO(4) (–) coordination. Furthermore, the two new phenanthrolyl- and pyridyl-receptors serve as models of the bipyridyl-based receptor, elucidating accurate stepwise association constants for 1 : 2 host/guest binding by this receptor, and suggest that oxoanions prefer the embrace of a “U” conformation in 1 : 1 complexes. Royal Society of Chemistry 2014-07-03 2014-05-23 /pmc/articles/PMC4068745/ /pubmed/24976946 http://dx.doi.org/10.1039/c4sc00950a Text en This journal is © The Royal Society of Chemistry 2014 http://creativecommons.org/licenses/by-nc/2.0/uk/ This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Gavette, Jesse V. Evoniuk, Christopher J. Zakharov, Lev N. Carnes, Matthew E. Haley, Michael M. Johnson, Darren W. Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors |
title | Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors
|
title_full | Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors
|
title_fullStr | Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors
|
title_full_unstemmed | Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors
|
title_short | Exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors
|
title_sort | exploring anion-induced conformational flexibility and molecular switching in a series of heteroaryl-urea receptors |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4068745/ https://www.ncbi.nlm.nih.gov/pubmed/24976946 http://dx.doi.org/10.1039/c4sc00950a |
work_keys_str_mv | AT gavettejessev exploringanioninducedconformationalflexibilityandmolecularswitchinginaseriesofheteroarylureareceptors AT evoniukchristopherj exploringanioninducedconformationalflexibilityandmolecularswitchinginaseriesofheteroarylureareceptors AT zakharovlevn exploringanioninducedconformationalflexibilityandmolecularswitchinginaseriesofheteroarylureareceptors AT carnesmatthewe exploringanioninducedconformationalflexibilityandmolecularswitchinginaseriesofheteroarylureareceptors AT haleymichaelm exploringanioninducedconformationalflexibilityandmolecularswitchinginaseriesofheteroarylureareceptors AT johnsondarrenw exploringanioninducedconformationalflexibilityandmolecularswitchinginaseriesofheteroarylureareceptors |