Cargando…

A Protein Data Bank Survey Reveals Shortening of Intermolecular Hydrogen Bonds in Ligand-Protein Complexes When a Halogenated Ligand Is an H-Bond Donor

Halogen bonding in ligand-protein complexes is currently widely exploited, e.g. in drug design or supramolecular chemistry. But little attention has been directed to other effects that may result from replacement of a hydrogen by a strongly electronegative halogen. Analysis of almost 30000 hydrogen...

Descripción completa

Detalles Bibliográficos
Autores principales: Poznański, Jarosław, Poznańska, Anna, Shugar, David
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4059718/
https://www.ncbi.nlm.nih.gov/pubmed/24933273
http://dx.doi.org/10.1371/journal.pone.0099984
_version_ 1782321275121696768
author Poznański, Jarosław
Poznańska, Anna
Shugar, David
author_facet Poznański, Jarosław
Poznańska, Anna
Shugar, David
author_sort Poznański, Jarosław
collection PubMed
description Halogen bonding in ligand-protein complexes is currently widely exploited, e.g. in drug design or supramolecular chemistry. But little attention has been directed to other effects that may result from replacement of a hydrogen by a strongly electronegative halogen. Analysis of almost 30000 hydrogen bonds between protein and ligand demonstrates that the length of a hydrogen bond depends on the type of donor-acceptor pair. Interestingly, lengths of hydrogen bonds between a protein and a halogenated ligand are visibly shorter than those estimated for the same family of proteins in complexes with non-halogenated ligands. Taking into account the effect of halogenation on hydrogen bonding is thus important when evaluating structural and/or energetic parameters of ligand-protein complexes. All these observations are consistent with the concept that halogenation increases the acidity of the proximal amino/imino/hydroxyl groups and thus makes them better, i.e. stronger, H-bond donors.
format Online
Article
Text
id pubmed-4059718
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher Public Library of Science
record_format MEDLINE/PubMed
spelling pubmed-40597182014-06-19 A Protein Data Bank Survey Reveals Shortening of Intermolecular Hydrogen Bonds in Ligand-Protein Complexes When a Halogenated Ligand Is an H-Bond Donor Poznański, Jarosław Poznańska, Anna Shugar, David PLoS One Research Article Halogen bonding in ligand-protein complexes is currently widely exploited, e.g. in drug design or supramolecular chemistry. But little attention has been directed to other effects that may result from replacement of a hydrogen by a strongly electronegative halogen. Analysis of almost 30000 hydrogen bonds between protein and ligand demonstrates that the length of a hydrogen bond depends on the type of donor-acceptor pair. Interestingly, lengths of hydrogen bonds between a protein and a halogenated ligand are visibly shorter than those estimated for the same family of proteins in complexes with non-halogenated ligands. Taking into account the effect of halogenation on hydrogen bonding is thus important when evaluating structural and/or energetic parameters of ligand-protein complexes. All these observations are consistent with the concept that halogenation increases the acidity of the proximal amino/imino/hydroxyl groups and thus makes them better, i.e. stronger, H-bond donors. Public Library of Science 2014-06-16 /pmc/articles/PMC4059718/ /pubmed/24933273 http://dx.doi.org/10.1371/journal.pone.0099984 Text en © 2014 Poznański et al http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are properly credited.
spellingShingle Research Article
Poznański, Jarosław
Poznańska, Anna
Shugar, David
A Protein Data Bank Survey Reveals Shortening of Intermolecular Hydrogen Bonds in Ligand-Protein Complexes When a Halogenated Ligand Is an H-Bond Donor
title A Protein Data Bank Survey Reveals Shortening of Intermolecular Hydrogen Bonds in Ligand-Protein Complexes When a Halogenated Ligand Is an H-Bond Donor
title_full A Protein Data Bank Survey Reveals Shortening of Intermolecular Hydrogen Bonds in Ligand-Protein Complexes When a Halogenated Ligand Is an H-Bond Donor
title_fullStr A Protein Data Bank Survey Reveals Shortening of Intermolecular Hydrogen Bonds in Ligand-Protein Complexes When a Halogenated Ligand Is an H-Bond Donor
title_full_unstemmed A Protein Data Bank Survey Reveals Shortening of Intermolecular Hydrogen Bonds in Ligand-Protein Complexes When a Halogenated Ligand Is an H-Bond Donor
title_short A Protein Data Bank Survey Reveals Shortening of Intermolecular Hydrogen Bonds in Ligand-Protein Complexes When a Halogenated Ligand Is an H-Bond Donor
title_sort protein data bank survey reveals shortening of intermolecular hydrogen bonds in ligand-protein complexes when a halogenated ligand is an h-bond donor
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4059718/
https://www.ncbi.nlm.nih.gov/pubmed/24933273
http://dx.doi.org/10.1371/journal.pone.0099984
work_keys_str_mv AT poznanskijarosław aproteindatabanksurveyrevealsshorteningofintermolecularhydrogenbondsinligandproteincomplexeswhenahalogenatedligandisanhbonddonor
AT poznanskaanna aproteindatabanksurveyrevealsshorteningofintermolecularhydrogenbondsinligandproteincomplexeswhenahalogenatedligandisanhbonddonor
AT shugardavid aproteindatabanksurveyrevealsshorteningofintermolecularhydrogenbondsinligandproteincomplexeswhenahalogenatedligandisanhbonddonor
AT poznanskijarosław proteindatabanksurveyrevealsshorteningofintermolecularhydrogenbondsinligandproteincomplexeswhenahalogenatedligandisanhbonddonor
AT poznanskaanna proteindatabanksurveyrevealsshorteningofintermolecularhydrogenbondsinligandproteincomplexeswhenahalogenatedligandisanhbonddonor
AT shugardavid proteindatabanksurveyrevealsshorteningofintermolecularhydrogenbondsinligandproteincomplexeswhenahalogenatedligandisanhbonddonor