Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity

Adenine, one of the components of DNA/RNA helices, has an ability to form self-organizing structures with cyclic hydrogen bonds (A4), similar to guanine quartets. Here, we report a computational investigation of the effect of substituents (X = NO2, Cl, F, H, Me, NH2) on electronic structure of 9H-ad...

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Autores: Szatylowicz, Halina, Marek, Paulina H., Stasyuk, Olga A., Krygowski, Tadeusz M., Solà i Puig, Miquel
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2020
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/18271
Acesso em linha:http://hdl.handle.net/10256/18271
Access Level:acceso abierto
Palavra-chave:Aromaticitat (Química)
Aromaticity (Chemistry)
Enllaços d'hidrogen
Hydrogen bonding
Funcional de densitat, Teoria del
Density functionals
Adenina
Adenine
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oai_identifier_str oai:recercat.cat:10256/18271
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network_name_str España
repository_id_str
spelling Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticitySzatylowicz, HalinaMarek, Paulina H.Stasyuk, Olga A.Krygowski, Tadeusz M.Solà i Puig, MiquelAromaticitat (Química)Aromaticity (Chemistry)Enllaços d'hidrogenHydrogen bondingFuncional de densitat, Teoria delDensity functionalsAdeninaAdenineAdenine, one of the components of DNA/RNA helices, has an ability to form self-organizing structures with cyclic hydrogen bonds (A4), similar to guanine quartets. Here, we report a computational investigation of the effect of substituents (X = NO2, Cl, F, H, Me, NH2) on electronic structure of 9H-adenine and its quartets (A4-N1, A4-N3, and A4-N7). DFT calculations were used to show the relationships between electronic nature of the substituents, strength of H-bonds in the quartets, and aromaticity of five- and six-membered rings of adenine. We demonstrated how the remote substituent X modifies the proton-donating properties of the NH2 group involved in the H-bonds within quartets and how the position of the substituent and its electronic nature affect the stability of the quartets. We also showed the possible changes in substituent electronic properties and aromaticity of both adenine rings caused by tetramer formation. The results indicate that the observed relationships depend on the A4 type. Moreover, the same substituent can both strengthen or weaken intermolecular interactions, depending on the substitution positionH. S. and T. M. K. thank the National Science Centre of Poland for supporting this work under the grant no. UMO-2016/23/B/ ST4/00082. P. H. M. would like to acknowledge Operational Project Knowledge Education Development 2014–2020 co-financed by European Social Fund. The work has been performed under the Project HPC-EUROPA3 (INFRAIA-2016-1- 730897), with the support of the EC Research Innovation Action under the H2020 Programme; in particular, P. H. M. gratefully acknowledges the support of the Institute of Computational Chemistry and Catalysis of the University of Girona and the computer resources and technical support provided by Barcelona Supercomputing Center. M. S. and O. A. S. are grateful to the Ministerio de Econom´ıa y Competitividad (MINECO) of Spain (project CTQ2017-85341-P and Juan de la Cierva formación contract FJCI-2017-32757 to O. A. S.) and the Generalitat de Catalunya (project 2017SGR39)Royal Society of Chemistry (RSC)Ministerio de Economía y Competitividad (Espanya)2020info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionpeer-reviewed9 p.application/pdfhttp://hdl.handle.net/10256/18271http://hdl.handle.net/10256/18271RSC Advances, 2020, vol. 10, núm. 39, p. 23350-23358Articles publicats (D-Q)Szatylowicz, Halina Marek, Paulina H. Stasyuk, Olga A. Krygowski, Tadeusz M. Solà i Puig, Miquel 2020 Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity RSC Advances 10 39 23350 23358reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1039/D0RA04585Cinfo:eu-repo/semantics/altIdentifier/issn/2046-2069info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-PReconeixement 4.0 Internacionalhttp://creativecommons.org/licenses/by/4.0info:eu-repo/semantics/openAccessoai:recercat.cat:10256/182712026-05-29T05:05:01Z
dc.title.none.fl_str_mv Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity
title Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity
spellingShingle Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity
Szatylowicz, Halina
Aromaticitat (Química)
Aromaticity (Chemistry)
Enllaços d'hidrogen
Hydrogen bonding
Funcional de densitat, Teoria del
Density functionals
Adenina
Adenine
title_short Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity
title_full Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity
title_fullStr Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity
title_full_unstemmed Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity
title_sort Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity
dc.creator.none.fl_str_mv Szatylowicz, Halina
Marek, Paulina H.
Stasyuk, Olga A.
Krygowski, Tadeusz M.
Solà i Puig, Miquel
author Szatylowicz, Halina
author_facet Szatylowicz, Halina
Marek, Paulina H.
Stasyuk, Olga A.
Krygowski, Tadeusz M.
Solà i Puig, Miquel
author_role author
author2 Marek, Paulina H.
Stasyuk, Olga A.
Krygowski, Tadeusz M.
Solà i Puig, Miquel
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (Espanya)
dc.subject.none.fl_str_mv Aromaticitat (Química)
Aromaticity (Chemistry)
Enllaços d'hidrogen
Hydrogen bonding
Funcional de densitat, Teoria del
Density functionals
Adenina
Adenine
topic Aromaticitat (Química)
Aromaticity (Chemistry)
Enllaços d'hidrogen
Hydrogen bonding
Funcional de densitat, Teoria del
Density functionals
Adenina
Adenine
description Adenine, one of the components of DNA/RNA helices, has an ability to form self-organizing structures with cyclic hydrogen bonds (A4), similar to guanine quartets. Here, we report a computational investigation of the effect of substituents (X = NO2, Cl, F, H, Me, NH2) on electronic structure of 9H-adenine and its quartets (A4-N1, A4-N3, and A4-N7). DFT calculations were used to show the relationships between electronic nature of the substituents, strength of H-bonds in the quartets, and aromaticity of five- and six-membered rings of adenine. We demonstrated how the remote substituent X modifies the proton-donating properties of the NH2 group involved in the H-bonds within quartets and how the position of the substituent and its electronic nature affect the stability of the quartets. We also showed the possible changes in substituent electronic properties and aromaticity of both adenine rings caused by tetramer formation. The results indicate that the observed relationships depend on the A4 type. Moreover, the same substituent can both strengthen or weaken intermolecular interactions, depending on the substitution position
publishDate 2020
dc.date.none.fl_str_mv 2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
peer-reviewed
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/18271
http://hdl.handle.net/10256/18271
url http://hdl.handle.net/10256/18271
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/D0RA04585C
info:eu-repo/semantics/altIdentifier/issn/2046-2069
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-P
dc.rights.none.fl_str_mv Reconeixement 4.0 Internacional
http://creativecommons.org/licenses/by/4.0
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Reconeixement 4.0 Internacional
http://creativecommons.org/licenses/by/4.0
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 9 p.
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry (RSC)
publisher.none.fl_str_mv Royal Society of Chemistry (RSC)
dc.source.none.fl_str_mv RSC Advances, 2020, vol. 10, núm. 39, p. 23350-23358
Articles publicats (D-Q)
Szatylowicz, Halina Marek, Paulina H. Stasyuk, Olga A. Krygowski, Tadeusz M. Solà i Puig, Miquel 2020 Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity RSC Advances 10 39 23350 23358
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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