Substituted adenine quartets: interplay between substituent effect, hydrogen bonding and aromaticity
| Autor: | Miquel Solà, Halina Szatylowicz, Olga A. Stasyuk, Paulina H. Marek, Tadeusz M. Krygowski |
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| Přispěvatelé: | Ministerio de Economía y Competitividad (Espanya) |
| Rok vydání: | 2020 |
| Předmět: |
Hydrogen bonding
Funcional de densitat Teoria del Hydrogen bond Chemistry General Chemical Engineering Adenine Intermolecular force Substituent Aromaticity Adenina General Chemistry Electronic structure Aromaticity (Chemistry) Crystallography chemistry.chemical_compound Tetramer Guanine-Quartets Aromaticitat (Química) Enllaços d'hidrogen DNA Density functionals |
| Zdroj: | 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 DUGiDocs – Universitat de Girona instname |
| Popis: | 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 H. 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) |
| Databáze: | OpenAIRE |
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