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dc.contributor.authorChawla, Mohit
dc.contributor.authorMinenkov, Yury
dc.contributor.authorVu, Khanh B
dc.contributor.authorOliva, Romina
dc.contributor.authorCavallo, Luigi
dc.date.accessioned2019-04-18T12:42:47Z
dc.date.available2019-04-18T12:42:47Z
dc.date.issued2019-04-15
dc.identifier.citationChawla M, Minenkov Y, Vu KB, Oliva R, Cavallo L (2019) Structural and Energetic Impact of Non-natural 7-Deaza-8-Azaguanine, 7-Deaza-8-Azaisoguanine and their 7-Substituted Derivatives on H-bonding Pairing with Cytosine and Isocytosine. ChemBioChem. Available: http://dx.doi.org/10.1002/cbic.201900245.
dc.identifier.issn1439-4227
dc.identifier.issn1439-7633
dc.identifier.doi10.1002/cbic.201900245
dc.identifier.urihttp://hdl.handle.net/10754/631946
dc.description.abstractWe theoretically characterized the impact that the 7-deaza-8-azaguanine (DAG) and 7-deaza-8-azaisoguanine (DAiG) modifications have on the geometry and stability of the G:C Watson-Crick (cWW) base pair and of the G:iC and iG:C reverse Watson-Crick (tWW) base pairs. In addition, we investigated the effect on the same base pairs of seven C7-substituted DAG and DAiG, some of which have been previously experimentally characterized. Our calculations indicate that all these modifications have a negligible impact on the geometry of the above base pairs, and that the modification of the heterocycle skeleton has small impact on the base pair interaction energies. Instead, base pair interaction energies are dependent on the nature of the C7 substituent. For the 7-substituted DAG-C cWW systems we found a linear correlation between the base pair interaction energy and the Hammett constant of the 7-substituent, with higher interaction energies corresponding to more electron-withdrawing substituents. Therefore, the explored modifications are expected to be accommodated in both parallel and antiparallel nucleic acid duplexes without perturbing their geometry, while the strength of a base pair (and duplex) featuring a DAG modification can in principle be tuned by incorporating different substituents at the C7 position.
dc.description.sponsorshipLC thanks the King Abdullah University of Science and Technology (KAUST) for financial support. For computer time, this research used the resources of the Supercomputing Laboratory at KAUST.
dc.publisherWiley
dc.relation.urlhttps://onlinelibrary.wiley.com/doi/abs/10.1002/cbic.201900245
dc.rightsArchived with thanks to ChemBioChem
dc.subjectDensity functional theory
dc.subjectModified Nucleotides
dc.subjectH-bond Interaction
dc.subjectNucleic Acids Base Pairing
dc.titleStructural and Energetic Impact of Non-natural 7-Deaza-8-Azaguanine, 7-Deaza-8-Azaisoguanine and their 7-Substituted Derivatives on H-bonding Pairing with Cytosine and Isocytosine
dc.typeArticle
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Division
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.identifier.journalChemBioChem
dc.eprint.versionPost-print
dc.contributor.institutionMoscow Institute of Physics and Technology, Institutskiy Pereulok 9, Dolgoprudny, Moscow Region 141700, Russia, RUSSIAN FEDERATION.
dc.contributor.institutionNTT Hi-Tech Institute, Nguyen Tat Thanh University, 298-300A Nguyen Tat Thanh Street, Ho Chi Minh City, Viet Nam, VIET NAM.
dc.contributor.institutionDepartment of Sciences and Technologies, University Parthenope of Naples, Centro Direzionale Isola C4, I-80143, Naples, Italy,
kaust.personChawla, Mohit
kaust.personCavallo, Luigi


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