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dc.contributor.authorChawla, Mohit
dc.contributor.authorCredendino, Raffaele
dc.contributor.authorChermak, Edrisse
dc.contributor.authorOliva, Romina
dc.contributor.authorCavallo, Luigi
dc.date.accessioned2016-02-21T14:16:57Z
dc.date.available2016-02-21T14:16:57Z
dc.date.issued2016-02-25
dc.identifier.citationTheoretical Characterization of the H-Bonding and Stacking Potential of Two Non-Standard Nucleobases Expanding the Genetic Alphabet 2016 The Journal of Physical Chemistry B
dc.identifier.issn1520-6106
dc.identifier.issn1520-5207
dc.identifier.pmid26882210
dc.identifier.doi10.1021/acs.jpcb.6b00125
dc.identifier.urihttp://hdl.handle.net/10754/596860
dc.description.abstractWe report a quantum chemical characterization of the non-natural (synthetic) H-bonded base pair formed by 6-amino-5-nitro-2(1H)-pyridone (Z) and 2-amino-imidazo [1,2-a]-1,3,5-triazin-4(8H)-one (P). The Z:P base pair, orthogonal to the classical G:C base pair, has been introduced in DNA molecules for expanding the genetic code. Our results indicate that the Z:P base pair closely mimics the G:C base pair both in terms of structure and stability. To clarify the role of the NO2 group on the C5 position of the Z base, we compared the stability of the Z:P base pair with that of base pairs having different functional group on the C5 position of Z. Our results indicate that the electron donating/withdrawing properties of the group in the C5 position has a clear impact on the stability of the Z:P base pair, with the strong electron withdrawing nitro group achieving the largest stabilizing effect on the H-bonding interaction, and the strong electron donating NH2 group destabilizing the Z:P pair by almost 4 kcal/mol. Finally, our gas phase and in water calculations confirm that the Z-nitro group reinforce the stacking interaction with its adjacent purine or pyrimidine ring.
dc.description.sponsorshipThe research reported in this publication was supported by funding from King Abdullah University of Science and Technology (KAUST).
dc.language.isoen
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/acs.jpcb.6b00125
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Physical Chemistry B, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/acs.jpcb.6b00125.
dc.titleTheoretical Characterization of the H-Bonding and Stacking Potential of Two Non-Standard Nucleobases Expanding the Genetic Alphabet
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Division
dc.identifier.journalThe Journal of Physical Chemistry B
dc.eprint.versionPost-print
dc.contributor.institutionDepartment of Sciences and Technologies, University Parthenope of Naples, Centro Direzionale Isola C4, I-80143, Naples, Italy
dc.contributor.affiliationKing Abdullah University of Science and Technology (KAUST)
kaust.personChawla, Mohit
kaust.personCredendino, Raffaele
kaust.personChermak, Edrisse
kaust.personCavallo, Luigi
refterms.dateFOA2017-02-16T00:00:00Z
dc.date.published-online2016-02-25
dc.date.published-print2016-03-10


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