A high-level G4(MP2) thermochemical study of the relative energies of the N-chlorinated isomers formed upon chlorination of cytosine

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dc.contributor.authorStambekova, Dana
dc.contributor.authorO'Reilly, Robert J.
dc.creatorDana, Stambekova
dc.date.accessioned2017-12-15T03:08:09Z
dc.date.available2017-12-15T03:08:09Z
dc.date.issued2017-08-01
dc.description.abstractAbstract Although the relative energies of the various tautomers of cytosine and 5-chlorocytosine have been studied in detail, little is known about the relative energies of the N-chlorinated isomers of cytosine. N-chlorination of cytosine is known to occur when cytosine is exposed to hypochlorous acid, a potent oxidant that is formed during the inflammatory process, and is presumed to have consequences concerning, for example, the structural integrity of DNA and RNA. In this study, the high-level G4(MP2) thermochemical protocol has been employed in studying the relative gas-phase free energies of thirty isomers that may be formed upon N-chlorination of cytosine. Using free energy of solvation corrections obtained by way of continuum models (CPCM and SMD), an approximation of the effect of aqueous solvation on the relative energies of the isomers has also been taken into account. In both the gas- and aqueous-phases, the lowest energy isomer is an exocyclic N-chloroimino derivative.en_US
dc.identifierDOI:10.1016/j.cdc.2017.07.002
dc.identifier.citationDana Stambekova, Robert J. O'Reilly, A high-level G4(MP2) thermochemical study of the relative energies of the N-chlorinated isomers formed upon chlorination of cytosine, In Chemical Data Collections, Volumes 9–10, 2017, Pages 220-228en_US
dc.identifier.issn24058300
dc.identifier.urihttps://www.sciencedirect.com/science/article/pii/S2405830017300599
dc.identifier.urihttp://nur.nu.edu.kz/handle/123456789/2908
dc.language.isoenen_US
dc.publisherChemical Data Collectionsen_US
dc.relation.ispartofChemical Data Collections
dc.rights.license© 2017 Elsevier B.V. All rights reserved.
dc.subjectN-chlorocytosineen_US
dc.subjectMyeloperoxidaseen_US
dc.subjectG4(MP2)en_US
dc.subjectDNAen_US
dc.subjectNucleobasesen_US
dc.titleA high-level G4(MP2) thermochemical study of the relative energies of the N-chlorinated isomers formed upon chlorination of cytosineen_US
dc.typeArticleen_US
elsevier.aggregationtypeJournal
elsevier.coverdate2017-08-01
elsevier.coverdisplaydateAugust 2017
elsevier.endingpage228
elsevier.identifier.doi10.1016/j.cdc.2017.07.002
elsevier.identifier.eid1-s2.0-S2405830017300599
elsevier.identifier.piiS2405-8300(17)30059-9
elsevier.identifier.scopusid85021940809
elsevier.openaccess0
elsevier.openaccessarticlefalse
elsevier.openarchivearticlefalse
elsevier.startingpage220
elsevier.teaserAlthough the relative energies of the various tautomers of cytosine and 5-chlorocytosine have been studied in detail, little is known about the relative energies of the N-chlorinated isomers of cytosine....
elsevier.volume9–10
workflow.import.sourcescience

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