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Deamination features of 5-hydroxymethylcytosine, a radical and enzymatic DNA oxidation product

dc.contributor.authorGrand A.
dc.contributor.authorJorge N.
dc.contributor.authorMorell C.
dc.contributor.authorCadet J.
dc.contributor.authorEriksson L.A.
dc.date.accessioned2020-09-02T22:19:26Z
dc.date.available2020-09-02T22:19:26Z
dc.date.issued2014
dc.identifier10.1007/s00894-014-2290-9
dc.identifier.citation20, 6, -
dc.identifier.issn16102940
dc.identifier.urihttps://hdl.handle.net/20.500.12728/4741
dc.descriptionThe 5-methylcytosine derivative 5-hydroxymethylcytosine (5hmCyt), which is generated via enzymatic oxidation, is sometimes referred to as the sixth nucleobase due to its widespread presence in the DNA of brain and embryonic stem cells. In this study, we used density functional based methods and reactivity indices from conceptual DFT to explore the mechanism and key features of the hydrolytic deamination of 5hmCyt. The data obtained are used to compare and contrast this deamination reaction with those of other cytosine derivatives. The deamination process for 5hmCyt is similar to the corresponding processes for other unsaturated derivatives in that the amino form is the reactive one and water addition is the rate-limiting step. However, several differences due to the rotameric asymmetry of the current system are also noted. © Springer-Verlag 2014.
dc.language.isoen
dc.publisherSpringer Verlag
dc.subject5-Hydroxymethylcytosine
dc.subjectDeamination
dc.subjectEnzymatic dna oxidation
dc.subjectMutation
dc.subjectRadical oxidation
dc.subject5 hydroxymethylcytosine
dc.subjectcytosine derivative
dc.subjectDNA
dc.subjectnucleic acid base
dc.subject5-hydroxymethylcytosine
dc.subjectcytosine
dc.subjectDNA
dc.subjectwater
dc.subjectarticle
dc.subjectdeamination
dc.subjectdensity functional theory
dc.subjecthydrolysis
dc.subjectoxidation
dc.subjectpriority journal
dc.subjectreaction analysis
dc.subjectanalogs and derivatives
dc.subjectchemical model
dc.subjectchemical structure
dc.subjectchemistry
dc.subjectcomputer simulation
dc.subjectdeamination
dc.subjectenergy transfer
dc.subjectmetabolism
dc.subjectoxidation reduction reaction
dc.subjectquantum theory
dc.subjectstructure activity relation
dc.subjectComputer Simulation
dc.subjectCytosine
dc.subjectDeamination
dc.subjectDNA
dc.subjectEnergy Transfer
dc.subjectHydrolysis
dc.subjectModels, Chemical
dc.subjectModels, Molecular
dc.subjectMolecular Structure
dc.subjectOxidation-Reduction
dc.subjectQuantum Theory
dc.subjectStructure-Activity Relationship
dc.subjectWater
dc.titleDeamination features of 5-hydroxymethylcytosine, a radical and enzymatic DNA oxidation product
dc.typeArticle


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