Prebiotic route to thymine from formamide - A combined experimental–theoretical study

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dc.contributor.authorPetera, Lukášcs
dc.contributor.authorMráziková, Klaudiacs
dc.contributor.authorNejdl, Lukášcs
dc.contributor.authorZemánková, Kristýnacs
dc.contributor.authorVaculovičová, Markétacs
dc.contributor.authorPastorek, Adamcs
dc.contributor.authorCiviš, Svatoplukcs
dc.contributor.authorKubelík, Petrcs
dc.contributor.authorHeays, Alancs
dc.contributor.authorCassone, Giuseppecs
dc.contributor.authorŠponer, Jiřícs
dc.contributor.authorFerus, Martincs
dc.contributor.authorŠponer, Juditcs
dc.coverage.issue8cs
dc.coverage.volume26cs
dc.date.accessioned2021-05-27T06:54:12Z
dc.date.available2021-05-27T06:54:12Z
dc.date.issued2021-04-30cs
dc.description.abstractSynthesis of RNA nucleobases from formamide is one of the recurring topics of prebiotic chemistry research. Earlier reports suggest that thymine, the substitute for uracil in DNA, may also be synthesized from formamide in the presence of catalysts enabling conversion of formamide to formaldehyde. In the current paper, we show that to a lesser extent conversion of uracil to thymine may occur even in the absence of catalysts. This is enabled by the presence of formic acid in the reaction mixture that forms as the hydrolysis product of formamide. Under the reaction conditions of our study, the disproportionation of formic acid may produce formaldehyde that hydroxymethylates uracil in the first step of the conversion process. The experiments are supplemented by quantum chemical modeling of the reaction pathway, supporting the plausibility of the mechanism suggested by Saladino and coworkers.en
dc.formattextcs
dc.format.extent1-9cs
dc.format.mimetypeapplication/pdfcs
dc.identifier.citationMOLECULES. 2021, vol. 26, issue 8, p. 1-9.en
dc.identifier.doi10.3390/molecules26082248cs
dc.identifier.issn1420-3049cs
dc.identifier.other171639cs
dc.identifier.urihttp://hdl.handle.net/11012/196780
dc.language.isoencs
dc.relation.ispartofMOLECULEScs
dc.relation.urihttps://doi.org/10.3390/molecules26082248cs
dc.rightsCreative Commons Attribution 4.0 Internationalcs
dc.rights.accessopenAccesscs
dc.rights.sherpahttp://www.sherpa.ac.uk/romeo/issn/1420-3049/cs
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/cs
dc.subjectformamideen
dc.subjectthymineen
dc.subjecturacilen
dc.subjectprebiotic chemistryen
dc.subjectorigin of lifeen
dc.titlePrebiotic route to thymine from formamide - A combined experimental–theoretical studyen
dc.type.driverarticleen
dc.type.statusPeer-revieweden
dc.type.versionpublishedVersionen
sync.item.dbidVAV-171639en
sync.item.dbtypeVAVen
sync.item.insts2021.11.20 00:53:04en
sync.item.modts2021.11.20 00:16:32en
thesis.grantorVysoké učení technické v Brně. Středoevropský technologický institut VUT. Chytré nanonástrojecs
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