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Prebiotic Route to Thymine from Formamide-A Combined Experimental-Theoretical Study
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SYSNO ASEP 0542518 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Prebiotic Route to Thymine from Formamide-A Combined Experimental-Theoretical Study Author(s) Petera, Lukáš (UFCH-W) ORCID
Mráziková, Klaudia (BFU-R) ORCID
Nejdl, L. (CZ)
Zemánková, K. (CZ)
Vaculovičová, M. (CZ)
Pastorek, Adam (UFCH-W) ORCID
Civiš, Svatopluk (UFCH-W) RID, ORCID, SAI
Kubelík, Petr (UFCH-W) RID, ORCID
Heays, Alan (UFCH-W) ORCID, RID, SAI
Cassone, Giuseppe (BFU-R) ORCID
Šponer, Jiří (BFU-R) RID, ORCID
Ferus, Martin (UFCH-W) ORCID, RID
Šponer, Judit E. (BFU-R) RID, ORCIDArticle number 2248 Source Title Molecules. - : MDPI
Roč. 26, č. 8 (2021)Number of pages 9 s. Language eng - English Country CH - Switzerland Keywords formamide ; thymine ; uracil ; prebiotic chemistry ; origin of life Subject RIV CF - Physical ; Theoretical Chemistry OECD category Physical chemistry Subject RIV - cooperation Institute of Biophysics - Biochemistry R&D Projects GA19-03314S GA ČR - Czech Science Foundation (CSF) EF16_019/0000778 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UFCH-W - RVO:61388955 ; BFU-R - RVO:68081707 UT WOS 000644587500001 EID SCOPUS 85105179448 DOI 10.3390/molecules26082248 Annotation Synthesis 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. Workplace J. Heyrovsky Institute of Physical Chemistry Contact Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Year of Publishing 2022 Electronic address http://hdl.handle.net/11104/0319915
Number of the records: 1