Prebiotic Route to Thymine from Formamide-A Combined Experimental-Theoretical Study

0542518 - ÚFCH JH 2022 RIV CH eng J - Journal Article
Petera, Lukáš - Mráziková, Klaudia - Nejdl, L. - Zemánková, K. - Vaculovičová, M. - Pastorek, Adam - Civiš, Svatopluk - Kubelík, Petr - Heays, Alan - Cassone, Giuseppe - Šponer, Jiří - Ferus, Martin - Šponer, Judit E.
Prebiotic Route to Thymine from Formamide-A Combined Experimental-Theoretical Study.
Molecules. Roč. 26, č. 8 (2021), č. článku 2248. E-ISSN 1420-3049
R&D Projects: GA ČR GA19-03314S; GA MŠMT EF16_019/0000778
Institutional support: RVO:61388955 ; RVO:68081707
Keywords : formamide * thymine * uracil * prebiotic chemistry * origin of life
OECD category: Physical chemistry; Biochemistry and molecular biology (BFU-R)
Impact factor: 4.927, year: 2021
Method of publishing: Open access

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.
Permanent Link: http://hdl.handle.net/11104/0319915