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

0542518 - ÚFCH JH 2022 RIV CH eng J - Článek v odborném periodiku
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
Grant CEP: GA ČR GA19-03314S; GA MŠMT EF16_019/0000778
Institucionální podpora: RVO:61388955 ; RVO:68081707
Klíčová slova: formamide * thymine * uracil * prebiotic chemistry * origin of life
Obor OECD: Physical chemistry; Biochemistry and molecular biology (BFU-R)
Impakt faktor: 4.927, rok: 2021
Způsob publikování: 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.
Trvalý link: http://hdl.handle.net/11104/0319915