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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F21%3A00542518" target="_blank" >RIV/61388955:_____/21:00542518 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/68081707:_____/21:00542518 RIV/62156489:43210/21:43919803 RIV/00216305:26620/21:PU140900

Výsledek na webu

<a href="http://hdl.handle.net/11104/0319915" target="_blank" >http://hdl.handle.net/11104/0319915</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules26082248" target="_blank" >10.3390/molecules26082248</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Molecules

ISSN

1420-3049

e-ISSN

1420-3049

Svazek periodika

26

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

9

Strana od-do

2248

Kód UT WoS článku

000644587500001

EID výsledku v databázi Scopus

2-s2.0-85105179448