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Photochemistry of 2-thiooxazole: a plausible prebiotic precursor to RNA nucleotides

Bertram, Lauren; Roberts, Samuel J; Powner, Matthew W; Szabla, Rafał; (2022) Photochemistry of 2-thiooxazole: a plausible prebiotic precursor to RNA nucleotides. Physical Chemistry Chemical Physics 10.1039/d2cp03167a. (In press). Green open access

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Abstract

Potentially prebiotic chemical reactions leading to RNA nucleotides involve periods of UV irradiation, which are necessary to promote selectivity and destroy biologially irrelevant side products. Nevertheless, UV light has only been applied to promote specific stages of prebiotic reactions and its effect on complete prebiotic reaction sequences has not been extensively studied. Here, we report on an experimental and computational investigation of the photostability of 2-thiooxazole (2-TO), a potential precursor of pyrimidine and 8-oxopurine nucleotides on early Earth. Our UV-irradiation experiments resulted in rapid decomposition of 2-TO into unidentified small molecule photoproducts. We further clarify the underlying photochemistry by means of accurate ab initio calculations and surface hopping molecular dynamics simulations. Overall, the computational results show efficient rupture of the aromatic ring upon the photoexcitation of 2-TO via breaking of the C-O bond. Consequently, the initial stage of the divergent prebiotic synthesis of pyrimidine and 8-oxopurine nucleotides would require periodic shielding from UV light either with sun screening chromophores or through a planetary scenario that would protect 2-TO until it is transformed into a more stable intermediate compound, e.g. oxazolidinone thione.

Type: Article
Title: Photochemistry of 2-thiooxazole: a plausible prebiotic precursor to RNA nucleotides
Location: England
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/d2cp03167a
Publisher version: https://doi.org/10.1039/D2CP03167A
Language: English
Additional information: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
UCL classification: UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL
URI: https://discovery.ucl.ac.uk/id/eprint/10155253
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