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A prebiotically plausible synthesis of pyrimidine β-ribonucleosides and their phosphate derivatives involving photoanomerization
Open accessAbstract
Previous research has identified ribose aminooxazoline as a potential intermediate in the prebiotic synthesis of the pyrimidine nucleotides with remarkable properties. It crystallizes spontaneously from reaction mixtures, with an enhanced enantiomeric excess if initially enantioenriched, which suggests that reservoirs of this compound might have accumulated on the early Earth in an optically pure form. Ribose aminooxazoline can be converted efficiently into α-ribocytidine by way of 2,2'-anhydroribocytidine, although anomerization to β-ribocytidine by ultraviolet irradiation is extremely inefficient. Our previous work demonstrated the synthesis of pyrimidine β-ribonucleotides, but at the cost of ignoring ribose aminooxazoline, using arabinose aminooxazoline instead. Here we describe a long-sought route through ribose aminooxazoline to the pyrimidine β-ribonucleosides and their phosphate derivatives that involves an extraordinarily efficient photoanomerization of α-2-thioribocytidine. In addition to the canonical nucleosides, our synthesis accesses β-2-thioribouridine, a modified nucleoside found in transfer RNA that enables both faster and more-accurate nucleic acid template-copying chemistry.
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“However, the search for a prebiotically plausible mechanism that can both induce and amplify a chiral bias in an RNA precursor from a fully racemic starting material has remained to be an open problem.”
From Origin of biological homochirality by crystallization of an RNA precursor on a magnetic surface (2023) · cites this paper as [25]
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“Follow-up studies highlighted ribo-aminooxazoline (RAO) as a key compound to resolve the origin of homochirality due to its centrality in the synthesis of nucleotides and crystallization properties (22, 25–27).”
From Origin of biological homochirality by crystallization of an RNA precursor on a magnetic surface (2023) · cites this paper as [25]
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“then, it was shown that RAO could be converted to pyrimidine nucleotides by a reaction sequence involving a photochemical inversion of the anomeric stereocenter (25).”
From Origin of biological homochirality by crystallization of an RNA precursor on a magnetic surface (2023) · cites this paper as [25]
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Metadata
- Authors
- Xu, J., Tsanakopoulou, M., Magnani, C. J., Szabla, R., Šponer, J. E., Šponer, J., Góra, R. W., & Sutherland, J. D.
- Affiliations
- MRC Laboratory of Molecular Biology (GB)
- Czech Academy of Sciences (CZ)
- Wrocław University of Science and Technology (PL)
- Corresponding author
- Szabla, Rafał
- Sutherland, John D.
- ORCID
- Venue
- Nature Chemistry
- Published
- 2016-11-21
- Volume
- 9
- Issue
- 4
- Pages
- 303-309
- ISSN
- 1755-4330 (ISSN-L)
- 1755-4349
- PMC
- PMC5576532
- OpenAlex
- W2554800362
- Cited by
- 133
- References
- 25
- Citations by year
- 2026: 6 · 2025: 13 · 2024: 8 · 2023: 13 · 2022: 11 · 2021: 16 · 2020: 16 · 2019: 16 · 2018: 18 · 2017: 16
- FWCI
- 7.96
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Licence
- www.springer.com/tdm (tdm)
- Locations
- Nature Chemistry (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- ASEP (submittedVersion, public-domain)
- Funders
- Grantová Agentura České Republiky (14?12010S, CEITEC 2020, LQ1601)
- Central European Institute of Technology (LQ1601)
- Medical Research Council (MC UP A024 1009)
- Wroclawskie Centrum Sieciowo-Superkomputerowe, Politechnika Wroclawska
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › RNA and protein synthesis mechanisms
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Keywords
- prebiotic synthesis, pyrimidine nucleosides, nucleotide phosphates, enantiomeric excess, UV irradiation, origin of life
- MeSH terms
- Molecular Conformation, Oxazoles, Phosphates, Pyrimidines, Ribonucleosides, Ribose, Evolution, Chemical, Photochemical Processes
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