The DOI matches its Crossref record; 25 of the 25 references it cites were found in a registry or an index.
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.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
The cited source says what the claim attributes to it.
In the citing paper
“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]
The cited source says what the claim attributes to it.
In the citing paper
“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]
The cited source says what the claim attributes to it.
In the citing paper
“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]
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Principles of Nucleic Acid Structure
Neidle, S., & Sanderson, M. (2008) · Elsevier eBooks · doi:10.1016/b978-0-12-369507-9.x5001-8 · Cited by 4,519
Principles of Nucleic Acid Structure
Saenger, W. (1984) · Springer advanced texts in chemistry · doi:10.1007/978-1-4612-5190-3 · Cited by 4,271
Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions.
Powner, M. W., Gerland, B., & Sutherland, J. D. (2009) · Nature · doi:10.1038/nature08013 · Cited by 1,383
Self-citationThe case for an ancestral genetic system involving simple analogues of the nucleotides.
Joyce, G. F., Schwartz, A. W., Miller, S. L., & Orgel, L. E. (1987) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.84.13.4398 · Cited by 387
Grosjean, H., de Crécy‐Lagard, V., & Marck, C. (2009) · FEBS Letters · doi:10.1016/j.febslet.2009.11.052 · Cited by 308
Prebiotic Synthesis of Simple Sugars by Photoredox Systems Chemistry
Ritson, D., & Sutherland, J. D. (2012) · Nature Chemistry · doi:10.1038/nchem.1467 · Cited by 258
Self-citationStudies in prebiotic synthesis
Sanchez, R. A., & Orgel, L. E. (1970) · Journal of Molecular Biology · doi:10.1016/0022-2836(70)90320-7 · Cited by 250
Urea-Inorganic Phosphate Mixtures as Prebiotic Phosphorylating Agents
Lohrmann, R., & Orgel, L. E. (1971) · Science · doi:10.1126/science.171.3970.490 · Cited by 245
Martínez‐Fernández, L., Corral, I., Granucci, G., & Persico, M. (2013) · Chemical Science · doi:10.1039/c3sc52856a · Cited by 139
Intersystem Crossing Pathways in the Noncanonical Nucleobase 2-Thiouracil: A Time-Dependent Picture
Mai, S., Marquetand, P., & González, L. (2016) · The Journal of Physical Chemistry Letters · doi:10.1021/acs.jpclett.6b00616 · Cited by 139
Cited by
Sorted by citations
Protocells and RNA Self-Replication
Joyce, G. F., & Szostak, J. W. (2018) · Cold Spring Harbor Perspectives in Biology · doi:10.1101/cshperspect.a034801 · Cited by 308
Systems protobiology: origin of life in lipid catalytic networks
Lancet, D., Zidovetzki, R., & Markovitch, O. (2018) · Journal of The Royal Society Interface · doi:10.1098/rsif.2018.0159 · Cited by 182
Selective prebiotic formation of RNA pyrimidine and DNA purine nucleosides
Xu, J., Chmela, V., Green, N. J., Russell, D. A., Janicki, M. J., Góra, R. W., Szabla, R., Bond, A. D., & Sutherland, J. D. (2020) · Nature · doi:10.1038/s41586-020-2330-9 · Cited by 176
Self-citationEnhanced Nonenzymatic RNA Copying with 2-Aminoimidazole Activated Nucleotides
Li, L., Prywes, N., Tam, C. P., O’Flaherty, D. K., Lelyveld, V. S., Izgu, E. C., Pal, A., & Szostak, J. W. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.6b13148 · Cited by 176
The origin of RNA precursors on exoplanets
Rimmer, P. B., Xu, J., Thompson, S. J., Gillen, E., Sutherland, J. D., & Queloz, D. P. (2018) · Science Advances · doi:10.1126/sciadv.aar3302 · Cited by 180
Self-citation
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
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
