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Cited by 113Origins and Evolution of LifeRNA and protein synthesis mechanismsDNA and Nucleic Acid Chemistry

Divergent prebiotic synthesis of pyrimidine and 8-oxo-purine ribonucleotides

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Stairs, Shaun, Nikmal, Arif, Bučar, Dejan-Krešimir, Zheng, Shao-Liang, Szostak, Jack W., Powner, Matthew W.·2017·Nature Communications
DOI 10.1038/ncomms15270PMC PMC5454461
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Abstract

Understanding prebiotic nucleotide synthesis is a long standing challenge thought to be essential to elucidating the origins of life on Earth. Recently, remarkable progress has been made, but to date all proposed syntheses account separately for the pyrimidine and purine ribonucleotides; no divergent synthesis from common precursors has been proposed. Moreover, the prebiotic syntheses of pyrimidine and purine nucleotides that have been demonstrated operate under mutually incompatible conditions. Here, we tackle this mutual incompatibility by recognizing that the 8-oxo-purines share an underlying generational parity with the pyrimidine nucleotides. We present a divergent synthesis of pyrimidine and 8-oxo-purine nucleotides starting from a common prebiotic precursor that yields the β-ribo-stereochemistry found in the sugar phosphate backbone of biological nucleic acids. The generational relationship between pyrimidine and 8-oxo-purine nucleotides suggests that 8-oxo-purine ribonucleotides may have played a key role in primordial nucleic acids prior to the emergence of the canonical nucleotides of biology.

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  • Two alternative approaches that have been explored recently involve either ribosylation of formamidopyrimidine, which is selective for the N9 position, but gives a mixture of α/β-furanosides and pyranosides, and a route from 2-thiooxazole to the pentose amino-oxazolidinone thiones and ultimately to the corresponding 8-oxopurine nucleotides.

    “Two alternative approaches that have been explored recently involve either ribosylation of formamidopyrimidine, which is selective for the N9 position, but gives a mixture of α/β-furanosides and pyranosides (Becker et al. 2016), and a route from 2-thiooxazole to the pentose amino-oxazolidinone thiones and ultimately to the corresponding 8-oxopurine nucleotides (Stairs et al. 2017).”

    From Protocells and RNA Self-Replication (2018) · cites this paper as Stairs et al. 2017

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Cited by

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Authors
Stairs, S., Nikmal, A., Bučar, D.-K., Zheng, S.-L., Szostak, J. W., & Powner, M. W.
Affiliations
  • University College London (GB)
  • Harvard University (US)
  • Howard Hughes Medical Institute (US)
Corresponding author
Powner, Matthew W.
ORCID
Venue
Nature Communications
Publisher
Springer Science and Business Media LLC
Published
2017-05-19
Volume
8
Issue
1
Pages
15270-15270
ISSN
2041-1723 (ISSN-L)
DOI
10.1038/ncomms15270
PMC
PMC5454461
OpenAlex
W2616496046
Cited by
113
References
9
Citations by year
2026: 10 · 2025: 5 · 2024: 12 · 2023: 11 · 2022: 10 · 2021: 16 · 2020: 12 · 2019: 16 · 2018: 16 · 2017: 5
FWCI
7.33
Type
journal article
Language
en
Open access
Licence
Locations
  • Nature Communications (publishedVersion, cc-by)
  • Europe PMC (PubMed Central) (publishedVersion, cc-by)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • Digital Access to Scholarship at Harvard (DASH) (Harvard University) (submittedVersion, cc-by)
  • RePEc: Research Papers in Economics (submittedVersion)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
  • UCL Discovery (University College London) (submittedVersion)
Funders
  • Howard Hughes Medical Institute
  • Simons Foundation (290363, 318881)
  • Engineering and Physical Sciences Research Council (EP/K004980/1)
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
purine ribonucleotides, divergent synthesis, origin of life
MeSH terms
Sugars, Furans, Oxazoles, Pentoses, Phosphorylation, Purine Nucleotides, Purines, Pyrimidines, Ribonucleotides, Stereoisomerism, Thiones, Prebiotics

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