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Cited by 176Origins and Evolution of LifeRNA and protein synthesis mechanismsDNA and Nucleic Acid Chemistry

Selective prebiotic formation of RNA pyrimidine and DNA purine nucleosides

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Xu, Jianfeng, Chmela, Václav, Green, Nicholas J., Russell, David A., Janicki, Mikołaj J., Góra, Robert W., Szabla, Rafał, Bond, Andrew D. +1 more·2020·Nature
DOI 10.1038/s41586-020-2330-9PMC PMC7116818
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Abstract

The nature of the first genetic polymer is the subject of major debate 1. Although the 'RNA world' theory suggests that RNA was the first replicable information carrier of the prebiotic era-that is, prior to the dawn of life 2,3-other evidence implies that life may have started with a heterogeneous nucleic acid genetic system that included both RNA and DNA 4. Such a theory streamlines the eventual 'genetic takeover' of homogeneous DNA from RNA as the principal information-storage molecule, but requires a selective abiotic synthesis of both RNA and DNA building blocks in the same local primordial geochemical scenario. Here we demonstrate a high-yielding, completely stereo-, regio- and furanosyl-selective prebiotic synthesis of the purine deoxyribonucleosides: deoxyadenosine and deoxyinosine. Our synthesis uses key intermediates in the prebiotic synthesis of the canonical pyrimidine ribonucleosides (cytidine and uridine), and we show that, once generated, the pyrimidines persist throughout the synthesis of the purine deoxyribonucleosides, leading to a mixture of deoxyadenosine, deoxyinosine, cytidine and uridine. These results support the notion that purine deoxyribonucleosides and pyrimidine ribonucleosides may have coexisted before the emergence of life 5.

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Crossref · 10.1038/s41586-020-2330-9

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  • 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 an open problem.

    “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 [26]

    The Results and Discussion (Prebiotic Route to Purine Deoxyribonucleosides; page unavailable) says ribo-aminooxazoline can crystallize enantiopure from minimally enantioenriched starting materials, supporting amplification of an existing bias. It does not establish that inducing a bias from fully racemic material remains an open problem; the route described starts with some enantioenrichment. (LLM, conf=0.78)

    Experimental — accuracy not yet measured

  • RAO is a key compound to resolve the origin of homochirality due to its centrality in the synthesis of nucleotides and crystallization properties.

    “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 [26]

    In Results and Discussion, under “Prebiotic Route to Purine Deoxyribonucleosides” (page not available), the paper identifies RAO as a precursor in its nucleoside-synthesis routes and says it crystallizes enantiopure from minimally enantioenriched solutions. It describes the production of enantiopure nucleosides as a potential outcome, however; it does not show that RAO resolves the origin of homochirality or demonstrate nucleotide synthesis from RAO. (LLM, conf=0.82)

    Experimental — accuracy not yet measured

  • Glyceraldehyde is the starting product in a sequence of reactions that produce both purine and pyrimidine (deoxy)ribonucleosides through intermediates 15-18.

    “Glyceraldehyde is also the starting product in a sequence of reactions that produce through intermediates 15–18 both purine and pyrimidine (deoxy)ribonucleosides”

    From The protometabolic nature of prebiotic chemistry (2023) · cites this paper as [103]

    The Results and Discussion section describes a route from ribo-aminooxazoline (RAO) 10 to pyrimidine nucleosides and, via compounds 15, 16 and 18, to a purine deoxynucleoside. It does not identify glyceraldehyde as the starting material, and compound 17 proved unreactive rather than serving as an intermediate in that route. Page numbers are unavailable in our copy. (LLM, conf=0.85)

    Experimental — accuracy not yet measured

  • The Powner-Sutherland pathway was further elaborated to include the synthesis of purine deoxyribonucleosides.

    “In a recent publication, this pathway was further elaborated to include the synthesis of purine deoxyribonucleosides [110].”

    From Prebiotic Reaction Networks in Water (2020) · cites this paper as [110]

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1 of the 50 references couldn’t be matched to a known paper.

Research works printed but not linked: 2

  1. [27]Vorbrüggen H Ruh-Pohlenz C Handbook of nucleoside synthesis Wiley 2001
  2. [29]Sanchez RA Ferris JP Orgel LE Studies in prebiotic synthesis II: Synthesis of purine precursors and amino acids from aqueous hydrogen cyanide J Mol Biol 1967 80 223 253 4297187

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Authors
Xu, J., Chmela, V., Green, N. J., Russell, D. A., Janicki, M. J., Góra, R. W., Szabla, R., Bond, A. D., & Sutherland, J. D.
Affiliations
  • MRC Laboratory of Molecular Biology (GB)
  • Wrocław University of Science and Technology (PL)
  • Institute of Physics (PL)
  • University of Cambridge (GB)
Corresponding author
Sutherland, John D.
ORCID
Venue
Nature
Publisher
Springer Science and Business Media LLC
Published
2020-06-03
Volume
582
Issue
7810
Pages
60-66
ISSN
  • 0028-0836 (ISSN-L)
  • 1476-4687
DOI
10.1038/s41586-020-2330-9
PMC
PMC7116818
OpenAlex
W3029443600
Cited by
176
References
50
Citations by year
2026: 15 · 2025: 26 · 2024: 33 · 2023: 23 · 2022: 26 · 2021: 35 · 2020: 18
FWCI
11.37
Type
journal article
Language
en
Open access
Licence
Locations
  • Nature (publishedVersion)
  • PubMed (publishedVersion)
  • PubMed Central (acceptedVersion)
  • RePEc: Research Papers in Economics (submittedVersion)
  • Edinburgh Research Explorer (University of Edinburgh) (submittedVersion, other-oa)
Funders
  • 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, RNA world, origin of life, deoxyadenosine, deoxyinosine, cytidine, uridine, stereo- and regioselectivity
MeSH terms
Origin of Life, Adenosine, Cytidine, DNA, Oxidation-Reduction, Purine Nucleosides, Pyrimidine Nucleosides, RNA, Uridine, Evolution, Chemical

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