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Cited by 23Origins and Evolution of LifeChemical Reaction MechanismsOrganophosphorus compounds synthesis

Mixed Anhydride Intermediates in the Reaction of 5(4 H)‐Oxazolones with Phosphate Esters and Nucleotides

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Liu, Ziwei, Rigger, Lukas, Rossi, Jean‐Christophe, Sutherland, John D., Pascal, Robert·2016·Chemistry – A European Journal
DOI 10.1002/chem.201602697PMC PMC5074369
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Abstract

5(4 H)‐Oxazolones can be formed through the activation of acylated α‐amino acids or of peptide C termini. They constitute potentially activated intermediates in the abiotic chemistry of peptides that preceded the origin of life or early stages of biology and are capable of yielding mixed carboxylic‐phosphoric anhydrides upon reaction with phosphate esters and nucleotides. Here, we present the results of a study aimed at investigating the chemistry that can be built through this interaction. As a matter of fact, the formation of mixed anhydrides with mononucleotides and nucleic acid models is shown to take place at positions involving a mono‐substituted phosphate group at the 3’‐ or 5’‐terminus but not at the internal phosphodiester linkages. In addition to the formation of mixed anhydrides, the subsequent intramolecular acyl or phosphoryl transfers taking place at the 3’‐terminus are considered to be particularly relevant to the common prebiotic chemistry of α‐amino acids and nucleotides.

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  • Several important classes of biomolecules, such as plausible prebiotic amino acids precursors, 2',3'-cyclic pyrimidine nucleotides, and glycerol phosphate, may have hydrogen cyanide and formaldehyde as common chemical precursors in the cyanosulfidic pathway.

    “They have shown that several important classes of biomolecules, such as plausible prebiotic amino acids precursors (Piotto et al., 2019), 2',3'-cyclic pyrimidine nucleotides, and glycerol phosphate, may have hydrogen cyanide ( 1 ) and formaldehyde as common chemical precursors in the aforementioned 'cyanosulfidic' pathway.”

    From The Origin and Early Evolution of Life: Homochirality Emergence in Prebiotic Environments (2023) · cites this paper as Liu et al., 2016

    The Introduction (page unavailable) says that essential biochemical building blocks can arise through similar processes, but it does not identify shared chemical precursors. Searches for hydrogen cyanide, formaldehyde, the cyanosulfidic pathway, glycerol phosphate, and cyclic pyrimidine nucleotides found no passage addressing the claimed route. (LLM, conf=0.73)

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Authors
Liu, Z., Rigger, L., Rossi, J., Sutherland, J. D., & Pascal, R.
Affiliations
  • École Nationale Supérieure de Chimie de Montpellier (FR)
  • MRC Laboratory of Molecular Biology (GB)
Corresponding author
Pascal, Robert
ORCID
Venue
Chemistry – A European Journal
Publisher
Wiley
Published
2016-08-18
Volume
22
Issue
42
Pages
14940-14949
ISSN
  • 0947-6539 (ISSN-L)
  • 1521-3765
DOI
10.1002/chem.201602697
PMC
PMC5074369
OpenAlex
W2512994687
Cited by
23
References
60
Citations by year
2026: 1 · 2024: 1 · 2023: 2 · 2022: 1 · 2021: 3 · 2020: 5 · 2019: 4 · 2018: 4 · 2017: 1 · 2016: 1
FWCI
1.59
Type
journal article
Language
en
Open access
Licence
Locations
  • Chemistry - A European Journal (publishedVersion, cc-by-nc)
  • Europe PMC (PubMed Central) (publishedVersion, cc-by-nc)
  • PubMed Central (publishedVersion, cc-by-nc)
  • PubMed (publishedVersion)
  • HAL (submittedVersion, cc-by-nc)
Funders
  • Simons Foundation (293065)
  • Agence Nationale de la Recherche (ANR-14-CE33-0020-01)
Topics
  • Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
  • Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
  • Physical Sciences › Chemistry › Organic Chemistry › Organophosphorus compounds synthesis
Keywords
5(4H)-oxazolones, mixed anhydrides, phosphate esters, nucleotides, mononucleotides, nucleic acid models, prebiotic chemistry, origin of life, acyl transfer, phosphoryl transfer, α-amino acids
MeSH terms
Anhydrides, Esters, Nucleic Acids, Nucleotides, Oxazolone, Peptides, Phosphates

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