ArticleScientific reports2014
Evolutionary importance of the intramolecular pathways of hydrolysis of phosphate ester mixed anhydrides with amino acids and peptides.
Article in Scientific reports, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Chirality Makes or Breaks Chemically Driven Self-Assembly.Angewandte Chemie (International ed. in English) · 2025Article
- Selective peptide bond formation via side chain reactivity and self-assembly of abiotic phosphates.Nature communications · 2025Article
- RNA-directed peptide synthesis across a nicked loop.Nucleic acids research · 2024Article
- From the RNA-Peptide World: Prebiotic Reaction Conditions Compatible with Lipid Membranes for the Formation of Lipophilic Random Peptides in the Presence of Short Oligonucleotides, and More.Life (Basel, Switzerland) · 2024Article
- "Sea Water" Supplemented with Calcium Phosphate and Magnesium Sulfate in a Long-Term Miller-Type Experiment Yields Sugars, Nucleic Acids Bases, Nucleosides, Lipids, Amino Acids, and Oligopeptides.Life (Basel, Switzerland) · 2023Article
- The Origin of Translation: Bridging the Nucleotides and Peptides.International journal of molecular sciences · 2022Review
- Emergent properties as by-products of prebiotic evolution of aminoacylation ribozymes.Nature communications · 2022Article
- Potentially Prebiotic Synthesis of Aminoacyl-RNA via a Bridging Phosphoramidate-Ester Intermediate.Journal of the American Chemical Society · 2022Article
- Nonenzymatic assembly of active chimeric ribozymes from aminoacylated RNA oligonucleotides.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- A Potential Role for Aminoacylation in Primordial RNA Copying Chemistry.Biochemistry · 2021Article
- pH-Dependent peptide bond formation by the selective coupling of α-amino acids in water.Chemical communications (Cambridge, England) · 2021Article
- Harnessing chemical energy for the activation and joining of prebiotic building blocks.Nature chemistry · 2020Article
- Mapping a Systematic Ribozyme Fitness Landscape Reveals a Frustrated Evolutionary Network for Self-Aminoacylating RNA.Journal of the American Chemical Society · 2019Article
- The Chemical Likelihood of Ribonucleotide-α-Amino acid Copolymers as Players for Early Stages of Evolution.Journal of molecular evolution · 2019Article
- How Prebiotic Chemistry and Early Life Chose Phosphate.Life (Basel, Switzerland) · 2019Review
- Tuning the reactivity of nitriles using Cu(ii) catalysis - potentially prebiotic activation of nucleotides.Chemical science · 2018Article
- Reciprocal Nucleopeptides as the Ancestral Darwinian Self-Replicator.Molecular biology and evolution · 2018Article
- Chemical roots of biological evolution: the origins of life as a process of development of autonomous functional systems.Open biology · 2017Review
- Mixed Anhydride Intermediates in the Reaction of 5(4H)-Oxazolones with Phosphate Esters and Nucleotides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Fatty acids' double role in the prebiotic formation of a hydrophobic dipeptide.Chemical science · 2016Article
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4 authors.
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Abstract
Aminoacyl adenylates (aa-AMPs) constitute essential intermediates of protein biosynthesis. Their polymerization in aqueous solution has often been claimed as a potential route to abiotic peptides in spite of a highly efficient CO2-promoted pathway of hydrolysis. Here we investigate the efficiency and relevance of this frequently overlooked pathway from model amino acid phosphate mixed anhydrides including aa-AMPs. Its predominance was demonstrated at CO2 concentrations matching that of physiological fluids or that of the present-day ocean, making a direct polymerization pathway unlikely. By contrast, the occurrence of the CO2-promoted pathway was observed to increase the efficiency of peptide bond formation owing to the high reactivity of the N-carboxyanhydride (NCA) intermediate. Even considering CO2 concentrations in early Earth liquid environments equivalent to present levels, mixed anhydrides would have polymerized predominantly through NCAs. The issue of a potential involvement of NCAs as biochemical metabolites could even be raised. The formation of peptide-phosphate mixed anhydrides from 5(4H)-oxazolones (transiently formed through prebiotically relevant peptide activation pathways) was also observed as well as the occurrence of the reverse cyclization process in the reactions of these mixed anhydrides. These processes constitute the core of a reaction network that could potentially have evolved towards the emergence of translation.
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