ArticleChemistry (Weinheim an der Bergstrasse, Germany)2016
Mixed Anhydride Intermediates in the Reaction of 5(4H)-Oxazolones with Phosphate Esters and Nucleotides.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed, 21 citations in OpenAlex.
- Prebiotic chiral transfer from self-aminoacylating ribozymes may favor either handedness.Nature communications · 2024Article
- Discovering pathways through ribozyme fitness landscapes using information theoretic quantification of epistasis.RNA (New York, N.Y.) · 2023Article
- Emergent properties as by-products of prebiotic evolution of aminoacylation ribozymes.Nature communications · 2022Article
- Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives.Molecules (Basel, Switzerland) · 2021Article
- Harnessing chemical energy for the activation and joining of prebiotic building blocks.Nature chemistry · 2020Article
- Templates direct the sequence-specific anchoring of theChemical science · 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
- Formation of Non-Natural α,α-Disubstituted Amino Esters via Catalytic Michael Addition.Organic letters · 2018Article
- Tuning the reactivity of nitriles using Cu(ii) catalysis - potentially prebiotic activation of nucleotides.Chemical science · 2018Article
- Mixed Anhydride Intermediates in the Reaction of 5(4H)-Oxazolones with Phosphate Esters and Nucleotides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
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Authors and funding
5 authors at 3 institutions in 2 countries.
Funding
Abstract
5(4H)-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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