ArticleOrigins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life2016
The Activation of Free Dipeptides Promoted by Strong Activating Agents in Water Does not Yield Diketopiperazines.
Article in Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Prebiotic Peptide Synthesis: How Did Longest Peptide Appear?Journal of molecular evolution · 2025Review
- Role of metal(ii) hexacyanocobaltate(iii) surface chemistry for prebiotic peptides synthesis.RSC advances · 2025Article
- The Effect of Goethites on the Polymerization of Glycine and Alanine Under Prebiotic Chemistry Conditions.Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life · 2021Article
- Harnessing chemical energy for the activation and joining of prebiotic building blocks.Nature chemistry · 2020Article
- Article
- Environmental control programs the emergence of distinct functional ensembles from unconstrained chemical reactions.Proceedings of the National Academy of Sciences of the United States of America · 2019Article
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Authors and funding
5 authors.
Funding
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Abstract
The activation of dipeptides was studied in the perspective of the abiotic formation of oligopeptides of significant length as a requirement for secondary structure formation. The formation of piperazin-2,5-diones (DKP), previously considered as a dead end when activating free dipeptides, was shown in this work to be efficiently suppressed when using strong activating agents (e.g., carbodiimides). This behaviour was explained by the fast formation of a 5(4H)-oxazolone intermediate at a rate that exceeds the time scale of the rotation of the peptide bond from the predominant trans-conformation into the cis-isomer required for DKP formation. No DKP was observed when using strong activating agents whereas phosphate mixed anhydrides or moderately activated esters were observed to predominantly yield DKP. The DKP side-reaction no longer constitutes a drawback for the C-terminus elongation of peptides. These results are considered as additional evidence that pathways involving strong activation are required to drive the emergence of living entities rather than close to equilibrium processes.
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Registered trials
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