ArticleProceedings of the National Academy of Sciences of the United States of America2019
Selective incorporation of proteinaceous over nonproteinaceous cationic amino acids in model prebiotic oligomerization reactions.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 55 papers.
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55 citing papers in PubMed, 130 citations in OpenAlex.
- Functional abiotic metabolite assembly hypothesis for the early events in the origin of life.Nature communications · 2026Review
- From Meteorites to Membrane Rafts: Ganglioside-Incorporating Prebiotic Vesicles and the Emergence of Membrane Domain Organization.The Journal of membrane biology · 2026Article
- Hydroxy acid conjugation to lipids increases structural and hydrolytic stability.Nature communications · 2026Article
- Stringent selection on kinetics of condensation reactions: early steps in chemical evolution.Physical chemistry chemical physics : PCCP · 2026Article
- Molecular war and peace: the concurrent path to antibiosis and antibiotic resistance.Frontiers in microbiology · 2026Review
- Coenzyme-protein interactions since early life.eLife · 2025Article
- Protopeptide backbone affects assembly in aqueous solutions.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Evolution of complex chemical mixtures reveals combinatorial compression and population synchronicity.Nature chemistry · 2025Article
- Biological Polymers: Evolution, Function, and Significance.Accounts of chemical research · 2025Article
- Catalytic peptide/hemin complex from ester-amide exchange reaction mediated by deep eutectic solvents.RSC advances · 2025Article
- On the Origin of Life on Earth: The Nanozymes Hypothesis, and More.Research (Washington, D.C.) · 2025Review
- Similarity Analysis of Computer-Generated and Commercial Libraries for Targeted Biocompatible Coded Amino Acid Replacement.International journal of molecular sciences · 2024Article
- From Catalysis of Evolution to Evolution of Catalysis.Accounts of chemical research · 2024Article
- The astrochemical evolutionary traits of phospholipid membrane homochirality.Nature reviews. Chemistry · 2024Review
- Alternative Pathways in Astrobiology: Reviewing and Synthesizing Contingency and Non-Biomolecular Origins of Terrestrial and Extraterrestrial Life.Life (Basel, Switzerland) · 2024Review
- Phosphoric acid salts of amino acids as a source of oligopeptides on the early Earth.Communications chemistry · 2024Article
- Protocellular Heme and Iron-Sulfur Clusters.Accounts of chemical research · 2024Review
- Peptides En Route from Prebiotic to Biotic Catalysis.Accounts of chemical research · 2024Article
- A Concept of Complementarity Between Complexity and Redundancy can Account for Kant's Biological Teleology and Unify Mechanistic and Finalistic Biology.Journal of molecular evolution · 2024Article
- Qualitative Monitoring of Proto-Peptide Condensation by Differential FTIR Spectroscopy.ACS earth & space chemistry · 2024Article
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Authors and funding
9 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Numerous long-standing questions in origins-of-life research center on the history of biopolymers. For example, how and why did nature select the polypeptide backbone and proteinaceous side chains? Depsipeptides, containing both ester and amide linkages, have been proposed as ancestors of polypeptides. In this paper, we investigate cationic depsipeptides that form under mild dry-down reactions. We compare the oligomerization of various cationic amino acids, including the cationic proteinaceous amino acids (lysine, Lys; arginine, Arg; and histidine, His), along with nonproteinaceous analogs of Lys harboring fewer methylene groups in their side chains. These analogs, which have been discussed as potential prebiotic alternatives to Lys, are ornithine, 2,4-diaminobutyric acid, and 2,3-diaminopropionic acid (Orn, Dab, and Dpr). We observe that the proteinaceous amino acids condense more extensively than these nonproteinaceous amino acids. Orn and Dab readily cyclize into lactams, while Dab and Dpr condense less efficiently. Furthermore, the proteinaceous amino acids exhibit more selective oligomerization through their α-amines relative to their side-chain groups. This selectivity results in predominantly linear depsipeptides in which the amino acids are α-amine-linked, analogous to today's proteins. These results suggest a chemical basis for the selection of Lys, Arg, and His over other cationic amino acids for incorporation into proto-proteins on the early Earth. Given that electrostatics are key elements of protein-RNA and protein-DNA interactions in extant life, we hypothesize that cationic side chains incorporated into proto-peptides, as reported in this study, served in a variety of functions with ancestral nucleic acid polymers in the early stages of life.
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