ArticleCommunications chemistry2022
Elucidating N-acyl amino acids as a model protoamphiphilic system.
Article in Communications chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 16 citations in OpenAlex.
- Biomimetic Construction of Abiotic Membranes Through Acylation of Cationic Diamino Acids.Chembiochem : a European journal of chemical biology · 2026Article
- Organocatalyzed bottom-up formation of protocells.Nature communications · 2026Article
- Entropy-Driven Amino Acid-Based Coacervates with Enzyme-Free Metabolism and Prebiotic Robustness.Journal of the American Chemical Society · 2025Article
- A Novel Eco-Friendly Process for the Synthesis and Purification of Ascorbyl-6-Oleates.Foods (Basel, Switzerland) · 2024Article
- The astrochemical evolutionary traits of phospholipid membrane homochirality.Nature reviews. Chemistry · 2024Review
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Protoamphiphiles are prebiotically-plausible moieties that would have constituted protocell membranes on early Earth. Although prebiotic soup would have contained a diverse set of amphiphiles capable of generating protocell membranes, earlier studies were mainly limited to fatty acid-based systems. Herein, we characterize N-acyl amino acids (NAAs) as a model protoamphiphilic system. To the best of our knowledge, we report a new abiotic route in this study for their synthesis under wet-dry cycles from amino acids and monoglycerides via an ester-amide exchange process. We also demonstrate how N-oleoyl glycine (NOG, a representative NAA) results in vesicle formation over a broad pH range when blended with a monoglyceride or a fatty acid. Notably, NOG also acts as a substrate for peptide synthesis under wet-dry cycles, generating different lipopeptides. Overall, our study establishes NAAs as a promising protoamphiphilic system, and highlights their significance in generating robust and functional protocell membranes on primitive Earth.
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Registered trials
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