Elucidating N-acyl amino acids as a model protoamphiphilic system.

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 synth

SUBMITTER: Joshi MP 

PROVIDER: S-EPMC9814278 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature