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.

原始两亲分子是生命起源前合理的部分，可能构成早期地球上的原始细胞膜。尽管益生元汤含有多种能够产生原始细胞膜的两亲物，但早期的研究主要限于基于脂肪酸的系统。在此，我们将 N-酰基氨基酸 (NAA) 描述为模型原两亲系统。据我们所知，我们在这项研究中报告了一种新的非生物途径，通过酯酰胺交换过程在干湿循环下从氨基酸和单甘油酯合成它们。我们还展示了 N-油酰甘氨酸（NOG，一种代表性的 NAA）与单酸甘油酯或脂肪酸混合时如何在较宽的 pH 范围内导致囊泡形成。值得注意的是，NOG 还可作为干湿循环下肽合成的底物，产生不同的脂肽。总体而言，我们的研究将 NAA 确立为一种有前途的原两亲系统，并强调了它们在原始地球上生成坚固且功能性的原始细胞膜方面的重要性。