Self-assembly versatility of N-acyl amino acids

N -acyl amino acids (NAAAs) are prebiotically plausible amphiphiles that can emerge from simple fatty acids and amino acids under abiotic conditions. As hybrid molecules combining two fundamental classes of prebiotic building blocks, NAAAs may have contributed to the emergence of structurally and functionally diverse molecular assemblies during early chemical evolution. However, how amino acid side chains influence their self-assembly behavior remains poorly understood. Here, we systematically investigated the self-assembly of three structurally distinct N -octanoyl amino acids— N -octanoyl-glycine (OA-G-OH), N -octanoyl-L-threonine (OA-T-OH), and N -octanoyl-L-phenylalanine (OA-F-OH)—to evaluate how amino acid side chains affect aggregation propensity and supramolecular structure. Our results indicate that NAAAs differ remarkably in aggregation propensity and generate distinct higher-order structures, potentially conferring functional diversity relevant to prebiotic chemistry and applications in drug delivery, biomedicine, and materials science.