Fatty acids, as amphiphilic molecules, are widely recognized for their self-assembly behaviors, which are influenced by the hydrophilic and hydrophobic components of their structure. In biological systems, the conjugates of fatty acids with various biomolecules play important biological roles. In addition, synthetic conjugates of fatty acids with other molecules such as peptides can modulate their self-assembly properties, enabling the design of functional materials for diverse applications in drug delivery, biomedicine, and materials science. In this study, we explored the self-assembly behavior of a series of fatty acid-amino acid conjugates which were synthesized through N-acylation of glycine (Gly), threonine (Thr) and phenylalanine (Phe) respectively with Octanoic acid (OA). We at first determined the critical aggregation concentration (CAC) of the conjugates by using pyrene as the fluorescent probe. The CAC of the three conjugates varies which strongly depends on the amino acid residue. Transmission electron microscopy (TEM) further demonstrates that the conjugates self-assemble to both particle-like structures and fibrous structures. This study showcases the potential of fatty acid-amino acid conjugates as tunable amphiphiles and their potential applications in drug delivery, biomedicine, and material design.

中文翻译：

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脂肪酸-氨基酸偶联物的自组装多功能性


脂肪酸作为两亲性分子，因其自组装行为而被广泛认可，这些行为受其结构的亲水和疏水成分的影响。在生物系统中，脂肪酸与各种生物分子的偶联物起着重要的生物学作用。此外，脂肪酸与其他分子（如肽）的合成偶联物可以调节其自组装特性，从而能够为药物递送、生物医学和材料科学中的各种应用设计功能性材料。在本研究中，我们探讨了通过甘氨酸 （Gly）、苏氨酸 （Thr） 和苯丙氨酸 （Phe） 分别与辛酸 （OA） 的 N-酰化合成的一系列脂肪酸-氨基酸偶联物的自组装行为。我们首先使用芘作为荧光探针来确定偶联物的临界聚集浓度 （CAC）。三种偶联物的 CAC 不同，这在很大程度上取决于氨基酸残基。透射电子显微镜 （TEM） 进一步证明，偶联物自组装到颗粒状结构和纤维结构上。本研究展示了脂肪酸-氨基酸偶联物作为可调两亲物的潜力及其在药物递送、生物医学和材料设计中的潜在应用。