Positional Fluorination of Fmoc-Phenylalanine Modulates Hydrogel Structure and Antibacterial Activity.

ABSTRACT: The rise of antibiotic-resistant bacteria emphasizes the urgent need for alternative therapeutic strategies. Self-assembling nanostructures, such as fluorenylmethoxycarbonyl-pentafluoro-l-phenylalanine (Fmoc-F₅-Phe), have shown promising antibacterial activity by selectively targeting bacterial membranes. However, the influence of fluorine positioning on hydrogel's physical and biological properties remains poorly understood. Here, we evaluate three single-fluorinated Fmoc-phenylalanine derivatives, each featuring a fluorine substitution at a different aromatic position. We demonstrate that even subtle positional changes dramatically affect self-assembly kinetics, nanostructure morphology, mechanical properties, and antibacterial performance. While Fmoc-F₅-Phe hydroge

SUBMITTER: Doitch O 

PROVIDER: S-EPMC12421518 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature