Halogen Bond-Tuning of Responsive Supramolecular Amino Acid Hydrogels.

ABSTRACT: N-Fmoc-pentafluoro-L-phenylalanine (F₅) forms stable supramolecular hydrogels, mainly through π-π stacking of its aromatic groups. Hydrogen bonding-driven co-assembly of F₅ with suitable partner molecules has been reported to affect the gel's properties, in accordance with what is observed in their corresponding co-crystal structures. Herein, we extended this hydrogel modulation strategy to halogen bonding (XB) interactions by introducing an XB-donating iodine atom in the para-position of the F₅ phenyl ring. Under conditions mimicking biological environments, both crystal packing and hydrogelation of the resulting N-Fmoc-4-iodo-tetrafluoro-phenylalanine (IF₄), were significantly affected by iodine-π interactions. Slower fibril formation kinetics

SUBMITTER: Veronese E 

PROVIDER: S-EPMC12462227 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature