Synthesis of Tetrafluorinated Aromatic Amino Acids with Distinct Signatures in ¹⁹F NMR

Abstract

Fluorinated amino acids serve as powerful tools in protein chemistry. We synthesized a series of <i>para</i>-substituted tetrafluorophenylalanines via the regioselective S_NAr chemistry of the commercially available pentafluorophenylalanine Boc-Z. These novel unnatural amino acids display distinct ¹⁹F NMR signatures, making them powerful tools for analyzing protein–membrane interactions with NMR spectroscopy