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A practical synthesis of the novel highly fluorinated amino acid Fmoc-perfluoro-tert-butyl tyrosine was developed. The sequence proceeds in two steps from commercially available Fmoc-4-NH 2 -phenylalanine via diazotization followed by diazonium coupling reaction with perfluoro-tert-butanol. In peptides, perfluoro-tert-butyl tyrosine was detected in 30 s by NMR spectroscopy at 500 nM peptide concentration due to nine chemically equivalent fluorines that are a sharp singlet by 19 F NMR. Perfluoro-tert-butyl ether has an estimated σ p Hammett substituent constant of +0.30.

Synthesis of Perfluoro-tert-butyl Tyrosine, for Application in 19F NMR, via a Diazonium-Coupling Reaction

Synthesis of Perfluoro-tert-butyl Tyrosine, for Application in ¹⁹F NMR, via a Diazonium-Coupling Reaction