title: Synthesis of Perfluoro-tert-butyl Tyrosine, for Application in19F NMR, via a Diazonium-Coupling Reaction.
abstract: 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-NH2-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 by19F NMR. Perfluoro-tert-butyl ether has an estimated σpHammett substituent constant of +0.30.
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Caitlin M
authors.initials: CM
authors.lastname: Tressler
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Neal J
authors.identifier: 0000-0002-7417-8085
authors.initials: NJ
authors.lastname: Zondlo
mesh_terms: D003979:Diazonium Compounds / Q000737:chemistry*; D005461:Fluorine; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003979:Diazonium Compounds; D005461:Fluorine; D014443:Tyrosine