Synthesis of photoactive p-azidotetrafluorophenylalanine containing peptide by solid-phase Fmoc methodology.
[structure: see text] N-Fmoc-L-p-azidotetrafluorophenylalanine was prepared from achiral starting materials using an acetamidomalonate synthesis and enzymatic resolution. A photoactive peptide containing this fluorinated residue could be assembled using solid-phase Fmoc chemistry.
Redman
James E
JE
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA.
Ghadiri
M Reza
MR
D000595:Amino Acid Sequence; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D010777:Photochemistry
D001386:Azides; C470820:N-Fmoc-azidotetrafluorophenylalanine; D010455:Peptides; D010649:Phenylalanine