Fmoc-Phe(4-I)-OH [82565-68-2] HEADING_TITLE


Other Names: Fmoc-Phe(p-I)-OH; Fmoc-para-iodophenylalanine

Catalog Number: UFF122 CAS Number: 82565-68-2
Formula: C24H20INO4 M.W.: 513.3













Fmoc-Phe(4-I)-OH is utilized to prepare peptides containing the versatile Phe(4-I) residue.  4-Iodophenylalanine has been used to prepare substrates for 125I incorporation to be used in radiolabeling studies (DR Harding, WS Hancock, JT Sparrow, Int. J. Pept. Protein Res., 1985, 26, 208-13).  Phe(4-I) residues have been used in x-ray chrystallographic structure determination (RK Spencer, H Li, JS Nowick, J. Am. Chem. Soc., 2014, Just Accepted) and as spectroscopic probes to study the orientation of peptide binding to receptor pockets (V De Filippis, et al., Protein Sci., 2007, 16, 1257-65).  4-Iodophenylalanine has also been utilized in the preparation of thiophenylalanine-containing peptides (CR Forbes, NJ Zondlo, Org. Lett., 2012, 14, 464-7).  Phe(4-I) residues can be converted to alkynyl-phenylalanines by the Sonogashira reaction (U. Hoffmans, N Metzler-Nolte, Bioconjugate Chem., 2006, 17, 204-13) or to a variety of biarylalanines through Suzuki coupling (S Chen, et al., Biochemistry, 2013, 52, 8580-9; C Mapelli, et al., J. Med. Chem., 2009, 52, 7788-99).

4-Substituted Phenylalanines

H-Bip-OH   Boc-Bip-OH   Fmoc-Bip-OH
H-D-Bip-OH   Boc-D-Bip-OH   Fmoc-D-Bip-OH
H-Bpa-OH   Boc-Bpa-OH   Fmoc-Bpa-OH
H-D-Bpa-OH   Boc-D-Bpa-OH   Fmoc-D-Bpa-OH
H-Phe(4-Br)-OH   Boc-Phe(4-Br)-OH   Fmoc-Phe(4-Br)-OH
H-D-Phe(4-Br)-OH   Boc-D-Phe(4-Br)-OH   Fmoc-D-Phe(4-Br)-OH
H-Phe(4-Cl)-OH   Boc-Phe(4-Cl)-OH   Fmoc-Phe(4-Cl)-OH
H-D-Phe(4-Cl)-OH   Boc-D-Phe(4-Cl)-OH   Fmoc-D-Phe(4-Cl)-OH
H-Phe(4-F)-OH   Boc-Phe(4-F)-OH   Fmoc-Phe(4-F)-OH
H-D-Phe(4-F)-OH HCl   Boc-D-Phe(4-F)-OH   Fmoc-D-Phe(4-F)-OH
H-Phe(4-I)-OH   Boc-Phe(4-I)-OH   Fmoc-Phe(4-I)-OH
H-D-Phe(4-I)-OH   Boc-D-Phe(4-I)-OH   Fmoc-D-Phe(4-I)-OH
H-Phe(4-CN)-OH   Boc-Phe(4-CN)-OH   Fmoc-Phe(4-CN)-OH
H-D-Phe(4-CN)-OH   Boc-D-Phe(4-CN)-OH   Fmoc-D-Phe(4-CN)-OH
H-Phe(4-Me)-OH   Boc-Phe(4-Me)-OH   Fmoc-Phe(4-Me)-OH
H-D-Phe(4-Me)-OH   Boc-D-Phe(4-Me)-OH   Fmoc--D-Phe(4-Me)-OH
H-Phe(4-CF3)-OH   Boc-Phe(4-CF3)-OH   Fmoc-Phe(4-CF3)-OH
H-D-Phe(4-CF3)-OH   Boc-D-Phe(4-CF3)-OH   Fmoc-D-Phe(4-CF3)-OH
H-Phe(4-NO2)-OH   Boc-Phe(4-NO2)-OH   Fmoc-Phe(4-NO2)-OH
H-D-Phe(4-NO2)-OH   Boc-D-Phe(4-NO2)-OH   Fmoc-D-Phe(4-NO2)-OH
H-Phe(4-NH2)-OH   Boc-Phe(4-NH2)-OH   Fmoc-Phe(4-NH2)-OH
H-D-Phe(4-NH2)-OH   Boc-D-Phe(4-NH2)-OH   Fmoc-D-Phe(4-NH2)-OH