Fmoc-Phe(2-Br)-OH [220497-47-2] HEADING_TITLE

Fmoc-2-bromo-L-phenylalanine

Other Names: Fmoc-Phe(ortho-Br)-OH; Fmoc-Phe(o-Br)-OH; Fmoc-ortho-bromo-L-phenylalanine

Catalog #: UFF131 CAS #: 220497-47-2
Formula: C24H20BrNO4 M.W.: 466.3

Fmoc-Phe(2-Br)-OH

 

 

 

 

 

 

 

Fmoc-Phe(2-Br)-OH is suitable for solid phase peptide synthesis.  Phe(2-Br) residues are found in sperm activating peptides from the egg jelly of the sea urchin Tripneustes gratilla (K Yoshino, et al., Biochemistry, 1991, 30, 6203-9). The bromine atom of 2-bromophenylalanine can be substituted by nucleophiles in metal catalyzed reactions.  The ketodipiperazine composed of Phe(2-Br) and Val undergoes intramolecular N-arylation when treated with CuI and CsOAc in DMSO (HJ Lim, JC Gallucci, TV RajanBabu, Org. Lett., 2010, 12, 2162-5).  Suitably protected 2-bromophenylalanine derivates can undergo Suzuki cross coupling with aryl boronic acid derivates to produce 2-arylphenylalanines (W Wang, et al., Tetrahedron, 2002, 58, 3101-10, W Wang, et. al., Tetrahedron, 2002, 58, 7365-74).

Brominated Phenylalanines

Cat. # Product Cat. # Product Cat. # Product
UHF131 H-Phe(2-Br)-OH UBF131 Boc-Phe(2-Br)-OH UFF131 Fmoc-Phe(2-Br)-OH
UHF231 H-D-Phe(2-Br)-OH UBF231 Boc-D-Phe(2-Br)-OH UFF231 Fmoc-D-Phe(2-Br)-OH
UHF166 H-Phe(3-Br)-OH UBF166 Boc-Phe(3-Br)-OH UFF166 Fmoc-Phe(3-Br)-OH
UHF266 H-D-Phe(3-Br)-OH UBF266 Boc-D-Phe(3-Br)-OH UFF266 Fmoc-D-Phe(3-Br)-OH
UHF111 H-Phe(4-Br)-OH UBF111 Boc-Phe(4-Br)-OH UFF111 Fmoc-Phe(4-Br)-OH
UHF211 H-D-Phe(4-Br)-OH UBF211 Boc-D-Phe(4-Br)-OH UFF211 Fmoc-D-Phe(4-Br)-OH

2-Substituted Phenylalanines

H-Phe(2-Br)-OH
H-Phe(2-Cl)-OH
H-Phe(2-F)-OH
Boc-Phe(2-Br)-OH
 Boc-Phe(2-Cl)-OH
Boc-Phe(2-F)-OH
Fmoc-Phe(2-Br)-OH
Fmoc-Phe(2-Cl)-OH
Fmoc-Phe(2-F)-OH
H-D-Phe(2-Br)-OH
H-D-Phe(2-Cl)-OH
H-D-Phe(2-f)-OH HCl
Boc-D-Phe(2-Br)-OH
Boc-D-Phe(2-Cl)-OH
Boc-D-Phe(2-F)-OH
Fmoc-D-Phe(2-Br)-OH
Fmoc-D-Phe(2-Cl)-OH
Fmoc-D-Phe(2-F)-OH
H-Phe(2-CN)-OH
H-Phe(2-Me)-OH
H-Phe(2-CF3)-OH
Boc-Phe(2-CN)-OH
Boc-Phe(2-Me)-OH
Boc-Phe(2-CF3)-OH
Fmoc-Phe(2-CN)-OH
Fmoc-Phe(2-Me)-OH
Fmoc-Phe(2-CF3)-OH
H-D-Phe(2-CN)-OH
H-D-Phe(2-Me)-OH
H-D-Phe(2-CF3)-OH
Boc-D-Phe(2-CN)-OH
Boc-D-Phe(2-Me)-OH
Boc-D-Phe(2-CF3)-OH
Fmoc-D-Phe(2-CN)-OH
Fmoc-D-Phe(2-Me)-OH
Fmoc-D-Phe(2-CF3)-OH

 

MSDS