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

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

2-Substituted Phenylalanines

 

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