Fmoc-Phe(3-CN)-OH [205526-36-9] HEADING_TITLE

N-Fmoc-3-cyano-L-phenylalanine

Other Names: Fmoc-Phe(m-CN)-OH; Fmoc-meta-cyanophenylalanine

Catalog Number: UFF118 CAS Number: 205526-36-9
Formula: C25H20N2O4 M.W.: 412.4

Fmoc-Phe(3-CN)-OH

 

 

 

 

 

Fmoc-Phe(3-CN)-OH is used to introduce 3-cyanophenylalanine into synthetic peptides.  In addition to their use in SAR studies, Phe(3-CN) residues can be converted to 3-tetrazole phenylalanine (Z-R Qu, et al., Inorg. Chem., 2003, 42, 7710-2) or 3-amidinophenylalanine.  3-Amidinophenylalanine is an arginine analog in several enzyme inhibitors, including thromin (J Stürzebecher, J. Med. Chem., 1997, 40, 3091-9), urokinase (J Stürzebecher, et al., Bioorg. Med. Chem. Lett., 1999, 9, 3147-52) and matriptase (T. Steinmetzer, et al., J Med. Chem., 2006, 49, 4116-26; T Steinmetzer, et al., Bioorg. Med. Chem. Lett., 2009, 19, 67-73; A Steinmetzer, et al., Bioorg. Med. Chem. Lett., 2009, 19, 1960-5).

Cyanophenylalanines

Cat. Product Cat. Product Cat. Product
UHF138 H-Phe(2-CN)-OH UBF138 Boc-Phe(2-CN)-OH UFF138 Fmoc-Phe(2-CN)-OH
UHF238 H-D-Phe(2-CN)-OH UBF238 Boc-D-Phe(2-CN)-OH UFF238 Fmoc-D-Phe(2-CN)-OH
UHF118 H-Phe(3-CN)-OH UBF118 Boc-Phe(3-CN)-OH UFF118 Fmoc-Phe(3-CN)-OH
UHF218 H-D-Phe(3-CN)-OH UBF218 Boc-D-Phe(3-CN)-OH UFF218 Fmoc-D-Phe(3-CN)-OH
UHF119 H-Phe(4-CN)-OH UBF119 Boc-Phe(4-CN)-OH UFF119 Fmoc-Phe(4-CN)-OH
UHF219 H-D-Phe(4-CN)-OH UBF219 Boc-D-Phe(4-CN)-OH UFF219 Fmoc-D-Phe(4-CN)-OH

3-Substituted Phenylalanines

H-Phe(3-Br)-OH   Boc-Phe(3-Br)-OH   Fmoc-Phe(3-Br)-OH
H-D-Phe(3-Br)-OH   Boc-D-Phe(3-Br)-OH   Fmoc-D-Phe(3-Br)-OH
H-Phe(3-Cl)-OH   Boc-Phe(3-Cl)-OH   Fmoc-Phe(3-Cl)-OH
H-D-Phe(3-Cl)-OH   Boc-D-Phe(3-Cl)-OH   Fmoc-D-Phe(3-Cl)-OH
H-Phe(3-F)-OH   Boc-Phe(3-F)-OH   Fmoc-Phe(3-F)-OH
H-D-Phe(3-F)-OH    Boc-D-Phe(3-F)-OH   Fmoc-D-Phe(3-F)-OH
H-Phe(3-CN)-OH   Boc-Phe(3-CN)-OH   Fmoc-Phe(3-CN)-OH
H-D-Phe(3-CN)-OH   Boc-D-Phe(3-CN)-OH   Fmoc-D-Phe(3-CN)-OH
H-Phe(3-Me)-OH   Boc-Phe(3-Me)-OH   Fmoc-Phe(3-Me)-OH
H-D-Phe(3-Me)-OH   Boc-D-Phe(3-Me)-OH   Fmoc-D-Phe(3-Me)-OH
H-Phe(3-CF3)-OH   Boc-Phe(3-CF3)-OH   Fmoc-Phe(3-CF3)-OH
H-D-Phe(3-CF3)-OH   Boc-D-Phe(3-CF3)-OH   Fmoc-D-Phe(3-CF3)-OH

MSDS