title: Synthesis of p-amino-L-phenylalanine derivatives with protected p-amino group for preparation of p-azido-L-phenylalanine peptides.
abstract: For the synthesis of p-azidophenylalanine peptides, the p-amino group of p-amino-L-phenylalanine is protected with the Z- or Boc residue via the copper complex or by specific acylation at pH 4.6. The alpha-amino or alpha-carboxy group is blocked by a protecting group (Boc, Ddz, OMe respectively Z, Nps, Ddz), which can be removed selectively. The synthesis of nine derivatives of p-amino-L-phenylalanine for incorporation into the peptide chain is described. The p-amino-phenylalanine is converted to p-azidophenylalanine without affecting disulfide bridges.
mesh_terms: D000595:Amino Acid Sequence; D001386:Azides; D006863:Hydrogen-Ion Concentration; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D001386:Azides; C009722:4-aminophenylalanine; C027162:4-azidophenylalanine; D010649:Phenylalanine