Synthesis of p-amino-L-phenylalanine derivatives with protected p-amino group for preparation of p-azido-L-phenylalanine peptides.

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.