A facile synthesis of peptide para -nitroanilides was developed using
a novel urethane linked para -aminoanilide resin 3 and solid phase pep
tide synthesis. Conversion of the resulting peptide para -aminoanilide
s to the corresponding peptide para -nitroanilides was achieved by oxi
dation with sodium perborate. With the exception of sequences containi
ng methionine, tryptophan and cysteine, all amino acid residues can be
used. A representative synthesis of the tetrapeptide para -nitroanili
de succinyl-Ala-Ala-Pro-Arg-PNA is described.