USE OF OZONOLYSIS IN THE SYNTHESIS OF C-TERMINAL PEPTIDE ALDEHYDES ONSOLID SUPPORT

A new strategy for the synthesis of peptide aldehydes on solid support is presented. Reaction of a N-protected aminoaldehyde with carboethox ymethylene triphenylphosphorane yielded an alpha-beta-unsaturated delt a-amino derivative. After saponification, the resulting alpha-beta-uns aturated delta-aminoacid was anchored to a solid support by an ester l inkage (Merrifield resin) or by an amide linkage (MBHA, Expansin). Aft er elongation of the peptide chain, ozonolysis yielded quite pure C-te rminal peptide aldehydes in a good yield with no detectable racemizati on of the C-terminal residue. (C) 1997 Elsevier Science Ltd.