Use of ozonolysis in the synthesis of C-terminal peptide aldehydes on solid support

Article abstract of DOI:10.1016/S0040-4039(97)10086-7

A new strategy for the synthesis of peptide aldehydes on solid support is presented. Reaction of a N-protected aminoaldehyde with caboethoxymethylene triphenylphosphorane yielded an α-β-unsaturated δ- amino derivative. After saponification, the resulting α-β-unsaturated δ- aminoacid was anchored to a solid support by an ester linkage (Merrifield resin) or by an amide linkage (MBHA, Expansin). After elongation of the peptide chain, ozonolysis yielded quite pure C-terminal peptide aldehydes in a good yield with no detectable racemization of the C-terminal residue.