MODIFIED CHEMOTACTIC PEPTIDES - SYNTHESIS AND ACTIVITY OF AN AZATIC-CONTAINING FMLP-OME ANALOG

The synthesis and the biological activity of a pseudopeptide analogue of the chemotactic N-formyltripeptide fMLP-OMe, containing the azaTic (3,4-dihydro-2(1H)-phthalazinecarboxylic acid) residue replacing the n ative phenylalanine, is described. Whereas pseudopeptides containing l inear alpha-azaamino acids are currently studied, data on the new grou p of analogues containing cyclic alpha-aza residues capable of limitin g the rotameric distribution of the side chains (topological control) are just emerging in the literature. At our best knowledge, the here d escribed [azaTic(3)]fMLP-OMe represents the first example of the intro duction of this new type of alpha-aza residue into a natural bioactive peptide.