Solid-phase synthesis of chemotactic peptides using alpha-amido acids

Four chemotactic peptides, For-Met-Xxx-Phe-OMe. with an alpha,alpha-disubst ituted amino acid at position 2 have been synthesized by the azido acid met hod [Meldal M, Juliano MA, Jansson AM. 1997, Azido acids in a novel method of solid-phase peptide synthesis. Tetrahedron Lett, 38: 2531-2534] on solid -phase, and were tested for biological activity. Dipropylglycine in the cen tral position (Xxx) was found to be as active as the natural chemotactic pe ptide for chemotactic activity toward human neutrophils. Higher yields were obtained than previously reported solution-phase syntheses of chemotactic peptides, and EEDQ was used successfully for the difficult solid-phase form ylation of amino groups. Copyright (C) 2000 European Peptide Society and Jo hn Wiley & Sons, Ltd.