Chemotactic Peptide Analogues The Role of (Z)-2,3-Didehydrophenylalanine and Phenylalanine C-Terminal Residues in Determining the Chemotactic Activity of Formylpeptides

✍ Scribed by Ines Torrini; Giampiero Pagani Zecchini; Mario Paglialunga Paradisi; Susanna Spisani

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 495 KB
• Volume: 329
• Category: Article
• ISSN: 0365-6233
• DOI: 10.1002/ardp.19963290306

✦ Synopsis

Several forrnylpeptides, analogs of the chemotactic agent HCO-Met-Leu-Phe-OMe, having the HCO-Xaa-Leu-A'Phe-OMe and HCO-Xaa-Leu-A'Phe-Phe-OMe structures (A' Phe = (Z)-2,3-didehydrophenylalanine), have been synthesized. The biological activity of these ligands has been determined on human neutrophils and compared to that of the corresponding HCO-Xaa-Leu-Phe-OMe derivatives not containing the unsaturated residue. The replacement of the C-terminal Phe with A' Phe causes, in all the examined tripeptides, the loss of any biological activity. On the other hand, the introduction into the A' Phe containing models of an additional C-terminal Phe residue leads to the formyltetrapeptides HCO-Xaa-Leu-A'Phe-Phe-OMe which show a biological activity very similar to that exhibited by the corresponding HCO-Xaa-Leu-Phe-OMe analogues.