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Chemotactic Peptide Analogues The Role of ( Z )‐2,3‐Didehydrophenylalanine and Phenylalanine C ‐Terminal Residues in Determining the Chemotactic Activity of Formylpeptides
Author(s) -
Torrini Ines,
Zecchini Giampiero Pagani,
Paradisi Mario Paglialunga,
Spisani Susanna
Publication year - 1996
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19963290306
Subject(s) - chemotaxis , peptide , chemistry , phenylalanine , stereochemistry , biochemistry , oligopeptide , terminal (telecommunication) , peptide synthesis , amino acid , receptor , telecommunications , computer science
Several formylpeptides, analogs of the chemotactic agent HCO‐Met‐Leu‐Phe‐OMe, having the HCO‐Xaa‐Leu‐Δ z Phe‐OMe and HCO‐Xaa‐Leu‐Δ z Phe‐Phe‐OMe structures (Δ z 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 Δ z Phe causes, in all the examined tripeptides, the loss of any biological activity. On the other hand, the introduction into the Δ z Phe containing models of an additional C ‐terminal Phe residue leads to the formyltetrapeptides HCO‐Xaa‐Leu‐Δ z Phe‐Phe‐OMe which show a biological activity very similar to that exhibited by the corresponding HCO‐Xaa‐Leu‐Phe‐OMe analogues.