Amino Acids

, Volume 35, Issue 2, pp 329–338 | Cite as

Chemotactic tripeptides incorporating at position 2 α-aminoacid residues with unsaturated side chains

  • G. Lucente
  • M. P. Paradisi
  • C. Giordano
  • A. Sansone
  • D. Torino
  • S. Spisani


New N-For-Met-Leu-Phe-OMe (fMLF-OMe) analogues incorporating three different γ-δ-didehydro-α-aminoacid residues (namely: Alg = (S)-Allylglycine; Dag = Diallylglycine; Cpg = 1-Aminocyclopent-3-ene-1-carboxylic acid) replacing the native (S)-Leucine have been synthesized and their activity towards human neutrophils has been evaluated in comparison with that shown by the reference tripeptide fMLF-OMe. Chemotaxis, lysozyme release and superoxide anion production have been measured. 1H NMR titration experiments and NOESY spectrum of the Cpg containing model 10 have been discussed in order to ascertain the preferred solution conformations. A fully extended (C5) conformation at position 2 and a folded conformation with two consecutive γ-turns (C7 structure) have been proposed for the Dag and Cpg containing tripeptides, respectively.

Keywords: Aminoacids with unsaturated side chains – Chemotactic peptides – Cyclopentenyl aminoacids – Conformation – Grubbs reaction – Human neutrophils 





(benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate




1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride


ethyl 2-ethoxy-1,2-dihydro-1-quinolinecarboxylate




Krebs-Ringer phosphate containing 0.1% w/v d-glucose


ring-closing metathesis




trifluoroacetic acid


thin-layer chromatography


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Copyright information

© Springer-Verlag 2007

Authors and Affiliations

  • G. Lucente
    • 1
    • 2
  • M. P. Paradisi
    • 1
    • 2
  • C. Giordano
    • 2
  • A. Sansone
    • 1
  • D. Torino
    • 1
  • S. Spisani
    • 3
  1. 1.Dipartimento di Studi FarmaceuticiUniversità degli Studi di Roma ‘La Sapienza’RomeItaly
  2. 2.Istituto di Chimica Biomolecolare del CNR, c/o Dipartimento di Studi FarmaceuticiUniversità degli Studi di Roma ‘La Sapienza’RomeItaly
  3. 3.Dipartimento di Biochimica e Biologia MolecolareUniversità di FerraraFerraraItaly

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