Chemotactic tripeptides incorporating at position 2 [alpha]-aminoacid residues with unsaturated side chains

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 hum...

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Bibliographic Details
Published in:Amino acids 2008-08, Vol.35 (2), p.329
Main Authors: Lucente, G, Paradisi, M P, Giordano, C, Sansone, A, Torino, D, Spisani, S
Format: Article
Language:English
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Proteins
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Summary: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. ^sup 1^H 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 (C^sub 5^) conformation at position 2 and a folded conformation with two consecutive γ-turns (C^sub 7^ structure) have been proposed for the Dag and Cpg containing tripeptides, respectively.[PUBLICATION ABSTRACT]
ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-007-0621-1