Synthesis, conformation, and biological activity of two fMLP-OMe analogues containing the new 2-[2′-(methylthio) ethyl] methionine residue

Autor: Susanna Spisani, Fernando Mazza, Serena Traniello, G. Pochetti, Gino Lucente, E. Gavuzzo, Ines Torrini, M. Paglialunga Paradisi, G. Pagani Zecchini
Rok vydání: 1997
Předmět:
Zdroj: Biopolymers. 42:415-426
ISSN: 1097-0282
0006-3525
DOI: 10.1002/(sici)1097-0282(19971005)42:4<415::aid-bip5>3.0.co;2-t
Popis: The new C alpha-tetrasubstituted alpha-amino acid residue 2-[2'-(methylthio)ethyl]methionine (Dmt) has been introduced into the reference chemotactic tripeptide HCO-Met-Leu-Phe-OMe (fMLP-OMe) in place of the leucine or methionine, respectively. The biological activity of the new analogues [Dmt2]fMLP-OMe (2) and [Dmt1]fMLP-OMe (3) has been determined; whereas 2 is active toward human neutrophils, stimulating directed migration, superoxide anion generation, and lysozyme release, 3 results practically inactive in all tested assays. A conformational analysis on 2 and 3 has been performed in solution by using ir absorption and 1H-nmr. The conformation of 2 was also examined in the crystal by x-ray diffraction methods. Both 2 and 3 adopt fully extended conformation in correspondence with the Dmt residue. Biological and conformational results are discussed and compared with related previously studied models.
Databáze: OpenAIRE
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