title: Synthetic formyl tripeptide chemoattractants: a C(alpha,alpha)-dialkylated, amphiphilic glycyl residue at position 1.
abstract: The two diastereomeric tripeptides f-(S)-HmMet-Leu-Phe-OMe and f-(R)-HmMet-Leu-Phe-OMe, analogues of the prototypical chemoattractant f-Met-Leu-Phe-OH, were synthesized in solution by classical methods and fully characterized. A conformational study was performed in solution by 1H-NMR. Concomitantly, the two peptides were tested for their ability to induce chemotaxis, superoxide anion production and lysozyme secretion from human neutrophils. The conformational and biological data are discussed with regard to the proposed model of the chemotactic receptor on neutrophils.
authors.affiliation: Institute of Organic Chemistry, Technical University of Lodz, 90-924 Lodz, Poland.
authors.forename: Renata
authors.initials: R
authors.lastname: Witkowska
authors.forename: Janusz
authors.initials: J
authors.lastname: Zabrocki
authors.forename: Susanna
authors.initials: S
authors.lastname: Spisani
authors.forename: Maria Sofia
authors.initials: MS
authors.lastname: Falzarano
authors.forename: Claudio
authors.initials: C
authors.lastname: Toniolo
authors.forename: Fernando
authors.initials: F
authors.lastname: Formaggio
mesh_terms: D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000494:pharmacology; D005998:Glycine / Q000737:chemistry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009113:Muramidase / Q000378:metabolism; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects / Q000378:metabolism; D011487:Protein Conformation; D013481:Superoxides / Q000378:metabolism
chemical_list: D004791:Enzyme Inhibitors; D013481:Superoxides; D009240:N-Formylmethionine Leucyl-Phenylalanine; D009113:Muramidase; D005998:Glycine