title: Synthesis and chemotactic activity of the fMLP analog HCO-Hmb-Leu-Phe-OMe.
abstract: The new fMLP analog HCO-Hmb-Leu-Phe-OMe (1), containing (S)-2-hydroxy-4-(methylthio)butyric acid (Hmb) in place of L-methionine at the N-terminal position, has been synthesized and fully characterized. The peptide 1 has been designed in order to improve the understanding of the role exerted by the formamido group in the binding interaction with the formylpeptide chemotactic receptors. Chemotaxis, superoxide anion production, and lysozyme release have been measured for both 1 and its deformylated analog Hmb-Leu-Phe-OMe 2. Results indicate that a strong hydrogen bond of the OH....O = C type may complement a weak H-bonding interaction involving the formylic proton as H-bond donor.
authors.affiliation: Dipartimento di Studi Farmaceutici, Università La Sapienza, Roma, Italy.
authors.forename: G P
authors.initials: GP
authors.lastname: Zecchini
authors.forename: M P
authors.initials: MP
authors.lastname: Paradisi
authors.forename: I
authors.initials: I
authors.lastname: Torrini
authors.forename: G
authors.initials: G
authors.lastname: Lucente
authors.forename: S
authors.initials: S
authors.lastname: Traniello
authors.forename: S
authors.initials: S
authors.lastname: Spisani
mesh_terms: D000595:Amino Acid Sequence; D002634:Chemotaxis, Leukocyte / Q000187:drug effects*; D006801:Humans; D066298:In Vitro Techniques; D008969:Molecular Sequence Data; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects
chemical_list: C083613:2-(formyloxy)-4-(methylthio)butyryl-leucyl-phenylalanine methyl ester; D009240:N-Formylmethionine Leucyl-Phenylalanine