title: Modified chemotactic peptides: synthesis and activity of an azaTic-containing fMLP-OMe analogue.
abstract: The synthesis and the biological activity of a pseudopeptide analogue of the chemotactic N-formyltripeptide fMLP-OMe, containing the azaTic (3,4-dihydro-2(1H)-phthalazinecarboxylic acid) residue replacing the native phenylalanine, is described. Whereas pseudopeptides containing linear alpha-azaamino acids are currently studied, data on the new group of analogues containing cyclic alpha-aza residues capable of limiting the rotameric distribution of the side chains (topological control) are just emerging in the literature. At our best knowledge, the here described [azaTic3]fMLP-OMe represents the first example of the introduction of this new type of alpha-aza residue into a natural bioactive peptide.
authors.affiliation: Dipartimento di Studi Farmaceutici, Università La Sapienza, Roma, Italy.
authors.forename: G
authors.initials: G
authors.lastname: Pagani Zecchini
authors.forename: I
authors.initials: I
authors.lastname: Torrini
authors.forename: M
authors.initials: M
authors.lastname: Paglialunga Paradisi
authors.forename: G
authors.initials: G
authors.lastname: Lucente
authors.forename: G
authors.initials: G
authors.lastname: Mastropietro
authors.forename: S
authors.initials: S
authors.lastname: Spisani
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002634:Chemotaxis, Leukocyte; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D010793:Phthalazines / Q000737:chemistry*
chemical_list: C116873:3,4-dihydro-2(H)-phthalazine carboxylic acid; D002264:Carboxylic Acids; D010793:Phthalazines; D009240:N-Formylmethionine Leucyl-Phenylalanine; C042932:formylmethionyl-leucyl-phenylalanine methyl ester