title: A conformation-activity study of the [L-(alpha Me)Phe]3 analog of the formyl methionyl tripeptide chemoattractant.
abstract: CHO-L-Met-L-Leu-L-(alpha Me)Phe-OMe, an analog of the formyl methionyl tripeptide chemoattractant CHO-L-Met-L-Leu-L-Phe-OH, was synthesized by solution methods and fully characterized. This compound was prepared to determine the effect of the incorporation of a conformationally restricted C alpha,alpha-disubstituted alpha-amino acid residue at position 3 on the relation of three-dimensional structure to biological activity. The peptide was tested for its ability to induce granule enzyme secretion from rabbit peritoneal polymorphonuclear leukocytes. In parallel, a conformational analysis was performed in the crystal state by x-ray diffraction and in organic solution by infrared absorption and 1H nuclear magnetic resonance. These biological and conformational data are discussed in relation to those of the prototype tripeptide and its methyl ester.
authors.affiliation: C.N.R., Department of Organic Chemistry, University of Padova, Italy.
authors.forename: C
authors.initials: C
authors.lastname: Toniolo
authors.forename: M
authors.initials: M
authors.lastname: Crisma
authors.forename: S
authors.initials: S
authors.lastname: Pegoraro
authors.forename: G
authors.initials: G
authors.lastname: Valle
authors.forename: G M
authors.initials: GM
authors.lastname: Bonora
authors.forename: E L
authors.initials: EL
authors.lastname: Becker
authors.forename: S
authors.initials: S
authors.lastname: Polinelli
authors.forename: W H
authors.initials: WH
authors.lastname: Boesten
authors.forename: H E
authors.initials: HE
authors.lastname: Schoemaker
authors.forename: E M
authors.initials: EM
authors.lastname: Meijer
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D001681:Biological Assay; D002630:Chemotactic Factors / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D011487:Protein Conformation; D011817:Rabbits; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D014961:X-Ray Diffraction
chemical_list: D002630:Chemotactic Factors; C074708:formylmethionyl-leucyl-alpha-methyl(phenylalanine) methyl ester; D009240:N-Formylmethionine Leucyl-Phenylalanine