title: Total synthesis in solution and conformational analysis of the peptaibol cervinin and selected analogues.
abstract: The total synthesis in solution and chemical characterization of the antibacterial undecamer peptaibol cervinin, its C-terminal (Lol-Ac) derivative, also naturally occurring, and three selected analogues modified at the N- and/or C-terminus(i) to improve the affinity to the membrane environment, are described. A solution conformational analysis in different media, performed by the combined use of FT-IR, CD, and 2D-NMR techniques, clearly shows a significant 3(10)-like helicity for these Aib-Pro rich peptides. The hydrophilicity/lipophilicity characteristics of the final compounds significantly influence their membrane-modifying properties.
authors.affiliation: Institute of Biomolecular Chemistry, Padova Unit, CNR, Department of Chemistry, University of Padova, Padova, Italy.
authors.forename: Chiara
authors.initials: C
authors.lastname: Baldini
authors.forename: Massimo
authors.initials: M
authors.lastname: Bellanda
authors.forename: Cristina
authors.initials: C
authors.lastname: Peggion
authors.forename: Albert Legrand
authors.initials: AL
authors.lastname: Djontu
authors.forename: Come
authors.initials: C
authors.lastname: Atagua
authors.forename: Stefano
authors.initials: S
authors.lastname: Mammi
authors.forename: Claudio
authors.initials: C
authors.lastname: Toniolo
mesh_terms: D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D012996:Solutions; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000900:Anti-Bacterial Agents; D010455:Peptides; D012996:Solutions; C484925:cervinin