Total synthesis in solution and conformational analysis of the peptaibol cervinin and selected analogues.
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.
Baldini
Chiara
C
Institute of Biomolecular Chemistry, Padova Unit, CNR, Department of Chemistry, University of Padova, Padova, Italy.
Bellanda
Massimo
M
Peggion
Cristina
C
Djontu
Albert Legrand
AL
Atagua
Come
C
Mammi
Stefano
S
Toniolo
Claudio
C
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
D000900:Anti-Bacterial Agents; D010455:Peptides; D012996:Solutions; C484925:cervinin