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 310-like helicity for these Aib-Pro rich peptides. The hydrophilicity/lipophilicity characteristics of the final compounds significantly influence their membrane-modifying properties.
Total Synthesis in Solution and Conformational Analysis of the Peptaibol Cervinin and Selected Analogues
BELLANDA, MASSIMO;PEGGION, CRISTINA;MAMMI, STEFANO;TONIOLO, CLAUDIO
2009
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 310-like helicity for these Aib-Pro rich peptides. The hydrophilicity/lipophilicity characteristics of the final compounds significantly influence their membrane-modifying properties.
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