Total synthesis of Septocylindrin B and C-terminus modified analogues

The total synthesis is reported of the peptaibol Septocylindrin B which is related to the well documented channel forming peptaibol antibiotic Alamethicin. Several analogues were synthesized with a modified C-terminus, to investigate the SAR of the terminal residue Phaol. All these peptides were tes...

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Veröffentlicht in:	PloS one 2012-12, Vol.7 (12), p.e51708-e51708
Hauptverfasser:	Nelissen, Jo, Nuyts, Koen, De Zotti, Marta, Lavigne, Rob, Lamberigts, Chris, De Borggraeve, Wim M
Format:	Artikel
Sprache:	eng
Schlagworte:	Alamethicin - analogs & derivatives Alamethicin - chemical synthesis Alamethicin - pharmacology Alcohol Amino acids Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacology Antibacterial activity Antibacterial agents Antibiotics Antifungal agents Bacteria - drug effects Biology C-Terminus Cell Membrane - drug effects Chemistry Chromatography, High Pressure Liquid Fluorescence Fluorescent indicators Laboratories Magnetic Resonance Spectroscopy Organic compound synthesis Peptaibols - chemical synthesis Peptaibols - pharmacology Peptides Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Structure-Activity Relationship Synthesis
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Beschreibung
Zusammenfassung:	The total synthesis is reported of the peptaibol Septocylindrin B which is related to the well documented channel forming peptaibol antibiotic Alamethicin. Several analogues were synthesized with a modified C-terminus, to investigate the SAR of the terminal residue Phaol. All these peptides were tested for their membrane perturbation properties by fluorescent dye leakage assay and for their antibacterial activity.
ISSN:	1932-6203 1932-6203
DOI:	10.1371/journal.pone.0051708