Synthesis of the Major Component of Alamethicin

Article abstract of DOI:10.1021/ja00411a018

Alamethicin (ALA), a natural membrane-active antibiotic, consists of several components.The major component, ALA I, was isolated in pure form and compared with the synthetic peptide acetyl-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu-Gln-Phol obtained by stepwise segment condensation on a polystyrene support.The synthetic and natural products appeared essentially identical by amino acid analysis, high performance liquid chromatography, 600-MHz proton nuclear magnetic resonance spectroscopy, mass spectrometry, electrical activity in lipid bilayer membranes, and antimicrobial activity.It is concluded that ALA I has the structure indicated above.