Synthesis and Characterization of the Major Component of Alamethicin

T. M. Balasubramanian, Nancy C.E. Kendrick, Melissa Taylor, Garland R. Marshall, James E. Hall, Igor Vodyanoy, Fritz Reusser

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67 Scopus citations

Abstract

Natural alamethicin has been purified on a high-performance liquid chromatography (HPLC) system developed to purify and characterize synthetic peptides corresponding to the proposed structures of alamethicin. Five of the twelve components detectable by UV absorption at 210 nm were isolated in pure form and were characterized for their antibacterial and ionophoric properties. Low-resolution electron-impact mass spectrometry (LREIMS) indicates that the purified major component and a synthetic preparation based on the recently proposed structure are identical in their primary structures. This major component, along with another fraction of the natural alamethicin mixture, closely demonstrates the spectrum of antibiotic activity possessed by the mixture. All fractions are equally potent in producing conductances of 30µS/cm2 in lipid bilayers, but the current-voltage curves induced by the different fractions have different slopes. Thus, their potencies at higher conductance levels can be expected to diverge. The synthetic peptide shows a close correspondence to the major component by all criteria examined.

Original languageEnglish
Pages (from-to)6127-6132
Number of pages6
JournalJournal of the American Chemical Society
Volume103
Issue number20
DOIs
StatePublished - Oct 1981

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