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PMID: 5449129 Published · ppublish English Journal Article

The primary structure of alamethicin.

The Biochemical journal ·Vol. 117 ·No. 4 ·1970-05-00 ·Pages 757-66

Payne JW, Jakes R, Hartley BS

Abstract

Alamethicin, an antibiotic that can transport cations and induce action potentials in synthetic membranes, is shown to be a cyclic peptide with 18 residues including 7-alpha-aminoisobutyric acid residues, two glutamine residues and one free carboxyl group. The composition indicates microheterogeneity. Alamethicin itself and many peptides derived from it are immune to enzymic digestion, but specific partial acid cleavages have allowed determination of the complete sequence. Diborane reduction has shown that the alpha-carboxyl group of glutamine-18 is free, but the ring is formed by a peptide bond between the imino group of proline-1 and the gamma-carboxyl group of glutamic acid-17. The structure is contrasted with that of other cation-transporting antibiotics. Model building allows a structure that could stack to form a tunnel with a lipophilic exterior and hydrophilic interior and flexible internal arms formed by the pendant C-terminal glutamine residue.

MeSH Terms
Action Potentials Amino Acid Sequence Anti-Bacterial Agents/pharmacology Biological Transport, Active Chemical Phenomena Chemistry Electrophoresis Glutamine/analysis Models, Structural Peptide Hydrolases Peptides
Chemicals
Anti-Bacterial Agents Peptides Glutamine Peptide Hydrolases
Authors & Affiliations
3 authors, click to expand affiliations / ORCID
Payne J W
Jakes R
Hartley B S
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31 references, click to expand
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Article Info
Journal
The Biochemical journal
Abbr.
Biochem J
ISSN
0264-6021
DOI
10.1042/bj1170757
Published
1970-05-00
Pages
757-66
Language
English
Region
England
NLM ID
2984726R
PMCID
PMC1179028
Subset
IM
External Links
PubMed source DOI: 10.1042/bj1170757 PMC Full Text View journal details
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