Alamethicin

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Alamethicin[1]
Alamethicin.png
Identifiers
CAS number 27061-78-5 N
PubChem 16132042
ChemSpider 17288702 YesY
ChEMBL CHEMBL438243 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C92H150N22O25
Molar mass 1964.31 g/mol
Appearance Off white solid
Melting point 255-270 °C
Solubility in water Insoluble
Solubility in DMSO, methanol, ethanol Soluble
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Alamethicin is a peptide antibiotic, produced by the fungus Trichoderma viride. It belongs to peptaibol peptides which contain the non-proteinogenic amino acid residue Aib (2-aminoisobutyric acid). This residue strongly induces formation of alpha-helical structure. The peptide sequence is:

Ac-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu-Gln-Phl

(Ac = acetyl, Phl = phenylalaninol, Aib = 2-Aminoisobutyric acid)

In cell membranes, it forms voltage-dependent ion channels by aggregation of four to six molecules.

References[edit]

Further reading[edit]

  • LR Jones, SW Maddock and HR Besch Jr. Unmasking effect of alamethicin on the (Na+,K+)-ATPase, beta-adrenergic receptor-coupled adenylate cyclase, and cAMP-dependent protein kinase activities of cardiac sarcolemmal vesicles. J. Biol. Chem., Vol. 255, Issue 20, 9971-9980, Oct, 1980.
  • Explore structures of Alamethicin at the protein data bank
  • Alamethicin in Norine
    • From "A voltage-gated ion channel model inferred from the crystal structure of alamethicin at 1.5-A resolution." Fox Jr, RO; Richards, FM (1982). "A voltage-gated ion channel model inferred from the crystal structure of alamethicin at 1.5-A resolution". Nature 300 (5890): 325–30. Bibcode:1982Natur.300..325F. doi:10.1038/300325a0. PMID 6292726.  edit