Alamethicin

Alamethicin[1]
IUPAC name	N-​acetyl-​2-​methylalanyl-​L-​prolyl-​2-​methylalanyl-​L-​alanyl-​2-​methylalanyl-​L-​alanyl-​L-​glutaminyl-​2-​methylalanyl-​L-​valyl-​2-​methylalanylglycyl-​D-​leucyl-​2-​methylalanyl-​L-​prolyl-​L-​valyl-​2-​methylalanyl-​2-​methylalanyl-​L-​α-​glutamyl-​N1-​[(1S)-​1-​benzyl-​2-​hydroxyethyl]-​L-​glutamamide
Identifiers
CAS number	[27061-78-5]
PubChem	16132042
SMILES	CC(C)C[C@@H](C(=O)NC(C)(C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC2=CC=CC=C2)CO)NC(=O)CNC(=O)C(C)(C)NC(=O)[C@H](C(C)C)NC(=O)C(C)(C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]3CCCN3C(=O)C(C)(C)NC(=O)C
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, 100 kPa) Infobox references

Alamethicin is a peptide antibiotic, produced by the fungus Trichoderma viride. It contains the non-proteinogenic amino acid 2-aminoisobutyric acid (Aib), which strongly induces helical peptide structures. 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)

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

References

Further reading

• 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.

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