Alamethicin

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Reference= [ [http://www.fermentek.co.il/alamethicin.htm Alamethicin product page] from Fermentek]
ImageFile=Alamethicin.pngImageSize=250px
IUPACName=
OtherNames=
Section1=Chembox Identifiers
CASNo=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
Section2=Chembox Properties
Formula=C₉₂H₁₅₀N₂₂O₂₅
MolarMass=1964.31 g/mol
Appearance=Off white solid
Density=
MeltingPt=255-270 °C
BoilingPt=
Solubility=Insoluble
SolubleOther = Soluble
Solvent = DMSO, methanol, ethanol

Section3=Chembox Hazards
MainHazards=
FlashPt=
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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)

It has UV spectrum maxima at 265 and 257 nm.

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

References