A peptaibol antibiotic
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Alamethicin F50

Item No. 23141

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
18-L-glutamine-alamethicin I
CAS Number
56165-93-6
Synonyms
  • 18-L-Glutamine Alamethicin I
Molecular Formula
C92H151N23O24
Formula Weight
1963.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
CC(C[C@H](NC(CNC(C(C)(NC([C@@H](NC(C(C)(NC([C@@H](NC([C@@H](NC(C(C)(NC([C@@H](NC(C(C)(NC([C@H]1N(C(C(C)(C)NC(C)=O)=O)CCC1)=O)C)=O)C)=O)C)=O)C)=O)CCC(N)=O)=O)C)=O)C(C)C)=O)C)=O)=O)C(NC(C)(C(N2[C@H](C(N[C@@H](C(C)C)C(NC(C)(C)C(NC(C)(C)C(N[C@H](CCC(N)=O)C(N[C@H](CCC(N)=O)C(N[C@H](CO)CC3=CC=CC=C3)=O)=O)=O)=O)=O)=O)CCC2)=O)C)=O)C
InChi Code
InChI=1S/C92H151N23O24/c1-47(2)43-58(72(127)109-92(24,25)84(139)114-41-29-33-59(114)73(128)104-65(48(3)4)75(130)112-90(20,21)82(137)113-89(18,19)80(135)103-56(36-39-62(94)119)70(125)102-55(35-38-61(93)118)69(124)99-54(46-116)44-53-31-27-26-28-32-53)100-64(121)45-96-77(132)85(10,11)111-76(131)66(49(5)6)105-81(136)88(16,17)108-71(126)57(37-40-63(95)120)101-67(122)50(7)97-78(133)86(12,13)107-68(123)51(8)98-79(134)87(14,15)110-74(129)60-34-30-42-115(60)83(138)91(22,23)106-52(9)117/h26-28,31-32,47-51
InChi Key
YPZSDWIWYLTCKG-NQYXTXNHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Alamethicin F50 is a peptaibol isolated from Trichoderma.1 It is a polymer of 20 amino acids that includes modified and non-proteinogenic amino acids.2 Alamethicin F50 is a mixture of 13 different peptides, with the most abundant designated as alamethicin F50/5. Alamethicin F50 forms voltage-dependent ion channels in lipid membranes and acts as a lytic agent.3,4 It induces lysis of leukocytes (IC50 = 54 and 80 μM for rat mast cells and mouse spleen lymphocytes, respectively) and exhibits antibacterial activity against a panel of 8 mollicutes (MICs = 1.56-12.5 μM).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Meyer, C.E., and Reusser, F. A polypeptide antibacterial agent isolated from Trichoderma viride. Experientia 23(2), 85-86 (1967).

    2. Kirschbaum, J., Krause, C., Winzheimer, R.K., et al. Sequences of alamethicins F30 and F50 reconsidered and reconciled. J. Pept. Sci. 9(11-12), 799-809 (2003).

    3. Béven, L., Duval, D., Rebuffat, S., et al. Membrane permeabilisation and antimycoplasmic activity of the 18-residue peptaibols, trichorzins PA. Biochim. Biophys. Acta 1372(1), 78-90 (1998).

    4. Bessler, W.G., Ottenbreit, B., Irmscher, G., et al. Interaction of membrane modifying peptide antibiotics from Trichoderma viride with leukocytes. Biochem. Biophys. Res. Commun. 87(1), 99-105 (1979).