A membrane active peptide antibiotic
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Alamethicin

Item No. 11425

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,12R)-1-((S)-1-((6S,12S,15S,21S,30S)-1-((R)-1-(2-acetamido-2-methylpropanoyl)pyrrolidin-2-yl)-15-(3-amino-3-oxopropyl)-30-isobutyl-21-isopropyl-3,3,6,9,9,12,18,18,24,24,33,33-dodecamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaoxo-2,5,8,11,14,17,20,23,26,29,32-undecaazatetratriacontan-34-oyl)pyrrolidin-2-yl)-12-(((R)-5-amino-1-(((S)-1-hydroxy-3-phenylpropan-2-yl)amino)-1,5-dioxopentan-2-yl)carbamoyl)-3-isopropyl-6,6,9,9-tetramethyl-1,4,7,10-tetraoxo-2,5,8,11-tetraazapentadecan-15-oic acid
CAS Number
27061-78-5
Synonyms
  • Antibiotic U-22324
Molecular Formula
C92H150N22O25
Formula Weight
1964.3
Purity
≥98% (mixture of isoforms)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlMethanol: 10 mg/ml
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]1CCCN1C(C(C)(NC(C)=O)C)=O)=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(N2CCC[C@H]2C(N[C@H](C(NC(C)(C(NC(C)(C(N[C@@H](C(N[C@@H](C(N[C@H](CO)CC3=CC=CC=C3)=O)CCC(N)=O)=O)CCC(O)=O)=O)C)=O)C)=O)C(C)C)=O)=O)C)=O)C
InChi Code
InChI=1S/C92H150N22O25/c1-47(2)43-58(72(127)108-92(24,25)84(139)113-41-29-33-59(113)73(128)103-65(48(3)4)75(130)111-90(20,21)82(137)112-89(18,19)80(135)102-56(37-40-64(120)121)70(125)101-55(35-38-61(93)117)69(124)98-54(46-115)44-53-31-27-26-28-32-53)99-63(119)45-95-77(132)85(10,11)110-76(131)66(49(5)6)104-81(136)88(16,17)107-71(126)57(36-39-62(94)118)100-67(122)50(7)96-78(133)86(12,13)106-68(123)51(8)97-79(134)87(14,15)109-74(129)60-34-30-42-114(60)83(138)91(22,23)105-52(9)116/h26-28,31-32,47-51,54-60,65-66,115H,29-30,33-46H2,1-25H3,(H2,93,117)(H2,94,118)(H,95,132)(H,96,133)(H,97,134)(H,98,124)(H,99,119)(H,100,122)(H,101,125)(H,102,135)(H,103,128)(H,104,136)(H,105,116)(H,106,123)(H,107,126)(H,108,127)(H,109,129)(H,110,131)(H,111,130)(H,112,137)(H,120,121)/t50-,51-,54-,55+,56+,57-,58-,59-,60+,65-,66-/m0/s1
InChi Key
LGHSQOCGTJHDIL-PPYNOJTFSA-N
Origin
Fungus/Trichoderma viride
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $61

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    5 mg

    $197

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    10 mg

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    Product Description

    Alamethicin is an antibiotic peptide belonging to a class of membrane active peptides of fungal origin called peptaibols.1 It contains an unusual amphiphilic amino acid, 2-aminoisobutyric acid, which strongly induces helical peptide structures and forms voltage-gated ion channels in the lipid bilayers of cell membranes.1 Alamethicin is often used to study ion channel assembly, voltage gating, and peptide-membrane interactions.2,3,4,5 Alamethicin is also widely used as agent to induce various physiological and defense responses in eukaryotic cells including plants.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Maischak, H., Zimmermann, M.R., Felle, H.H., et al. Alamethicin-induced electrical long distance signaling in plants. Plant Signal. Behav. 5(8), 988-990 (2010).

    2. Kessel, A., Cafiso, D.S., and Ben-Tal, N. Continuum solvent model calculations of alamethicin-membrane interactions: Thermodynamic aspects. Biophys. J. 78(2), 571-583 (2000).

    3. Pan, J., Tristram-Nagle, S., and Nagle, J.F. Alamethicin aggregation in lipid membranes. J. Membr. Biol. 231(1), 1-36 (2009).

    4. Jones, L.R., Maddock, S.W., and Besch, H.R., Jr. Unmasking effect of alamethicin on the (Na+,K+)-ATPase, β-adrenergic receptor-coupled adenylate cyclase, and cAMP-dependent protein kinase activities of cardiac sarcolemmal vesicles. The Journal of Biological Chemisty 255(20), 9971-9980 (1980).

    5. Walsky, R.L., Bauman, J.N., Bourcier, K., et al. Optimized assays for human UDP-glucuronosyltransferase (UGT) activities: Altered alamethicin concentration and utility to screen for UGT inhibitors. Drug Metab. Dispos. 40(5), 1051-1065 (2012).