Alamethicin

Alamethicin is an antibiotic peptide belonging to a class of membrane active peptides of fungal origin called peptaibols. 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. Alamethicin is often used to study ion channel assembly, voltage gating, and peptide-membrane interactions. Alamethicin is also widely used as agent to induce various physiological and defense responses in eukaryotic cells including plants.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: >90% (mixture of isoforms). Formulation: (Request formulation change), A crystalline solid. Solubility: DMSO: 10 mg/ml, Methanol: 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.