Alamethicin - ≥98% , CAS No.27061-78-5

CAS: 27061-78-5 Cat. No.: A132913 Summenformel: C₉₂H₁₅₀N₂₂O₂₅ Molekulargewicht: 1964.34 Beilstein Registry Number: 5213858 EG-Nummer: 608-040-6 PubChem CID: 53229968

GRADE & PURITY ≥98%

Synonyms

MFCD00151517 | ALAMETHICIN | Alamethicin from Trichoderma viride | Alamethicin from Trichoderma viride, >=98% (HPLC) | Antibiotic U 22324

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Alamethicin (U-22324) is a polypeptide natural product antibiotic supplied as a mixture of homologs: Alamethicin and Alamethicin I. These compounds form voltage-dependent ion channels in the lipid bilayer, through the spontaneous assembly of units into a multimeric barrel-stave structure spanning the membrane. This formation results in a hydrophilic pore which permits non-specific ion efflux through the membrane. The non-specific ion efflux obliterates the normal electrochemical gradient of the cell, producing the antibiotic property of Alamethicin. Substantiated by experiments with covalently tethered molecules of Alamethicin, It is suggested that different multimeric aggregation states create varying pore sizes with varying stabilities, correlating to differential specificity for ions. This channel-forming activity has been exploited as a tool for introducing hydrophilic small molecules into mitochondria without disrupting the integrity of the membrane.
Alamethicin is a monovalent cation ionophore which can mimic nerve action potential across artificial membranes. Alamethicin has also been used for studying membrane interactions of antimicrobial peptides.

Specifications

Synonyme

MFCD00151517 | ALAMETHICIN | Alamethicin from Trichoderma viride | Alamethicin from Trichoderma viride, >=98% (HPLC) | Antibiotic U 22324

Spezifikationen & Reinheit

≥98%

Biochemische und physiologische Mechanismen

Monovalent cation ionophore; can mimic nerve action potential across artificial membranes.Peptide antibiotic from the fungus Trichoderma viride. Forms voltage-dependent ion channels in the lipid bilayer of cell membranes. Inhibits non-specific ion efflux

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Hinweis

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one week. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Reinheit

≥98%

Namen und Kennungen

Pubchem Sid

504771108

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504771108

Kanonisches Lächeln

CC(C)CC(C(=O)NC(C)(C)C(=O)N1CCCC1C(=O)NC(C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)N)C(=O)NC(CC2=CC=CC=C2)CO)NC(=O)CNC(=O)C(C)(C)NC(=O)C(C(C)C)NC(=O)C(C)(C)NC(=O)C(CCC(=O)N)NC(=O)C(C)NC(=O)C(C)(C)NC(=O)C(C)NC(=O)C(C)(C)NC(=O)C3CCCN3C(=O)C(C)(C)NC(=O)C

IUPAC Name

(4S)-4-[[2-[[2-[[(2S)-2-[[(2S)-1-[2-[[(2S)-2-[[2-[[2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[2-[[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidine-2-carbonyl]amino]-2-methylpropanoyl]amino]propanoyl]amino]-2-methylpropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoyl]amino]-2-methylpropanoyl]amino]-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-2-methylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]-5-[[(2S)-5-amino-1-[[(2R)-1-hydroxy-3-phenylpropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-5-oxopentanoic acid

InChIKey

LGHSQOCGTJHDIL-SLKIUSOBSA-N

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

Isomere SMILES

C[C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)NC(C)(C)C(=O)N[C@@H](C(C)C)C(=O)NC(C)(C)C(=O)NCC(=O)N[C@@H](CC(C)C)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)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

WGK Deutschland

3

PubChem CID

53229968

Molekulargewicht

1964.34

Beilstein

5213858

Chemische und physikalische Eigenschaften

• Löslichkeit: Soluble in DMSO and ethanol，Methanol
• Empfindlichkeit: light sensitive & Moisture sensitive
• Schmelzpunkt (°C): 252°C-272°C