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

CAS: 27061-78-5 Cat. No.: A132913 Molecular Weight: 1964.34 Beilstein Registry Number: 5213858 EC Number: 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

Overview

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

Synonyms

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

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

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

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

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.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504771108
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504771108
• Canonical Smiles: 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
• Isomeric 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 Germany: 3
• PubChem CID: 53229968
• Molecular Weight: 1964.34
• Beilstein: 5213858

Chemical and Physical Properties

• Solubility: Soluble in DMSO and ethanol，Methanol
• Sensitivity: light sensitive & Moisture sensitive
• Melt Point(°C): 252°C-272°C

References

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