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Merck
CN

A5361

Alamethicin

from Trichoderma viride, ≥98% (HPLC), antibiotic, DMSO solution

别名:

U-22324

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关于此项目

化学文摘社编号:
27061-78-5
MDL number:
MFCD00151517
UNSPSC Code:
12352200
EC Number:
200-664-3
NACRES:
NA.77

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产品名称

Alamethicin, Ready Made Solution from Trichoderma viride, 5 mg/mL in DMSO

SMILES string

N2([C@@H](CCC2)C(=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](CO)Cc3ccccc3)C(=O)C(NC(=O)[C@@H](NC(=O)CNC(=O)C(NC(=O)[C@@H](NC(=O)C(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(NC(=O)[C@@H](NC(=O)C(NC(=O)[C@H]1N(

InChI key

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

assay

≥98% (HPLC)

form

DMSO solution

concentration

5 mg/mL in DMSO

antibiotic activity spectrum

Gram-positive bacteria

mode of action

cell membrane | interferes

shipped in

wet ice

storage temp.

−20°C

Quality Level

200

相关类别

Application

Alamethicin is a 20-amino acid channel-forming peptide antibiotic that can function as a monovalent cation ionophore. Alamethicin has been used to develop methods for the routine assessment of potential new drug candidates to elicit their pharmacokinetic drug interactions.
Alamethicin, Ready Made Solution from Trichoderma viride has been used :
  • In the uridine 5′-diphospho-glucuronosyltransferase activity assay.
  • To determine the Na, K-ATPase activity in permeabilized bovine nonpigmented epithelium cells.
  • In methylcrotonyl-CoA carboxylase activity assay.

Biochem/physiol Actions

Alamethicin is a 20-amino acid channel-forming peptide antibiotic isolated from the fungus Trichoderma viride. Alamethicin consists of several isoforms, for which structural information has been published. Alamethicin forms voltage-dependent channels across lipid bilayer membranes. The Alamethicin channel is built by a bundle of helical monomers forming a water filled transmembrane pore. The conductivity level of the channel is determined by the number of associated helical monomers (3-12), which generates a non aligned supermolecular structure with an aqueous core through which ions can cross lipid membranes. Alamethicin catalyzes the exchange of protons for monovalent cations with little difference in affinities and has the ability to transport cations through biological and artificial lipid membranes. Alamethicin can be used for the permeabilization of mitochondria without affecting the outer or inner membranes.

General description

Alamethicin belongs to the peptaibol family of antimicrobial peptides. It is mainly composed of hydrophobic amino acids. It possess a helical structure with a movable hinge region at Gly-11 position.

Physical form

The product contains a mixture of alamethicin isoforms. It is supplied as a 5 mg/mL, 0.2 μm filtered solution in DMSO.

存储类别

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 2

flash_point_f

188.6 °F - closed cup

flash_point_c

87 °C - closed cup

法规信息

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分析证书(COA)

Lot/Batch Number
0000148430
0000152805
0000284781
0000254795
0000152805

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Structure and alignment of the membrane-associated peptaibols ampullosporin A and alamethicin by oriented 15N and 31P solid-state NMR spectroscopy
Salnikov ES, et al.
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