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Alamethicin F50 (Synonyms: 18-L-Glutamine Alamethicin I)

Catalog No.GC42763

Alamethicin F50 is a peptaibol isolated from Trichoderma.

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Alamethicin F50 Chemical Structure

Cas No.: 56165-93-6

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500μg
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1mg
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5mg
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Sample solution is provided at 25 µL, 10mM.

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Background

Alamethicin F50 is a peptaibol isolated from Trichoderma. It is a polymer of 20 amino acids that includes modified and non-proteinogenic amino acids. Alamethicin F50 is a mixture of 13 different peptides, with the most abundant designated as alamethicin F50/5. Alamethicin F50 forms voltage-dependent ion channels in lipid membranes and acts as a lytic agent. It induces lysis of leukocytes (IC50 = 54 and 80 μM for rat mast cells and mouse spleen lymphocytes, respectively) and exhibits antibacterial activity against a panel of 8 mollicutes (MICs = 1.56-12.5 μM).

Chemical Properties

Cas No. 56165-93-6 SDF
Synonyms 18-L-Glutamine Alamethicin I
Formula C92H151N23O24 M.Wt 1963.3
Solubility DMF: Soluble,DMSO: Soluble,Ethanol: Soluble,Methanol: Soluble Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.
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Research Update

Enhancing the Antimicrobial Activity of Alamethicin F50/5 by Incorporating N-terminal Hydrophobic Triazole Substituents

Chemistry 2017 Dec 19;23(71):17964-17972.PMID:28922505DOI:10.1002/chem.201703569.

A simple and efficient strategy is proposed to significantly improve the antibacterial activity of peptaibols and other antimicrobial peptides by N-terminal capping with 1,2,3-triazole bearing various hydrophobic substituents on C-4. Such N-terminal insertions on Alamethicin F50/5 could enhance its antimicrobial activity on Gram-positive bacteria without modification of its overall three-dimensional structure. Although the native peptide and its analogues shared comparable helical contents, the crystal structure of one of the most active derivative showed a local slight distortion of the N-terminal extremity, which was also observed in solution using NMR spectroscopy. Importantly, fluorescence studies showed that the N-capped derivatives had increased affinity for liposomes, which may indicate they interacted more strongly with the bacterial membrane than Alamethicin F50/5.

Conformational analysis of TOAC-labelled Alamethicin F50/5 analogues

Chem Biodivers 2007 Jun;4(6):1256-68.PMID:17589864DOI:10.1002/cbdv.200790108.

In the preceding paper in this issue, we reported the total syntheses in solution of a set of four TOAC-containing analogues of the [L-Glu(OMe)(7,18,19)] F50/5 component of alamethicin, the prototype of peptaibol antibiotics forming channels in the biological membranes. In this article, we have expanded this work to the examination of their preferred conformation in solution by use of a combination of CD, FT-IR absorption, and NMR spectroscopies. The results are strongly in favor of the view that replacement of the Aib residues at positions 1, 8, and 16 with TOAC (both are members of the helicogenic sub-class of C(alpha)-tetrasubstituted alpha-amino acids) does not significantly affect the overwhelmingly populated alpha-helical 3D structure of alamethicin. The X-ray diffraction crystal structure of the N(alpha)-protected, C-terminal, hexapeptide amide segment Z-L-Pro-L-Val-(Aib)(2)-[L-Glu(OMe)](2)-Fol lends further support to our conformational conclusions.

Total synthesis in solution of Alamethicin F50/5 by an easily tunable segment condensation approach

Biopolymers 2004;76(6):485-93.PMID:15499566DOI:10.1002/bip.20161.

A total synthesis in solution of the 19-mer peptide component F50/5 of alamethicin, the most extensively investigated among the channel-former peptaibol antibiotics, is reported. Three peptide segments (A, B, C) were prepared and assembled, followed by incorporation of the acetylated N-terminal amino acid. The synthetic modules B and C are characterized by three Glu(OMe) residues (at positions 7, 18, and 19) that, after completion of the synthesis, were reacted with ammonia to provide Alamethicin F50/5. By use of this general strategy, we also prepared the [Gln7, Glu(OMe)18,19] Alamethicin F50/5 analogue. The purity and conformation of the final products were assessed by chromatographic, spectrometric, and spectroscopic techniques. This tunable segment condensation approach will pave the way for an easy synthesis of alamethicin analogues bearing amino acid residues with desired side-chain probes even at the N-terminus and in internal positions of the sequence.

Pore-forming properties of Alamethicin F50/5 inserted in a biological membrane

Chem Biodivers 2007 Jun;4(6):1338-46.PMID:17589885DOI:10.1002/cbdv.200790114.

The pore-forming properties of native and synthetic alamethicins were investigated in photoreceptor rod outer segments (OS) isolated from frog retina, and recorded in whole-cell configuration. The peptaibols were applied (and removed) to (from) the OS within less than 50 ms by means of a computer-controlled micro-perfusion system. Once blocked with light, the main OS endogenous conductance, the OS membrane resistance was >1 GOmega, allowing low-noise and high-resolution recordings. Currents of ca. 700 pA were recorded in symmetric K(+) (100 mM) and Ca(2+) (1 mM), upon applying 1 microM of Alamethicin F50/5 or its [L-Glu(OMe)(7,18,19)] analogue to the OS membrane (clamped at -20 mV). In the latter peptide, the Gln residues at positions 7, 18, and 19 were substituted with side-chain esterified Glu residues. For both peptides, the current activated exponentially, with a delay from peptide application, and exponentially returned to zero without any delay, upon removing the peptide from the external solution. The delay as well as the activation (tau(a)) and deactivation (tau(d)) time constants of the current produced by the modified alamethicin were much slower, and the current noise was much larger, with respect to the corresponding values for Alamethicin F50/5. Therefore, the above three Gln residues are not a key factor for pore formation, but the [L-Glu(OMe)(7,18,19)] analogue produces larger pores with a lower probability of formation.

Solution synthesis, conformational analysis, and antimicrobial activity of three Alamethicin F50/5 analogs bearing a trifluoroacetyl label

Chem Biodivers 2014 Aug;11(8):1163-91.PMID:25146762DOI:10.1002/cbdv.201300394.

We prepared, by solution-phase methods, and fully characterized three analogs of the membrane-active peptaibiotic Alamethicin F50/5, bearing a single trifluoroacetyl (Tfa) label at the N-terminus, at position 9 (central region) or at position 19 (C-terminus), and with the three Gln at positions 7, 18, and 19 replaced by Glu(OMe) residues. To add the Tfa label at position 9 or 19, a γ-trifluoroacetylated α,γ-diaminobutyric acid (Dab) residue was incorporated as a replacement for the original Val(9) or Glu(OMe)(19) amino acid. We performed a detailed conformational analysis of the three analogs (using FT-IR absorption, CD, 2D-NMR, and X-ray diffraction), which clearly showed that Tfa labeling does not introduce any dramatic backbone modification in the predominantly α-helical structure of the parent peptaibiotic. The results of an initial solid-state (19)F-NMR study on one of the analogs favor the conclusion that the Tfa group is a very promising reporter for the analysis of peptaibioticmembrane interactions. Finally, we found that the antimicrobial activities of the three newly synthesized analogs depend on the position of the Tfa label in the peptide sequence.

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