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A4665

Sigma-Aldrich

Alamethicin from Trichoderma viride

≥98% (HPLC)

Synonym(s):

Antibiotic U-22324

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About This Item

CAS Number:
27061-78-5
Beilstein:
5213858
MDL number:
MFCD00151517
UNSPSC Code:
12352209
PubChem Substance ID:
24890893
NACRES:
NA.77

Quality Level

300

Assay

≥98% (HPLC)

form

powder

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

CC(C)C[C@H](NC(=O)CNC(=O)C(C)(C)NC(=O)[C@@H](NC(=O)C(C)(C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@H](C)NC(=O)C(C)(C)NC(=O)[C@@H]1CCCN1C(=O)C(C)(C)NC(C)=O)C(C)C)C(=O)NC(C)(C)C(=O)N2CCC[C@H]2C(=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(N)=O)C(=O)N[C@@H](CO)Cc3ccccc3

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-SLKIUSOBSA-N

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General description

Alamethicin is an antibiotic and a cytolytic peptide capable of forming an amphipathic α-helical structure in biological membranes. It is a linear peptaibol, made up of 20 amino acid residues. It belongs to the class of Nonribosomal peptides (NRP) and is loaded with alpha-amino isobutyric acid.

Application

Alamethicin from Trichoderma viride has been used:
  • to examine the effect of glutamate transporters on the Na+/K+-ATPase dependent extracellular K+ transient during neuronal activity
  • to investigate the formation of anion-permeable channels in planar lipid bilayers by magainin I obtained from Xenopus skin
  • to study the permeability of root apical meristem and epidermis and cellulase induced resistance to Alamethicin in Arabidopsis thaliana
  • to study the cytotoxic effects of the phycotoxin okadaic acid and mycotoxins on human intestinal (HT-29) and neuroblastoma (SH-SY5Y) cell lines
  • to analyze the structural variations and biological activity of peptaibols obtained from the Longibrachiatum clade belonging to the genus of filamentous fungi Trichoderma

Biochem/physiol Actions

Alamethicin is responsible for eliciting resistance in plants and is harmful to them by causing lesions and rapid death associated with ribosomal ribonucleic acid (rRNA) cleavage. It can cause permeability of the apical meristem and epidermis in A. thaliana roots. Alamethicin leads to the coiling of tendrils in Bryonia dioica induced by jasmonates.

Quality

A mixture of alamethicin homologs

Sequence

Ac-2-MeAla-L-Pro-2-MeAla-L-Ala-2-MeAla-L-Ala-L-Glu(NH2)-2-MeAla-L-Val-2-MeAla-Gly-L-Leu-2-MeAla-L-Pro-L-Val-2-MeAla-2-MeAla-L-Glu-L-Glu(NH2)-phenylalaninol

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

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D P Tieleman et al.
Biophysical journal, 76(6), 3186-3191 (1999-06-04)
Alamethicin is an amphipathic alpha-helical peptide that forms ion channels. An early event in channel formation is believed to be the binding of alamethicin to the surface of a lipid bilayer. Molecular dynamics simulations are used to compare the structural
Bradley R Dotson et al.
BMC plant biology, 18(1), 165-165 (2018-08-12)
Trichoderma fungi live in the soil rhizosphere and are beneficial for plant growth and pathogen resistance. Several species and strains are currently used worldwide in co-cultivation with crops as a biocontrol alternative to chemical pesticides even though little is known
Burkhard Bechinger et al.
Chemistry and physics of lipids, 165(3), 282-301 (2012-03-01)
Solid-state NMR spectroscopic techniques provide valuable information about the structure, dynamics and topology of membrane-inserted polypeptides. In particular antimicrobial peptides (or 'host defence peptides') have early on been investigated by solid-state NMR spectroscopy and many technical innovations in this domain
Alexey G Kruglov et al.
Chemical research in toxicology, 22(3), 565-573 (2009-02-06)
A novel mycotoxin named acrebol, consisting of two closely similar peptaibols (1726 and 1740 Da), was isolated from an indoor strain of the mitosporic ascomycete fungus Acremonium exuviarum. This paper describes the unique mitochondrial toxicity of acrebol, not earlier described
H Duclohier et al.
Biophysical journal, 56(5), 1017-1021 (1989-11-01)
The ionophore properties of magainin I, an antimicrobial and amphipathic peptide from the skin of Xenopus, were investigated in planar lipid bilayers. Circular dichroism studies, performed comparatively with alamethicin, in small or large unilamellar phospholipidic vesicles, point to a smaller
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