A4665

Alamethicin from Trichoderma viride

≥98% (HPLC)

• Synonym(s): Antibiotic U-22324
• CAS Number: 27061-78-5
• Beilstein: 5213858
• MDL number: MFCD00151517
• UNSPSC Code: 12352209
• PubChem Substance ID: 24890893
• NACRES: NA.77

Properties

• 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

Description

General description

Alamethicin is an antibiotic and a cytolytic peptide capable of forming an amphipathic α-helical structure in biological membranes.[1] 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.[2]

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[3]
• to investigate the formation of anion-permeable channels in planar lipid bilayers by magainin I obtained from Xenopus skin[1]
• to study the permeability of root apical meristem and epidermis and cellulase induced resistance to Alamethicin in Arabidopsis thaliana[2]
• to study the cytotoxic effects of the phycotoxin okadaic acid and mycotoxins on human intestinal (HT-29) and neuroblastoma (SH-SY5Y) cell lines[4]
• to analyze the structural variations and biological activity of peptaibols obtained from the Longibrachiatum clade belonging to the genus of filamentous fungi Trichoderma[5]

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.[5]

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

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves