Alamethicin from Trichoderma viride

SIGMA/A4665 - ≥98% (HPLC)

Synonym: Antibiotic U-22324

CAS Number: 27061-78-5
MDL Number: MFCD00151517
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-A4665-5MG	5 mg	$299.00 1/EA	Add To Favorites
45-A4665-10MG	10 mg	$510.00 1/EA	Add To Favorites
45-A4665-25MG	25 mg	$1020.00 1/EA	Add To Favorites

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Properties
Descriptions
Safety Info.
Basic Data

antibiotic activity spectrum	Gram-positive bacteria
assay	≥98% (HPLC)
form	powder
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
mode of action	cell membrane \| interferes
Quality Level	300
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
storage temp.	2-8°C

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.
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.
Packaging:	5, 10, 25 mg in glass bottle
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

Symbol	GHS06
Signal word	Danger
Hazard statements	H301
Precautionary statements	P301 + P310 + P330
Hazard Codes	T
Risk Statements	25
Safety Statements	45
RIDADR	UN 3462 6.1 / PGIII
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥98% (HPLC)
Storage Temp.	2-8°C
UNSPSC	12352209

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