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Merck
CN

05125

Alamethicin from Trichoderma viride

≥50 % by HPLC (main component)

Synonym(s):

Antibiotic U-22324

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About This Item

CAS Number:
27061-78-5
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
5213858
MDL number:
MFCD00151517

Key Documents

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composition

, ≥50% HPLC (main component)

Quality Level

100

storage temp.

−20°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

Other Notes

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
Alamethicin-mediated fusion of lecithin vesicles

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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A L Lau et al.
Proceedings of the National Academy of Sciences of the United States of America, 72(6), 2170-2174 (1975-06-01)
It was recently shown that alamethicin greatly facilitates the fusion of small, sonicated, lecithin bilayer vesicles. In the present work the details of this fusion process have been followed by monitoring the inner and outer choline methyl signals separately by
Upendra A Argikar et al.
Drug metabolism and disposition: the biological fate of chemicals, 37(1), 229-236 (2008-10-08)
Valproic acid (VPA) is a widely used anticonvulsant that is also approved for mood disorders, bipolar depression, and migraine. In vivo, valproate is metabolized oxidatively by cytochromes P450 and beta-oxidation, as well as conjugatively via glucuronidation. The acyl glucuronide conjugate
Md Ashrafuzzaman et al.
Biochimica et biophysica acta, 1778(12), 2814-2822 (2008-09-24)
We examined the permeabilization of lipid bilayers by the beta-sheet, cyclic antimicrobial decapeptide gramicidin S (GS) in phospholipid bilayers formed either by mixtures of zwitterionic diphytanoylphosphatidylcholine and anionic diphytanoylphosphatidylglycerol or by single zwitterionic unsaturated phosphatidylcholines having various hydrocarbon chain lengths
Elena N Dedkova et al.
The Journal of physiology, 587(Pt 4), 851-872 (2008-12-24)
We used laser scanning confocal microscopy in combination with the nitric oxide (NO)-sensitive fluorescent dye DAF-2 and the reactive oxygen species (ROS)-sensitive dyes CM-H(2)DCF and MitoSOX Red to characterize NO and ROS production by mitochondrial NO synthase (mtNOS) in permeabilized
Mari Aidemark et al.
BMC plant biology, 9, 27-27 (2009-03-17)
The cell wall component callose is mainly synthesized at certain developmental stages and after wounding or pathogen attack. Callose synthases are membrane-bound enzymes that have been relatively well characterized in vitro using isolated membrane fractions or purified enzyme. However, little

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