生物来源
Pseudomonas syringae B-301D
方案
>95% (HPLC)
表单
solution
抗生素抗菌谱
fungi
作用机制
cell membrane | interferes
运输
dry ice
储存温度
−20°C
SMILES字符串
[H]\C(CC)=C1\NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CCC\N=C(\N)N)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CO)NC(=O)[C@H](COC(=O)[C@@]([H])(NC(=O)[C@H](NC1=O)[C@H](O)C(O)=O)[C@H](O)CCl)NC(=O)CC(O)CCCCCCCC
InChI
1S/C53H85ClN14O17/c1-3-5-6-7-8-12-17-30(70)25-39(72)60-37-28-85-52(84)40(38(71)26-54)67-50(81)41(42(73)51(82)83)68-46(77)31(14-4-2)61-47(78)35(24-29-15-10-9-11-16-29)65-43(74)32(18-13-23-59-53(57)58)62-44(75)33(19-21-55)63-45(76)34(20-22-56)64-48(79)36(27-69)66-49(37)80/h9-11,14-16,30,32-38,40-42,69-71,73H,3-8,12-13,17-28,55-56H2,1-2H3,(H,60,72)(H,61,78)(H,62,75)(H,63,76)(H,64,79)(H,65,74)(H,66,80)(H,67,81)(H,68,77)(H,82,83)(H4,57,58,59)/b31-14-/t30?,32-,33-,34-,35-,36-,37-,38+,40-,41+,42?/m0/s1
InChI key
YMFYPHGOLKNWQN-WMJMADPPSA-N
应用
Syringomycin E from Pseudomonas syringae may be used in proton pumps and membrane potential studies.
生化/生理作用
Phytotoxin of the cyclic lipodepsinonapeptides class. Potent biosurfactant, which is toxic to many plants and fungi and is implicated as a virulence factor in several major plant diseases. Inhibits the growth of several yeast strains including Rhodotorula pilimanae and Saccharomyces cerevisiae and is also effective against human pathogenic fungi.
Syringomycin E (SR-E) is a phytotoxin of the cyclic lipodepsinonapeptides class composed of a 3-hydroxy fatty acid tail attached to a polar peptide head that contains nine amino acid residues. SR-E is a potent biosurfactant, which is toxic to many plants and fungi and is implicated as a virulence factor in several major plant diseases such as holcus spot disease of maize and bacterial canker of stone fruits. Syringomycin E inhibits the growth of several yeast strains including Rhodotorula pilimanae and Saccharomyces cerevisiae and is also effective against human pathogenic fungi. Syringomycin E targets the plant and fungal plasma membrane altering several of its functions such as membrane potential, protein phosphorylation, H+-ATPase activity, and ion fluxes. All of these effects are related to SR-E pore formation in the host membrane. At least six molecules of syringomycin E compose a channel with a radius of ~1 nm and individual channels can become aggregated into clusters that exhibit synchronous opening and closing. Remarkably, the host membrane composition influences the sensitivity to syringomycin E and membrane lipids directly participate in the channel gating. Syringomycin E is reported to cause lysis of erythrocytes of different origin.
特点和优势
2-[(3S,6S,12S,15S,18S,21S,24S,27S)-18,21-Bis(2-aminoethyl)-12-benzyl-3-[(1R)-2-chloro-1-hydroxy-ethyl]-15-[3-(diaminomethylideneamino)propyl]-24-(hydroxymethyl)-27-(3-hydroxyundecanoylamino)-2,5,8,11,14,17,20,23,26-nonaoxo-9-propylidene-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-6-yl]-2-hydroxy-acetic acid
外形
Supplied as a 0.5 mg/mL solution in 1 mM hydrochloric acid.
储存分类代码
12 - Non Combustible Liquids
WGK
WGK 1
闪点(°F)
Not applicable
闪点(°C)
Not applicable
个人防护装备
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
法规信息
新产品
此项目有
Ludmila V Schagina et al.
Bioelectrochemistry (Amsterdam, Netherlands), 60(1-2), 21-27 (2003-08-02)
To elucidate the voltage gating of syringomycin E (SRE) ion channels in lipid bilayers, the effective gating charge q was measured under different conditions. It was shown that q and its sign are dependent on membrane surface charge, dipole potential
Sheri Woo et al.
Antonie van Leeuwenhoek, 81(1-4), 353-356 (2002-11-27)
The interactions between biocontrol fungi and bacteria may play a key role in the natural process of biocontrol, although the molecular mechanisms involved are still largely unknown. Synergism can occur when different agents are applied together, and cell wall degrading
Frédéric H Vaillancourt et al.
Proceedings of the National Academy of Sciences of the United States of America, 102(29), 10111-10116 (2005-07-09)
The nine-residue lipodepsipeptide syringomycin E, elaborated as a phytotoxin by Pseudomonas syringae pv. syringae B301D contains a 4-Cl-L-Thr-9 moiety where failure to chlorinate results in a 3-fold drop in biological activity. The proteins SyrB1 and SyrB2 encoded by the biosynthetic
Andrey N Bessonov et al.
European biophysics journal : EBJ, 35(5), 382-392 (2006-02-14)
The bacterial lipodepsipeptide syringomycin E (SRE) added to one (cis-) side of bilayer lipid membrane forms voltage dependent ion channels. It was found that G-actin increased the SRE-induced membrane conductance due to formation of additional SRE-channels only in the case
Zsófia Szabó et al.
Biochimica et biophysica acta, 1660(1-2), 118-130 (2004-02-06)
Interaction of pore-forming toxins, syringopeptin22A (SP22A), syringomycin E (SRE) and syringotoxin (ST), with model membranes were investigated. Liposomes were prepared from saturated phospholipids (DPPC or DMPC) or from binary mixtures of DPPC with varying amount of DOPC or cholesterol. The
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