S6946
Syringomycin E
from Pseudomonas syringae B-301D, >95% (HPLC), solution
别名:
SR-E
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关于此项目
经验公式（希尔记法）:
C53H85ClN14O17
化学文摘社编号:
分子量:
1225.78
PubChem Substance ID:
UNSPSC Code:
12352200
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
SMILES string
[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
biological source
Pseudomonas syringae B-301D
assay
>95% (HPLC)
form
solution
antibiotic activity spectrum
fungi
mode of action
cell membrane | interferes
shipped in
dry ice
storage temp.
−20°C
Application
Syringomycin E from Pseudomonas syringae may be used in proton pumps and membrane potential studies.
Biochem/physiol Actions
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.
Features and Benefits
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
Physical form
Supplied as a 0.5 mg/mL solution in 1 mM hydrochloric acid.
存储类别
12 - Non Combustible Liquids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
法规信息
新产品
此项目有
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
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
E Mátyus et al.
European biophysics journal : EBJ, 35(6), 459-467 (2006-03-18)
Syringomycin-E (SR-E) is a cyclic lipodepsinonapeptide produced by certain strains of the bacterium Pseudomonas syringae pv. syringae. It shows inhibitory effects against many fungal species, including human pathogens. Its primary biological target is the plasma membrane, where it forms channels
Olga S Ostroumova et al.
FEBS letters, 581(5), 804-808 (2007-02-10)
To probe the size of the ion channel formed by Pseudomonas syringae lipodepsipeptide syringomycin E, we use the partial blockage of ion current by penetrating poly(ethylene glycol)s. Earlier experiments with symmetric application of these polymers yielded a radius estimate of
Vincenzo Fogliano et al.
Molecular plant-microbe interactions : MPMI, 15(4), 323-333 (2002-05-25)
Pseudomonas syringae pv. syringae strain B359 secreted two main lipodepsipeptides (LDPs), syringomycin E (SRE) and syringopeptin 25A (SP25A), together with at least four types of cell wall-degrading enzymes (CWDEs). In antifungal bioassays, the purified toxins SRE and SP25A interacted synergistically
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