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Merck
CN

S6946

Sigma-Aldrich

Syringomycin E

from Pseudomonas syringae B-301D, >95% (HPLC), solution

Synonym(s):

SR-E

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About This Item

Empirical Formula (Hill Notation):
C53H85ClN14O17
CAS Number:
124888-22-8
Molecular Weight:
1225.78
UNSPSC Code:
12352200
PubChem Substance ID:
24899726

Key Documents

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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

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

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

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.

Storage Class Code

12 - Non Combustible Liquids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
086K4000

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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
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
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
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
Yang Ju Im et al.
FEMS microbiology letters, 223(2), 199-203 (2003-06-28)
Both bacterial cyclic lipodepsipeptide syringomycin E and plant defensin DmAMP1 were shown previously to require expression of the yeast gene IPT1 for fungicidal action against Saccharomyces cerevisiae. IPT1 encodes a sphingolipid biosynthetic pathway glycotransferase that produces the terminal sphingolipid mannosyldiinositolphosphoceramide.
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Data Sheet - S6946

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