Key Documents

View All Documentation

S6946

Syringomycin E

Name: Syringomycin E
Brand: SIGMA

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

Synonym(s):

SR-E

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₅₃H₈₅ClN₁₄O₁₇

CAS Number:

124888-22-8

Molecular Weight:

1225.78

PubChem Substance ID:

24899726

UNSPSC Code:

12352200

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

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

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)

Regulatory Information

新产品

This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

086K4000

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Actin and amphiphilic polymers influence on channel formation by Syringomycin E in lipid bilayers.

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

Dichlorination and bromination of a threonyl-S-carrier protein by the non-heme Fe(II) halogenase SyrB2.

Frédéric H Vaillancourt et al.

Chembiochem : a European journal of chemical biology, 7(5), 748-752 (2006-03-11)

Effective gating charge of ion channels induced by toxin syringomycin E in lipid bilayers.

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

Molecular dynamics of the cyclic lipodepsipeptides' action on model membranes: effects of syringopeptin22A, syringomycin E, and syringotoxin studied by EPR technique.

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

IPT1-independent sphingolipid biosynthesis and yeast inhibition by syringomycin E and plant defensin DmAMP1.

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.

View All Related Papers