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S6946

Syringomycin E

Name: Syringomycin E
Brand: SIGMA

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:

124888-22-8

分子量:

1225.78

PubChem Substance ID:

24899726

UNSPSC Code:

12352200

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属性

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

说明

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

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

086K4000

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