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Syringomycin E

Catalog No. S6946 Name Sigma Aldrich
CAS Number 124888-22-8 Website http://www.sigmaaldrich.com
M. F. C53H85ClN14O17 Telephone 1-800-521-8956
M. W. 1225.7786 Fax
Purity >95% (HPLC) Email
Storage Chembase ID: 154036

SYNONYMS

IUPAC name
2-[(3S,6R,12S,15S,18S,21S,24S,27S)-18,21-bis(2-aminoethyl)-12-benzyl-3-[(1S)-2-chloro-1-hydroxyethyl]-15-{3-[(diaminomethylidene)amino]propyl}-24-(hydroxymethyl)-27-(3-hydroxyundecanamido)-2,5,8,11,14,17,20,23,26-nonaoxo-9-propylidene-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosan-6-yl]-2-hydroxyacetic acid
IUPAC Traditional name
[(3S,6R,12S,15S,18S,21S,24S,27S)-18,21-bis(2-aminoethyl)-12-benzyl-3-[(1S)-2-chloro-1-hydroxyethyl]-15-{3-[(diaminomethylidene)amino]propyl}-24-(hydroxymethyl)-27-(3-hydroxyundecanamido)-2,5,8,11,14,17,20,23,26-nonaoxo-9-propylidene-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosan-6-yl](hydroxy)acetic acid
Synonyms
SR-E

DATABASE IDS

CAS Number 124888-22-8
PubChem SID 24899726
EC Number 231-791-2

PROPERTIES

Storage Temperature -20°C
MSDS Link Download
Personal Protective Equipment Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
Biological Source from Pseudomonas syringae B-301D
Empirical Formula (Hill Notation) C53H85ClN14O17
Purity >95% (HPLC)
Shipped in dry ice
Apperance solution

DETAILS

Description (English)
Physical form
Supplied as a 0.5 mg/mL solution in 1 mM hydrochloric acid.
Biochem/physiol Actions
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.
Specifications
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
Description (简体中文)
Physical form
Supplied as a 0.5 mg/mL solution in 1 mM hydrochloric acid.
Biochem/physiol Actions
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.
Specifications
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

REFERENCES