Key Documents

View All Documentation

L5399

Lipid A, diphosphoryl from Escherichia coli F583 (Rd mutant)

Name: Lipid A, diphosphoryl from <I>Escherichia coli</I> F583 (Rd mutant)
Brand: SIGMA

Synonym(s):

Diphosphoryl Lipid A from E.Coli.

Select a Size

Change View

About This Item

NACRES:

NA.25

PubChem Substance ID:

24896402

UNSPSC Code:

12352211

MDL number:

MFCD00131510

Technical Service

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

Let Us Assist

biological source

Escherichia coli (F583 Rd mutant)

Quality Level

200

form

lyophilized powder

shipped in

ambient

storage temp.

2-8°C

SMILES string

CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)C(OCC2OC(OP(O)(O)=O)C(NC(=O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)OC(CO)C1OP(O)(O)=O

InChI

1S/C94H178N2O25P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)115-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)119-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)114-83(102)67-61-55-49-43-36-30-24-18-12-6)93(116-79(73-97)90(92)120-122(107,108)109)113-74-80-89(106)91(118-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(94(117-80)121-123(110,111)112)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-94,97-99,106H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,107,108,109)(H2,110,111,112)

InChI key

GZQKNULLWNGMCW-UHFFFAOYSA-N

Related Categories

Biochemicals

Chemistry & Biochemicals

General description

Lipid A is the fundamental structure of lipopolysaccharides (LPS), present in bacteria.

Application

Lipid A, diphosphoryl from Escherichia coli F583 (Rd mutant) has been used:

to study the effect of various lipid A molecules on lung pericyte proliferation in vitro
to test on THP-1 and J774A.1 cells for neopterin and nitrite formation respectively
as lipopolysaccharides (LPS) derivatives in binding experiments
to stimulate the spleen cells and as a mitogen stimulation for toll like receptor 4 (TLR4)

Biochem/physiol Actions

Lipid A is mainly essential for the robust immunostimulatory activities of lipopolysaccharides (LPS) in human. Lipid A is the hydrophobic domain of LPS helps in anchoring LPS to the plasma membrane of bacteria. It is immunologically active and an important constituent of LPS recognised by immune system.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

0000486028

0000406510

0000367391

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

Tumor regression caused by endotoxins and mycobacterial fractions.

E E Ribi et al.

Journal of the National Cancer Institute, 55(5), 1253-1257 (1975-11-01)

A transplantable hepatocarcinoma of guinea pigs was used as an experimental model for immunotherapy of cancer. Earlier work showed that complete regression of 6- to 7-day-old tumors could be obtained in about 60% of cases by inoculation of the tumors

Purification and structural determination of nontoxic lipid A obtained from the lipopolysaccharide of Salmonella typhimurium.

N Qureshi et al.

The Journal of biological chemistry, 257(19), 11808-11815 (1982-10-10)

Endotoxin extracted from the heptose-less mutant of Salmonella typhimurium was hydrolyzed in 0.1 N HCl in methanol/water (1:1, v/v) at 100 degrees C to yield lipid A, which was then fractionated on a Sephadex LH-20 column to yield a major

Position of ester groups in the lipid A backbone of lipopolysaccharides obtained from Salmonella typhimurium.

N Qureshi et al.

The Journal of biological chemistry, 258(21), 12947-12951 (1983-11-10)

Lipopolysaccharides extracted from the heptoseless mutant of Salmonella typhimurium G30/C21 were hydrolyzed with either 0.1 N HCl at 100 degrees C or treated twice with 20 mM sodium acetate, pH 4.5, at 100 degrees C for 45 min and finally

Enhancement of endotoxic shock by N-acetylmuramyl-L-alanyl-(L-seryl)-D-isoglutamine (muramyl dipeptide).

E E Ribi et al.

Cancer research, 39(11), 4756-4759 (1979-11-01)

We described elsewhere that the synergistic antitumor activity of endotoxic extracts from Re mutants of gram-negative bacteria and trehalose mycolate against guinea pig syngeneic line 10 tumor was abrogated after peptide substances accompanying these extracts had been removed. This activity

Shiga toxin-associated hemolytic uremic syndrome: combined cytotoxic effects of shiga toxin and lipopolysaccharide (endotoxin) on human vascular endothelial cells in vitro.

C B Louise et al.

Infection and immunity, 60(4), 1536-1543 (1992-04-01)

This study explores the in vitro relationship between Shiga toxin-producing Shigella spp. and Escherichia coli and the development of vascular complications in humans following bacillary dysentery. We propose that lipopolysaccharide (LPS; endotoxin) may combine with Shiga toxin to facilitate vascular

View All Related Papers

Global Trade Item Number

SKU	GTIN
L5399-1MG	04061826677414
L5399-5MG	04061833274972

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service