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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.

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About This Item

NACRES:

NA.25

PubChem Substance ID:

24896402

UNSPSC Code:

12352211

MDL number:

MFCD00131510

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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)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

L5399-1MG: + L5399-5MG-PW: + L5399-1MG-PW: + L5399-BULK: + L5399-VAR: + L5399-5MG:

jan

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Adipokinetic hormone enhances nodule formation and phenoloxidase activation in adult locusts injected with bacterial lipopolysaccharide.

Graham Goldsworthy et al.

Journal of insect physiology, 49(8), 795-803 (2003-07-26)

Interactions between the locust endocrine and immune systems have been studied in vivo in relation to nodule formation and activation of the prophenoloxidase cascade in the haemolymph. Injection of bacterial lipopolysaccharide (LPS) extracted from Escherichia coli induces nodule formation in

Biological activities of lipid A complexed with bovine-serum albumin.

C Galanos et al.

European journal of biochemistry, 31(2), 230-233 (1972-12-04)

Effects of Endotoxin on Lung Pericytesin Vitro

Khoury J and Langleben D

Microvascular Research, 56(2), 71-84 (1998)

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

Attacin-an insect immune protein-binds LPS and triggers the specific inhibition of bacterial outer-membrane protein synthesis

Carlsson A, et al.

Microbiology, 144(8), 2179-2188 (1998)

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