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1246298-62-3

1246298-62-3 Structure

1246298-62-3 Structure
IdentificationBack Directory
[Name]

Di[3-deoxy-D-Manno-octulosonyl]-lipid A (aMMoniuM salt)
[CAS]

1246298-62-3
[Synonyms]

Kdo2-Lipid A
Kdo2-Lipid A (KLA)
Kdo2-Lipid A ammonium
Di[3-deoxy-D-Manno-octulosonyl]-lipid A (aMMoniuM salt)
DI[3-DEOXY-D-MANNO-OCTULOSONYL]-LIPID A (AMMONIUM SALT);KDO2-LIPID A
Di[3-deoxy-D-manno-octulosonyl]-lipid A sodium salt - 0.5mg/ml aqueous solution
O-3-Deoxy-alpha-D-altro-2-octulopyranosonosyl-(2-4)-O-3-deoxy-alpha-D-altro-2-octulopyranosonosyl-(2-6)-O-2-deoxy-2-[[(3R)-1-oxo-3-[(1-oxododecyl)oxy]tetradecyl]amino]-3-O-[(3R)-1-oxo-3-[(1-oxotetradecyl)oxy]tetradecyl]-4-O-phosphono-beta-D-glucopyranosyl-(1-6)-2-deoxy-2-[[(3R)-3-hydroxy-1-oxotetradecyl]amino]-alpha-D-glucopyranose 1-(dihydrogen phosphate) 3-[(3R)-3-hydroxytetradecanoate] ammonium salt (1:4)
[Molecular Formula]

C110H214N6O39P2
[MDL Number]

MFCD22416704
[MOL File]

1246298-62-3.mol
[Molecular Weight]

2306.84
Chemical PropertiesBack Directory
[storage temp. ]

-20°C
[form ]

solid
[color ]

White to off-white
[biological source]

Escherichia coli
Safety DataBack Directory
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

Kdo2-Lipid A (KLA) has been used:
  • as a toll like receptor (TLR) ligand source in immortalized murine macrophage culture media
  • in 2H-,13C-,15N-labeled OprHΔL1ΔL4 in 1,2-dihexanoyl-sn-glycero-3-phosphocholine (DHPC) micelles, to determine the specific residues of OprHΔL1ΔL4 interacting with lipopolysaccharides (LPS) source
  • as a component of LPS stock to study its role in lipopolysaccharide induced prion protein conversion

[Uses]

Kdo2-Lipid A (KLA) is a nearly homogeneous Re lipopolysaccharide (LPS) substracture with endotoxin activity equal to tha of native LPS. KLA is comparable to LPS and its activity is reduced by >10^3 in cells fro TLR-4 deficient mice.
[General Description]

3-deoxy-D-manno-octulosonic acid (Kdo2-Lipid A) is the essential component of lipopolysaccharide in most Gram-negative bacteria and the minimal structural component to sustain bacterial viability. It serves as the active component of lipopolysaccharide to stimulate potent host immune responses through the complex of Toll-like-receptor 4 (TLR4) and myeloid differentiation protein 2 (MD2). Therefore, Kdo2-lipid A is an important stimulator for studying the mechanism of the innate immune system and for developing bacterial vaccine adjuvants. Kdo2 Lipid A/TLR4 antagonists can also be applied in anti-inflammatory interventions. Kdo2-lipid A, induces de novo sphingolipid biosynthesis in RAW264.7 macrophages, which is essential for induction of autophagy. Kdo2-Lipid A has been used in animal atherosclerosis model.
[Biochem/physiol Actions]

Kdo2-Lipid A might be useful to stimulate inflammatory response.
[in vivo]

KDO2-Lipid A (i.t.) activates toll-like receptor 4 (TLR4) in rats[1].

Animal Model:Rats (Male Holzman Sprague-Dawley, 300–400 g) [1]
Dosage:0.1 to 10 μg
Administration:I.T.; 0.1-10 μg; prior and 15, 30, 60, 90 and 120 min after injection of Kdo2-Lipid A.
Result:Intrathecal injection of 1 μg Kdo2-Lipid A induces allodynia, and the animals appeared to be sick after i.t. injection of Kdo2-Lipid A.
[IC 50]

TLR4
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