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SML2430

Sigma-Aldrich

Kdo2-Lipid A (KLA)

≥90% (HPLC)

Synonym(s):

Di[3-deoxy-D-manno-octulosonyl]-lipid A (ammonium salt), KLA, Kdo2-LipidA

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About This Item

Empirical Formula (Hill Notation):
C110H202N2O39P2 · xNH3
CAS Number:
Molecular Weight:
2238.72 (free acid basis)
UNSPSC Code:
12352211
NACRES:
NA.77

biological source

Escherichia coli

assay

≥90% (HPLC)

form

solid

storage temp.

−20°C

SMILES string

O=C(O)[C@@]1(O[C@H]2[C@@H](O)C([C@H](O)CO)O[C@](C(O)=O)(OC[C@H]3O[C@@H](OC[C@H]4O[C@H](OP(O)(O)=O)[C@@H](NC(C[C@@H](CCCCCCCCCCC)O)=O)C(OC(C[C@@H](CCCCCCCCCCC)O)=O)[C@H]4O)C(NC(C[C@@H](CCCCCCCCCCC)OC(CCCCCCCCCCC)=O)=O)[C@@H](OC(C[C@@H](CCCCCCCCCCC)OC(CCCCC

Related Categories

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.

Other Notes

Solubility: Kdo2 -Lipid A can be dissolved in a solution of 0.1-0.5% Triethylamine (Sigma Cat# 90335) at 1 mg/ml (In case of percipitation use sonication). Use sonication to directly solublized in cell culture medium. Storage: Once Kdo2-lipidA is dissolved in 0.1-0.5% Triethylamine (Sigma Cat# 90335) aliquot and store at -20°C. The solution is stable for 2 months in -20°C.

wgk_germany

WGK 3

flash_point_f

No data available

flash_point_c

No data available


Certificates of Analysis (COA)

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Kacee Sims et al.
The Journal of biological chemistry, 285(49), 38568-38579 (2010-09-30)
Activation of RAW264.7 cells with a lipopolysaccharide specific for the TLR4 receptor, Kdo(2)-lipid A (KLA), causes a large increase in cellular sphingolipids, from 1.5 to 2.6 × 10(9) molecules per cell in 24 h, based on the sum of subspecies
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The LIPID MAPS Consortium (www.lipidmaps.org) is developing comprehensive procedures for identifying all lipids of the macrophage, following activation by endotoxin. The goal is to quantify temporal and spatial changes in lipids that occur with cellular metabolism and to develop bioinformatic

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