95991-05-2

Basic information

• Product Name: LIPID A, DIPHOSPHORYL FROM ESCHERICHIA COLI F-583 (RD MUTANT)
• Synonyms: LIPID A, DIPHOSPHORYL FROM ESCHERICHIA COLI F-583 (RD MUTANT);LIPID A, DIPHOSPHORYL FROM SALMONELLA MINNESOTA RE-595 (R MUTANTS);LIPID A, DIPHOSPHORYL FROM SALMONELLA*MI NNESOTA RE-;lipid a, diphosphoryl from salmonella enterica serotype minnesota re 595 (re mutant);lipid A, diphosphoryl
• CAS NO: 95991-05-2
• Molecular Formula: H4O7P2
• Molecular Weight: 177.975082
• Product Categories: Complex Lipids;Glycolipids;Others
• Mol File: 95991-05-2.mol
• Article Data: 5

Chemical Properties

• Appearance: White to tan powder
• Density: 1.13±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 1.73±0.10(Predicted)
• CAS DataBase Reference: LIPID A, DIPHOSPHORYL FROM ESCHERICHIA COLI F-583 (RD MUTANT)(CAS DataBase Reference)
• NIST Chemistry Reference: LIPID A, DIPHOSPHORYL FROM ESCHERICHIA COLI F-583 (RD MUTANT)(95991-05-2)
• EPA Substance Registry System: LIPID A, DIPHOSPHORYL FROM ESCHERICHIA COLI F-583 (RD MUTANT)(95991-05-2)

Safety Data

• Hazard Codes: Xn
• WGK Germany: 3
• Hazardous Substances Data: 95991-05-2(Hazardous Substances Data)

Usage

Description

Lipid A, diphosphoryl from Escherichia coli F-583 (RD mutant) is a modified form of the lipopolysaccharide (LPS) component found in the outer membrane of gram-negative bacteria. It plays a crucial role in the immune response and has been extensively studied for its potential applications in various fields.

Uses

Used in Biomedical Research:
Lipid A, diphosphoryl from Escherichia coli F-583 (RD mutant) is used as a research tool for studying the effect of various lipid A molecules on lung pericyte proliferation in vitro. This helps in understanding the underlying mechanisms of cell growth and proliferation.
Used in Cell Line Studies:
This lipid A derivative is used in testing on THP-1 and J774A.1 cells for neopterin and nitrite formation, respectively. These tests are essential for evaluating the immune response and inflammatory processes in these cell lines.
Used in Binding Experiments:
Lipid A, diphosphoryl from Escherichia coli F-583 (RD mutant) is used as a lipopolysaccharide (LPS) derivative in binding experiments. This helps in investigating the interactions between LPS and various cellular receptors, such as toll-like receptor 4 (TLR4), which play a significant role in the immune response.
Used in Immunological Applications:
This lipid A variant is used to stimulate spleen cells and acts as a mitogen, which can activate the immune system. This application is crucial for studying the immune response and developing potential therapeutic strategies for various diseases.

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.

Upstream product

• 96020-49-4 C₁₄₂H₂₁₈N₂O₂₆P₂ 
• 230966-96-8 C₁₄₄H₂₂₀N₂O₂₅P₂ 

Relevant articles and documents

Nuclear magnetic resonance of lipid A - The influence of solvents on spin relaxation and spectral quality

Nuclear magnetic resonance (NMR) spectroscopy of lipid A is limited by rapid transversal relaxation and subsequent line broadening caused by the tendency of these glycolipids to form aggregates in all solvents. To examine the influence of solvents on NMR spectra, hexa-acyl lipid A from Escherichia coli F515 was investigated. Line widths at half height, longitudinal relaxation times, and transversal relaxation times were measured in different solvents, lipid A concentrations, and temperatures. Chloroform-d, dioxane-d8, and pyridine-d5 each mixed with 25% methanol-d4 as well as sole DMSO-d6 and 0.1M triethylamine-d15 (TEA-d 15) in D2O caused good spectral resolutions and allowed structure analysis. ROESY and HMBC spectra gave an insight into the influence of transversal relaxation times on spectral quality in two-dimensional spectra. Solvent depending differences of interglycosidic NOEs indicated dissimilarities of the conformations in the interglycosidic linkage and allowed conclusions about the lipid A solution state.

A divergent synthesis of lipid A and its chemically stable unnatural analogues

Lipid A and its two chemically stable analogues, wherein the glycosidic phosphoryl groups in lipid A is replaced with 2-(phosphonooxy)ethyl or carboxymethyl groups, have been synthesized by an improved and divergent route via a common allyl glycoside intermediate in which the 4-hydroxy group was protected as a benzyl ether. The total yields were more than 20% for 11 or 12 steps starting from allyl 4,6-O-benzylidene-2-deoxy-2- (trichloroethoxycarbonylamino)-D-glucopyranoside. These synthetic chemically stable analogues induce interleukin-6 and tumor necrosis factor a in human peripheral whole blood cells with potencies comparable to those by natural- type synthetic lipid A. The Limulus activities of both analogues were found to be even stronger than the activity of the natural-type one.

TOTAL SYNTHESIS OF ESCHERICHIA COLI LIPID A

The first total synthesis of E. coli lipid A (1) is described.The synthetic compound was identical with a natural specimen and exhibited the full endotoxic activity.It was thus conclusively proved by this chemical synthesis that lipid A is the active prin