Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

Safety Information

L5399

Sigma-Aldrich

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

Synonym(s):

Diphosphoryl Lipid A from E.Coli.

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

MDL number:
MFCD00131510
UNSPSC Code:
12352211
PubChem Substance ID:
24896402
NACRES:
NA.25

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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.

JAN Code

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
099M4055V
12190417
039M4043V
12180801
028M4081V

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

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)
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)
View All Related Papers

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