Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

L0774

Sigma-Aldrich

Lipid A, diphosphoryl from Salmonella enterica serotype minnesota Re 595 (Re mutant)

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

CAS Number:
95991-05-2
MDL number:
MFCD00131510
UNSPSC Code:
12352211
PubChem Substance ID:
24896265
NACRES:
NA.25

biological source

Salmonella enterica (serotype minnesota Re 595 Re mutant)

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

Application

Lipid A molecules compose the lipid membrane anchoring core components of endotoxins produced by Gram-negative bacteria. Lipid A molecules induce immune responses. Structually, lipid A molecules are composed of two glucosamine unites with varied, species dependent, fatty acyl chain number and identity and degree of phosphorylation.
Lipid A, diphosphoryl from Salmonella entericaserotype Minnesota Re 595 may be used in comparative assessment of the antigenicity of specific structures within different LPA molecules and analogues.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
019M4139V
12151001
046M4037V
087M4065V
074M4025V

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

Hayat Zerrouki et al.
PloS one, 10(3), e0116083-e0116083 (2015-04-04)
Lipid A is a major hydrophobic component of lipopolysaccharides (endotoxin) present in the membrane of most Gram-negative bacteria, and the major responsible for the bioactivity and toxicity of the endotoxin. Previous studies have demonstrated that the late afterglow region of
Natsuko Tanimura et al.
International immunology, 26(6), 307-314 (2014-01-02)
TLR4/MD-2 senses lipid A, activating the MyD88-signaling pathway on the plasma membrane and the TRIF-signaling pathway after CD14-mediated TLR4/MD-2 internalization into endosomes. Monophosphoryl lipid A (MPL), a detoxified derivative of lipid A, is weaker than lipid A in activating the
H Takada et al.
Critical reviews in microbiology, 16(6), 477-523 (1989-01-01)
For the past ten years, several groups were engaged in synthetic studies of lipid A, namely the lipid portion of bacterial lipopolysaccharides (LPS) that has been assumed to be the bioactive center of LPS, but has not been unanimously approved.
J Y Homma et al.
Advances in experimental medicine and biology, 256, 101-119 (1990-01-01)
Some synthetic compounds of the nonreducing part of lipid A were found to preserve significant immunopharmacological activities of the endotoxin, at the same time showing very slight if any endotoxic activity such as pyrogenicity lethality or Shwartzman reactivity. Thus, divers
D S Kabanov et al.
Biochemistry. Biokhimiia, 75(4), 383-404 (2010-07-14)
This review covers data on composition and structure of lipid A, core, and O-polysaccharide of the known lipopolysaccharides from Gram-negative bacteria. The relationship between the structure and biological activity of lipid A is discussed. The data on roles of core
View All Related Papers

Questions

Reviews

No rating value

Active Filters

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