P0503

O-Phosphorylethanolamine

Name: <I>O</I>-Phosphorylethanolamine
Brand: SIGMA

Synonym(s):

2-Aminoethyl dihydrogen phosphate, O-Phosphocolamine, O-Phosphoethanolamine, Colaminephosphoric acid

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About This Item

Linear Formula:

NH₂CH₂CH₂OPO₃H₂

CAS Number:

1071-23-4

Molecular Weight:

141.06

UNSPSC Code:

12161700

NACRES:

NA.25

PubChem Substance ID:

24898109

EC Number:

213-988-5

Beilstein/REAXYS Number:

1758916

MDL number:

MFCD00008178

InChI key

SUHOOTKUPISOBE-UHFFFAOYSA-N

InChI

1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)

SMILES string

NCCOP(O)(O)=O

form

powder

storage temp.

−20°C

Quality Level

200

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Application

O-Phosphorylethanolamine has been used:

in LHC-8 medium as a supplement in culturing the transformed human liver epithelial (THLE)-2 and THLE-3 cells
in C-reactive protein (CRP) binding sucrose flotation experiment
to incubate phosphomonoesters with anion-exchange chromatography (AEC) fractions for the detection of phosphatase activity
to add in the washed beads for the preparation of phosphorylethanolamine (Pet) -conjugated sepharose column for chromatographic purification of mutant CRP

Biochem/physiol Actions

Phosphorylethanolamine participates in phospholipid metabolism. Its release can be stimulated occasionally by depolarizing stimuli. Reduction of phosphorylethanolamine levels has been observed in Alzheimer′s and Huntington′s disease.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Phosphoethanolamine-complexed C-reactive protein: a pharmacological-like macromolecule that binds to native low-density lipoprotein in human serum

Singh SK, et al.

Clinica Chimica Acta; International Journal of Clinical Chemistry, 394(1-2), 94-98 (2008)

The phosphocholine-binding pocket on C-reactive protein is necessary for initial protection of mice against pneumococcal infection

Gang TB, et al.

Test, jbc-M112 (2012)

Phosphoethanolamine and ethanolamine are decreased in Alzheimer's disease and Huntington's disease

Ellison David W, et al.

Brain Research, 417(2), 389-392 (1987)

Novel Phospholipase A activity secreted byLegionella species

Flieger A, et al.

Journal of Bacteriology, 182(5), 1321-1327 (2000)

Cyclotides insert into lipid bilayers to form membrane pores and destabilize the membrane through hydrophobic and phosphoethanolamine-specific interactions.

Conan K Wang et al.

The Journal of biological chemistry, 287(52), 43884-43898 (2012-11-07)

Cyclotides are a family of plant-derived circular proteins with potential therapeutic applications arising from their remarkable stability, broad sequence diversity, and range of bioactivities. Their membrane-binding activity is believed to be a critical component of their mechanism of action. Using

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