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Phosphocholine

From Wikipedia, the free encyclopedia
Not to be confused withphosphatidylcholine.
Phosphocholine
Skeletal formula
Ball-and-stick model
Names
Other names
Choline phosphate
Identifiers
3D model (JSmol)
ChemSpider
MeSHPhosphocholine
UNII
  • InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9) ☒N
    Key: YHHSONZFOIEMCP-UHFFFAOYSA-N ☒N
  • InChI=1/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)
    Key: YHHSONZFOIEMCP-UHFFFAOYAD
  • C[N+](C)(C)CCOP(=O)(O)[O-]
Properties
C5H15NO4P
Molar mass184.151 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Phosphocholine is an intermediate in the synthesis ofphosphatidylcholine in tissues. Phosphocholine is made in a reaction, catalyzed bycholine kinase, that convertsATP andcholine into phosphocholine andADP. Phosphocholine is a molecule found, for example, inlecithin.

Innematodes and humanplacentas, phosphocholine is selectively attached to other proteins as aposttranslational modification to suppress an immune response by their hosts.[1][2]

It is also one of the binding targets ofC-reactive protein (CRP).[3] Thus, when a cell is damaged, CRP binds to phosphocholine, beginning the recognition and phagocytotic immunologic response.

Phosphocholine is a natural constituent of hens' eggs (and many other eggs) often used in biomimetic membrane studies.[4][5]

See also

[edit]

References

[edit]
  1. ^Lovell TM, Woods RJ, Butlin DJ, et al. (September 2007)."Identification of a novel mammalian post-translational modification, phosphocholine, on placental secretory polypeptides".Journal of Molecular Endocrinology.39 (3):189–98.doi:10.1677/JME-07-0007.PMC 2189575.PMID 17766644.
  2. ^"Placenta 'fools body's defences'".BBC News. 2007-11-10. Retrieved2010-05-22.
  3. ^Thompson D, Pepys MB, Wood SP (1999)."The physiological structure of human C-reactive protein and its complex with phosphocholine".Structure.7 (2):169–77.doi:10.1016/S0969-2126(99)80023-9.PMID 10368284.
  4. ^Rose L, Jenkins AT (2006). "The effect of the ionophore valinomycin on biomimetic solid supported lipid DPPTE/EPC membranes".Bioelectrochemistry.70 (2):387–93.doi:10.1016/j.bioelechem.2006.05.009.PMID 16875886.
  5. ^Pambou, Elias; Crewe, John; Yaseen, Mohammed; Padia, Faheem N.; Rogers, Sarah; Wang, Dong; Xu, Hai; Lu, Jian R. (2015-09-15). "Structural Features of Micelles of Zwitterionic Dodecyl-phosphocholine (C12PC) Surfactants Studied by Small-Angle Neutron Scattering".Langmuir.31 (36):9781–9789.doi:10.1021/acs.langmuir.5b02077.ISSN 0743-7463.PMID 26301341.

External links

[edit]
General
N terminus
C terminus
Single specificAAs
Serine/Threonine
Tyrosine
Cysteine
Aspartate
Glutamate
Asparagine
Glutamine
Lysine
Arginine
Proline
Histidine
Tryptophan
Crosslinks between twoAAs
CysteineCysteine
MethionineHydroxylysine
LysineTyrosine
TryptophanTryptophan
Crosslinks between threeAAs
SerineTyrosineGlycine
HistidineTyrosineGlycine
AlanineSerineGlycine
Crosslinks between fourAAs
AllysineAllysineAllysineLysine
Glycerol backbone
(Glycerophospholipids/
Phosphoglycerides
)
Phosphatidyl-:
Phosphoinositides:
Ether lipids:
Sphingosine backbone
Metabolites
PAFRTooltip Platelet-activating factor receptor
Agonists
Antagonists
Others
Precursors
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