Phosphocholine

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title: "Phosphocholine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["post-translational-modification", "quaternary-ammonium-compounds", "organophosphates", "zwitterions"] topic_path: "general/post-translational-modification" source: "https://en.wikipedia.org/wiki/Phosphocholine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 416271641 | ImageFile = Phosphocholine.png | ImageSize = 180px | ImageAlt = Skeletal formula | ImageFile1 = Phosphocholine-zwitterion-3D-balls.png | ImageSize1 = 200 | ImageAlt1 = Ball-and-stick model | IUPACName = | OtherNames = Choline phosphate | Section1 = {{Chembox Identifiers | CASNo_Ref = | CASNo = 107-73-3 | UNII_Ref = | UNII = 96AN057F7A | PubChem = 1014 | SMILES = CN+(C)CCOP(=O)(O)[O-] | ChemSpiderID_Ref = | ChemSpiderID = 119298 | InChI = 1/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9) | InChIKey = YHHSONZFOIEMCP-UHFFFAOYAD | StdInChI_Ref = | StdInChI = 1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9) | StdInChIKey_Ref = | StdInChIKey = YHHSONZFOIEMCP-UHFFFAOYSA-N | MeSHName = Phosphocholine | Section2 = {{Chembox Properties | Formula = C5H15NO4P | MolarMass = 184.151 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

Phosphocholine is an intermediate in the synthesis of phosphatidylcholine in tissues. Phosphocholine is made in a reaction, catalyzed by choline kinase, that converts ATP and choline into phosphocholine and ADP. Phosphocholine is a molecule found, for example, in lecithin.

In nematodes and human placentas, phosphocholine is selectively attached to other proteins as a posttranslational modification to suppress an immune response by their hosts.

It is also one of the binding targets of C-reactive protein (CRP). 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.

References

References

  1. (September 2007). "Identification of a novel mammalian post-translational modification, phosphocholine, on placental secretory polypeptides". Journal of Molecular Endocrinology.
  2. (2007-11-10). "Placenta 'fools body's defences'". BBC News.
  3. (1999). "The physiological structure of human C-reactive protein and its complex with phosphocholine.". Structure.
  4. (2006). "The effect of the ionophore valinomycin on biomimetic solid supported lipid DPPTE/EPC membranes". Bioelectrochemistry.
  5. (2015-09-15). "Structural Features of Micelles of Zwitterionic Dodecyl-phosphocholine (C12PC) Surfactants Studied by Small-Angle Neutron Scattering". Langmuir.

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post-translational-modificationquaternary-ammonium-compoundsorganophosphateszwitterions