{{distinguish|phosphatidylcholine}} {{chembox | 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 = {{cascite|correct|CAS}} | CASNo = 107-73-3 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = 96AN057F7A | PubChem = 1014 | SMILES = C[N+](C)(C)CCOP(=O)(O)[O-] | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | 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 = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = YHHSONZFOIEMCP-UHFFFAOYSA-N | MeSHName = Phosphocholine }} | Section2 = {{Chembox Properties | Formula = C<sub>5</sub>H<sub>15</sub>NO<sub>4</sub>P | 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.<ref>{{cite journal |vauthors=Lovell TM, Woods RJ, Butlin DJ, etal |title=Identification of a novel mammalian post-translational modification, phosphocholine, on placental secretory polypeptides |journal= Journal of Molecular Endocrinology|volume=39 |issue=3 |pages=189–98 |date=September 2007 |pmid=17766644 |pmc=2189575 |doi=10.1677/JME-07-0007 }}</ref><ref>{{cite news| url=https://news.bbc.co.uk/2/hi/health/7081298.stm | work=BBC News | title=Placenta 'fools body's defences' | date=2007-11-10 | access-date=2010-05-22}}</ref>
It is also one of the binding targets of C-reactive protein (CRP).<ref>{{cite journal|vauthors=Thompson D, Pepys MB, Wood SP |title=The physiological structure of human C-reactive protein and its complex with phosphocholine.|journal=Structure |volume=7|issue=2|pages=169–77|year=1999|pmid=10368284|doi=10.1016/S0969-2126(99)80023-9|doi-access=free}}</ref> 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.<ref>{{cite journal |vauthors=Rose L, Jenkins AT |title=The effect of the ionophore valinomycin on biomimetic solid supported lipid DPPTE/EPC membranes |journal= Bioelectrochemistry|year=2006 |volume=70 |issue=2 |pages=387–93 |pmid=16875886 |doi=10.1016/j.bioelechem.2006.05.009}}</ref><ref>{{Cite journal|last1=Pambou|first1=Elias|last2=Crewe|first2=John|last3=Yaseen|first3=Mohammed|last4=Padia|first4=Faheem N.|last5=Rogers|first5=Sarah|last6=Wang|first6=Dong|last7=Xu|first7=Hai|last8=Lu|first8=Jian R.|date=2015-09-15|title=Structural Features of Micelles of Zwitterionic Dodecyl-phosphocholine (C12PC) Surfactants Studied by Small-Angle Neutron Scattering|journal=Langmuir|volume=31|issue=36|pages=9781–9789|doi=10.1021/acs.langmuir.5b02077|pmid=26301341|issn=0743-7463}}</ref>
==See also== * Alkylphosphocholines * Choline * Phosphoethanolamine
==References== {{Reflist|2}}
==External links== *[http://www.ch.ic.ac.uk/chemime/tests/chemapp/index.html Phosphocholine 3D Structure Viewer]
{{Protein primary structure}} {{Phospholipids}} {{PAF signaling}}
Category:Post-translational modification Category:Quaternary ammonium compounds Category:Organophosphates Category:Zwitterions