phosphocholine

{{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 = 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.{{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 }}{{cite news| url=http://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}}

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