Phosphocholine

Phosphocholine
Names
	Other names Choline phosphate
Identifiers
CAS Number	107-73-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	119298 ;
MeSH	Phosphocholine
PubChem CID	1014;
UNII	96AN057F7A ;
CompTox Dashboard (EPA)	DTXSID30861727 ;
	InChI InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9) Key: YHHSONZFOIEMCP-UHFFFAOYSA-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;
	SMILES C[N+](C)(C)CCOP(=O)(O)[O-];
Properties
Chemical formula	C5H15NO4P
Molar mass	184.151 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[1]^[2]

It is also one of the binding targets of C-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]

^ 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.
^ "Placenta 'fools body's defences'". BBC News. 2007-11-10. Retrieved 2010-05-22.
^ 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.
^ 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.
^ 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.

[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. Retrieved 2010-05-22.

[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.

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