ホスホコリン、コリンリン酸
- 関
- phosphorylcholine
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/12/01 22:49:31」(JST)
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Phosphocholine
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Names |
Other names
Choline phosphate
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Identifiers |
CAS Number
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107-73-3 Y |
ChemSpider |
119298 |
InChI
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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
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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
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Jmol interactive 3D |
Image |
MeSH |
Phosphocholine |
PubChem |
1014 |
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Properties |
Chemical formula
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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).
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Y verify (what is YN ?) |
Infobox references |
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- Not to be confused with phosphatidylcholine.
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.
It is also used by nematodes and human placentas 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]
See also
- Alkylphosphocholines
- Choline
- Phosphoethanolamine
References
- ^ Lovell TM, Woods RJ, Butlin DJ, et al. (September 2007). "Identification of a novel mammalian post-translational modification, phosphocholine, on placental secretory polypeptides". J. Mol. Endocrinol. 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 ATA (2006). "The effect of the ionophore valinomycin on biomimetic solid supported lipid DPPTE/EPC membranes". Bioelectrochem. 70 (2): 387–93. doi:10.1016/j.bioelechem.2006.05.009. PMID 16875886.
External links
- Phosphocholine 3D Structure Viewer
Protein primary structure and posttranslational modifications
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General |
- Peptide bond
- Protein biosynthesis
- Proteolysis
- Racemization
- N-O acyl shift
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N terminus |
- Acetylation
- Carbamylation
- Formylation
- Glycation
- Methylation
- Myristoylation (Gly)
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C terminus |
- Amidation
- Glycosyl phosphatidylinositol (GPI)
- O-methylation
- Detyrosination
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Single specific AAs |
Serine/Threonine
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- Phosphorylation
- Dephosphorylation
- Glycosylation
- Methylidene-imidazolone (MIO) formation
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Tyrosine
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- Phosphorylation
- Dephosphorylation
- Sulfation
- Porphyrin ring linkage
- Adenylylation
- Flavin linkage
- Topaquinone (TPQ) formation
- Detyrosination
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Cysteine
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- Palmitoylation
- Prenylation
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Aspartate
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Glutamate
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- Carboxylation
- Methylation
- Polyglutamylation
- Polyglycylation
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Asparagine
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- Deamidation
- Glycosylation
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Glutamine
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Lysine
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- Methylation
- Acetylation
- Acylation
- Adenylylation
- Hydroxylation
- Ubiquitination
- Sumoylation
- ADP-ribosylation
- Deamination
- Oxidative deamination to aldehyde
- O-glycosylation
- Imine formation
- Glycation
- Carbamylation
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Arginine
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- Citrullination
- Methylation
- ADP-ribosylation
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Proline
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Histidine
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- Diphthamide formation
- Adenylylation
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Tryptophan
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Crosslinks between two AAs |
Cysteine-Cysteine
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Methionine-Hydroxylysine
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Lysine-Tyrosylquinone
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- Lysine tyrosylquinone (LTQ) formation
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Tryptophan-Tryptophylquinone
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- Tryptophan tryptophylquinone (TTQ) formation
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Three consecutive AAs
(chromophore formation) |
Serine–Tyrosine–Glycine
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- p-Hydroxybenzylidene-imidazolinone formation
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Histidine–Tyrosine–Glycine
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- 4-(p-hydroxybenzylidene)-5-imidazolinone formation
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Crosslinks between four AAs |
Allysine-Allysine-Allysine-Lysine
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Index of genetics
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Description |
- Gene expression
- DNA
- replication
- cycle
- recombination
- repair
- binding proteins
- Transcription
- factors
- regulators
- nucleic acids
- RNA
- RNA binding proteins
- ribonucleoproteins
- repeated sequence
- modification
- Translation
- ribosome
- modification
- nexins
- Proteins
- domains
- Structure
- primary
- secondary
- tertiary
- quaternary
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Disease |
- Replication and repair
- Transcription factor
- Transcription
- Translation
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Lipids: phospholipids
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Glycerol backbone
(Glycerophospholipids/
Phosphoglycerides) |
Phosphatidyl-: |
- -ethanolamine/cephalin (PE)
- -choline/lecithin (PC)
- -serine (PS)
- -glycerol (PG)
- -inositol (PI)
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Phosphoinositides: |
- PIP PI(3)P
- PIP2 (PI(3,4)P2
- PIP3
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Ether lipids: |
- Plasmalogen
- Platelet-activating factor
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Sphingosine backbone |
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Metabolites |
- Inositol phosphate
- Inositol
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- Choline
- Phosphocholine
- Citicoline
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Index of inborn errors of metabolism
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Description |
- Metabolism
- Enzymes and pathways: citric acid cycle
- pentose phosphate
- glycoproteins
- glycosaminoglycans
- phospholipid
- cholesterol and steroid
- sphingolipids
- eicosanoids
- amino acid
- urea cycle
- nucleotide
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Disorders |
- Citric acid cycle and electron transport chain
- Glycoprotein
- Proteoglycan
- Fatty-acid
- Phospholipid
- Cholesterol and steroid
- Eicosanoid
- Amino acid
- Purine-pyrimidine
- Heme metabolism
- Symptoms and signs
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Treatment |
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Index of biochemical families
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Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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Nucleic acids |
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Proteins |
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Other |
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PAF signaling
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PAF |
Agonists
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Antagonists
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- A-85783
- ABT-491
- Apafant
- BN-50739
- BN-52063
- Cetirizine
- CV-3988
- CV-6209
- Etizolam
- Ginkgolide B (BN-52021)
- Israpafant
- Kadsurenone
- L-652
- Lexipafant
- Loratadine
- PCA-4248
- Rupatadine
- SM-12502
- SR-27417
- SRI 63-441
- Terfenadine
- WEB-2086
- Yangambin
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Others |
Precursors
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- Choline
- ATP
- Phosphocholine
- PC
- LPC
- AAG
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UpToDate Contents
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English Journal
- ToF-SIMS analysis of amyloid beta aggregation on different lipid membranes.
- Yokoyama Y1, Aoyagi S1, Shimanouchi T2, Iwamura M2, Iwai H3.
- Biointerphases.Biointerphases.2016 Jun 28;11(2):02A314. doi: 10.1116/1.4940706.
- Amyloid beta (Aβ) peptides are considered to be strongly related to Alzheimer's disease. Aβ peptides form a β-sheet structure on hard lipid membranes and it would aggregate to form amyloid fibrils, which are toxic to cells. However, the aggregation mechanism of Aβ is not fully understood. To eva
- PMID 26822505
- Mass spectrometric profiling of lipids in intestinal tissue from rats fed cereals processed for medical conditions.
- Dowlatshahi Pour M1, Jennische E2, Lange S2, Ewing AG3, Malmberg P1.
- Biointerphases.Biointerphases.2016 Jun 11;11(2):02A310. doi: 10.1116/1.4939599.
- Time-of-flight secondary ion mass spectrometry (ToF-SIMS) was used for lipid profiling of intestine tissue sections from rats fed specially processed cereals and rats fed ordinary feed as a control. This cereal is known to increase the activity of antisecretory factor in plasma and the exact mechani
- PMID 26753787
- Non-invasive in vivo imaging of early metabolic tumor response to therapies targeting choline metabolism.
- Mignion L1, Danhier P1, Magat J1, Porporato PE2, Masquelier J3, Gregoire V4, Muccioli GG3, Sonveaux P2, Gallez B1, Jordan BF1.
- International journal of cancer. Journal international du cancer.Int J Cancer.2016 Apr 15;138(8):2043-9. doi: 10.1002/ijc.29932. Epub 2015 Dec 9.
- The cholinic phenotype, characterized by elevated phosphocholine and a high production of total-choline (tCho)-containing metabolites, is a metabolic hallmark of cancer. It can be exploited for targeted therapy. Non-invasive imaging biomarkers are required to evaluate an individual's response to tar
- PMID 26595604
Japanese Journal
- Effect of dispersants of multi-walled carbon nanotubes on cellular uptake and biological responses
- Haniu Hisao,Saito Naoto,Matsuda Yoshikazu,Kim Yoong-Ahm,Park Ki Chul,Tsukahara Tamotsu,Usui Yuki,Aoki Kaoru,Shimizu Masayuki,Ogihara Nobuhide,Hara Kazuo,Takanashi Seiji,Okamoto Masanori,Ishigaki Norio,Nakamura Koichi,Kato Hiroyuki
- International Journal of Nanomedicine 1(6), 3295-3307, 2011-12-09
- … assay), as well as intracellular MWCNT concentration and cytokine secretion (measured by flow cytometry) in human bronchial epithelial cells (BEAS-2B) exposed to a type of highly purified MWCNT vapor grown carbon fiber (VGCF®, Showa Denko Kabushiki-gaisha, Tokyo, Japan) in three different dispersants (gelatin, carboxylmethyl cellulose, and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine). …
- NAID 120003674279
- Interactions between Sex Hormones and a 1,2-Di-O-myristoyl-sn-glycero-3-phosphocholine Molecular Layer : Characteristics of the Liposome, Surface Area versus Surface Pressure of the Monolayer, and Microscopic Observation
- NAKATA Satoshi,IKEGUCHI Ayaka,SHIOTA Takaya,KOMORI Ryouhei,KUMAZAWA Noriyuki,TSUTSUMI Moe,DENDA Mitsuhiro
- Bulletin of the Chemical Society of Japan 84(3), 283-289, 2011-03-15
- NAID 10028046236
Related Links
- phosphocholine phos·pho·cho·line (fŏs'fō-kō'lēn') n. An intermediate in the synthesis of phosphatidylcholine in tissues.
- For MWCNTs, the CPPs performed additional experiments using BEGM medium (for BEAS-2B cells), showing that the combination of BSA and 1,2-dipalmitoyl-snglycero-3 phosphocholine (DPPC) provided optimal suspension ...
★リンクテーブル★
[★]
- 英
- phosphocholine、phosphorylcholine
- 関
- ホスホコリン、ホスホリルコリン
[★]
- 英
- [[]]
- 同
- phosphocholine
- 関
- [[]]
- 同
- phosphocholine
[★]
1-アルキル-2-アセチルグリセロホスホコリンエステラーゼ
- 関
- lipoprotein-associated phospholipase A2、Lp-PLA2、PAF acetylhydrolase
[★]
1-アシルグリセロホスホコリン-O-アシルトランスフェラーゼ
[★]
アルキルホスホコリン APCs
[★]
アルキルホスホコリン