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P0503 Sigma

O-Phosphorylethanolamine

Synonym: 2-Aminoethyl dihydrogen phosphate, O-Phosphocolamine, O-Phosphoethanolamine, Colaminephosphoric acid

  • CAS Number 1071-23-4

  • Linear Formula NH2CH2CH2OPO3H2

  • Molecular Weight 141.06

  •  Beilstein Registry Number 1758916

  •  EC Number 213-988-5

  •  MDL number MFCD00008178

  •  PubChem Substance ID 24898109

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Description

Packaging

1 g in poly tube

Bottomless glass bottle. Contents are inside inserted fused cone.

10 mg in autosample vial

5, 25, 100, 500 g in poly bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P0503.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

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Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
34
Safety Statements (Europe) 
26-36/37/39-45
RIDADR 
UN 3261 8 / PGII
WGK Germany 
3
RTECS 
KJ5830000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

Lipidomics of familial longevity. Gonzalez-Covarrubias V, Beekman M, Uh HW, et al. Aging Cell 12(3), 426-34, (2013)

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Shear-stress sensitive lenticular vesicles for targeted drug delivery. Holme MN, Fedotenko IA, Abegg D, et al. Nat. Nanotechnol. 7(8), 536-43, (2012)

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A novel plasmid-encoded serotype conversion mechanism through addition of phosphoethanolamine to the O-antigen of Shigella flexneri. Sun Q, Knirel YA, Lan R, et al. PLoS ONE 7(9), e46095, (2012)

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Modification of the Campylobacter jejuni N-linked glycan by EptC protein-mediated addition of phosphoethanolamine. Scott NE, Nothaft H, Edwards AV, et al. J. Biol. Chem. 287(35), 29384-96, (2012)

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Cyclotides insert into lipid bilayers to form membrane pores and destabilize the membrane through hydrophobic and phosphoethanolamine-specific interactions. Wang CK, Wacklin HP, and Craik DJ J. Biol. Chem. 287(52), 43884-98, (2012)

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O-antigen structure of Shigella flexneri serotype Yv and effect of the lpt-O gene variation on phosphoethanolamine modification of S. flexneri O-antigens. Knirel YA, Lan R, Senchenkova SN, et al. Glycobiology 23(4), 475-85, (2013)

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Matrix metalloprotease 2-responsive multifunctional liposomal nanocarrier for enhanced tumor targeting. Zhu L, Kate P, and Torchilin VP ACS Nano 6(4), 3491-8, (2012)

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ECNI GC-MS analysis of picolinic and quinolinic acids and their amides in human plasma, CSF, and brain tissue. Smythe GA, Poljak A, Bustamante S, et al. Adv. Exp. Med. Biol. 527, 705-12, (2003)

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Molecular identification of hydroxylysine kinase and of ammoniophospholyases acting on 5-phosphohydroxy-L-lysine and phosphoethanolamine. Veiga-da-Cunha M, Hadi F, Balligand T, et al. J. Biol. Chem. 287(10), 7246-55, (2012)

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An alternative mechanism for the methylation of phosphoethanolamine catalyzed by Plasmodium falciparum phosphoethanolamine methyltransferase. Saen-Oon S, Lee SG, Jez JM, et al. J. Biol. Chem. 289(49), 33815-25, (2014)

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Nanoassisted laser desorption-ionization-MS imaging of tumors. Tata A, Fernandes AM, Santos VG, et al. Anal. Chem. 84(15), 6341-5, (2012)

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The structure of the neisserial lipooligosaccharide phosphoethanolamine transferase A (LptA) required for resistance to polymyxin. Wanty C, Anandan A, Piek S, et al. J. Mol. Biol. 425(18), 3389-402, (2013)

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Assessment of antioxidant reserves and oxidative stress in cerebrospinal fluid after severe traumatic brain injury in infants and children. Bayir H, Kagan VE, Tyurina YY, et al. Pediatr. Res. 51(5), 571-8, (2002)

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1H and (13)C NMR spectroscopic analysis of human saliva. Silwood CJ, Lynch E, Claxson AW, et al. J. Dent. Res. 81(6), 422-7, (2002)

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Anti-angiogenic and anti-metastatic activity of synthetic phosphoethanolamine. Ferreira AK, Freitas VM, Levy D, et al. PLoS ONE 8(3), e57937, (2013)

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EptC of Campylobacter jejuni mediates phenotypes involved in host interactions and virulence. Cullen TW, O'Brien JP, Hendrixson DR, et al. Infect. Immun. 81(2), 430-40, (2013)

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Iron supplementation dose for perinatal iron deficiency differentially alters the neurochemistry of the frontal cortex and hippocampus in adult rats. Rao R, Tkac I, Unger EL, et al. Pediatr. Res. 73(1), 31-7, (2013)

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STED microscopy detects and quantifies liquid phase separation in lipid membranes using a new far-red emitting fluorescent phosphoglycerolipid analogue. Honigmann A, Mueller V, Hell SW, et al. Faraday Discuss. 161, 77-89; discussion 113-50, (2013)

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Thiolated DAB dendrimer/ZnSe nanoparticles for C-reactive protein recognition in human serum. Algarra M, Campos BB, Gomes D, et al. Talanta 99, 574-9, (2012)

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Phosphoethanolamine residues on the lipid A moiety of Neisseria gonorrhoeae lipooligosaccharide modulate binding of complement inhibitors and resistance to complement killing. Lewis LA, Shafer WM, Dutta Ray T, et al. Infect. Immun. 81(1), 33-42, (2013)

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CdSe and ZnSe quantum dots capped with PEA for screening C-reactive protein in human serum. Gomes D, Algarra M, Diez de los Rios MJ, et al. Talanta 93, 411-4, (2012)

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Sphingosine-1-phosphate lyase has a central role in the development of Dictyostelium discoideum. Li G, Foote C, Alexander S, et al. Development 128(18), 3473-83, (2001)

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Structural determinants of activity at the GABAB receptor. A comparison of phosphoethanolamine and related GABA analogs. Klunk WE, McClure RJ, Xu CJ, et al. Mol. Chem. Neuropathol. 26(1), 15-30, (1995)

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Phosphoethanolamine decoration of Neisseria gonorrhoeae lipid A plays a dual immunostimulatory and protective role during experimental genital tract infection. Packiam M, Yedery RD, Begum AA, et al. Infect. Immun. 82(6), 2170-9, (2014)

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Current analytical strategies for C-reactive protein quantification in blood. Algarra M, Gomes D, and Esteves da Silva JC Clin. Chim. Acta 415, 1-9, (2013)

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Molecular and structural basis of inner core lipopolysaccharide alterations in Escherichia coli: incorporation of glucuronic acid and phosphoethanolamine in the heptose region. Klein G, Müller-Loennies S, Lindner B, et al. J. Biol. Chem. 288(12), 8111-27, (2013)

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Synthetic phosphoethanolamine has in vitro and in vivo anti-leukemia effects. Ferreira AK, Santana-Lemos BA, Rego EM, et al. Br. J. Cancer 109(11), 2819-28, (2013)

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Synthetic phosphoethanolamine a precursor of membrane phospholipids reduce tumor growth in mice bearing melanoma B16-F10 and in vitro induce apoptosis and arrest in G2/M phase. Ferreira AK, Meneguelo R, Marques FL, et al. Biomed. Pharmacother. 66(7), 541-8, (2012)

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An ethanolamine-phosphate modified glycolipid in Clostridium acetobutylicum that responds to membrane stress. Tian B, Guan Z, and Goldfine H Biochim. Biophys. Acta 1831(6), 1185-90, (2013)

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Metabolomic analysis to discover candidate therapeutic agents against acute pancreatitis. Sakai A, Nishiumi S, Shiomi Y, et al. Arch. Biochem. Biophys. 522(2), 107-20, (2012)

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Methylation of ethanolamine groups in phosphoethanolamines is relevant for L-arginine insertion in lipid membranes. Bouchet A, Lairion F, and Disalvo A Biochim. Biophys. Acta 1818(5), 1395-401, (2012)

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Meclizine inhibits mitochondrial respiration through direct targeting of cytosolic phosphoethanolamine metabolism. Gohil VM, Zhu L, Baker CD, et al. J. Biol. Chem. 288(49), 35387-95, (2013)

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Inactivity of phosphoethanolamine, an endogenous GABA analog decreased in Alzheimer's disease, at GABA binding sites. Klunk WE, Debnath ML, McClure RJ, et al. Life Sci. 56(26), 2377-83, (1995)

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Cerebrospinal fluid taurine after traumatic brain injury. Seki Y, Kimura M, Mizutani N, et al. Neurochem. Res. 30(1), 123-8, (2005)

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Transient cell function disruption by low dose acute exposure of ionizing radiation. Saxena P, Bhatnagar A, Nishad DK, et al. Indian J. Exp. Biol. 49(12), 895-903, (2011)

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Phosphoethanolamine normal range in pediatric urines for hypophosphatasia screening. Imbard A, Alberti C, Armoogum-Boizeau P, et al. Clin. Chem. Lab Med. 50(12), 2231-3, (2012)

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Nanomedicine: Shake up the drug containers. Barenholz Y Nat. Nanotechnol. 7(8), 483-4, (2012)

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Formation of Schiff bases of O-phosphorylethanolamine and O-phospho-DL-serinewith pyridoxal 5'-phosphate. Experimental and theoretical studies. Vilanova B, Gallardo JM, Caldés C, et al. J. Phys. Chem. A 116(8), 1897-905, (2012)

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Beil. 4,IV,1415

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