aminoethylphosphonic acid

Summary

Summary: An organophosphorus compound isolated from human and animal tissues.

Top Publications

  1. Au K, Ren J, Walter T, Harlos K, Nettleship J, Owens R, et al. Structures of an alanine racemase from Bacillus anthracis (BA0252) in the presence and absence of (R)-1-aminoethylphosphonic acid (L-Ala-P). Acta Crystallogr Sect F Struct Biol Cryst Commun. 2008;64:327-33 pubmed publisher
    ..work, the structures of an alanine racemase (BA0252) in the presence and absence of the inhibitor (R)-1-aminoethylphosphonic acid (L-Ala-P) have determined by X-ray crystallography to resolutions of 2.1 and 1.47 A, respectively...
  2. Ternan N, Quinn J. Phosphate starvation-independent 2-aminoethylphosphonic acid biodegradation in a newly isolated strain of Pseudomonas putida, NG2. Syst Appl Microbiol. 1998;21:346-52 pubmed
    A strain of Pseudomonas putida that utilized the biogenic organophosphonate 2-aminoethylphosphonic acid as sole carbon and energy, nitrogen and phosphorus source contained 2-aminoethylphosphonic acid: pyruvate aminotransferase and ..
  3. Stamper G, Morollo A, Ringe D, Stamper C. Reaction of alanine racemase with 1-aminoethylphosphonic acid forms a stable external aldimine. Biochemistry. 1998;37:10438-45 pubmed
    R)-1-Aminoethylphosphonic acid (L-Ala-P), a synthetic L-alanine analogue, has antibacterial activity and is a time-dependent inactivator of all purified Gram-positive bacterial alanine racemases that have been tested...
  4. Cai Y, Lu Y, Yu C, Lyu H, Miao Z. Combined C-H functionalization/O-H insertion reaction to form tertiary ?-alkoxy substituted ?-aminophosphonates catalyzed by [Cu(MeCN)4]PF6. Org Biomol Chem. 2013;11:5491-9 pubmed publisher
    ..This process provides straightforward access to tertiary ?-alkoxy substituted ?-aminophosphonate derivatives with moderate to good yields. ..
  5. Chen S, Hu L, Zhang Y, Deng P, Li C, Chen X, et al. (AEDPH3)·(BtaH): a novel supramolecular plaster with formaldehyde adsorption and formaldehyde/ultraviolet ray-induced luminescence switching performance. Chem Commun (Camb). 2012;48:552-4 pubmed publisher
    ..It can adsorb and eliminate formaldehyde (HCHO) with high efficiency and exhibits very interesting HCHO/ultraviolet ray-induced luminescence switching. ..
  6. Carreira J, Jones C, Wait R, Previato J, Mendonça Previato L. Structural variation in the glycoinositolphospholipids of different strains of Trypanosoma cruzi. Glycoconj J. 1996;13:955-66 pubmed
    ..are substituted at the third mannose distal to inositol (Man 3) by ethanolamine-phosphate or 2-aminoethylphosphonic acid, as are some glycosyl-phosphatidylinositol-protein anchors of T. cruzi...
  7. Ong J, Kerr D, Abbenante J, Prager R. Short-chain baclofen analogues are GABAB receptor antagonists in the guinea-pig isolated ileum. Eur J Pharmacol. 1991;205:319-22 pubmed
    ..0). The corresponding des-chloro analogues were all less active. These compounds represent another class of GABAB receptor antagonists which may cross the blood-brain barrier. ..
  8. Kariotoglou D, Mastronicolis S. Sphingophosphonolipid molecular species from edible mollusks and a jellyfish. Comp Biochem Physiol B Biochem Mol Biol. 2003;136:27-44 pubmed
    ..5% of hydroxy FA and +12.3% of trihydroxy bases. The compositions of CAEP-IIM and CAEP-IIE appear to be specific of each organism, while the composition of molluscan or jellyfish major sphingophosphonolipids appears not specific. ..
  9. Toukach F, Shashkov A, Katzenellenbogen E, Kocharova N, Czarny A, Knirel Y, et al. Structure of the O-specific polysaccharide of Hafnia alvei PCM 1222 containing 2-aminoethyl phosphate. Carbohydr Res. 1996;295:117-26 pubmed
    ..35 to 0.55 and that of the O-acetyl groups from 0.05 to 0.4 per repeating unit. It was tentatively suggested that the O-acetyl group is located at position 4 of a rhamnosyl residue. ..

More Information

Publications52

  1. Patterson C, Smith J. Differential modification of activities of the high-affinity and low-affinity insulin receptors of 3T3-L1 fibroblasts by phosphonolipids in vivo. Biochem Biophys Res Commun. 1996;228:75-80 pubmed
    ..The results suggest that this specific cellular phospholipid modification will be useful in dissecting the specific functions of the two forms of the mammalian insulin receptor. ..
  2. Hård K, Van Doorn J, Thomas Oates J, Kamerling J, Van der Horst D. Structure of the asn-linked oligosaccharides of apolipophorin III from the insect Locusta migratoria. Carbohydrate-linked 2-aminoethylphosphonate as a constituent of a glycoprotein. Biochemistry. 1993;32:766-75 pubmed
    ..L. migratoria apolipophorin III is the first example of a glycoprotein containing carbohydrate-linked 2-aminoethylphosphonate. The structures of the major oligosaccharides were established to be the following: [formula: see text] ..
  3. Ishii S, Hayashi H, Okamoto A, Kagamiyama H. Aromatic L-amino acid decarboxylase: conformational change in the flexible region around Arg334 is required during the transaldimination process. Protein Sci. 1998;7:1802-10 pubmed
    ..From these results we propose that the conformational change in the flexible region is required during the transaldimination process. ..
  4. Ricci L, Frosini M, Gaggelli N, Valensin G, Machetti F, Sgaragli G, et al. Inhibition of rabbit brain 4-aminobutyrate transaminase by some taurine analogues: a kinetic analysis. Biochem Pharmacol. 2006;71:1510-9 pubmed
    ..These include (+/-)piperidine-3-sulfonic acid (PSA), 2-aminoethylphosphonic acid (AEP), (+/-)2-acetylaminocyclohexane sulfonic acid (ATAHS) and 2-aminobenzenesulfonate (ANSA)...
  5. Chen C, Zhang H, Kim A, Howard A, Sheldrick G, Mariano Dunaway D, et al. Degradation pathway of the phosphonate ciliatine: crystal structure of 2-aminoethylphosphonate transaminase. Biochemistry. 2002;41:13162-9 pubmed
    ..Modeling of bound substrates and products reveals the structural basis for AEP recognition and the stereospecificity of proton elimination at the alpha-carbon and indicates conformational changes along the reaction pathway...
  6. Bruynseels K, Van Hecke P, Vanstapel F. Further observations on the uptake and effects of phosphonates in perfused rat liver studied by (31)P-NMR. NMR Biomed. 1999;12:275-85 pubmed
    ..The monocarboxylate analogue, PhePo (10 mM), did not significantly interfere with disposal of lactate (0.3-5 mM). ..
  7. Tellman K, Palmer C. Polymers of sodium-N-undec-10-ene-1-oyl taurate and sodium-N-undec-10-ene-1-oyl aminoethyl-2-phosphonate as pseudostationary phases for electrokinetic chromatography. Electrophoresis. 1999;20:152-61 pubmed
    ..The polymers do exhibit unique selectivity, but the differences in selectivity are not significant for the majority of compounds studied. ..
  8. Chintalapati M, Truax R, Stout R, Portier R, Losso J. In vitro and in vivo anti-angiogenic activities and inhibition of hormone-dependent and -independent breast cancer cells by ceramide methylaminoethylphosphonate. J Agric Food Chem. 2009;57:5201-10 pubmed publisher
    ..This is the first report on CMAEPn-inhibited angiogenesis both in vitro and in vivo. ..
  9. Hidaka T, Goda M, Kuzuyama T, Takei N, Hidaka M, Seto H. Cloning and nucleotide sequence of fosfomycin biosynthetic genes of Streptomyces wedmorensis. Mol Gen Genet. 1995;249:274-80 pubmed
    ..Nucleotide sequencing of a large fragment revealed the presence of ten open reading frames, including the four biosynthetic genes and six genes with unknown functions. ..
  10. Abe S, Araki S, Satake M, Fujiwara N, Kon K, Ando S. Structure of triphosphonoglycosphingolipid containing N-acetylgalactosamine 6-O-2-aminoethylphosphonate in the nervous system of Aplysia kurodai. J Biol Chem. 1991;266:9939-43 pubmed
  11. Klimek Ochab M, Obojska A, Picco A, Lejczak B. Isolation and characterization of two new microbial strains capable of degradation of the naturally occurring organophosphonate - ciliatine. Biodegradation. 2007;18:223-31 pubmed
    ..Enzymatic activity involved in ciliatine degradation studied in the fungal cell-free extract proved to be distinct from bacterial pathway described before...
  12. Copie V, Faraci W, Walsh C, Griffin R. Inhibition of alanine racemase by alanine phosphonate: detection of an imine linkage to pyridoxal 5'-phosphate in the enzyme-inhibitor complex by solid-state 15N nuclear magnetic resonance. Biochemistry. 1988;27:4966-70 pubmed
    ..We also report the pH dependence of Ala-P binding to alanine racemase. ..
  13. Tan S, Tan L. Distribution of ciliatine (2-aminoethylphosphonic acid) and phosphonoalanine (2-amino-3-phosphonopropionic acid) in human tissues. Clin Physiol Biochem. 1989;7:303-9 pubmed
    Ciliatine (2-aminoethylphosphonic acid) was detected in the human brain, heart, kidney, liver, intestine, spleen, adrenal glands, and aorta...
  14. Brenot F, Aubry L, Martin J, Satre M, Klein G. Kinetics of endosomal acidification in Dictyostelium discoideum amoebae. 31P-NMR evidence for a very acidic early endosomal compartment. Biochimie. 1992;74:883-95 pubmed
    ..3) before reaching a less acidic late endosomal/prelysosomal compartment (pH 5.8-6.0) from where they are immediately transported to, and trapped in, the cytoplasm (pH 7.3). ..
  15. Ross R, Roeder R. Binding affinity of surface functionalized gold nanoparticles to hydroxyapatite. J Biomed Mater Res A. 2011;99:58-66 pubmed publisher
    ..to a mean particle size of 10-15 nm and surface functionalized with either L-glutamic acid, 2-aminoethylphosphonic acid, or alendronate, which exhibit a primary amine for binding gold opposite carboxylate, phosphonate, or ..
  16. Danhorn T, Hentzer M, Givskov M, Parsek M, Fuqua C. Phosphorus limitation enhances biofilm formation of the plant pathogen Agrobacterium tumefaciens through the PhoR-PhoB regulatory system. J Bacteriol. 2004;186:4492-501 pubmed
    ..tumefaciens surface interactions. ..
  17. Ankrah P, Loerch S, Dehority B. Occurrence of 2-aminoethylphosphonic acid in feeds, ruminal bacteria and duodenal digesta from defaunated sheep. J Anim Sci. 1989;67:1061-9 pubmed
    A quantitative method of analysis for 2-aminoethylphosphonic acid (AEP) was developed using reverse-phase HPLC...
  18. Hurley J, Bunde T, Dell J, Kirkpatrick D, Bishop S. Phosphonoglycoprotein from Metridium senile--heterogeneity of glycoproteins containing aminoethylphosphonic acid. Comp Biochem Physiol B. 1977;58:253-9 pubmed
    ..wt components. 4. Phosphonoglycoproteins appear to be acidic connective tissue components with AEP linked to hexosamine containing oligosaccharide side chains. ..
  19. Castronovo F, Kopiwoda S, Peterson M. 2-aminoethylphosphonic acid: biodistribution of a naturally occurring phosphonate after labelling with technetium-99m. Nucl Med Commun. 1996;17:902-6 pubmed
    ..Nevertheless, a natural phosphonate derivative, 2-aminoethylphosphonic acid (2-AEP), has been detected in animal and human tissue...
  20. Barry R, Bowman E, McQueney M, Dunaway Mariano D. Elucidation of the 2-aminoethylphosphonate biosynthetic pathway in Tetrahymena pyriformis. Biochem Biophys Res Commun. 1988;153:177-82 pubmed
    ..80% yield. However, the maximum yield of 2-aminoethylphosphonic acid obtained by use of phosphonopyruvate was only 15%...
  21. Sparkes M, Dixon H, Geoghegan K, Visedo Gonzalez E. Application of the synthetic method to other amines. Biochem J. 1989;260:296-7 pubmed
    Taurine and 2-aminoethylphosphonic acid were synthesized by the method of the main paper [Geoghegan & Dixon (1989) Biochem. J. 260, 295-296], i.e...
  22. de Souza L, Iacomini M, Gorin P, Sari R, Haddad M, Sassaki G. Glyco- and sphingophosphonolipids from the medusa Phyllorhiza punctata: NMR and ESI-MS/MS fingerprints. Chem Phys Lipids. 2007;145:85-96 pubmed
    ..The probable origin of MGDG and SQDG in the jellyfish is the result of an endosymbiotic association with a microalga of the Dinoflagellate group, since these lipids are commonly found in photosynthetic membranes. ..
  23. Meneses P, Glonek T, Henderson T. Metabolism of 2-aminoethylphosphonic acid during embryonic development of the schistosomal vector Biomphalaria glabrata. Comp Biochem Physiol B. 1987;88:969-75 pubmed
    1. Egg masses of the Planorbid snail Biomphalaria glabrata contain 2-aminoethylphosphonic acid (AEP) in three different chemical environments, as determined by 31P nuclear magnetic resonance spectroscopy, giving signals at 20.9, 21...
  24. Matsubara T, Morita M, Hayashi A. Determination of the presence of ceramide aminoethylphosphonate and ceramide N-methylaminoethylphosphonate in marine animals by fast atom bombardment mass spectrometry. Biochim Biophys Acta. 1990;1042:280-6 pubmed
    ..the positive ion mode and at m/z 124 and 138 in the negative ion mode, were used to distinguish between aminoethylphosphonic acid and N-methylaminoethylphosphonic acid in CAEPn and CMAEPn...
  25. Ploux O, Breyne O, Carillon S, Marquet A. Slow-binding and competitive inhibition of 8-amino-7-oxopelargonate synthase, a pyridoxal-5'-phosphate-dependent enzyme involved in biotin biosynthesis, by substrate and intermediate analogs. Kinetic and binding studies. Eur J Biochem. 1999;259:63-70 pubmed
  26. Sarkar M, Hamilton C, Fairlamb A. Properties of phosphoenolpyruvate mutase, the first enzyme in the aminoethylphosphonate biosynthetic pathway in Trypanosoma cruzi. J Biol Chem. 2003;278:22703-8 pubmed
    ..cruzi cells. Southern and Western analysis suggests that PEP mutase is unique to T. cruzi and is not present in the other medically important parasites, Trypanosoma brucei and Leishmania spp. ..
  27. Kim A, Baker A, Dunaway Mariano D, Metcalf W, Wanner B, Martin B. The 2-aminoethylphosphonate-specific transaminase of the 2-aminoethylphosphonate degradation pathway. J Bacteriol. 2002;184:4134-40 pubmed
    ..Site-directed mutagenesis demonstrated the importance of three selected residues (Asp168, Lys194, and Arg340) in AEPT catalysis...
  28. Vidal G, Thiaudiere E, Canioni P, Gallis J. Aminomethylphosphonate and 2-aminoethylphosphonate as (31)P-NMR pH markers for extracellular and cytosolic spaces in the isolated perfused rat liver. NMR Biomed. 2000;13:289-96 pubmed
    ..Therefore, NEthPo could be considered as an interesting cytosolic pH probe suitable for (31)P-NMR measurements, especially when experimental conditions prevent reliable observation of cytosolic Pi resonance. ..
  29. Fathi R, Huang Q, Coppola G, Delaney W, Teasdale R, Krieg A, et al. Oligonucleotides with novel, cationic backbone substituents: aminoethylphosphonates. Nucleic Acids Res. 1994;22:5416-24 pubmed
    ..2-Aminoethyl)phosphonates represent a novel approach to the introduction of positive charges into the backbone of oligonucleotides. ..
  30. Jiang W, Metcalf W, Lee K, Wanner B. Molecular cloning, mapping, and regulation of Pho regulon genes for phosphonate breakdown by the phosphonatase pathway of Salmonella typhimurium LT2. J Bacteriol. 1995;177:6411-21 pubmed
    ..Complementation studies indicate that the S. typhimurium phn locus probably includes genes both for phosphonate transport and for catalysis of C-P bond cleavage. ..
  31. Shoguchi E, Tanaka M, Takeuchi T, Shinzato C, Satoh N. Probing a coral genome for components of the photoprotective scytonemin biosynthetic pathway and the 2-aminoethylphosphonate pathway. Mar Drugs. 2013;11:559-70 pubmed publisher
    ..The results suggest that de novo synthesis of carbon-phosphorus compounds is performed in corals. ..
  32. Cooley N, Kulakova A, Villarreal Chiu J, Gilbert J, McGrath J, Quinn J. Phosphonoacetate biosynthesis: in vitro detection of a novel NADP(+)-dependent phosphonoacetaldehyde-oxidizing activity in cell-extracts of the marine Roseovarius nubinhibens ISM. Mikrobiologiia. 2011;80:329-34 pubmed
    ..activity was detected in cell-extracts of the marine bacterium Roseovarius nubinhibens ISM grown on 2-aminoethylphosphonic acid (2-AEP; ciliatine). Extracts also contained 2-AEP transaminase and phosphonoacetate hydrolase activities...
  33. Borisova S, Christman H, Metcalf M, Zulkepli N, Zhang J, van der Donk W, et al. Genetic and biochemical characterization of a pathway for the degradation of 2-aminoethylphosphonate in Sinorhizobium meliloti 1021. J Biol Chem. 2011;286:22283-90 pubmed publisher
    ..This pathway is likely not limited to S. meliloti as suggested by the presence of homologous gene clusters in other bacterial genomes. ..
  34. Le Grand F, Kraffe E, Marty Y, Donaghy L, Soudant P. Membrane phospholipid composition of hemocytes in the Pacific oyster Crassostrea gigas and the Manila clam Ruditapes philippinarum. Comp Biochem Physiol A Mol Integr Physiol. 2011;159:383-91 pubmed publisher
    ..Hemolymph cell monolayer observations and flow-cytometric analyses revealed species-specific hemocyte morphology and sub-populations which could account for some of the observed species-specific membrane lipid compositions. ..
  35. Urai M, Nakamura T, Uzawa J, Baba T, Taniguchi K, Seki H, et al. Structural analysis of O-glycans of mucin from jellyfish (Aurelia aurita) containing 2-aminoethylphosphonate. Carbohydr Res. 2009;344:2182-7 pubmed publisher
    ..To the best of our knowledge, this is the first example of an O-glycan structure of glycoproteins containing AEP. This exceptionally simple structure of Q-mucin and its potential use in material science and technology are revealed. ..
  36. Krzysko Lupicka T, Strof W, Kubś K, Skorupa M, Wieczorek P, Lejczak B, et al. The ability of soil-borne fungi to degrade organophosphonate carbon-to-phosphorus bonds. Appl Microbiol Biotechnol. 1997;48:549-52 pubmed
    ..The strains of Trichoderma harzianum, Scopulariopsis sp. and Aspergillus niger chosen for more detailed study show the ability to degrade ciliatine, glyphosate and also amino(3-methoxyphenyl)methylphosphonic acid effectively. ..
  37. Zhukova N. Lipid classes and fatty acid composition of the tropical nudibranch mollusks Chromodoris sp. and Phyllidia coelestis. Lipids. 2007;42:1169-75 pubmed
    ..7 and 34%), which could have originated from the dietary origin or symbiotic bacteria. This is the first report on lipid and FA composition of nudibranchs...
  38. Iqbal S, Parker G, Davidson H, Moslehi Rahmani E, Robson R. Reversible phase variation in the phnE gene, which is required for phosphonate metabolism in Escherichia coli K-12. J Bacteriol. 2004;186:6118-23 pubmed
  39. Kursula I, Partanen S, Lambeir A, Antonov D, Augustyns K, Wierenga R. Structural determinants for ligand binding and catalysis of triosephosphate isomerase. Eur J Biochem. 2001;268:5189-96 pubmed
    ..Comparison of the TIM-IPP and the TIM-PGH structures with other liganded and unliganded structures also highlights the conformational flexibility of the ligand and the active site, as well as the conserved mode of ligand binding. ..
  40. Pessina F, Matteucci G, Esposito L, Gorelli B, Valoti M, Sgaragli G. Protection of intrinsic nerves of guinea-pig detrusor strips against anoxia/glucopenia and reperfusion injury by taurine. Adv Exp Med Biol. 2000;483:325-33 pubmed
    ..On the contrary, neither 0.1 nor 10 mM taurine had significant effects. It is concluded that taurine can partially counteract the ischaemia-reperfusion injury in the guinea-pig urinary bladder. ..
  41. Ibáñez M, Pozo O, Sancho J, Lopez F, Hernandez F. Residue determination of glyphosate, glufosinate and aminomethylphosphonic acid in water and soil samples by liquid chromatography coupled to electrospray tandem mass spectrometry. J Chromatogr A. 2005;1081:145-55 pubmed
    ..The method developed has been applied to the determination of these compounds in real water and soil samples from different areas. All the detections were confirmed by acquiring two transitions for each compound. ..
  42. Lacoste A, Dumora C, Ali B, Neuzil E, Dixon H. Utilization of 2-aminoethylarsonic acid in Pseudomonas aeruginosa. J Gen Microbiol. 1992;138:1283-7 pubmed
    ..The two arsonates inhibited the growth of this bacterium when 2-aminoethylphosphonic acid (AEP) but not alanine or NH4Cl, was supplied as the only other nitrogen source...
  43. Yamada S, Araki S, Abe S, Kon K, Ando S, Satake M. Structural analysis of a novel triphosphonoglycosphingolipid from the egg of the sea hare, Aplysia kurodai. J Biochem. 1995;117:794-9 pubmed
    ..By comparing 1H-NMR spectra of native and HF-treated glycolipids, steric interactions of two residues of 2-AEP with ring protons of the glucose and the internal galactose were indicated. ..