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Chemical Compound Review

acetyl-P     acetyloxyphosphonic acid

Synonyms: CHEBI:15350, HMDB01494, bmse000261, AR-1H6470, AKOS006329198, ...
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Disease relevance of acetyloxyphosphonic acid


High impact information on acetyloxyphosphonic acid


Chemical compound and disease context of acetyloxyphosphonic acid


Biological context of acetyloxyphosphonic acid

  • Formation of the phosphoenzyme from acetyl phosphate in the forward reaction was only weakly inhibited, but hydrolysis of the phosphoenzyme was strongly inhibited [11].
  • ATP and acetyl phosphate induces molecular events near the ATP binding site and the membrane domain of Na+,K+-ATPase. The tetrameric nature of the enzyme [12].
  • The extent of the decrease in the BIPM fluorescence and the increase in the amount of phosphoenzyme both showed monophasic kinetics with a similar dependence on the concentration of acetyl phosphate (K0.5 = 4 mM), while that of FITC fluorescence showed a biphasic decrease (K 0.5 greater than 10 mM) [13].
  • Ca(2+)-ATPase and Na+,K(+)-ATPase are phosphorylated from both ATP and acetyl phosphate (ACP) and dephosphorylated, resulting in active ion transport [14].
  • The effects of varying the intracellular amounts of acetyl phosphate on chemotaxis and the osmo-response were also investigated [15].

Anatomical context of acetyloxyphosphonic acid


Associations of acetyloxyphosphonic acid with other chemical compounds

  • With human hemoglobin A, methyl acetyl phosphate competes with 2,3-diphosphoglycerate and acetylates only Val-1(beta), Lys-82(beta), and Lys-144(beta) within or near the cleft that binds this organic phosphate (Ueno, H., Pospischil, M. A., Manning, J. M., and Kluger, R. (1986) Arch Biochem. Biophys. 244, 795) [21].
  • Several lines of evidence, including the finding that ATP- and not acetyl phosphate- or Pi-dependent phosphorylation is blocked by derivatization, suggest that the lysyl residue is at the catalytic nucleotide binding site, but is not directly involved in phosphoryl transfer [22].
  • Purified UhpA was phosphorylated by acetyl phosphate in a reaction that was dependent on Mg2+ and on the presence of aspartate 54, the site of phosphorylation in homologous response regulators [23].
  • Active site ligands such as acetyl phosphate, phosphate, and p-nitrophenyl phosphate were also ineffective at increasing the Ca2+ affinity [24].
  • Reaction of protein C with iodoacetate inhibits its ability to decompose acetyl phosphate, but this inactivation of the enzyme by alkylation is prevented in the presence of the substrate indicating the formation of an unreactive enzyme-bound acetylthiol ester [25].

Gene context of acetyloxyphosphonic acid


Analytical, diagnostic and therapeutic context of acetyloxyphosphonic acid

  • A radioactive tracer and rapid filtration method was applied to the study of Ca2+ release from sarcoplasmic reticulum (SR) vesicles which were preloaded passively (equilibration with millimolar Ca2+) or actively (in the presence of ATP or acetyl phosphate) [31].
  • Thus 83% of untreated oxygenated sickle cells had densities greater than 1.098 gm/ml, whereas after treatment with methyl acetyl phosphate, 52% of the cells were in this density range [32].
  • This model is composed of five units: a substrate unit consisting of substrate solutions--AMP, ATP, and acetyl phosphate (AcOP)--an enzymatic reactor unit consisting of AK and AdK immobilized to Sepharose 4B, an auto sampler unit, an analytical unit made up of high-performance liquid chromatography, and a control unit made up of a microcomputer [33].


  1. Requirements of acetyl phosphate for the binding protein-dependent transport systems in Escherichia coli. Hong, J.S., Hunt, A.G., Masters, P.S., Lieberman, M.A. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
  2. Glycine reductase mechanism. Andreesen, J.R. Current opinion in chemical biology. (2004) [Pubmed]
  3. RpoS synthesis is growth rate regulated in Salmonella typhimurium, but its turnover is not dependent on acetyl phosphate synthesis or PTS function. Cunning, C., Elliott, T. J. Bacteriol. (1999) [Pubmed]
  4. Control of poly-beta-hydroxybutyrate synthase mediated by acetyl phosphate in cyanobacteria. Miyake, M., Kataoka, K., Shirai, M., Asada, Y. J. Bacteriol. (1997) [Pubmed]
  5. Intracellular butyryl phosphate and acetyl phosphate concentrations in Clostridium acetobutylicum and their implications for solvent formation. Zhao, Y., Tomas, C.A., Rudolph, F.B., Papoutsakis, E.T., Bennett, G.N. Appl. Environ. Microbiol. (2005) [Pubmed]
  6. C-terminal DNA binding stimulates N-terminal phosphorylation of the outer membrane protein regulator OmpR from Escherichia coli. Ames, S.K., Frankema, N., Kenney, L.J. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  7. Phosphorylation of bacterial response regulator proteins by low molecular weight phospho-donors. Lukat, G.S., McCleary, W.R., Stock, A.M., Stock, J.B. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  8. The N-terminal input domain of the sensor kinase KdpD of Escherichia coli stabilizes the interaction between the cognate response regulator KdpE and the corresponding DNA-binding site. Heermann, R., Altendorf, K., Jung, K. J. Biol. Chem. (2003) [Pubmed]
  9. Partial purification of ferredoxin from Ruminococcus albus and its role in pyruvate metabolism and reduction of nicotinamide adenine dinucleotide by H2. Glass, T.L., Bryant, M.P., Wolin, M.J. J. Bacteriol. (1977) [Pubmed]
  10. Methyl acetyl phosphate, a new type of antisickling agent: site-specific acetylating agent toward the 2,3-DPG binding site in hemoglobin S. Ueno, H., Manning, J.M. The American journal of pediatric hematology/oncology. (1988) [Pubmed]
  11. Modification of histidine 5 in sarcoplasmic reticulum Ca2+-ATPase by diethyl pyrocarbonate causes strong inhibition of formation of the phosphoenzyme intermediate from inorganic phosphate. Yamasaki, K., Daiho, T., Saino, T., Kanazawa, T. J. Biol. Chem. (1997) [Pubmed]
  12. ATP and acetyl phosphate induces molecular events near the ATP binding site and the membrane domain of Na+,K+-ATPase. The tetrameric nature of the enzyme. Tsuda, T., Kaya, S., Yokoyama, T., Hayashi, Y., Taniguchi, K. J. Biol. Chem. (1998) [Pubmed]
  13. Microenvironment of two different extrinsic fluorescence probes in Na+,K+-ATPase changes out of phase during sequential appearance of reaction intermediates. Taniguchi, K., Tosa, H., Suzuki, K., Kamo, Y. J. Biol. Chem. (1988) [Pubmed]
  14. The energy transduction mechanism is different among P-type ion-transporting ATPases. Acetyl phosphate causes uncoupling between hydrolysis and ion transport in H+,K(+)-ATPase. Asano, S., Kamiya, S., Takeguchi, N. J. Biol. Chem. (1992) [Pubmed]
  15. Acetyl phosphate and the activation of two-component response regulators. McCleary, W.R., Stock, J.B. J. Biol. Chem. (1994) [Pubmed]
  16. Independence of two conformations of sarcoplasmic reticulum Ca2+-ATPase molecules in hydrolyzing acetyl phosphate. A two-pair model of the ATPase structural unit. Nakamura, J., Tajima, G. J. Biol. Chem. (1997) [Pubmed]
  17. Phosphorylation-dependent binding of BvgA to the upstream region of the cyaA gene of Bordetella pertussis. Karimova, G., Bellalou, J., Ullmann, A. Mol. Microbiol. (1996) [Pubmed]
  18. Intestinal short-chain fatty acids alter Salmonella typhimurium invasion gene expression and virulence through BarA/SirA. Lawhon, S.D., Maurer, R., Suyemoto, M., Altier, C. Mol. Microbiol. (2002) [Pubmed]
  19. Inhibition of the gelation of extracellular and intracellular hemoglobin S by selective acetylation with methyl acetyl phosphate. Ueno, H., Benjamin, L.J., Pospischil, M.A., Manning, J.M. Biochemistry (1987) [Pubmed]
  20. Modulation of flagellar expression in Escherichia coli by acetyl phosphate and the osmoregulator OmpR. Shin, S., Park, C. J. Bacteriol. (1995) [Pubmed]
  21. Methyl acetyl phosphate as a covalent probe for anion-binding sites in human and bovine hemoglobins. Ueno, H., Pospischil, M.A., Manning, J.M. J. Biol. Chem. (1989) [Pubmed]
  22. 2',3'-O-(2,4,6-trinitrophenyl)-8-azido-AMP and -ATP photolabel Lys-492 at the active site of sarcoplasmic reticulum Ca(2+)-ATPase. McIntosh, D.B., Woolley, D.G., Berman, M.C. J. Biol. Chem. (1992) [Pubmed]
  23. Protein phosphorylation affects binding of the Escherichia coli transcription activator UhpA to the uhpT promoter. Dahl, J.L., Wei, B.Y., Kadner, R.J. J. Biol. Chem. (1997) [Pubmed]
  24. Calcium binding to the H+,K(+)-ATPase. Evidence for a divalent cation site that is occupied during the catalytic cycle. Mendlein, J., Ditmars, M.L., Sachs, G. J. Biol. Chem. (1990) [Pubmed]
  25. Glycine reductase protein C. Properties and characterization of its role in the reductive cleavage of Se-carboxymethyl-selenoprotein A. Stadtman, T.C., Davis, J.N. J. Biol. Chem. (1991) [Pubmed]
  26. Regulation of RssB-dependent proteolysis in Escherichia coli: a role for acetyl phosphate in a response regulator-controlled process. Bouché, S., Klauck, E., Fischer, D., Lucassen, M., Jung, K., Hengge-Aronis, R. Mol. Microbiol. (1998) [Pubmed]
  27. Cloning and characterization of a new purine biosynthetic enzyme: a non-folate glycinamide ribonucleotide transformylase from E. coli. Marolewski, A., Smith, J.M., Benkovic, S.J. Biochemistry (1994) [Pubmed]
  28. The Escherichia coli CpxA-CpxR envelope stress response system regulates expression of the porins ompF and ompC. Batchelor, E., Walthers, D., Kenney, L.J., Goulian, M. J. Bacteriol. (2005) [Pubmed]
  29. The Cpx two-component signal transduction pathway is activated in Escherichia coli mutant strains lacking phosphatidylethanolamine. Mileykovskaya, E., Dowhan, W. J. Bacteriol. (1997) [Pubmed]
  30. Control of diauxic growth of Azotobacter vinelandii on acetate and glucose. Tauchert, K., Jahn, A., Oelze, J. J. Bacteriol. (1990) [Pubmed]
  31. Rapid filtration measurements of Ca2+ release from cisternal sarcoplasmic reticulum vesicles. Sumbilla, C., Inesi, G. FEBS Lett. (1987) [Pubmed]
  32. Effects of methyl acetyl phosphate, a covalent antisickling agent, on the density profiles of sickle erythrocytes. Ueno, H., Yatco, E., Benjamin, L.J., Manning, J.M. J. Lab. Clin. Med. (1992) [Pubmed]
  33. Construction of a system for the regeneration of adenosine 5'-triphosphate, which supplies energy to bioreactor. Kondo, H., Tomioka, I., Nakajima, H., Imahori, K. J. Appl. Biochem. (1984) [Pubmed]
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