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Chemical Compound Review

AG-D-81394     dihydroxy-oxido-oxo- phosphorane

Synonyms: CHEBI:39745, HMDB02105, AC1L1AIK, AC1Q7DKR, CTK4C2292, ...
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Disease relevance of dihydroxy-oxido-oxo-phosphorane

  • In an effort to determine whether the Na+-dependent Pi transport system of Ehrlich ascites tumor cells exhibits specificity for H2PO4- or HPO4(-2), Pi fluxes were determined by measuring 32Pi-Pi self-exchange [1].
  • The dimeric L-2-haloacid dehalogenase from Pseudomonas sp. YL, (subunit mass, 26179 Da), has been crystallized by vapor diffusion, supplemented by repetitive seeding, against a 50 mM potassium dihydrogenphosphate solution (pH 4.5) containing 15% (w/v) polyethylene glycol 8,000 and 1% (v/v) n-propanol [2].
  • Static exercise caused muscle acidosis and an increase in H2PO4-, whereas rhythmic exercise had no effect on muscle metabolism.(ABSTRACT TRUNCATED AT 250 WORDS)[3]
  • However, hypercapnic perfusion (70% CO2, pHo, 6.7, pHi 6.4-6.5) had no effect on peak tetanic force, and there was no significant correlation between pHi or [H2PO4-] during hypercapnia in either muscle [4].

High impact information on dihydroxy-oxido-oxo-phosphorane

  • The highly significant linear relationship between increases of H+ and H2PO4- and the decline of MVC strongly suggests that both H+ and H2PO4- are important determinants of human muscle fatigue [5].
  • Many of the essential metalloproteins are located in the cell, whose cytoplasmic fluid contains several small inorganic anions, such as Cl-, NO2-, NO3-, H2PO4-, and SO4(2-), that play an indispensable role in determining the cell's volume, regulating the cell's pH, signal transduction, muscle contraction, as well as cell growth and metabolism [6].
  • o-quinone alpha-phenylmethide was generated as a short-lived transient species in aqueous solution by flash photolysis of o-hydroxy-alpha-phenylbenzyl alcohol, and its rate of decay was measured in HClO4 and NaOH solutions as well as in CH3CO2H, H2PO4-, and HCO3- buffers [7].
  • Studies of the pH-dependence of phosphorylation show that H2PO4- and HPO4(2)- bind to the ATPase with equal affinity, but that only binding of H2PO4- leads to phosphorylation, described by an equilibrium constant of 2 [8].
  • Mixed-type inhibition with H2PO4- is actually of the type called "partially mixed competitive and non-competitive' as the inhibitor binds both to the catalytic site and to the allosteric site [9].

Biological context of dihydroxy-oxido-oxo-phosphorane

  • Thus, in both synthesis and hydrolysis of ATP, TFP and H2PO4- interact with a common site [10].
  • Analysis of the H-bonding network around the bound inhibitor indicates that phosphate is bound as the H2PO4- anion, and that an additional proton is present on the Odelta2 atom of Asp(alpha363), an active site residue involved in Ni coordination through Odelta1 [11].
  • Data on phosphate uptake during oxidative phosphorylation at several pH showed that H2PO4- is the true substrate for oxidative phosphorylation [10].
  • It is supposed that changes in molecular structure affect the H+- and H2PO4- ion transporting function and may be part of the "gating" mechanism in phosphate transport [12].

Anatomical context of dihydroxy-oxido-oxo-phosphorane

  • With a uniform pCO2 throughout the epithelium, the model variables include the concentrations of Na, K, Cl, HCO3, H2PO4, HPO4, and H, as well as hydrostatic pressure and electrical potential [13].
  • To differentiate the effects of high energy phosphates, pH, and [H2PO4-] on skeletal muscle fatigue, intracellular acidosis during handgrip exercise was attenuated by prolonged submaximal exercise [14].
  • Capillary zone electrophoresis was used for the separation of pilocarpine from its epimer, isopilocarpine, using coated fused-silica capillaries of 20 cm x 25 microm I.D., 8 kV running voltage, migration buffer of 0.1 M sodium dihydrogenphosphate pH 8, detection at 217 nm and injection by electromigration [15].
  • METHODS: 120 extracted human premolars were randomly assigned to eight groups for bonding with the following self-etching agents: Prompt-L Pop, Adper Prompt, Clearfil SE, Prime& Bond NT with NRC, Xeno111, One-Up Bond, AdheSe, or Prime & Bond NT using a total etch technique (36% H2PO4) [16].

Associations of dihydroxy-oxido-oxo-phosphorane with other chemical compounds

  • Inhibition by trifluoperazine of ATP synthesis and hydrolysis by particulate and soluble mitochondrial F1: competition with H2PO4- [10].
  • The analytical method for the measurement of the fluorescent compound employed a Tosoh ODS 80 column eluted with 10 mM potassium dihydrogenphosphate (pH 4.5) and acetonitrile (3:2, v/v) and detection at an excitation wavelength of 375 nm (10 nm bandpass) and an emission wavelength of 455 nm (10 nm bandpass) [17].
  • Aliquots of each solution were chromatographed on a reversed-phase column using a mobile phase of methanol-20 mM potassium dihydrogenphosphate (pH 6.4) (linear gradient from 0 to 100% methanol at 3%/min with a flow-rate of 1.5 ml/min) on a liquid chromatograph equipped with an ultraviolet absorbance detector (254 nm) [18].
  • On-line microdialysate was directly injected into a microbore column using a methanol-100 mM sodium dihydrogenphosphate (30:70, v/v, pH 2.5 adjusted with orthophosphoric acid) as the mobile phase and ultraviolet detection at 325 nm [19].
  • The mobile phase was methanol-0.08 M phosphate buffer (pH 7.6) (20:80), which contained 0.01 M tetrabutylammonium dihydrogenphosphate [20].

Gene context of dihydroxy-oxido-oxo-phosphorane

  • Thus VR1 and ASIC are likely to play a coordinated and interactive role in processing the muscle afferent response to H2PO4-. Furthermore, the physiological mechanisms mediating the response to H+ and H2PO4- are likely to be different [21].
  • Thus we examined the role played by purinergic receptors, vanilloid type 1 receptors (VR1), and acid-sensing ion channels (ASIC) in mediating H2PO4- -evoked pressor responses [21].
  • Separation of the investigated compound and internal standard was achieved on a Nucleosil 7 C18 column with a 0.01-M potassium dihydrogenphosphate buffer (pH 2.5)-methanol (60:40, v/v) mobile phase [22].
  • Single crystal X-ray structures of L1 and [RuII(bipy)2(L2H)](H2PO4)3.(CH3)2CO.0.8H2O were obtained, the latter revealing the presence of H2PO4- counter anions, the source of which is presumed to be hydrolysis of PF6- ions [23].
  • The on-line chromatographic separation was performed on a LiChrospher 100 RP8 5-microm particle size packed analytical column (25x0.4 cm I.D.). The mobile phase consisted of acetonitrile-0.01 M potassium dihydrogenphosphate (65:35, v/v) at a flow-rate of 0.8 ml/min [24].

Analytical, diagnostic and therapeutic context of dihydroxy-oxido-oxo-phosphorane

  • Positive ion fast atom bombardment mass spectrometry of the diphosphoryl lipid A TLC-3 (a highly acylated major band) showed a major component with (M + H)+ ion of mass 1798, which fragmented to yield a (M - H2PO4)+ ion of mass 1700 [25].
  • The HPLC separation was carried out on a Supersphere RP-18e column (125 X 4.0 mm I.D.) using 0.05 M sodium dihydrogenphosphate (pH 4.5)-acetonitrile (8:2) as the mobile phase at a flow-rate of 0.5 ml/min, and monitored with a photodiode-array detector [26].
  • 31P magic angle spinning NMR confirmed the XPS data and also showed that the chemical shift of the (H2PO4)- ions strongly depended on the crystallization degree of the Nb2O5 [27].
  • 1H NMR titrations demonstrated that while compound 1 hydrogen-bonded to H2PO4- forming simple 1 : 1 host-guest complex, further addition of F- induced the deprotonation of compound 1 [28].
  • Urinary modified nucleosides were determined by capillary electrophoresis using a 300 mM SDS-25 mM sodium tetraborate-50 mM sodium dihydrogenphosphate buffer [29].


  1. Evidence for monovalent phosphate transport in Ehrlich ascites tumor cells. Bowen, J.W., Levinson, C. J. Cell. Physiol. (1983) [Pubmed]
  2. Crystallization and preliminary x-ray crystallographic studies of L-2-haloacid dehalogenase from Pseudomonas sp. YL. Hisano, T., Hata, Y., Fujii, T., Liu, J.Q., Kurihara, T., Esaki, N., Soda, K. Proteins (1996) [Pubmed]
  3. Sympathetic nerve activity during prolonged rhythmic forearm exercise. Batman, B.A., Hardy, J.C., Leuenberger, U.A., Smith, M.B., Yang, Q.X., Sinoway, L.I. J. Appl. Physiol. (1994) [Pubmed]
  4. Hypercapnic acidosis and increased H2PO4- concentration do not decrease force in cat skeletal muscle. Adams, G.R., Fisher, M.J., Meyer, R.A. Am. J. Physiol. (1991) [Pubmed]
  5. 31P nuclear magnetic resonance studies of high energy phosphates and pH in human muscle fatigue. Comparison of aerobic and anaerobic exercise. Miller, R.G., Boska, M.D., Moussavi, R.S., Carson, P.J., Weiner, M.W. J. Clin. Invest. (1988) [Pubmed]
  6. Competition between protein ligands and cytoplasmic inorganic anions for the metal cation: a DFT/CDM study. Dudev, T., Lim, C. J. Am. Chem. Soc. (2006) [Pubmed]
  7. Flash photolytic generation of o-quinone alpha-phenylmethide and o-quinone alpha-(p-anisyl)methide in aqueous solution and investigation of their reactions in that medium. Saturation of acid-catalyzed hydration. Chiang, Y., Kresge, A.J., Zhu, Y. J. Am. Chem. Soc. (2002) [Pubmed]
  8. Effects of pH on phosphorylation of the Ca2+-ATPase of sarcoplasmic reticulum by inorganic phosphate. Khan, Y.M., East, J.M., Lee, A.G. Biochem. J. (1997) [Pubmed]
  9. Inhibition patterns of a model complex mimicking the reductive half-reaction of sulphite oxidase. Chaudhury, P.K., Das, S.K., Sarkar, S. Biochem. J. (1996) [Pubmed]
  10. Inhibition by trifluoperazine of ATP synthesis and hydrolysis by particulate and soluble mitochondrial F1: competition with H2PO4-. García, J.J., Tuena de Gómez-Puyou, M., Gómez-Puyou, A. J. Bioenerg. Biomembr. (1995) [Pubmed]
  11. Structure-based rationalization of urease inhibition by phosphate: novel insights into the enzyme mechanism. Benini, S., Rypniewski, W.R., Wilson, K.S., Ciurli, S., Mangani, S. J. Biol. Inorg. Chem. (2001) [Pubmed]
  12. Proton cycling through the mitochondrial phosphate transporter in energy transduction. Fonyó, A., Ligeti, E., Lukács, G. Prog. Clin. Biol. Res. (1982) [Pubmed]
  13. Nonequilibrium thermodynamic model of the rat proximal tubule epithelium. Weinstein, A.M. Biophys. J. (1983) [Pubmed]
  14. Human muscle fatigue after glycogen depletion: a 31P magnetic resonance study. Bertocci, L.A., Fleckenstein, J.L., Antonio, J. J. Appl. Physiol. (1992) [Pubmed]
  15. Analysis of pilocarpine and its trans epimer, isopilocarpine, by capillary electrophoresis. Baeyens, W., Weiss, G., Van Der Weken, G., Van Den Bossche, W. J. Chromatogr. (1993) [Pubmed]
  16. Influence of marginal bevels on microleakage around Class V cavities bonded with seven self-etching agents. Santini, A., Ivanovic, V., Ibbetson, R., Milia, E. American journal of dentistry. (2004) [Pubmed]
  17. High-performance liquid chromatographic determination of 3-hydroxykynurenine with fluorimetric detection; comparison of preovulatory phase and postovulatory phase urinary excretion. Shibata, K., Onodera, M. J. Chromatogr. (1991) [Pubmed]
  18. High-performance of liquid chromatographic determination of [3,4-di-(4-methoxyphenyl)-5-isoxazolyl]acetic acid and its metabolites in human plasma and urine. Marunaka, T., Maniwa, M. J. Chromatogr. (1987) [Pubmed]
  19. Determination of chlorogenic acid in rat blood by microdialysis coupled with microbore liquid chromatography and its application to pharmacokinetic studies. Tsai, T.H., Chen, Y.F., Shum, A.Y., Chen, C.F. Journal of chromatography. A. (2000) [Pubmed]
  20. Determination of amoxicillin in human plasma by high-performance liquid chromatography and solid phase extraction. Krauwinkel, W.J., Volkers-Kamermans, N.J., van Zijtveld, J. J. Chromatogr. (1993) [Pubmed]
  21. Vanilloid type 1 receptor and the acid-sensing ion channel mediate acid phosphate activation of muscle afferent nerves in rats. Gao, Z., Henig, O., Kehoe, V., Sinoway, L.I., Li, J. J. Appl. Physiol. (2006) [Pubmed]
  22. Validated liquid chromatographic method for the determination of N-3-(2,2,5,5-tetramethyl-3-pirrolin-3-carboxamidopropylphthalimide hydrochloride), a novel antiarrhythmic agent in human plasma. Róna, K., Ary, K., Ondi, S., Gachályi, B. Journal of chromatography. A. (1998) [Pubmed]
  23. Metal-to-ligand charge-transfer sensitisation of near-infrared emitting lanthanides in trimetallic arrays M2Ln (M=Ru, Re or Os; Ln=Nd, Er or Yb). Pope, S.J., Coe, B.J., Faulkner, S., Laye, R.H. Dalton transactions (Cambridge, England : 2003) (2005) [Pubmed]
  24. Automated quantitative determination of the new renin inhibitor CGP 60536 by high-performance liquid chromatography. Lefèvre, G., Gauron, S. J. Chromatogr. B Biomed. Sci. Appl. (2000) [Pubmed]
  25. Position of ester groups in the lipid A backbone of lipopolysaccharides obtained from Salmonella typhimurium. Qureshi, N., Takayama, K., Heller, D., Fenselau, C. J. Biol. Chem. (1983) [Pubmed]
  26. Identification and determination of sulphamethazine and N4-acetylsulphamethazine in meat by high-performance liquid chromatography with photodiode-array detection. Horie, M., Saito, K., Hoshino, Y., Nose, N., Hamada, N., Nakazawa, H. J. Chromatogr. (1990) [Pubmed]
  27. Surface modification with phosphoric acid of SiO2/Nb2O5 prepared by the sol-gel method: structural-textural and acid sites studies and an ion exchange model. Francisco, M.S., Cardoso, W.S., Gushikem, Y., Landers, R., Kholin, Y.V. Langmuir : the ACS journal of surfaces and colloids. (2004) [Pubmed]
  28. Host-guest complexation of a fluorescent and electrochemical chemsensor for fluoride anion. Zhang, B.G., Xu, J., Zhao, Y.G., Duan, C.Y., Cao, X., Meng, Q.J. Dalton transactions (Cambridge, England : 2003) (2006) [Pubmed]
  29. Application of capillary electrophoresis in clinical chemistry: the clinical value of urinary modified nucleosides. Liebich, H.M., Lehmann, R., Xu, G., Wahl, H.G., Häring, H.U. J. Chromatogr. B Biomed. Sci. Appl. (2000) [Pubmed]
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