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Chemical Compound Review

Oxonium     oxidanium

Synonyms: Hydronium ion, Hydronium, ion, AC1NUTDZ, AG-F-98856, CHEBI:29412, ...
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Disease relevance of oxonium


High impact information on oxonium

  • Bioenergetic coupling to protonmotive force: should we be considering hydronium ion coordination and not group protonation [4]?
  • The effect of the Ca2+-ATPase of sarcoplasmic reticulum upon activities of Na+, K+, and H3O+ ions [5].
  • A comparison by 220-MHz NMR of histidine hydronium ion titrations in porcine pancreatic ribonuclease and an extensively deglycosylated derivative [6].
  • The hydronium cation and the two triflate anions in 13 are associated into an anionic network through extensive hydrogen bonding surrounding stacks of the phosphonium cations [7].
  • Two close-lying minima are characterized, as well as two distinct transition states connecting them, either via H3O+ inversion or rotation, with barriers of 1.0 and 4.6 kcal/mol, respectively, at the BLYP/II'//BLYP/6-31G level [8].

Biological context of oxonium

  • A family of enantiomerically pure oxonium ions, that is O-protonated 1-aryl-1-methoxyethanes, has been generated in the gas phase by the (CH(3))(2)Cl(+) methylation of the corresponding 1-arylethanols [9].
  • The continuum from the concerted to stepwise mechanism is experimentally and theoretically verified in the present ene cyclization of the oxonium ion intermediate such as 4 [10].
  • Pretreatment with SA6 prevented mortality of 71% of day-old mice after intracranial injection of 100 LD50 of AHSV/4, while OH3 and ME11 significantly increased the average survival time of challenged animals [11].
  • Silicate glass and mineral dissolution: calculated reaction paths and activation energies for hydrolysis of a q3 si by H3O+ using ab initio methods [12].
  • This requires an understanding of the kinetics of hydrated hydronium ion formation, the involvement of mass discrimination in the analytical quadrupole mass spectrometer and the decreased diffusive loss of the heavier hydrates along the flow tube [13].

Anatomical context of oxonium

  • ESD spectra from the surface of red blood cells prepared from smears of whole blood show H+ as the predominant desorbed positive ion and O+, OH+, H3O+, Na+, and Cl+ as secondary species [14].

Associations of oxonium with other chemical compounds

  • The pD-dependent binding constants, determined by (1)H NMR spectroscopy, were analyzed according to a seven-state model, which included the CX4 tetra- and penta-anions, the protonated and unprotonated forms of the azoalkanes, the corresponding complexes, as well as the complex formed between CX4 and the deuteriated hydronium ion [15].
  • Our results indicate that the rate of degradation of NADPH is proportional most importantly to temperature and concentrations of hydronium ion, but also to concentrations of phosphate and acetate [16].
  • It has been proposed [Anton, D., Hedstrom, L., Fish, S., & Abeles, R. (1983) Biochemistry 22, 5903-5908; Steinrücken, H. C., & Amrhein, N. (1984) Eur. J. Biochem. 143, 351-357] that in this complex glyphosate functions as a transition-state analog of the putative phosphoenolpyruvoyl oxonium ion [17].
  • Anthraquinone-containing cyclic polyether hosts form 1:1 complexes with hydronium ion, producing large enhancements in luminescence via inversion of npi* and pipi* exited states [18].
  • The ESI/MS signal at m/z 803 is consistent with an oxonium ion for a glycan structure containing NeuAc, Gal, GlcNAc, and Fuc [19].

Gene context of oxonium

  • The atomic structure of mammalian AQP1 illustrates how this family of proteins is freely permeated by water but not protons (hydronium ions, H3O+) [20].
  • Some oxonium ions that were observed in the low-mass region, but that were not found in the PSD analyses (Mo, W.; et al. Anal. Chem. 1998, 70, 4520-4526), rendered a more detailed structural insight [21].
  • The oxonium ions at m/z 512.2, which are derived from the fucosylated oligosaccharides of immunoglobulin Y and thyroglobulin, were observed, suggesting that fucosylation had occurred proximal to the outer nonreducing terminus [21].
  • Efforts to establish the C10 and C13 spiroketal centers via an oxonium-initiated bis-spiroketalization under both kinetic and thermodynamic conditions have yielded the (10R,13S)-trioxadispiroketal 19 as the major product, which is diastereomeric with the (10R,13R) relative configuration assigned to the azaspiracids [22].
  • Our results confirm that OH3 and S11 are indeed T. gondii, but that N. caninum and T. gondii are likely to be separate species, thereby resolving previous uncertainties concerning the identity of these parasites [23].

Analytical, diagnostic and therapeutic context of oxonium

  • Oxonium ions (MH - CH3OH)+ were generated by liquid secondary ion mass spectrometry (LSIMS) and their decomposition was recorded on a tandem magnetic instrument [24].
  • This proposed HPLC method was applicable to separate/detect H3O+ from both strong and weak acidic samples [25].
  • Identification of new types of aluminium compounds by electrospray ionization mass spectrometry: oxonium cations [26].
  • First, using Raman spectroscopy, we found that an equilibrium of H2O + H2OCl+ <==> HOCl + H3O+ is unlikely because the "apparent pKa" increases monotonically from 1.25 to 2.11 as the analytical concentration is increased from 6.6 to 26.2 mM [27].
  • The serum phosphate levels were similar in CAPD and HD patients with smaller doses of OH3 AL in CAPD patients (p less than 0.001) [28].


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  4. Bioenergetic coupling to protonmotive force: should we be considering hydronium ion coordination and not group protonation? Boyer, P.D. Trends Biochem. Sci. (1988) [Pubmed]
  5. The effect of the Ca2+-ATPase of sarcoplasmic reticulum upon activities of Na+, K+, and H3O+ ions. Wiggins, P.M. J. Biol. Chem. (1980) [Pubmed]
  6. A comparison by 220-MHz NMR of histidine hydronium ion titrations in porcine pancreatic ribonuclease and an extensively deglycosylated derivative. Wang, F.F., Hirs, C.H. J. Biol. Chem. (1979) [Pubmed]
  7. Insignificance of P-H...P hydrogen bonding: structural chemistry of neutral and protonated 1,8-di(phosphinyl)naphthalene. Reiter, S.A., Nogai, S.D., Karaghiosoff, K., Schmidbaur, H. J. Am. Chem. Soc. (2004) [Pubmed]
  8. Hydronium ion complex of 18-crown-6: where are the protons? A density functional study of static and dynamic properties. Bühl, M., Wipff, G. J. Am. Chem. Soc. (2002) [Pubmed]
  9. Gas-phase activation and reaction dynamics of chiral ion-dipole complexes. Filippi, A., Speranza, M. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  10. (2,5)-Ene cyclization catalyzed by mesoporous solid acids: isotope labeling study and ab initio calculation for continuum from concerted to stepwise ene mechanism. Mikami, K., Ohmura, H., Yamanaka, M. J. Org. Chem. (2003) [Pubmed]
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  15. Analysis of host-assisted guest protonation exemplified for p-sulfonatocalix[4]arene--towards enzyme-mimetic pKa shifts. Bakirci, H., Koner, A.L., Schwarzlose, T., Nau, W.M. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  16. Stability of NADPH: effect of various factors on the kinetics of degradation. Wu, J.T., Wu, L.H., Knight, J.A. Clin. Chem. (1986) [Pubmed]
  17. Reevaluating glyphosate as a transition-state inhibitor of EPSP synthase: identification of an EPSP synthase.EPSP.glyphosate ternary complex. Sammons, R.D., Gruys, K.J., Anderson, K.S., Johnson, K.A., Sikorski, J.A. Biochemistry (1995) [Pubmed]
  18. Luminescence and structural comparisons of strong-acid sensor molecules. 2. Kampmann, B., Lian, Y., Klinkel, K.L., Vecchi, P.A., Quiring, H.L., Soh, C.C., Sykes, A.G. J. Org. Chem. (2002) [Pubmed]
  19. Site localization of sialyl Lewis(x) antigen on alpha1-acid glycoprotein by high performance liquid chromatography-electrospray mass spectrometry. Dage, J.L., Ackermann, B.L., Halsall, H.B. Glycobiology (1998) [Pubmed]
  20. Aquaporin water channels: molecular mechanisms for human diseases. Agre, P., Kozono, D. FEBS Lett. (2003) [Pubmed]
  21. Structural characterization of chemically derivatized oligosaccharides by nanoflow electrospray ionization mass spectrometry. Mo, W., Sakamoto, H., Nishikawa, A., Kagi, N., Langridge, J.I., Shimonishi, Y., Takao, T. Anal. Chem. (1999) [Pubmed]
  22. Synthetic studies toward the C5-C20 domain of the azaspiracids. Dounay, A.B., Forsyth, C.J. Org. Lett. (2001) [Pubmed]
  23. Differentiation of Toxoplasma gondii from closely related coccidia by riboprint analysis and a surface antigen gene polymerase chain reaction. Brindley, P.J., Gazzinelli, R.T., Denkers, E.Y., Davis, S.W., Dubey, J.P., Belfort, R., Martins, M.C., Silveira, C., Jamra, L., Waters, A.P. Am. J. Trop. Med. Hyg. (1993) [Pubmed]
  24. Differentiation of O-acetyl and O-carbamoyl esters of N-acetyl-glucosamine by decomposition of their oxonium ions. Application to the structure of the nonreducing terminal residue of Nod factors. Treilhou, M., Ferro, M., Monteiro, C., Poinsot, V., Jabbouri, S., Kanony, C., Promé, D., Promé, J.C. J. Am. Soc. Mass Spectrom. (2000) [Pubmed]
  25. Ion chromatographic analysis of hydronium ion using ODS modified with dodecylsulfate as the stationary phase. Hu, W., Hasebe, K., Tanaka, K., Inoue, S., Nagai, M. The Analyst. (2000) [Pubmed]
  26. Identification of new types of aluminium compounds by electrospray ionization mass spectrometry: oxonium cations. Bartók, M., Szabó, P.T., Bartók, T., Szöllösi, G., Balázsik, K. Rapid Commun. Mass Spectrom. (2001) [Pubmed]
  27. Monitoring the speciation of aqueous free chlorine from pH 1 to 12 with Raman spectroscopy to determine the identity of the potent low-pH oxidant. Cherney, D.P., Duirk, S.E., Tarr, J.C., Collette, T.W. Applied spectroscopy. (2006) [Pubmed]
  28. Diabetic patients on CAPD need less aluminum hydroxide as a phosphate binder than non-diabetics. Macia, M., Coronel, F., Torrente, J., Sanchez, A., Tornero, F., Barrientos, A. Advances in peritoneal dialysis. Conference on Peritoneal Dialysis. (1990) [Pubmed]
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