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Chemical Compound Review

Phosphit     trioxidophosphane

Synonyms: phosphite, Orthophosphite, Phosphite ions, AG-C-86600, CHEBI:45064, ...
 
 
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Disease relevance of trioxidophosphane

  • Genetic analysis indicates that Escherichia coli possesses two independent pathways for oxidation of phosphite (Pt) to phosphate [1].
  • The ptxD gene from Pseudomonas stutzeri WM88 encoding the novel phosphorus oxidizing enzyme NAD:phosphite oxidoreductase (trivial name phosphite dehydrogenase, PtxD) was cloned into an expression vector and overproduced in Escherichia coli [2].
  • Using solid-phase phosphite triester methods, we have synthesized both strands of the phage lambda OR3 DNA sequence, reannealed them, and studied the native operator duplex by high-resolution NMR at 500 MHz [3].
  • Enhanced utilization of phosphonate and phosphite by Klebsiella aerogenes [4].
  • One isolate that grew well with either hypophosphite or phosphite was identified by 16S rRNA gene analysis as a strain of Alcaligenes faecalis [5].
 

High impact information on trioxidophosphane

  • A new activity for an old enzyme: Escherichia coli bacterial alkaline phosphatase is a phosphite-dependent hydrogenase [1].
  • O-selectivity and utility of phosphorylation mediated by phosphite triester intermediates in the N-unprotected phosphoramidite method [6].
  • Improvement of the new phosphite method for the synthesis of oligodeoxyribonucleotides using the deoxyribonucleoside 3'-bis(1,1,1,3,3,3- hexafluoro-2-propyl) phosphite unit has been carried out via the hydrolysis and capping steps, without any side reaction products [7].
  • Synthetic DNA duplexes corresponding to the ribosome binding site (RBS) were synthesized through the phosphite method on solid support [8].
  • Rescue of root meristem activity in Pi-starved pdr2 by phosphite (Phi), a non-metabolizable Pi analog, and divided-root experiments suggest that pdr2 disrupts sensing of low external Pi availability [9].
 

Chemical compound and disease context of trioxidophosphane

 

Biological context of trioxidophosphane

 

Anatomical context of trioxidophosphane

 

Associations of trioxidophosphane with other chemical compounds

  • Thus, 10 ddNs were converted to their 5'-alphaB-betagammaCF(2)TPs via a sequence (one-pot) of reactions: formation of an activated phosphite, formation of a cyclic triphosphate, boronation, and hydrolysis [18].
  • Fluorophosphate (pKa = 4.7) and phosphite (pKa = 6.4) chemical shifts and coupling constants were found to be pH sensitive but at pH ranges too low to be useful for the study of fresh red cells [19].
  • Both operons individually support growth on methylphosphonate; however, the phn operon supports growth on aminoethylphosphonate and phosphite, as well [14].
  • Varying the biphenyl substituents in the phosphite moiety greatly affected the enantioselectivity in the hydrogenation reactions [20].
  • A method for determining enantiomeric excess by mass spectrometry was employed to screen a family of chiral phosphite P,N-ligands for activity in the rhodium-catalyzed asymmetric hydrosilylation of ketones [21].
 

Gene context of trioxidophosphane

  • Involvement of the Escherichia coli phn (psiD) gene cluster in assimilation of phosphorus in the form of phosphonates, phosphite, Pi esters, and Pi [22].
  • A gene coding for human stefin B was synthesized by the solid-phase phosphite method and cloned in the pUC8 cloning vector [23].
  • A gene coding for human Val8-calcitonin (Val8-hCT) was synthesized by the solid-phase phosphite approach and fused to a synthetic human immune interferon-gamma (IFN-gamma) gene [24].
  • Sequences consisting of the 17-bp nutL core flanked by two HindIII cohesive sites were synthesized by the phosphite coupling method, and cloned in proper orientation between the Pp promoter of pBR322 and lambda gene N followed by the tL1 terminator on a galK-expression plasmid [25].
  • This organism also has the htxB, htxC, and htxD genes that comprise an ABC-type transporter, presumably for hypophosphite and phosphite transport [5].
 

Analytical, diagnostic and therapeutic context of trioxidophosphane

References

  1. A new activity for an old enzyme: Escherichia coli bacterial alkaline phosphatase is a phosphite-dependent hydrogenase. Yang, K., Metcalf, W.W. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  2. Purification and characterization of a novel phosphorus-oxidizing enzyme from Pseudomonas stutzeri WM88. Costas, A.M., White, A.K., Metcalf, W.W. J. Biol. Chem. (2001) [Pubmed]
  3. Sequence-specific recognition of deoxyribonucleic acid. Chemical synthesis and nuclear magnetic resonance assignment of the imino protons of lambda OR3 operator deoxyribonucleic acid. Chou, S.H., Hare, D.R., Wemmer, D.E., Reid, B.R. Biochemistry (1983) [Pubmed]
  4. Enhanced utilization of phosphonate and phosphite by Klebsiella aerogenes. Imazu, K., Tanaka, S., Kuroda, A., Anbe, Y., Kato, J., Ohtake, H. Appl. Environ. Microbiol. (1998) [Pubmed]
  5. Genetic diversity and horizontal transfer of genes involved in oxidation of reduced phosphorus compounds by Alcaligenes faecalis WM2072. Wilson, M.M., Metcalf, W.W. Appl. Environ. Microbiol. (2005) [Pubmed]
  6. O-selectivity and utility of phosphorylation mediated by phosphite triester intermediates in the N-unprotected phosphoramidite method. Ohkubo, A., Ezawa, Y., Seio, K., Sekine, M. J. Am. Chem. Soc. (2004) [Pubmed]
  7. A convenient approach to the synthesis of medium size oligodeoxyribonucleotides by improved new phosphite method. Hosaka, H., Suzuki, Y., Sato, H., Gug-Kim, S., Takaku, H. Nucleic Acids Res. (1991) [Pubmed]
  8. Search for the optimal sequence of the ribosome binding site by random oligonucleotide-directed mutagenesis. Min, K.T., Kim, M.H., Lee, D.S. Nucleic Acids Res. (1988) [Pubmed]
  9. Arabidopsis pdr2 reveals a phosphate-sensitive checkpoint in root development. Ticconi, C.A., Delatorre, C.A., Lahner, B., Salt, D.E., Abel, S. Plant J. (2004) [Pubmed]
  10. Efficient regeneration of NADPH using an engineered phosphite dehydrogenase. Johannes, T.W., Woodyer, R.D., Zhao, H. Biotechnol. Bioeng. (2007) [Pubmed]
  11. Assignment of the non-exchangeable proton resonances of d(C-G-C-G-A-A-T-T-C-G-C-G) using two-dimensional nuclear magnetic resonance methods. Hare, D.R., Wemmer, D.E., Chou, S.H., Drobny, G., Reid, B.R. J. Mol. Biol. (1983) [Pubmed]
  12. New monodentate chiral phosphite ligands for asymmetric hydrogenation. Hannen, P., Militzer, H.C., Vogl, E.M., Rampf, F.A. Chem. Commun. (Camb.) (2003) [Pubmed]
  13. Molecular genetic analysis of phosphite and hypophosphite oxidation by Pseudomonas stutzeri WM88. Metcalf, W.W., Wolfe, R.S. J. Bacteriol. (1998) [Pubmed]
  14. Two C-P lyase operons in Pseudomonas stutzeri and their roles in the oxidation of phosphonates, phosphite, and hypophosphite. White, A.K., Metcalf, W.W. J. Bacteriol. (2004) [Pubmed]
  15. Laser flash photolysis evidence for styryl radical cation cyclization in the SET-induced photorearrangement of a p-methoxy-substituted 2-phenylallyl phosphite. Shukla, D., Lu, C., Schepp, N.P., Bentrude, W.G., Johnston, L.J. J. Org. Chem. (2000) [Pubmed]
  16. Evidence for anionic cation transport of lithium, sodium and potassium across the human erythrocyte membrane induced by divalent anions. Becker, B.F., Duhm, J. J. Physiol. (Lond.) (1978) [Pubmed]
  17. The temperature dependence of human erythrocyte transport of phosphate, phosphite and hypophosphite. Galanter, W.L., Labotka, R.J. Biochim. Biophys. Acta (1990) [Pubmed]
  18. Synthesis of 2',3'-dideoxynucleoside 5'-alpha-P-borano-beta,gamma-(difluoromethylene)triphosphates and their inhibition of HIV-1 reverse transcriptase. Boyle, N.A., Rajwanshi, V.K., Prhavc, M., Wang, G., Fagan, P., Chen, F., Ewing, G.J., Brooks, J.L., Hurd, T., Leeds, J.M., Bruice, T.W., Cook, P.D. J. Med. Chem. (2005) [Pubmed]
  19. A phosphate-analogue probe of red cell pH using phosphorus-31 nuclear magnetic resonance. Labotka, R.J., Kleps, R.A. Biochemistry (1983) [Pubmed]
  20. Highly enantioselective Rh-catalyzed hydrogenation based on phosphine-phosphite ligands derived from carbohydrates. Pàmies, O., Diéguez, M., Net, G., Ruiz, A., Claver, C. J. Org. Chem. (2001) [Pubmed]
  21. New catalysts for the asymmetric hydrosilylation of ketones discovered by mass spectrometry screening. Yao, S., Meng, J.C., Siuzdak, G., Finn, M.G. J. Org. Chem. (2003) [Pubmed]
  22. Involvement of the Escherichia coli phn (psiD) gene cluster in assimilation of phosphorus in the form of phosphonates, phosphite, Pi esters, and Pi. Metcalf, W.W., Wanner, B.L. J. Bacteriol. (1991) [Pubmed]
  23. Cloning a synthetic gene for human stefin B and its expression in E. coli. Jerala, R., Trstenjak, M., Lenarcic, B., Turk, V. FEBS Lett. (1988) [Pubmed]
  24. Chemical synthesis and expression in E. coli of a human Val8-calcitonin gene by fusion to a synthetic human interferon-gamma gene. Ivanov, I., Gigova, L., Jay, E. FEBS Lett. (1987) [Pubmed]
  25. Synthesis of the nutL DNA segments and analysis of antitermination and termination functions in coliphage lambda. Drahos, D., Galluppi, G.R., Caruthers, M., Szybalski, W. Gene (1982) [Pubmed]
  26. Chemical synthesis of a biologically active gene for human immune interferon-gamma. Prospect for site-specific mutagenesis and structure-function studies. Jay, E., MacKnight, D., Lutze-Wallace, C., Harrison, D., Wishart, P., Liu, W.Y., Asundi, V., Pomeroy-Cloney, L., Rommens, J., Eglington, L. J. Biol. Chem. (1984) [Pubmed]
  27. Site-directed mutagenesis of active site residues of phosphite dehydrogenase. Woodyer, R., Wheatley, J.L., Relyea, H.A., Rimkus, S., van der Donk, W.A. Biochemistry (2005) [Pubmed]
  28. Phosphite accelerates programmed cell death in phosphate-starved oilseed rape (Brassica napus) suspension cell cultures. Singh, V.K., Wood, S.M., Knowles, V.L., Plaxton, W.C. Planta (2003) [Pubmed]
  29. Purification of synthetic oligodeoxyribonucleotides by ion-exchange high-performance liquid chromatography. Scanlon, D., Haralambidis, J., Southwell, C., Turton, J., Tregear, G. J. Chromatogr. (1984) [Pubmed]
  30. Chemical synthesis and cloning of secretin gene. Qian, S.W., Chen, C.Q., Li, Z.P. Sci. Sin., Ser. B, Chem. Biol. Agric. Med. Earth Sci. (1988) [Pubmed]
 
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