phosphites

Summary

Summary: Inorganic salts or organic esters of phosphorous acid that contain the (3-)PO3 radical. (From Grant & Hackh's Chemical Dictionary, 5th ed)

Top Publications

  1. Nagai H, Sasaki K, Matsumura S, Toshima K. Environmentally benign beta-stereoselective glycosidations of glycosyl phosphites using a reusable heterogeneous solid acid, montmorillonite K-10. Carbohydr Res. 2005;340:337-53 pubmed
    Environmentally benign and stereoselective beta-glycosidations of glycopyranosyl phosphites and alcohols using a reusable heterogeneous solid acid, montmorillonite K-10, as an activator have been developed...
  2. López Arredondo D, Herrera Estrella L. Engineering phosphorus metabolism in plants to produce a dual fertilization and weed control system. Nat Biotechnol. 2012;30:889-93 pubmed
  3. Kataoka M, Hattori A, Okino S, Hyodo M, Asano M, Kawai R, et al. Ethyl(methyl)dioxirane as an efficient reagent for the oxidation of nucleoside phosphites into phosphates under nonbasic anhydrous conditions. Org Lett. 2001;3:815-8 pubmed
    A convenient method for the oxidation of nucleoside phosphites into phosphates under nonbasic and nonaqueous conditions using commercially available ethyl(methyl)dioxirane has been developed...
  4. Machinandiarena M, Lobato M, Feldman M, Daleo G, Andreu A. Potassium phosphite primes defense responses in potato against Phytophthora infestans. J Plant Physiol. 2012;169:1417-24 pubmed publisher
    ..Our results indicate that KPhi primes the plant for an earlier and more intense response to infection and that SA would mediate this response...
  5. Massoud K, Barchietto T, Le Rudulier T, Pallandre L, Didierlaurent L, Garmier M, et al. Dissecting phosphite-induced priming in Arabidopsis infected with Hyaloperonospora arabidopsidis. Plant Physiol. 2012;159:286-98 pubmed publisher
    ..We propose that Phi negatively regulates MPK4, thus priming SA-dependent defense responses following Hpa infection...
  6. Ticconi C, Delatorre C, Abel S. Attenuation of phosphate starvation responses by phosphite in Arabidopsis. Plant Physiol. 2001;127:963-72 pubmed
    ..Thus, the use of Phi may allow further dissection of phosphate signaling by genetic selection for constitutive phosphate starvation response mutants on media containing organophosphates as the only source of phosphorus...
  7. Berkowitz O, Jost R, Pearse S, Lambers H, Finnegan P, Hardy G, et al. An enzymatic fluorescent assay for the quantification of phosphite in a microtiter plate format. Anal Biochem. 2011;412:74-8 pubmed publisher
    ..Because phosphite is a widely used fungicide to protect plants from pathogenic oomycetes, the assay provides a cost-effective and easy-to-use method to monitor the fate of phosphite following application...
  8. Varadarajan D, Karthikeyan A, Matilda P, Raghothama K. Phosphite, an analog of phosphate, suppresses the coordinated expression of genes under phosphate starvation. Plant Physiol. 2002;129:1232-40 pubmed
    ..Synchronized suppression of multiple Pi starvation-induced genes by Phi points to its action on the early molecular events, probably signal transduction, in Pi starvation response...
  9. King M, Reeve W, Van der Hoek M, Williams N, McComb J, O Brien P, et al. Defining the phosphite-regulated transcriptome of the plant pathogen Phytophthora cinnamomi. Mol Genet Genomics. 2010;284:425-35 pubmed publisher
    ..The results of both the microscopic and molecular investigations are consistent with phosphite inhibiting the function of the cytoskeleton and cell wall synthesis...

More Information

Publications62

  1. Berkowitz O, Jost R, Kollehn D, Fenske R, Finnegan P, O Brien P, et al. Acclimation responses of Arabidopsis thaliana to sustained phosphite treatments. J Exp Bot. 2013;64:1731-43 pubmed publisher
    ..These alterations in amino acid pools provide novel insights for the understanding of phosphite-induced pathogen resistance...
  2. Guga P. P-chiral oligonucleotides in biological recognition processes. Curr Top Med Chem. 2007;7:695-713 pubmed
    ..Selected examples of application of diastereomerically pure P-chiral oligonucleotides for structural, biochemical and biological experiments are discussed...
  3. Fujita S, Oka N, Matsumura F, Wada T. Synthesis of oligo(?-D-glycosyl phosphate) derivatives by a phosphoramidite method via boranophosphate intermediates. J Org Chem. 2011;76:2648-59 pubmed publisher
  4. Nomeir A, Matthews H. Metabolism and disposition of dimethyl hydrogen phosphite in rats and mice. J Toxicol Environ Health. 1997;51:489-501 pubmed
    ..Therefore, the species-dependent variations in the carcinogenicity of DMHP are most likely attributable to factors other than metabolism and disposition...
  5. Holden C, Shum K, Gawkrodger D. Contact allergy to triphenyl phosphate: probable cross-reactivity to triphenyl phosphite present in an EN46001 System 22 clear oxygen facemask. Contact Dermatitis. 2006;54:299-300 pubmed
  6. Yang K, Metcalf W. A new activity for an old enzyme: Escherichia coli bacterial alkaline phosphatase is a phosphite-dependent hydrogenase. Proc Natl Acad Sci U S A. 2004;101:7919-24 pubmed
    ..Thus, BAP is a unique Pt-dependent, H2-evolving hydrogenase. This reaction is unprecedented in both P and H biochemistry, and it is likely to involve direct transfer of hydride from the substrate to water-derived protons...
  7. Kunda U, Balam S, Nemallapudi B, Chereddy S, Nayak S, Cirandur S. Facile synthesis, antioxidant and antimicrobial activity of amino methylene bisphosphonates. Chem Pharm Bull (Tokyo). 2012;60:104-9 pubmed
    ..The title compounds are characterized by IR, (1)H-, (13)C-, (31)P-NMR and mass spectra, also studied their antimicrobial and antioxidant activity...
  8. Lu Y, Shi Z, Li Z, Guan Z. Helical polymers based on intramolecularly hydrogen-bonded aromatic polyamides. Chem Commun (Camb). 2010;46:9019-21 pubmed publisher
    ..These polymers can fold into helical conformation different from their linear control. The chirality of helical conformation can further be tuned via acid-base complexation using chiral residues...
  9. Das B, Balasubramanyam P, Krishnaiah M, Veeranjaneyulu B, Reddy G. Iodine-catalyzed efficient hydrophosphonylation of N-tosyl aldimines. J Org Chem. 2009;74:4393-5 pubmed publisher
    Treatment of N-tosyl aldimines with dialkyl trimethylsilyl phosphites at 0 degrees C in the presence of iodine as a catalyst afforded the corresponding sulfonamide phosphonates in excellent yields within 1.5 to 2.5 h.
  10. Iuliano A, Losi D, Facchetti S. Stereochemical features making deoxycholic acid derived tropos biphenylphosphites efficient chiral ligands for rhodium: the asymmetric hydrogenation of dimethylitaconate as a case study. J Org Chem. 2007;72:8472-7 pubmed
    ..atropoisomeric binaphthyl analogues, together with NMR and CD measurements on the rhodium complexes of some phosphites, allowed us to shed light on the nature of the active catalytic species and on the asymmetric induction process ..
  11. Lopez Arredondo D, Herrera Estrella L. A novel dominant selectable system for the selection of transgenic plants under in vitro and greenhouse conditions based on phosphite metabolism. Plant Biotechnol J. 2013;11:516-25 pubmed publisher
  12. Relyea H, van der Donk W. Mechanism and applications of phosphite dehydrogenase. Bioorg Chem. 2005;33:171-89 pubmed
    ..The potential of the enzyme as a NAD(P)H cofactor regeneration system is discussed as well as efforts to engineer the cofactor specificity of the protein...
  13. Hua Z, Vassar V, Choi H, Ojima I. New biphenol-based, fine-tunable monodentate phosphoramidite ligands for catalytic asymmetric transformations. Proc Natl Acad Sci U S A. 2004;101:5411-6 pubmed
    ..The fine-tuning capability of these ligands plays a significant role in achieving high enantioselectivity in the asymmetric hydroformylation of allyl cyanide and the conjugate addition of diethylzinc to cycloalkenones...
  14. Kaur P, Wever W, Rajale T, Li G. Asymmetric hydrophosphylation of chiral N-phosphonyl imines provides an efficient approach to chiral ?-amino phosphonates. Chem Biol Drug Des. 2010;76:314-9 pubmed publisher
    Chiral N-phosphonylimines were found to react with lithium phosphites to provide various substituted chiral ?-amino phosphonates in excellent yields (94-97%) and diastereoselectivities (93:7-99:1)...
  15. Pike R, Starnes W, Carpenter G. Cubane tetrameric complexes of copper(I) chloride and bromide with triphenyl phosphite. Acta Crystallogr C. 1999;55 ( Pt 2):162-5 pubmed
    ..Both have distorted 'cubane' Cu4X4 cores. Distortion of the cubane structure is reflected in X-Cu-X angles > 90 degrees and Cu-X-Cu angles < 90 degrees, and is more pronounced in the bromide complex...
  16. Hu G, Chen W, Fu T, Peng Z, Qiao H, Gao Y, et al. Nickel-catalyzed C-P cross-coupling of arylboronic acids with P(O)H compounds. Org Lett. 2013;15:5362-5 pubmed publisher
    A novel and efficient Ni-catalyzed coupling of a wide range of arylboronic acids with H-phosphites, H-phosphinate esters, and H-phosphine oxides has been developed, providing a general and powerful tool for the synthesis of various aryl-..
  17. Böhrsch V, Serwa R, Majkut P, Krause E, Hackenberger C. Site-specific functionalisation of proteins by a Staudinger-type reaction using unsymmetrical phosphites. Chem Commun (Camb). 2010;46:3176-8 pubmed publisher
    Unsymmetrical phosphites react efficiently in a Staudinger reaction with p-azido-phenylalanine, which can be applied for the biotinylation of proteins, thereby expanding the scope of the chemoselective Staudinger-phosphite reaction of ..
  18. Mallakpour S, Mirkarimi F. Synthesis and characterization of novel, optically active polyamides derived from S-valine natural amino acid and bulky anthracenic side chain. Amino Acids. 2010;39:1255-63 pubmed publisher
    ..The obtained PAs exhibit good thermal stability up to 335°C for 10% weight loss in nitrogen atmosphere and glass transition temperatures fell in the rang of 177-185°C...
  19. Tanaka Y, Takahashi K, Sasao T, Kirigaya T, Hosoi S, Nagaoka N, et al. [Detection of tris(2,4-di-tert-butylphenyl)phosphite (Irgafos 168, antioxidant in plastics) and its oxide in commercial frozen vegetables]. Shokuhin Eiseigaku Zasshi. 2003;44:181-5 pubmed
    ..We analyzed Irgafos 168 and its oxide in 38 samples of commercial frozen vegetables, and they were detected from 4 samples (0.02-0.80 microgram/g as total amount of Irgafos 168 and its oxide)...
  20. Feingersch R, Philosof A, Mejuch T, Glaser F, Alalouf O, Shoham Y, et al. Potential for phosphite and phosphonate utilization by Prochlorococcus. ISME J. 2012;6:827-34 pubmed publisher
    ..Our results suggest that Prochlorococcus adapt to low-P environments by increasing the number of Pn transporters with different specificities towards phosphite and different Pns...
  21. White A, Metcalf W. Microbial metabolism of reduced phosphorus compounds. Annu Rev Microbiol. 2007;61:379-400 pubmed
  22. Bhanthumnavin W, Bentrude W. Effect of amino substituents on the stereochemical outcome of the photo-Arbuzov rearrangements of 1-arylethyl phosphorodiamidites. J Org Chem. 2005;70:4643-51 pubmed
    ..formed by carbon-oxygen bond scission (Scheme 1), which are somewhat longer lived than those from the analogous phosphites 5 and 6, is proposed...
  23. Pozgan F, Toupet L, Dixneuf P. Preparation of hexacoordinating benzimidazole containing ligand and hexakis(benzimidazole-ruthenium(II)) complex. Molecular structure of C6{CH2-(N-benzimidazole-RuCl2(p-cymene))}6. Dalton Trans. 2011;40:6619-22 pubmed publisher
    ..The reactivity of the prepared complex with phosphite and carbonate was investigated and revealed the weakness of (benzimidazole)N-Ru bonds and the release of the polydentate ligand...
  24. Kaboudin B, Arefi M, Emadi S, Sheikh Hasani V. Synthesis and inhibitory activity of ureidophosphonates, against acetylcholinesterase: pharmacological assay and molecular modeling. Bioorg Chem. 2012;41-42:22-7 pubmed publisher
  25. Yehudai Resheff S, Zimmer S, Komine Y, Stern D. Integration of chloroplast nucleic acid metabolism into the phosphate deprivation response in Chlamydomonas reinhardtii. Plant Cell. 2007;19:1023-38 pubmed
    ..This unusual phenomenon, which is phosphite- and PSR1-insensitive, may have evolved as a result of the polyploid nature of cpDNA and the requirement of P for cpRNA degradation by PNPase...
  26. Torresani C, Zendri E, Vescovi V, De Panfilis G. Contact urticaria syndrome from occupational triphenyl phosphite exposure. Contact Dermatitis. 2003;48:237-8 pubmed
  27. Xiang C, Bian Y, Mao X, Huang Z. Coupling reactions of heteroarenes with phosphites under silver catalysis. J Org Chem. 2012;77:7706-10 pubmed publisher
    ..cross-coupling reaction of substituted furans, thiophene, thioazole, and pyrrole 1a-e with dialkyl phosphites 2 was first developed to afford corresponding phosphonated products 3a-h with up to 89% yield and good ..
  28. Imani Shakibaei G, Feiz A, Ghahremanzadeh R, Bazgir A. Three-component synthesis of 2-oxoindolin-3-ylphosphonates. Chem Pharm Bull (Tokyo). 2010;58:896-900 pubmed
    ..The features of this procedure are mild reaction conditions, high yields of products, and operational simplicity...
  29. Diéguez M, Ruiz A, Claver C. Chiral diphosphites derived from D-glucose: new highly modular ligands for the asymmetric catalytic hydrogenation. J Org Chem. 2002;67:3796-801 pubmed
    ..Moreover, the presence of bulky substituents at the ortho-positions of the biaryl diphosphite moieties has a positive effect on enantioselectivity...
  30. Liu P, Li C, Liang X, Xu J, Lu G, Ji F. Advanced oxidation of hypophosphite and phosphite using a UV/H2O2 process. Environ Technol. 2013;34:2231-9 pubmed
    ..It is really a powerful and environmentally friendly treatment method for the wastewater containing hypophosphite and phosphite...
  31. Yamabe S, Tsuchida N, Yamazaki S. Correlation between the rate order and the number of molecules in the reaction of trimethyl phosphite with water in acetonitrile solvent. J Phys Chem A. 2010;114:11699-707 pubmed publisher
    ..Catalytic water molecules were added to the n = 2 and 3 bond-interchange circuits. Then route B with n = 2 + 2 was found to be best. By n = 2 + 10 and n = 3 + 12 models, the n = 2 based route B was confirmed to be likely...
  32. Kinebuchi H, Akimaru K, Noda S, Yamamoto K. Cholinesterase activity in quails of neuropathy caused by organophosphates. Ind Health. 1998;36:376-9 pubmed
  33. Evano G, Tadiparthi K, Couty F. Copper-mediated cross-coupling of 1,1-dibromo-1-alkenes with dialkyl phosphites: a convenient synthesis of 1-alkenylphosphonates. Chem Commun (Camb). 2011;47:179-81 pubmed publisher
    ..of E-1-alkenylphosphonates by copper-mediated cross-coupling between 1,1-dibromo-1-alkenes and dialkyl phosphites is reported...
  34. Overend G, Iggo J, Heaton B, Whyman R. The reaction of mixtures of [Rh4(CO)12] and triphenylphosphite with carbon monoxide or syngas as studied by high-resolution, high-pressure NMR spectroscopy. Magn Reson Chem. 2008;46 Suppl 1:S100-6 pubmed publisher
    ..The distribution of tetrameric species obtained is similar to that obtained under the same partial pressure of CO. On depressurisation/out-gassing of the sample, the original mixture of tetrameric clusters is obtained...
  35. Lipsitz L, Weber A, Bursian S, Aulerich R, Ramsey D, Duke T. A quantitative assessment of TPP-induced delayed neuropathy in the retina and lateral geniculate nucleus of the European ferret (Mustela putorius furo). Neurotoxicology. 2002;23:33-42 pubmed
    ..D.; 7d = 152 microm2 +/- 28S.D. versus control = 214 microm2 +/- 9S.D.). Cell size distributions for LGN neurons were shifted toward smaller cell sizes in both TPP-treated groups compared to control...
  36. Li L, Cheng K, Wang F, Zhang J. Ionothermal synthesis of chiral metal phosphite open frameworks with in situ generated organic templates. Inorg Chem. 2013;52:5654-6 pubmed publisher
    ..It is interesting that the organic template, Me2-DABCO, is in situ generated from the alkylation reaction of 1,4-diazabicyclo[2.2.2]octane and dimethyl phosphites.
  37. Morton S, Zhang Y, Edwards M. Implications of nutrient release from iron metal for microbial regrowth in water distribution systems. Water Res. 2005;39:2883-92 pubmed
    ..Consequently, it may not be possible to control regrowth on iron surfaces by limiting phosphorus in the bulk water...
  38. Khang G, Kong C, Rhee J, Lee H. Stabilization of nontoxic PVC formulation for gamma irradiation sterilization, I. Effect of additives. Biomed Mater Eng. 2002;12:135-47 pubmed
    ..The proposed mechanisms of stabilization and discolorization with various additives are also discussed...
  39. Rubio M, Pizzano A. Application of phosphine-phosphite ligands in the iridium catalyzed enantioselective hydrogenation of 2-methylquinoline. Molecules. 2010;15:7732-41 pubmed publisher
    The hydrogenation of 2-methylquinoline with Ir catalysts based on chiral phosphine-phosphites has been investigated. It has been observed that the reaction is very sensitive to the nature of the ligand...
  40. Bhanthumnavin W, Bentrude W. Photo-Arbuzov rearrangements of 1-arylethyl phosphites: stereochemical studies and the question of radical-pair intermediates. J Org Chem. 2001;66:980-90 pubmed
    The direct UV irradiation of the 1-arylethyl phosphites 7, 8, and 9 was carried out in acetonitrile, benzene, and cyclohexane, as was the triphenylene-sensitized reaction of 9...
  41. Maerten E, Cabrera S, Kjaersgaard A, Jørgensen K. Organocatalytic asymmetric direct phosphonylation of alpha,beta-unsaturated aldehydes: mechanism, scope, and application in synthesis. J Org Chem. 2007;72:8893-903 pubmed
    ..DFT calculations have been applied to explain the approach of the phosphite to the reactive carbon atom in the iminium intermediate in order to account for the observed absolute enantioselectivity in the reaction...
  42. Di Palma L, Merli C, Petrucci E. Innovative methods for removing phosphorus from wastewaters. Ann Chim. 2001;91:145-9 pubmed
    Wastewater containing a mixture of hypophosphites and phosphites was treated in order to assess the possibility of attaining high levels of phosphorus oxidation to phosphate...
  43. Bunik V, Denton T, Xu H, Thompson C, Cooper A, Gibson G. Phosphonate analogues of alpha-ketoglutarate inhibit the activity of the alpha-ketoglutarate dehydrogenase complex isolated from brain and in cultured cells. Biochemistry. 2005;44:10552-61 pubmed
  44. Kholodar S, Murkin A. DXP reductoisomerase: reaction of the substrate in pieces reveals a catalytic role for the nonreacting phosphodianion group. Biochemistry. 2013;52:2302-8 pubmed publisher
    ..2 kcal/mol of transition state stabilization for the truncated substrate. These results implicate a phosphate-driven conformational change involving loop closure over the DXR active site to generate an environment poised for catalysis...
  45. Han C, Geng J, Ren H, Gao S, Xie X, Wang X. Phosphite in sedimentary interstitial water of Lake Taihu, a large eutrophic shallow lake in China. Environ Sci Technol. 2013;47:5679-85 pubmed publisher
    ..Phosphite may be an important media in the P biogeochemical cycle in Lake Taihu and contribute to its internal P transportation...
  46. Zhang Q, Takacs J. Click-connected ligand scaffolds: macrocyclic chelates for asymmetric hydrogenation. Org Lett. 2008;10:545-8 pubmed publisher
    ..Enantioselectivity as high as 97% ee is obtained using these click ligands in rhodium-catalyzed asymmetric hydrogenation. Control experiments and spectroscopic data suggest that a 16-membered P,P-macrocyclic Rh(I) chelate is formed...
  47. Tsang W, Amyes T, Richard J. A substrate in pieces: allosteric activation of glycerol 3-phosphate dehydrogenase (NAD+) by phosphite dianion. Biochemistry. 2008;47:4575-82 pubmed publisher
  48. Singh S, Ma L, Hendry M. Characterization of aqueous lead removal by phosphatic clay: equilibrium and kinetic studies. J Hazard Mater. 2006;136:654-62 pubmed
    ..The exceptional capability of phosphatic clay to remove aqueous Pb demonstrated its potential as a cost effective way to remediate Pb-contaminated water, soils and sediments...
  49. Liu H, Xu J. Synthesis of 1-(N-ethoxycarbonylamino)alkylphosphonic monoesters. Amino Acids. 2005;29:241-3 pubmed
    ..A series of 1-(N-ethoxycarbonylamino)alkylphosphonic monoesters were synthesized via three-component Mannich-type condensation of ethyl carbamate, aldehydes and dichlorophosphites in benzene, followed by hydrolysis...
  50. Sasseville D, Moreau L. Allergic contact dermatitis from triphenyl phosphite. Contact Dermatitis. 2005;52:163-4 pubmed
  51. Gao F, Furlong O, Kotvis P, Tysoe W. Reaction of tributyl phosphite with oxidized iron: surface and tribological chemistry. Langmuir. 2004;20:7557-68 pubmed
    ..The resulting tribological film appears to be composed of a relatively hard polyphosphate glass formed by rapid diffusion of POx species into the oxide, covered by a low shear strength graphitic layer...
  52. Ercegovic T, Nilsson U, Magnusson G. A study of the donor properties of sialyl phosphites having an auxiliary 3-(S)-phenylseleno group. Carbohydr Res. 2001;331:255-63 pubmed
    ..The weak C-Se bond, possibly in combination with a steric hindrance, which disfavors alpha-nitrilium ion formation, seem to explain the unsuccessful sialylations of the less reactive acceptors...
  53. Burra D, Berkowitz O, Hedley P, Morris J, Resjö S, Levander F, et al. Phosphite-induced changes of the transcriptome and secretome in Solanum tuberosum leading to resistance against Phytophthora infestans. BMC Plant Biol. 2014;14:254 pubmed publisher
    ..Our study suggests that a rapid phosphite-triggered response is important to confer long-lasting resistance against P. infestans and gives molecular understanding of its successful field applications. ..