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PubMed2005

[Synthesis, structure characterization and, fluorescence studies of the complexes of europium with phenylglyoxylic acid, 1,10-phenanthroline and triphenyl phosphine oxide].

Three novel europium complexes, Eu-L, EuL3phen and EuL2 (TPPO)2NO3, were synthesized (HL = phenylglyoxylic, phen= 1,10-phenanthroline, and TPPO = triphenyl phosphine oxide). The complexes were characterized by elemental analysis, conductivity, IR, and 1H NMR. The IR spectra indicated that all the complexes have a larger deltaupsilon(upsilon(as) (CO2-) - upsilon(s)(CO2-) than that of NaL, and carboxylate ions in the phenylglyoxyate coordinated as unidentate ligands. And alpha-aeto also coordinated with the europium ions. In 1H NMR, the signals of hydrogens in the phenylglyoxyate shifted toward upfield, and those in phen or TPPO slightly shifted. The excitation and emission spectra were recorded at room temperature, and the excitation spectra showed that the optimum excitation wavelengths were 374.0, 358.2 and 383.4 nm, Five emission bands of the complexes due to 5D(0)-7F(0), 5D(0)-7F(1), 5D(0)-7F(2), 5D(0)-7F(3) and 5D(0)-7F(4) transitions were observed in the region of 550-720 nm (Eu-L: 577.8, 590.2, 614.0, 648.4 and 695.4 nm; EuL3phen: 578.0, 588.4, 591.6, 611.2, 617.0, 649.4, 687.6 and 698.6 nm; EuL2 (TPPO)2NO3: 577.8, 590.4, 614.6, 649.2 and 697.6 nm). The emission intensities of europium ions were obviously sensitized by TPPO.

English Abstract↗
PubMed1992

[ Dynamics of NAD-dependent isocitrate dehydrogenase activity in homogenized rat liver exposed to toxic products of the phosphorus industry].

Dynamic studies showed that the combined action of phosphine and hydrofluoric acid damages the Krebs cycle reactions, dehydrogenization of isocitrate and synthesis of citrate in homogenized rat liver. Yellow phosphorus harmed the citrate synthetic reaction of citric acid cycle in homogenized rat liver as well. That activated the alternative action principles in the cycle. The main cause of such disorders in the Krebs cycle in likely to be the abnormal fat metabolism induced by toxic products of phosphorus industry.

Animals↗
PubMed2005

Phosphine from rocks: mechanically driven phosphate reduction?

Natural rock and mineral samples released trace amounts of phosphine during dissolution in mineral acid. An order of magnitude more phosphine (average 1982 ng PH3 kg rock and maximum 6673 ng PH3/kg rock) is released from pulverized rock samples (basalt, gneiss, granite, clay, quartzitic pebbles, or marble). Phosphine was correlated to hardness and mechanical pulverization energy of the rocks. The yield of PH3 ranged from 0 to 0.01% of the total P content of the dissolved rock. Strong circumstantial evidence was gathered for reduction of phosphate in the rock via mechanochemical or "tribochemical" weathering at quartz and calcite/marble inclusions. Artificial reproduction of this mechanism by rubbing quartz rods coated with apatite-phosphate to the point of visible triboluminescence, led to detection of more than 70 000 ng/kg PH3 in the apatite. This reaction pathway may be considered a mechano-chemical analogue of phosphate reduction from lightning or electrical discharges and may contribute to phosphine production via tectonic forces and processing of rocks.

Geological Phenomena↗
PubMed2003

High asymmetric induction with beta-turn-derived palladium phosphine complexes.

[reaction: see text] Work toward the development of a bisphosphine ligand system for the palladium-catalyzed addition to cyclic allyl acetates is reported. A parallel approach using phosphine-containing amino acids in conjunction with natural amino acids was used to develop a selective ligand system. The ligand system was examined while attached to the polymer support as well as in solution. Selectivites with the difficult substrate 3-acetoxycyclopentene of up to 95% ee are reported.

Acetates↗
PubMed2001

Effect of Lewis acidity on the synthesis of RuHCl(CO)(phosphine)(2): subtle influence of steric and electronic effects among P(i)Pr(3), P(i)Pr(2)(3,5-(CF(3))(2)C(6)H(3)), and P(i)Pr(2)Me.

To evaluate the influence of steric, electronic, and synthetic factors, the synthesis of RuHCl(CO)[P(i)Pr(2)(3,5-(CF(3))(2)C(6)H(3))](2) was carried out, and its Lewis acidity toward Cl- was compared to that of RuHCl(CO)(P(i)Pr(3))(2). In this synthesis, Na(2)CO(3) was shown to be a more effective base than NEt(3), because Na+ can better mask the nucleophilicity of the potential ligand Cl-. An X-ray structure determination of the hydride-free species RuCl(2)(CO)(P(i)Pr(2)Me)(2) shows it to be a dimer, and this solid-state structure persists in solution, but as several different isomers. The synthesis of RuHCl(CO)(P(i)Pr(2)Me)(3) shows that three of this smaller phosphine can crowd around Ru, but dynamic NMR spectra show one phosphine to be weakly bound. The rate of reaction of Me(3)SiC(triple bond)CH with this molecule is suppressed by added free P(i)Pr(2)Me, indicating phosphine dissociation to be a mechanistic component.

Journal Article↗
PubMed1997

A new potassium channel toxin from the sea anemone Heteractis magnifica: isolation, cDNA cloning, and functional expression.

A new potassium channel toxin, HmK, has been isolated from the sea anemone Heteractis magnifica. It inhibits the binding of [125I]-alpha-dendrotoxin (a ligand for voltage-gated K channels) to rat brain synaptosomal membranes with a Ki of about 1 nM, blocks K+ currents through Kv 1.2 channels expressed in a mammalian cell line, and facilitates acetylcholine release at the avian neuromuscular junction. HmK comprises of 35 amino acids (Mr 4055) with the sequence R1TCKDLIPVS10ECTDIRCRTS20MKYRLNLCRK30TCGSC35. A full assignment of the disulfide linkages was made by using partial reduction with tri(2-carboxyethyl)phosphine (TCEP) at acid pH and rapid alkylation with iodoacetamide. The disulfide bridges were identified as Cys3-Cys35, Cys12-Cys28, and Cys17-Cys32. A cDNA clone encoding HmK was isolated using RT-PCR from the total RNA obtained from sea anemone tentacles, while the 5'- and 3'-flanking regions of the cDNA were amplified by RACE. The full-length cDNA was 563 bp long and contained a sequence encoding a signal peptide of 39 amino acids. The coding region for matured HmK toxin was cloned and expressed as a glutathione S-transferase (GST) fusion product in the cytoplasm of Escherichia coli. After affinity purification and cleavage, the recombinant toxin was shown to be identical to native HmK in its N-terminal sequence, chromatographic behavior, and binding to dendrotoxin binding sites on rat brain membranes.

Amino Acid Sequence↗
PubMed2004

Tris(2-carboxyethyl)phosphine stabilization of RNA: comparison with dithiothreitol for use with nucleic acid and thiophosphoryl chemistry.

We assessed the utility of the sulfhydryl reductant Tris(2-carboxyethyl)phosphine (TCEP) for both nucleic acid and thiophosphate chemistry, including its effects on organomercurial gel electrophoresis, RNA catalysis, RNA backbone stability, and the intrinsic stability of TCEP. The sulfhydryls of dithiothreitol (DTT) compete with thiophosphates for binding to the mercury within [(N-acryloylamino)phenyl] mercuric chloride (APM) polyacrylamide gels, whereas millimolar concentrations of TCEP gave no difference in the fraction of thiophosphorylated RNA retained on the APM interface relative to samples containing no reductant. Ribozyme activity in TCEP, assessed by the self-thiophosphorylating Kin.46 ribozyme, was unaffected by the presence of DTT or TCEP or by the absence of reductant, as measured on APM gels and evaluated by Michaelis-Menten kinetics. Unexpectedly, TCEP more than doubled the half-life of full-length RNA at 50 and 70 degrees C, whether in 5 or 50mM MgCl(2), relative to DTT and the absence of reductant. Under these same conditions, the 5(')-thiophosphate showed negligible decay, and TCEP was more stable than DTT. TCEP thermostability was equivalent in the presence of 5 or 50mM MgCl(2) and 10mM adenosine or ATP.

Base Sequence↗
PubMedDate not supplied

Efficient synthesis of sulfonic, phosphoric, and phosphinic esters employing alkylating polymer-bound reagents.

The efficient esterification of various sulfonic acids and sulfonates using polymer-bound triazenes based on the triazene T2 linker is described. Esterification of enantiopure alpha-substituted sodium sulfonates was performed in the presence of an alkylating resin without racemization. Racemization is a serious drawback in the esterification route via sulfonyl chlorides because of intermediate sulfene formation. To demonstrate the versatility of this protocol, phosphoric and phosphinic acids have been converted into the corresponding esters as well. All products were obtained in good yield and excellent purities without any further purification steps.

Journal Article↗
PubMed1994

Laboratory diagnosis of zinc phosphide poisoning.

Zinc phosphide, a readily-available rodenticide, poses a significant risk for intoxication in animals. Animals have been poisoned by ingesting treated bait or the carcasses of poisoned rodents. Toxicity is due to the liberation of phosphine gas in the stomach. Clinical signs include central nervous system excitation, depression and vomition. Similarities of clinical signs with other central nervous system toxicants make the diagnosis difficult without a specific diagnostic test. The procedure outlined in this paper detects phosphine liberated from zinc phosphide by the addition of hydrochloric acid as well as the phosphine previously generated by contact with stomach acid.

Animals↗
PubMed2002

Asymmetric synthesis of 2H-azirines derived from phosphine oxides using solid-supported amines. Ring opening of azirines with carboxylic acids.

A simple and efficient asymmetric synthesis of 2H-azirine-2-phosphine oxides 3 is described. The key step is a solid-phase bound achiral or chiral amine-mediated Neber reaction of beta-ketoxime tosylates derived from phosphine oxides 1. Reaction of 2H-azirines 3 and 11 with carboxylic acids 4 gives phosphorylated ketamides 5 and 12. Ring closure of ketamides 5 and 12 with triphenylphosphine and hexachloroethane in the presence of triethylamine leads to the formation of phosphorylated oxazoles 8 and 13.

Amines↗
PubMed1980

Mutagenicity tests of fabric-finishing agents in Salmonella typhimurium: fiber-reactive wool dyes and cotton flame retardants.

Thirty-nine fabric-finishing agents were tested for mutagenic activity in Salmonella typhimurium. Twenty-four fiber-reactive wool dyes and three acid dyes (not fiber-reactive) were screened by spot tests in strains TA100, TA98, TA1535, and TA1537. Among these dyes, seven bromoacrylamide dyes and one vinyl sulfone dye were mutagenic. Additionally, one of the three acid dyes was mutagenic in spot tests. The mutagenicity of the acid dye was due to an impurity or breakdown product rather than to the dye itself; the origin of the activities of the other dyes is unknown. No mutagenicity was observed among five chlorotriazine or four sulfonyl-ethane sulfonic acid dyes. Eight phosphorus-containing flame retardants (phosphonium, phosphine, phosphine oxide, and phosphonic acid derivatives) and methyl-N-methylolcarbamate, which is employed to obtain a flame-retardant finish on cotton, were tested for mutagenicity in strains TA100, TA98, TA1535, and TA1537, using quantitative incorporation assays. All were nonmutagenic. Two of three bromoalkyl-substituted triazine flame retardants were mutagenic in strains TA100 and TA1535. It is unknown whether this activity is due to impurities or to the parent compound. The flame retardants tested were either in actual commercial use or in experimental development for potential commercial processes. These results indicate the need for early testing of potential fabric-finishing agents and processes.

Animals↗
PubMed1999

Disulfide assignment of the C-terminal cysteine knot of agouti-related protein (AGRP) by direct sequencing analysis.

We have assigned the disulfide structure of Md-65 agouti-related protein (Md65-AGRP) using differential reduction and alkylation followed by direct sequencing analysis. The mature human AGRP is a single polypeptide chain of 112 amino acid residues, consisting of an N-terminal acidic region and a unique C-terminal cysteine-rich domain. The C-terminal domain, a 48 amino acid peptide named Md65-AGRP, was expressed in Escherichia coil cells and refolded under different conditions from the mature recombinant protein. The disulfide bonds in the cystine knot structure of Md65-AGRP were partially reduced using tris(2-carboxyethyl) phosphine (TCEP) under acidic conditions, followed by alkylation with N-ethylmaleimide (NEM). The procedure generated several isoforms with varying degrees of NEM alkylation. The multiple forms of Md65-AGRP generated by partial reduction and NEM modification were then completely reduced and carboxymethylated to identify unreactive disulfide bonds. Differentially labeled Md65-AGRP were directly sequenced and analyzed by MALDI mass spectrometry. The results confirmed that Md65-AGRP contained the same disulfide structure as that of Md5-AGRP reported previously [Bures, E. J., Hui, J. O., Young, Y. et al. (1998) Biochemistry 37, 12172-12177].

Agouti-Related Protein↗
PubMed2006

Phosphine-free cross-coupling reaction of arylboronic acids with carboxylic anhydrides or acyl chlorides in aqueous media.

The palladium acetate-catalyzed coupling reaction of aryl boronic acid with carboxylic anhydride or acyl chloride was carried out smoothly in water in the presence of poly(ethylene glycol) (PEG) or 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]) to give high yields of ketones without the use of phosphine ligands. The Pd(OAc)2-H2O-[bmim][PF6] catalytic system can be recovered and reused eight times with high efficiency for both carboxylic anhydride and acyl chloride.

Anhydrides↗
PubMedDate not supplied

Determination of phosphine: comparison of rates of desorption by purge-and-trap method and by sulfuric acid treatment.

Two methods were compared for quantitative determination of phosphine present on fumigated food and materials. The rate of desorption of PH3 by using a purge-and-trap method was shown to be much slower when compared with sulfuric acid treatment and was also simpler. Application of the modified sulfuric acid treatment for real samples is described.

Adsorption↗
PubMed2002

Water-soluble phosphines. 17.(1) novel water-soluble secondary and tertiary phosphines with disulfonated 1,1'-biphenyl backbones and dibenzophosphole moieties.

Reaction of 2,2'-difluoro-1,1'-biphenyl with chlorosulfonic acid and subsequent hydrolysis followed by neutralization with potassium or sodium hydroxide affords disodium or dipotassium 5,5'-disulfonato-2,2'-difluoro-1,1'-biphenyl (1a, 1b). On treatment of 1b with diphenyl- or phenylphosphine in the superbasic medium DMSO/KOH, phosphine ligand 2 or 3 with a disulfonated 1,1'-biphenyl backbone or a dibenzophosphole moiety is formed. The structure of the oxide of 5-phenyldibenzophosphole 3, which crystallizes as 4.2.5H(2)O in the monoclinic space group P2(1)/n with a = 13.799(3) A, b = 19.246(4) A, c = 17.764(4) A, beta = 105.63(3) degrees, and Z = 4, has been determined by X-ray analysis. Nucleophilic phosphination of 1a with NaPH(2) in liquid ammonia yields the sodium phosphide 5a which on protonation gives the water-soluble 5H-dibenzophosphole 5. Reaction of 1b with PH(3) in the superbasic medium DMSO/KOtBu affords 5b in addition to the oxidation product 6a. On oxidation of 5a or 5b with H(2)O(2), the sodium or potassium salts of the sulfonated phosphinic acids 6a or 6b, respectively, are formed. Alkylation of the sodium dibenzophospholide 5a with 2,2'-bis(chloromethyl)-1,1'-biphenyl or 1,4-di-O-p-toluenesulfonyl-2,3-O-isopropylidene-D-threitol yields the chiral water-soluble bidentate phosphine ligands 8 and 9, respectively.

Journal Article↗
PubMed1996

Dehydrochlorination of alpha-Chlorophosphines, a Simple and General Route to Phosphaalkenes.

Primary and secondary alpha-chlorophosphines 2a-g are prepared in ca. 70% yield by chemoselective reduction of the corresponding phosphonic and phosphinic esters with AlHCl(2) and are characterized by (31)P, (13)C, and (1)H NMR and by HMRS. They can be kept several weeks in the refrigerator after purification. They lead then to the corresponding phosphaalkenes 3a-g by HCl elimination. For the volatile alpha-chlorophosphines 2a-e HCl elimination occurs in the gas phase on solid potassium carbonate under VGSR conditions (vacuum gas-solid reactions); the corresponding phosphaalkenes 3a-e are characterized by real time HRMS analysis of the gaseous flow (VGSR/HRMS coupling) and by solid-phase IR spectroscopy after condensation of the gaseous flow on a KBr window cooled to 77 K. The decomposition of phosphaalkenes at this temperature is monitored by IR spectroscopy. The alpha-chlorophosphines 2a-g undergo a HCl elimination in the liquid phase in the presence of a Lewis base; the formation of the transient phosphaalkenes is monitored by (31)P FT-NMR. The temperature of HCl elimination is dependent both upon the P-H acidity of the phosphine precursors and the nature of the base. The (31)P NMR data of the simple phosphaalkenes 3a-g are for the first time reported. They are consistent with the proposed structure. The stereochemistry of the (Z)- and (E)-isomers is established according to the "cis-rule". Phosphaalkenes 3a-g are also characterized by chemical trapping in solution with various dienes, dipoles, or thiols. All of these experiments confirm the transient character of these species. The synthetic potential of this route is evaluated.

Journal Article↗