Protein Information

Name complex is
Synonyms 39kD; CI 39kD; Complex I; Complex I 39kD; NADH dehydrogenase (ubiquinone) Fe S protein 2 like; NADH ubiquinone oxidoreductase 39 kDa subunit mitochondrial; NADH ubiquinone oxidoreductase 39 kDa subunit; NDUFA 9…

Compound Information

Name phosphine
CAS phosphine

Reference List

PubMed Abstract RScore(About this table)
18251492 Marzano C, Gandin V, Pellei M, Colavito D, Papini G, Lobbia GG, Del Giudice E, Porchia M, Tisato F, Santini C: In vitro antitumor activity of the water soluble copper (I) complexes bearing the tris (hydroxymethyl) phosphine ligand. J Med Chem. 2008 Feb 28;51(4):798-808. Epub 2008 Feb 6.

Cytological stains and flow cytometric analyses indicated that the phosphine copper (I) complex is able to inhibit the growth of tumor cells via G2/M cell cycle arrest and paraptosis accompanied with the loss of mitochondrial transmembrane potential.
31(0,1,1,1) Details
19505129 Ignatov SK, Khalimon AY, Rees NH, Razuvaev AG, Mountford P, Nikonov GI: Beta-agostic silylamido and silyl-hydrido compounds of molybdenum and tungsten. Inorg Chem. 2009 Oct 19;48(20):9605-22.

A double phosphine dissociation pathway via the species (MeN)(2) Mo (PMe (3)) was ruled out because this complex is by 24.7 kcal mol (-1) less stable than (MeN)(2) Mo (PMe (3))(2).
6(0,0,1,1) Details
18630868 Fristrup P, Ahlquist M, Tanner D, Norrby PO: On the nature of the intermediates and the role of chloride ions in Pd-catalyzed allylic alkylations: added insight from density functional theory. J Phys Chem A. 2008 Dec 18;112(50):12862-7.

In the presence of both phosphine and chloride ligands, the allyl intermediate is in equilibrium between a cationic eta (3)-allylPd complex with two phosphine ligands, the corresponding neutral complex with one phosphine and one chloride ligand, and a neutral eta (1)-allylPd complex with one chloride and two phosphine ligands.
The eta (1)-complex is unreactive toward nucleophiles.
2(0,0,0,2) Details
17256842 Gilbertson JD, Szymczak NK, Crossland JL, Miller WK, Lyon DK, Foxman BM, Davis J, Tyler DR: Coordination chemistry of H2 and N2 in aqueous solution. Inorg Chem. 2007 Feb 19;46(4):1205-14. Epub 2007 Jan 26.

Reactivity and mechanistic studies using trans-FeII (P2) 2X2)-type complexes (P2 = a chelating, water-solubilizing phosphine)..
The reactions of the trans-Fe (DMeOPrPE) 2Cl2 complex (I; DMeOPrPE = 1,2-bis (bis (methoxypropyl) phosphino) ethane) and its derivatives were studied in aqueous and nonaqueous solvents with a particular emphasis on the binding and activation of H2 and N2.
2(0,0,0,2) Details
14692777 Yamashita M, Cuevas Vicario JV, Hartwig JF: Trans influence on the rate of reductive elimination. J Am Chem Soc. 2003 Dec 31;125(52):16347-60.

This result suggests that the geometry of the complex is equal in importance to the donating ability of the dative ligands.
Third, the difference in rate between the isomeric arylpalladium amido complexes was similar in magnitude to the differences in rates resulting from conventional variation of substituents on the symmetric phosphine ligands.
1(0,0,0,1) Details
20354611 Castineiras A, Pedrido R: A thiosemicarbazone ligand functionalized by a phosphine group: Reactivity toward coinage metal ions. Dalton Trans. 2010 Apr 21;39(15):3572-84. Epub 2010 Mar 11.

The complex is an interesting case of a pseudo-chloronium gold (i) complex.
1(0,0,0,1) Details
20089711 Zoer B, Cogolludo AL, Perez-Vizcaino F, De Mey JG, Blanco CE, Villamor E: Hypoxia sensing in the fetal chicken femoral artery is mediated by the mitochondrial electron transport chain. Am J Physiol Regul Integr Comp Physiol. 2010 Apr;298(4):R1026-34. Epub 2010 Jan 20.

Also, the K (+) channel inhibitors tetraethylammonium (nonselective), diphenyl phosphine oxide-1 (voltage-gated K (+) channel 1.5), glibenclamide (ATP-sensitive K (+) channel), iberiotoxin (large-conductance Ca (2+)-activated K (+) channel), and BaCl (2) (inward-rectifying K (+) channel), as well as ouabain (Na (+)-K (+)-ATPase inhibitor) did not affect hypoxia-induced relaxation.
Hypoxia-induced relaxation was abolished or significantly reduced by the mETC inhibitors rotenone (complex I), myxothiazol and antimycin A (complex III), and NaN (3) (complex IV).
1(0,0,0,1) Details
15237144 Batten MP, Canty AJ, Cavell KJ, Ruther T, Skelton BW, White AH: Bis [tris (1-methyl-1H-imidazol-2-yl) phosphine-kappa3N3] iron (II) tetrachloroferrate (II) methanol tetrasolvate (ca 153 K) and bis [tris (1-methyl-1H-imidazol-2-yl) methanol-kappa3N3] iron (III) bis [tetrachloroferrate (III)] chloride (redetermination, ca 153 K). Acta Crystallogr C. 2004 Jul;60(Pt 7):m311-3. Epub 2004 Jun 22.

The first of the title compounds, [Fe (C12H15N6P) 2][FeCl4].4CH4O, is the first homoleptic bis (ligand) iron (II) species reported for this phosphorus bridgehead ligand; interestingly, the complex is isomorphous with its tris (1-methyl-1H-imidazol-2-yl) methanol counterpart, the second of the title compounds, [Fe (C13H16N6O) 2][FeCl4] 2Cl.
1(0,0,0,1) Details
16417380 Barder TE: Synthesis, structural, and electron topographical analyses of a dialkylbiaryl phosphine/arene-ligated palladium (I) dimer: enhanced reactivity in Suzuki-Miyaura coupling reactions. J Am Chem Soc. 2006 Jan 25;128(3):898-904.

Additionally, this complex is a suitable precatalyst for high yielding Suzuki-Miyaura coupling reactions in short reaction times.
1(0,0,0,1) Details
19672503 Feng J, Zhou L, Song SY, Li ZF, Fan WQ, Sun LN, Yu YN, Zhang HJ: A study on the near-infrared luminescent properties of xerogel materials doped with dysprosium complexes. Dalton Trans. 2009 Sep 7;(33):6593-8. Epub 2009 Jun 30.

The results reveal that the dysprosium complex is successfully synthesized in situ in the corresponding xerogel.
The evidence showed that the neutral ligand triphenyl phosphine oxide (TPPO) could increase the emission intensity of the dysprosium complex while 1,10-phenanthroline (phen) gave the negative effect.
1(0,0,0,1) Details
17257007 Weir JJ, McDonough JE, Fortman G, Isrow D, Hoff CD, Scott B, Kubas GJ: Synthesis, structure, and thermochemistry of the formation of the metal-metal bonded dimers [Mo (mu-TeAr)(CO) 3 (PiP3)] 2 (Ar = phenyl, naphthyl) by phosphine elimination from *Mo (TePh)(CO) 3 (PiPr3) 2. Inorg Chem. 2007 Feb 5;46(3):652-9.

Kinetic studies show the rate of formation of the dimeric chalcogen bridged complex is best fit by a rate law first order in (*TeAr) Mo (CO) 3 (PiPr3) 2 and inhibited by added PiPr3.
1(0,0,0,1) Details
14640640 Pestovsky O, Bakac A: Direct kinetic studies of atom transfer and electron transfer reactions of hydroperoxo and high-valent oxo complexes of chromium. J Am Chem Soc. 2003 Dec 3;125(48):14714-5.

A macrocyclic hydroperoxo chromium complex reacts with triphenyl phosphine in an acid-catalyzed oxygen-atom transfer reaction, k = 850 M-2 s-1.
In a competing process, the hydroperoxo complex is converted to a dioxo chromium (V) species, which reacts with PPh3 by electron transfer, k = 4.4 x 105 M-1 s-1.
1(0,0,0,1) Details
19275142 Matsubara T: Dynamical behavior of the H2 molecule of the PtH (H2)[P (t-Bu) 3] 2 (+) complex. J Phys Chem A. 2009 Apr 2;113(13):3227-36.

The dynamical behavior of the coordinated H (2) molecule of the PtH (H (2))[P (t-Bu)(3)](2)](+) complex is examined by the ONIOM-molecular dynamics (MD) method that we recently developed.
The ONIOM-MD simulations reveal that the dynamical environmental effects of the t-Bu substituents of the phosphine ligands, which increase the magnitude of the energy fluctuations of the active part, significantly promote both rotation and dissociation of the coordinated H (2) molecule.
1(0,0,0,1) Details
20124678 Becker CA, Black RS, Forbes RP: Tris (tert-butyl isocyanide) bis [tris (4-methoxyphenyl) phosphine] cobalt (I) perchlorate dichloromethane disolvate and tris (tert-butyl isocyanide) bis [tris (4-methoxyphenyl) phosphine] cobalt (II) bis (perchlorate) dichloromethane disolvate: modification of a trigonal-bipyramidal structure with change of metal oxidation state. Acta Crystallogr C. 2010 Feb;66(Pt 2):m40-3. Epub 2010 Jan 15.

The cation of complex (I) has D (3h) site symmetry around the Co atom and the overall symmetry is C (3h).
1(0,0,0,1) Details
20060593 Xie F, Sutherland DE, Stillman MJ, Ogawa MY: Cu (I) binding properties of a designed metalloprotein. J Inorg Biochem. 2010 Mar;104(3):261-7. Epub 2009 Dec 16.

Absorption, emission, electrospray ionization mass spectrometry (ESI-MS), and circular dichroism (CD) experiments show that a 1:1 Cu-peptide complex is formed when Cu (I) is initially added to a solution of the monomeric peptide.
It was further found that the exogenous reductant tris (2-carboxyethyl) phosphine (TCEP) can competitively inhibit the binding of Cu (I) to the low affinity site of the peptide, but does not interact with Cu (I) clusters.
1(0,0,0,1) Details
19472292 Liu LP, Hammond GB: Reactions of cationic gold (I) with allenoates: synthesis of stable organogold (I) complexes and mechanistic investigations on gold-catalyzed cyclizations. Chem Asian J. 2009 Aug 3;4(8):1230-6.

The reaction of allenoates with cationic gold (I)-generated in situ from a phosphine gold chloride and a silver salt-formed unusual, room temperature stable vinyl gold (I) lactones under very mild conditions.
Controlled experiments for the cleavage of the gold-carbon bond by electrophiles indicated that this vinyl gold (I) complex is the likely intermediate in the gold-catalyzed reaction of carbon-carbon multiple bonds.
1(0,0,0,1) Details
12735970 Kothari KK, Raghuraman K, Pillarsetty NK, Hoffman TJ, Owen NK, Katti KV, Volkert WA: Syntheses, in vitro and in vivo characterization of a 99mTc-(I)-tricarbonyl-benzylamino-dihydroxymethyl phosphine (NP (2)) chelate. Appl Radiat Isot. 2003 May;58(5):543-9.

A single, well-defined 99mTc (CO)(3) NP (2) complex is formed at pH 7.5 within 10 min at 60 degrees C that exhibits high in vitro and in vivo stability.
1(0,0,0,1) Details
19785176 Gouverd C, Biaso F, Cataldo L, Berclaz T, Geoffroy M, Levillain E, Avarvari N, Fourmigue M, Sauvage FX, Wartelle C: Tetrathiafulvalene-phosphine-based iron and ruthenium carbonyl complexes: electrochemical and EPR studies. Phys Chem Chem Phys. 2005 Jan 7;7(1):85-93.

The stability of this complex is however modest and, after some minutes, the species resulting from the scission of a P-Fe bond is detected.
1(0,0,0,1) Details
18443708 Fernandez D, Garcia-Seijo MI, Bardaji M, Laguna A, Garcia-Fernandez ME: Gold (I) and silver (I) complexes containing a tripodal tetraphosphine ligand: influence of the halogen and stoichiometry on the properties. Dalton Trans. 2008 May 21;(19):2633-42. Epub 2008 Mar 31.

The influence of the halogen on the aurophilic contacts of compounds with a 4:1 metal to ligand ratio results in different photophysical properties, while and are luminescent complex is nonemissive.
Complexes of the type [Au2 (micro-PP3) 2] X2 [X=Cl (), Br (), I ()], [Ag2 (micro-PP3) 2](NO3) 2 (), Ag (PP3) Cl (), M3 (micro-PP3) X3 [M=Au, X=Cl (), Br (), I (); M=Ag, X=NO3 ()] and Au4 (micro-PP3) X4 [X=Cl (), Br (), I ()] have been prepared by interaction between gold (I) or silver (I) salts and the ligand tris [2-(diphenylphosphino) ethyl] phosphine (PP3) in the appropriate molar ratio.
1(0,0,0,1) Details
12823028 Dioumaev VK, Procopio LJ, Carroll PJ, Berry DH: Synthesis and reactivity of silyl ruthenium complexes: the importance of trans effects in C-H activation, Si-C bond formation, and dehydrogenative coupling of silanes. J Am Chem Soc. 2003 Jul 2;125(26):8043-58.

The longest Ru-P distance within a complex is always trans to Si, reflecting the strong trans influence of silicon.
The aptitude of phosphine dissociation in these complexes has been probed in reactions of 1a, 1c, and 7a with PMe (3)-d (9) and CO.
1(0,0,0,1) Details
16234939 Thapper A, Behrens A, Fryxelius J, Johansson MH, Prestopino F, Czaun M, Rehder D, Nordlander E: Synthesis and characterization of molybdenum oxo complexes of two tripodal ligands: reactivity studies of a functional model for molybdenum oxotransferases. Dalton Trans. 2005 Nov 7;(21):3566-71. Epub 2005 Sep 16.

The dioxo-molybdenum complex [MoO2 (L-O)]+ reacts with phosphines in methanol to afford phosphine oxides and an air-sensitive molybdenum complex, tentatively identified as [Mo (IV) O (L-O)(OCH3)].
The latter complex is capable of reducing biological oxygen donors such as DMSO or nitrate, thereby mimicking the activity of DMSO reductase and nitrate reductase.
1(0,0,0,1) Details
19746461 Christian GJ, Terrett RN, Stranger R, Cavigliasso G, Yates BF: Dinitrogen activation by Fryzuk's [Nb (P (2) N (2))] complex and comparison with the Laplaza-Cummins [Mo{N (R) Ar}(3)] and Schrock [Mo (N (3) N)] systems. Chemistry. 2009 Oct 26;15(42):11373-83.

The reaction profile of N (2) with Fryzuk's [Nb (P (2) N (2))] (P (2) N (2)=PhP (CH (2) SiMe (2) NSiMe (2) CH (2))(2) PPh) complex is explored by density functional calculations on the model [Nb (PH (3))(2)(NH (2))(2)] system.
The orientation of the amide and phosphine ligands has a significant effect on the overall reaction enthalpy and also the N--N bond cleavage step.
1(0,0,0,1) Details
19639941 Snelders DJ, van Koten G, Klein Gebbink RJ: Hexacationic Dendriphos ligands in the Pd-catalyzed Suzuki-Miyaura cross-coupling reaction: scope and mechanistic studies. J Am Chem Soc. 2009 Aug 19;131(32):11407-16.

Through control and poisoning experiments, it is concluded that a homogeneous Pd (0)-Dendriphos complex is the active species in this catalytic system.
Despite their triarylphosphine-based structure, Dendriphos ligands behave as very bulky phosphine ligands and lead to a preferential formation of coordinatively unsaturated and catalytically active Pd (0) species, which explains the observed high catalytic activity for these systems.
1(0,0,0,1) Details
15360258 Tutusaus O, Nunez R, Vinas C, Teixidor F, Mata I, Molins E: Synthesis, characterization, and dynamic studies of 12-vertex eta5-ruthenium (II) closo-phosphine complexes with monoanionic [10-L-nido-7-R-7,8-C2B9H9]- ligands. Inorg Chem. 2004 Sep 20;43(19):6067-74.

The Ru (II) atom in this complex is on the open face of the monoanionic charge-compensated ligand adopting a pseudooctahedral coordination.
1(0,0,0,1) Details
12974644 Brohawn SG, Miksa IR, Thorpe C: Avian sulfhydryl oxidase is not a metalloenzyme: adventitious binding of divalent metal ions to the enzyme. Biochemistry. 2003 Sep 23;42(37):11074-82.

The resulting zinc complex is modestly air-stable, reverting to a spectrum of the native protein with a t (1/2) of 40 min, whereas the four-electron-reduced native QSOX is reoxidized in less than a second under comparable conditions.
Using tris (2-carboxyethyl) phosphine hydrochloride (TCEP), an alternate substrate of QSOX that binds Zn (2+) relatively weakly (unlike dithiothreitol), allows rapid inhibition of oxidase activity to be demonstrated at low micromolar metal levels.
1(0,0,0,1) Details
16357969 Meyer C, Scherer M, Schonberg H, Ruegger H, Loss S, Gramlich V, Grutzmacher H: Coordination chemistry of phosphanyl amino acids: solid state and solution structures of neutral and cationic rhodium complexes. Dalton Trans. 2006 Jan 7;(1):137-48. Epub 2005 Nov 29.


The complexes [RhCl (cod)((Z) SerPhos)] and [RhCl (cod)((Boc) SerPhos)] show good activities in homogeneously catalyzed hydrogenations of olefins while the dipeptide complex is less active.
1(0,0,0,1) Details
17973285 Stephan GC, Sivasankar C, Studt F, Tuczek F: Energetics and mechanism of ammonia synthesis through the Chatt Cycle: conditions for a catalytic mode and comparison with the Schrock Cycle. Chemistry. 2008;14(2):644-52.

Moreover, the Mo I fluoro-dinitrogen complex is labile towards disproportionation.
The implications of these results with respect to the realization of a catalytic system on the basis of Mo and W phosphine complexes are discussed.
1(0,0,0,1) Details
19809739 Arunachalampillai A, Olsson D, Wendt OF: Synthesis and characterisation of PCsp3P phosphine and phosphinite iridium complexes. Dalton Trans. 2009 Oct 28;(40):8626-30. Epub 2009 Aug 20.

0(0,0,0,0) Details
18698441 Jones C, Mills DP, Rose RP, Stasch A: Synthesis and structural characterisation of group 10 metal (II) gallyl complexes: analogies with platinum diboration catalysts?. Dalton Trans. 2008 Sep 7;(33):4395-408. Epub 2008 Jul 3.


Reactions of the anionic gallium (i) heterocycle, [:Ga{[N (Ar) C (H)](2)}](-) (Ar = C (6) H (3) Pr (i)(2)-2,6), with a variety of mono- and bidentate phosphine, tmeda and 1,5-cyclooctadiene (COD) complexes of group 10 metal dichlorides are reported.
0(0,0,0,0) Details
15250684 Nemykin VN, Laskin J, Basu P: Isolation, characterization of an intermediate in an oxygen atom-transfer reaction, and the determination of the bond dissociation energy. J Am Chem Soc. 2004 Jul 21;126(28):8604-5.

The synthesis and structure of a phosphine oxide-bound intermediate molecule originating from a dioxo-molybdenum (VI) complex is described.
81(1,1,1,1) Details
15934775 Saito T, Sunaga T, Sakai N, Nakamura Y, Yamamoto S, Iriuchijima D, Yoza K: Oxygen atom transfer reactions from dioxygen to phosphines via a bridging sulfur dioxide in a trinuclear cluster complex of rhenium, [(Ph (3) P)(2) N][Re (3)(mu (3)-S)(mu-S)(2)(mu-SO (2)) Cl (6)(PMe (2) Ph)(3)]. Inorg Chem. 2005 Jun 13;44(12):4427-32.

The oxygen atoms on the SO (2) ligand react with phosphines or phosphites to form phosphine oxides or phosphates, and the original cluster complex is recovered.
31(0,1,1,1) Details
15732997 Yahav A, Goldberg I, Vigalok A: Difluoro complexes of platinum (II) and -(IV) with monodentate phosphine ligands: an exceptional stability of d6 octahedral organometallic fluorides. Inorg Chem. 2005 Mar 7;44(5):1547-53.

It was found that phosphine dissociation from the octahedral Pt (IV) complex is essential for the reductive elimination reaction to take place, the difluoro complex being kinetically stable even at 60 degrees C.
31(0,1,1,1) Details
15264874 Seifert S, Kunstler JU, Schiller E, Pietzsch HJ, Pawelke B, Bergmann R, Spies H: Novel procedures for preparing 99mTc (III) complexes with tetradentate/monodentate coordination of varying lipophilicity and adaptation to 188Re analogues. Bioconjug Chem. 2004 Jul-Aug;15(4):856-63.

At first the Tc (III)- or Re (III)-EDTA complex is formed which reacts in a second step with the tripodal ligand 2,2',2' '-nitrilotris (ethanethiol) (NS3) or its carboxyl derivative NS3COOH (a) and the monodentate phosphine ligands (triphenylphosphine L1, dimethylphenylphosphine L2) or isocyanides (tert-butyl isonitrile L3, methoxyisobutyl isonitrile L4, 4-isocyanomethylbenzoic acid-L-arginine L5, 4-isocyanomethylbenzoic acid-L-arginyl-L-arginine L6, 4-isocyanomethylbenzoic acid-neurotensin (8-13) L7) to the so-called '4+1' complex.
31(0,1,1,1) Details