17 research outputs found
The Catalytic Mechanism Of Indole-3-glycerol Phosphate Synthase (igps) Investigated By Electrospray Ionization (tandem) Mass Spectrometry
No full textAn enzymatic reaction has been monitored by on-line direct infusion electrospray ionization (tandem) mass spectrometry. Using this fast and sensitive technique, a key and transient intermediate of Mycobacterium tuberculosis indole-3-glycerol phosphate synthase (IGPS)-catalyzed reaction has been trapped. The reaction catalyzed by indole-3-glycerol phosphate synthase is part of the tryptophan biosynthetic pathway, and is not present in mammals, including humans. This peculiarity renders this enzyme a potential target for the development of biospecific agents with potential anti-TB activity. The present results indicate the presence of two intermediates in the mechanism of this enzymatic reaction. © 2008 Elsevier Ltd. All rights reserved.494159145917Raviglione, M.C., Smith, I.M., (2007) New Engl. J. Med., 356, p. 656World Health Organization. Surveillance, planning, financing, WHO Report, Geneva, Switzerland, WHO/HTM/TB/2005.349, 2005Smith, D.A., Parish, T., Stoker, N.G., Bancroft, G.J., (2001) Infect. Immun., 69, p. 1142Ducati, R.G., Ruffino-Netto, A., Basso, L.A., Santos, D.S., (2006) Mem. Inst. Oswaldo Cruz, 101, p. 697Maartens, G., Wilkinson, R.J., (2007) Lancet, 370, p. 2030Pablos-Mendez, A., Raviglione, M.C., Laszlo, A., Binkin, N., Rieder, H.L., Bustreo, F., Cohn, D.L., Nunn, P., (1998) New Engl. J. Med., 338, p. 1641Deng, H., Murkin, A.S., Schramm, V.L., (2006) J. Am. Chem. Soc., 128, p. 7765Lee, C.E., Goodfellow, C., Javid-Majd, F., Baker, E.N., Lott, J.S., (2006) J. Mol. Biol., 355, p. 784Parry, R.J., (1972) Chemistry of Heterocyclic Compounds in Indoles, Part II, 25. , Houlihan W.J. (Ed), Wiley-Interscience, New York pp 1-64Shivakumar, D.M., Bruice, T.C., (2004) Proc. Natl. Acad. Sci. U.S.A., 101, p. 14379Altamirano, M.M., Blackburn, J.M., Aguayo, C., Fersht, A.R., (2000) Nature, 403, p. 617Eberlin, M.N., (2007) Eur. J. Mass Spectrom., 13, p. 18Hsu, F.F., Turk, J., Owens, R.M., Rhoades, E.R., Russell, D.G., (2007) J. Am. Soc. Mass Spectrom., 18, p. 466Knight, W.B., Swiderek, K.M., Sakuma, T., Calaycay, J., Shively, J.E., Lee, T.D., Covey, T.R., Griffin, P.R., (1993) Biochemistry, 32, p. 2031Kirschner, K., Szadkowski, H., Jardetzky, T.S., Hager, V., (1987) Methods Enzymol., 142, p. 386Hennig, M., Darimont, B.D., Jansonius, J.N., Kirschner, K., (2002) J. Mol. Biol., 319, p. 757noteLapis, A.A.M., Neto, B.A.D., Scholten, J.D., Nachtigall, F.M., Eberlin, M.N., Dupont, J., (2006) Tetrahedron Lett., 47, p. 6775Santos, L.S., Neto, B.A.D., Consorti, C.S., Pavam, C.H., Almeida, W.P., Coelho, F., Eberlin, M.N., Dupont, J., (2006) J. Phys. Org. Chem., 19, p. 731Neto, B.A.D., Lapis, A.A.M., Mancilha, F.S., Vasconcelos, I.B., Thum, C., Basso, L.A., Santos, D.S., Dupont, J., (2007) Org. Lett., 9, p. 4001Russowsky, D., Neto, B.A.D., (2003) Tetrahedron Lett., 44, p. 2923Russowsky, D., Neto, B.A.D., (2004) Tetrahedron Lett., 45, pp. 1437-1440Pilli, R.A., Robello, L.G., Camilo, N.S., Dupont, J., Lapis, A.A.M., Neto, B.A.D., (2006) Tetrahedron Lett., 47, p. 166
Phosphine-free heck reaction: mechanistic insights and catalysis “on water” using a charge-tagged palladium complex
No full textA novel Pd-complex with a charge tag (imidazolium cation) was applied for online monitoring of the neutral Heck reaction by electrospray ionization (tandem) mass spectrometry-ESI-MS(/MS). The results shed light on the mechanism of the reaction, whereas the charge-tagged ligand also allowed the unprecedented MS monitoring of Pd2+ reduction to Pd0. Key reaction intermediates associated with Pd catalysis could also be detected and characterized due to the presence of the charge tag on the Pd-complex. DFT calculations supported the proposed mechanism. The new charge-tagged Pd-complex is also shown to function as an active catalyst "on water" with the advantage of using cheaper and less reactive aryl chloride substrates in a phosphine-free version of the Heck reaction. © the Partner Organisations 2014.A novel Pd-complex with a charge tag (imidazolium cation) was applied for online monitoring of the neutral Heck reaction by electrospray ionization (tandem) mass spectrometry – ESI-MS(/MS). The results shed light on the mechanism of the reaction, whereas38729582963CAPES - COORDENAÇÃO DE APERFEIÇOAMENTO DE PESSOAL DE NÍVEL SUPERIORCNPQ - CONSELHO NACIONAL DE DESENVOLVIMENTO CIENTÍFICO E TECNOLÓGICOFINEP - FINANCIADORA DE ESTUDOS E PROJETOSFAPESP - FUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE SÃO PAULOFsem informaçãosem informaçãosem informaçãosem informaçãosem informaçãosem informaçãoKandukuri, S.R., Schiffner, J.A., Oestreich, M., (2012) Angew. Chem., Int. Ed., 51, pp. 1265-1269Faulkner, A., Bower, J.F., (2012) Angew. Chem., Int. 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Solid, solution and gas phase interactions of an imidazolium-based task-specific ionic liquid derived from natural kojic acid
No full textAn imidazolium-based task-specific ionic liquid derived from the natural kojic acid had its supramolecular interactions investigated in solid, solution and gas phase. The use of a set of techniques formed by single-crystal X-ray diffraction, nuclear magnetic resonance (NMR) spectroscopy, UV-Vis spectrophotometry, conductivity measurements, small angle X-ray scattering (SAXS), electrospray (tandem) mass spectrometry (ESI-MS(/MS)), and theoretical calculations allowed a deep investigation of the structural organization of the task-specific ionic liquid and its supramolecular interactions.An imidazolium-based task-specific ionic liquid derived from the natural kojic acid had its supramolecular interactions investigated in solid, solution and gas phase. 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The Role Of Ionic Liquids In Co-catalysis Of Baylis-hillman Reaction: Interception Of Supramolecular Species Via Electrospray Ionization Mass Spectrometry
No full textThe Baylis-Hillman reaction is a general and multifaceted method for C - C bond formation in organic synthesis. Using electrospray ionization mass spectrometry in both the positive and negative ion modes, we performed on-line monitoring of the reaction in the presence of imidazolium ionic liquids. Loosely bonded supramolecular species formed by coordination of neutral reagents, products and the protonated forms of zwitterionic Baylis-Hillman intermediates with cations and anions of ionic liquids were gently and efficiently transferred directly from the solution to the gas phase. Mass measurements and structural characterization of these unprecedented species via collisioninduced dissociation in tandem mass spectrometry experiments were performed. The interception of several supramolecular species indicates that ionic liquids co-catalyze Baylis-Hillman reactions by activating the aldehyde toward nucleophilic enolate attack and by stabilizing the zwitterionic species that act as the main BH intermediates. Copyright © 2006 John Wiley & Sons, Ltd.1911731736Baylis, A.B., Hillman, M.E.D., (1972), German Patent 2155113Chem. Abstr. 197277: 34174qMorita, K., Suzuki, Z., Hirose, H., (1968) Bull. Chem. Soc. Jpn, 41, pp. 2815-2815Basavaiah, D., Rao, A.J., Satyanarayama, T., (2003) Chem. Rev, 103, pp. 811-891Almeida, W.P., Coelho, F., (2000) Quim. Nova, 23, pp. 98-101Chem. Abstr. 2000132: 236562Ciganek, E., (1997) Org. React, 51, pp. 201-350Basavaiah, D., Rao, P.D., Hyma, R.S., (1996) Tetrahedron, 52, pp. 8001-8062Silveira, G.P.C., Coelho, F., (2005) Tetrahedron Lett, 46, pp. 6477-6481Mateus, C.R., Coelho, F., (2005) J. Braz. Chem. 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Mass-selection was performed by Q1 using a unitary m/z window, and collisions were performed in the rf-only quadrupole collision cell, followed by mass analysis of product ions by the high-resolution orthogonalreflectron TOF analyzerSuarez, P.A.Z., Dullius, J.E., Einloft, S., DeSouza, R.F., Dupont, J., (1996) Polyhedron, 15, pp. 1217-121
Probing the mechanism of the ugi four-component reaction with charge-tagged reagents by ESI-MS(/MS)
No full textThe mechanism of the Ugi four-component reaction has been investigated by electrospray ionization (tandem) mass spectrometry using charge-tagged reagents (a carboxylic acid or an amine) to favour detection. Key intermediates were transferred directly via ESI(+) from the reaction solution to the gas phase and characterized by MS measurements and MS/MS collision induced dissociation. The Mumm rearrangement (final step) was also investigated by both travelling wave ion mobility mass spectrometry and DFT calculations. The data seem to consolidate the amazingly selective mechanism of this intricate four-component reaction. © 2013 The Royal Society of Chemistry.The mechanism of the Ugi four-component reaction has been investigated by electrospray ionization (tandem) mass spectrometry using charge-tagged reagents (a carboxylic acid or an amine) to favour detection. Key intermediates were transferred directly via503338340FAPDF - FUNDAÇÃO DE APOIO À PESQUISA NO DISTRITO FEDERALCAPES - COORDENAÇÃO DE APERFEIÇOAMENTO DE PESSOAL DE NÍVEL SUPERIORFAPESP - FUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE SÃO PAULOCNPQ - CONSELHO NACIONAL DE DESENVOLVIMENTO CIENTÍFICO E TEsem informaçãosem informaçãosem informaçãosem informaçãoDe Graaff, C., Ruijter, E., Orru, R.V.A., (2012) Chem. Soc. Rev., 41, pp. 3969-4009Hernandez, J.G., Juaristi, E., (2012) Chem. Commun., 48, pp. 5396-5409Domling, A., Wang, W., Wang, K., (2012) Chem. Rev., 112, pp. 3083-3135Van Berkel, S.S., Bogels, B.G.M., Wijdeven, M.A., Westermann, B., Rutjes, F., (2012) Eur. J. Org. Chem., pp. 3543-3559Vercillo, O.E., Andrade, C.K.Z., Wessjohann, L.A., (2008) Org. Lett., 10, pp. 205-208Basso, A., Banfi, L., Riva, R., (2010) Eur. J. Org. Chem., pp. 1831-1841Domling, A., (2006) Chem. Rev., 106, pp. 17-89Ugi, I., (1959) Angew. Chem., Int. Ed., 71, p. 386Cheron, N., Ramozzi, R., El Kaim, L., Grimaud, L., Fleurat-Lessard, P., (2012) J. Org. Chem., 77, pp. 1361-1366Coelho, F., Eberlin, M.N., (2011) Angew. Chem., Int. Ed., 50, pp. 5261-5263Li, R.M., Smith, R.L., Kenttamaa, H.I., (1996) J. Am. Chem. Soc., 118, pp. 5056-5061Dos Santos, M.R., Diniz, J.R., Arouca, A.M., Gomes, A.F., Gozzo, F.C., Tamborim, S.M., Parize, A.L., Neto, B.A.D., (2012) ChemSusChem, 5, pp. 716-726Oliveira, F.F.D., Dos Santos, M.R., Lalli, P.M., Schmidt, E.M., Bakuzis, P., Lapis, A.A.M., Monteiro, A.L., Neto, B.A.D., (2011) J. Org. Chem., 76, pp. 10140-10147Alvim, H.G.O., De Lima, T.B., De Oliveira, H.C.B., Gozzo, F.C., De MacEdo, J.L., Abdelnur, P.V., Silva, W.A., Neto, B.A.D., (2013) ACS Catal., 3, pp. 1420-1430Vikse, K.L., Henderson, M.A., Oliver, A.G., McIndoe, J.S., (2010) Chem. Commun., 46, pp. 7412-7414Limberger, J., Leal, B.C., Back, D.F., Dupont, J., Monteiro, A.L., (2012) Adv. Synth. Catal., 354, pp. 1429-1436Vikse, K.L., Ahmadi, Z., Manning, C.C., Harrington, D.A., McIndoe, J.S., (2011) Angew. Chem., Int. Ed., 50, pp. 8304-8306Gozzo, F.C., Santos, L.S., Augusti, R., Consorti, C.S., Dupont, J., Eberlin, M.N., (2004) Chem.-Eur. J., 10, pp. 6187-6193Lapthorn, C., Pullen, F., Chowdhry, B.Z., (2013) Mass Spectrom. Rev., 32, pp. 43-71Lalli, P.M., Corilo, Y.E., De Sa, G.F., Daroda, R.J., De Souza, V., Souza, G., Campuzano, I., Eberlin, M.N., (2011) ChemPhysChem, 12, pp. 1444-144
Structural organization and supramolecular interactions of the task-specific ionic liquid 1-methyl-3-carboxymethylimidazolium chloride: solid, solution, and gas phase structures
No full textUsing a set of different techniques, which included single crystal X-ray, NMR, UV-vis, conductivity measurements, SAXS (small angle X-rays), ESI-MS(/MS) (electrospray (tandem) mass spectrometry), and theoretical calculations, an ample study of the structural organization and supramolecular interaction of the task-specific ionic liquid 1-methyl-3-carboxymethylimidazolium chloride (named MAI.Cl) was conducted. All techniques allowed for comprehensive investigation in the solid state, solution, and gas-phase behavior of MAI.Cl. Most relevant interactions are demonstrated showing the importance of hydrogen bonding to supramolecular organization of MAI.Cl in different states and its tendency to aggregate in aqueous solutions. © 2014 American Chemical Society.Using a set of different techniques, which included single crystal X-ray, NMR, UV–vis, conductivity measurements, SAXS (small angle X-rays), ESI-MS(/MS) (electrospray (tandem) mass spectrometry), and theoretical calculations, an ample study of the structu118311787817889CAPES - COORDENAÇÃO DE APERFEIÇOAMENTO DE PESSOAL DE NÍVEL SUPERIORCNPQ - CONSELHO NACIONAL DE DESENVOLVIMENTO CIENTÍFICO E TECNOLÓGICOFINEP - FINANCIADORA DE ESTUDOS E PROJETOSFAPESP - FUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE SÃO PAULOFsem informaçãosem informaçãosem informaçãosem informaçãosem informaçãoHallett, J.P., Welton, T., Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2 (2011) Chem. 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Facts, Presumptions, And Myths On The Solvent-free And Catalyst-free Biginelli Reaction. What Is Catalysis For?
No full textThe current manuscript describes the role and importance of catalysis and solvent effects for the Biginelli multicomponent reaction. The overwhelming number of new catalysts and conditions recently published for the Biginelli synthesis, including in some manuscripts entitled catalyst-free and/or solvent-free have incentivized controversies and hot debates regarding the importance of developing new catalysts and reaction conditions to perform this very important multicomponent reaction. These so-called catalyst-free reports have generated much confusion in the field, requiring urgent elucidations. In this manuscript, we exemplify, demystify, and discuss the crucial role of catalysis, solvent effects, mechanisms, kinetics, facts, presumptions, and myths associated with the Biginelli reaction aiming to avoid current and future confusion and to stimulate new approaches. © 2014 American Chemical Society.79833833397Domling, A., Wang, W., Wang, K., (2012) Chem. 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Raw diffraction images of the first bromodomain of human BRD4 in complex with (+)-JD1
No full textRaw diffraction images of the first bromodomain of human BRD4 in complex with (+)-JD1, an Organometallic BET Bromodomain Inhibitor. The final structure is deposited in the Protein Data Bank under accession code 6SE4.
The structure is part of the following publication:
Hassell-Hart, S., Runcie, A., Krojer, T., Doyle, J., Lineham, E., Ocasio, C.A., Neto, B.A.D., Fedorov, O., Marsh, G., Maple, H., et al. (2019). Synthesis and Biological Investigation of (+)-JD1, an Organometallic BET Bromodomain Inhibitor. Organometallics. doi: 10.1021/acs.organomet.9b00750.
Additional information:
dataset: BRD4A-JD1_i03
beamline: Diamond Light Source I03
visit: mx19301-7
date: 25-11-2018
Flux: 2.03e+11
Ω Start: 0.0°
Ω Osc: 0.15°
Ω Overlap: 0°
No. Images: 1200
Resolution: 1.50Å
Wavelength: 0.9762Å
Exposure: 0.030s
Transmission: 100.00%
Beamsize: 80x20μm
datasets: BRD4A-JD1_i04
beamline: Diamond Light Source I04
visit: mx19301-9
date: 08-12-2018
Flux: 6.62e+11
Ω Start: 0.0°
Ω Osc: 0.50°
Ω Overlap: 0°
No. Images: 720
Resolution: 2.30Å
Wavelength: 1.7384Å
Exposure: 0.050s
Transmission: 100.00%
Beamsize: 32x20μm
Additionally, a cif file containing refinement restraints and a png file for the ligand JD1 is included.</p
N,N-dimethyl-4-amino-2,1,3-benzothiadiazole: synthesis and luminescent solvatochromism
No full text2,1,3-benzothiadiazole (BTD) derivatives were widely applied as herbicides, fungicides and antibacterial agents. The strong withdrawing ability of BTD and its fluorescent properties make it appealing also for the preparation of luminescent materials. Polymers containing the BTD fragment were successfully exploited for advances applications such as organic light-emitting diodes (OLEDs), dyes, solar and photovoltaic cells, as recently reported by B.A.D. Neto et al. [Eur. J. Org. Chem. (2013) 228].
To the best of our knowledge, a complete synthetic procedure for N,N-dimethyl-4-amino-2,1,3-benzothiadiazole (BTDNMe2) from the commercially available 2,1,3-benzothiadiazole was never reported. The only reference available dates back to 1976 and describes the thermal decomposition of the corresponding ammonium salt [N.M. Slavachevskaja et al., Pharm. Chem. J. 10 (1976) 327]. The synthetic route here proposed involves nitration of BTD in sulfonitric mixture, followed by reduction of the nitro-group and subsequent methylation with iodomethane. BTDNMe2 was isolated as dark red oil and it was fully characterized by means of nuclear magnetic resonance (NMR) and infrared spectroscopy. Solutions of BTDNMe2 in common organic solvents revealed to be appreciably luminescent in the visible range. The increase of dielectric constant caused a non-linear red shift of the absorption and emission maxima, an increase of the Stokes shift and a reduction of the photoluminescence quantum yield. The electronic transitions related to the absorption and emission properties were associated to the HOMO-LUMO energy gap by means of electrochemical measurements and DFT calculations. Finally, BTDNMe2 was successfully used for the preparation of luminescent doped polymethylmethacrylate samples with intense orange emission
Use of the Genealogical Sorting Index (GSI) to delineate species boundaries in the Neofusicoccum parvum-Neofusicoccum ribis species complex
No full textNeofusicoccum is a recently described genus of common endophytes and pathogens of woody hosts, previously placed in the genus Botryosphaeria. Many morphological characteristics routinely used to describe species overlap in Neofusicoccum, and prior to the use of molecular phylogenetics, isolates from different hosts and locations were often misidentified. Two cryptic species Neofusicoccum ribis and Neofusicoccum parvum were initially described from different continents and recently another four species within this complex were described using fixed nucleotide polymorphisms for differentiation. In a survey of eucalypt cankers in eastern Australia, a collection of morphologically similar Neofusicoccum isolates were obtained. This collection was analysed within the framework of the morphological (MSRC), ecological (ESRC) and phylogenetic (PSRC) species recognition concepts. Morphological data based on spore measurements (MSRC), together with pathogenicity trials (ESRC) were considered alongside molecular analysis (PSRC), which included multiple gene phylogenies constructed from four nuclear gene regions. We also used the Genealogical Sorting Index method to provide objective evidence for the status of terminal taxa in the phylogenetic analysis. The isolates examined exhibited overlapping morphological and culture characteristics, similar pathogenicity to excised stems and shared hosts within the same locations. Phylogenetic analysis separated isolates into 8 clades corresponding to six described species: N. ribis, N. parvum, Neofusicoccum kwambonambiense, Neofusicoccum cordaticola, Neofusicoccum umdonicola, Neofusicoccum batangarum, and two new species. GSI support indicated combined phylogenetic data were monophyletic for all clades and all p-values were significant allowing us to reject the null hypothesis that all groups were from a single mixed group. Consequently the description of Neofusicoccum occulatum is presented
