메뉴 건너뛰기




Volumn 27, Issue 7, 2013, Pages 816-824

Electronic structure and gas-phase chemistry of protonated α- And β-quinonoid compounds: A mass spectrometry and computational study

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; DIAGNOSIS; ELECTRONIC STRUCTURE; ELECTROSPRAY IONIZATION; GASES; IONIZATION OF GASES; IONS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULES; PROTONATION;

EID: 84875193627     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6519     Document Type: Article
Times cited : (9)

References (60)
  • 3
    • 17044437348 scopus 로고    scopus 로고
    • Down-regulation of cyclooxygenase-2 and telomerase activity by beta-lapachone in human prostate carcinoma cells
    • J. H. Lee, J. H. Cheong, Y. M. Park, Y. H. Choi,. Down-regulation of cyclooxygenase-2 and telomerase activity by beta-lapachone in human prostate carcinoma cells. Pharmacolog. Res. 2005, 51, 553.
    • (2005) Pharmacolog. Res. , vol.51 , pp. 553
    • Lee, J.H.1    Cheong, J.H.2    Park, Y.M.3    Choi, Y.H.4
  • 6
    • 33645463415 scopus 로고    scopus 로고
    • Preparation of alpha-diazocarbonyl compounds from beta-lapachone derivatives and other 1,2-naphthoquinones: Use of the 2D NMR H-1,N-15 and H-1,C-13 HMBC techniques in assigning regiochemistry
    • V. F. Ferreira, A. Jorqueira, K. Z. Leal, H. R. X. Pimentel, P. R. Seidl, M. N. Da Silva, M. C. B. V. De Souza, A. V. Pinto, J. L. Wardell, S. M. S. V. Wardell,. Preparation of alpha-diazocarbonyl compounds from beta-lapachone derivatives and other 1,2-naphthoquinones: use of the 2D NMR H-1,N-15 and H-1,C-13 HMBC techniques in assigning regiochemistry. Magn. Reson. Chem. 2006, 44, 481.
    • (2006) Magn. Reson. Chem. , vol.44 , pp. 481
    • Ferreira, V.F.1    Jorqueira, A.2    Leal, K.Z.3    Pimentel, H.R.X.4    Seidl, P.R.5    Da Silva, M.N.6    De Souza, M.C.B.V.7    Pinto, A.V.8    Wardell, J.L.9    Wardell, S.M.S.V.10
  • 7
    • 60349085566 scopus 로고    scopus 로고
    • Ex vivo activities of beta-lapachone and alpha-lapachone on macrophages: A quantitative pharmacological analysis based on amperometric monitoring of oxidative bursts by single cells
    • D. C. M. Ferreira, I. Tapsoba, S. Arbault, Y. Bouret, M. S. A. Moreira, A. V. Pinto, M. O. F. Goulart, C. Amatore,. Ex vivo activities of beta-lapachone and alpha-lapachone on macrophages: a quantitative pharmacological analysis based on amperometric monitoring of oxidative bursts by single cells. ChemBioChem. 2009, 10, 528.
    • (2009) ChemBioChem. , vol.10 , pp. 528
    • Ferreira, D.C.M.1    Tapsoba, I.2    Arbault, S.3    Bouret, Y.4    Moreira, M.S.A.5    Pinto, A.V.6    Goulart, M.O.F.7    Amatore, C.8
  • 10
    • 0034547932 scopus 로고    scopus 로고
    • In vitro leishmanicidal activity of monomeric and dimeric naphthoquinones
    • O. Kayser, A. F. Kiderlen, H. Laatsch, S. L. Croft,. In vitro leishmanicidal activity of monomeric and dimeric naphthoquinones. Acta Tropica 2000, 77, 307.
    • (2000) Acta Tropica , vol.77 , pp. 307
    • Kayser, O.1    Kiderlen, A.F.2    Laatsch, H.3    Croft, S.L.4
  • 11
    • 78751510668 scopus 로고    scopus 로고
    • Effects of quinone derivatives, such as 1,4-naphthoquinone, on DNA polymerase inhibition and anti-inflammatory action
    • K. Kobayashi, S. Nishiumi, M. Nishida, M. Hirai, T. Azuma, H. Yoshida, Y. Mizushina, M. Yoshida,. Effects of quinone derivatives, such as 1,4-naphthoquinone, on DNA polymerase inhibition and anti-inflammatory action. Med. Chem. 2011, 7, 37.
    • (2011) Med. Chem. , vol.7 , pp. 37
    • Kobayashi, K.1    Nishiumi, S.2    Nishida, M.3    Hirai, M.4    Azuma, T.5    Yoshida, H.6    Mizushina, Y.7    Yoshida, M.8
  • 13
    • 0038381447 scopus 로고    scopus 로고
    • An overview of the chemistry and pharmacology of naphthoquinones with emphasis on beta-lapachone and derivatives
    • M. N. Da Silva, V. F. Ferreira, M. C. B. V. De Souza,. An overview of the ch e mistry and pharmacology of naphthoquinones with emphasis on beta-lapachone and derivatives. Quim. Nova 2003, 26, 407.
    • (2003) Quim. Nova , vol.26 , pp. 407
    • Da Silva, M.N.1    Ferreira, V.F.2    De Souza, M.C.B.V.3
  • 14
    • 44849084454 scopus 로고    scopus 로고
    • Electrochemical parameters and techniques in drug development, with an emphasis on quinones and related compounds
    • E. A. Hillard, F. C. De Abreu, D. C. M. Ferreira, G. Jaouen, M. O. F. Goulart, C. Amatore,. Electrochemical parameters and techniques in drug development, with an emphasis on quinones and related compounds. Chem. Commun. 2008, 23, 2612.
    • (2008) Chem. Commun. , vol.23 , pp. 2612
    • Hillard, E.A.1    De Abreu, F.C.2    Ferreira, D.C.M.3    Jaouen, G.4    Goulart, M.O.F.5    Amatore, C.6
  • 15
    • 0041317054 scopus 로고    scopus 로고
    • Electrospray wings for molecular elephants (Nobel lecture)
    • J. B. Fenn,. Electrospray wings for molecular elephants (Nobel lecture). Angew. Chem. Int. Ed. 2003, 42, 3871.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 3871
    • Fenn, J.B.1
  • 16
    • 0037329401 scopus 로고    scopus 로고
    • Ion formation in MALDI: The cluster ionization mechanism
    • M. Karas, R. Kruger,. Ion formation in MALDI: the cluster ionization mechanism. Chem. Rev. 2003, 103, 427.
    • (2003) Chem. Rev. , vol.103 , pp. 427
    • Karas, M.1    Kruger, R.2
  • 17
    • 0035246248 scopus 로고    scopus 로고
    • Mass analysis at the advent of the 21st century
    • S. A. McLuckey, J. M. Wells,. Mass analysis at the advent of the 21st century. Chem. Rev. 2001, 101, 571.
    • (2001) Chem. Rev. , vol.101 , pp. 571
    • McLuckey, S.A.1    Wells, J.M.2
  • 22
    • 33749039189 scopus 로고    scopus 로고
    • Fragmentation studies of synthetic 2-acylamino-1,4-naphthoquinones by electrospray ionization mass spectrometry
    • R. Vessecchi, P. G. B. D. Nascimento, J. N. C. Lopes, N. P. Lopes,. Fragmentation studies of synthetic 2-acylamino-1,4-naphthoquinones by electrospray ionization mass spectrometry. J. Mass Spectrom. 2006, 41, 1219.
    • (2006) J. Mass Spectrom. , vol.41 , pp. 1219
    • Vessecchi, R.1    Nascimento, P.G.B.D.2    Lopes, J.N.C.3    Lopes, N.P.4
  • 23
    • 70349156431 scopus 로고    scopus 로고
    • Gas-phase dissociation of 1,4-naphthoquinone derivative anions by electrospray ionization tandem mass spectrometry
    • R. Vessecchi, C. A. Carollo, J. N. C. Lopes, A. E. M. Crotti, N. P. Lopes, S. E. Galembeck,. Gas-phase dissociation of 1,4-naphthoquinone derivative anions by electrospray ionization tandem mass spectrometry. J. Mass Spectrom. 2009, 44, 1224.
    • (2009) J. Mass Spectrom. , vol.44 , pp. 1224
    • Vessecchi, R.1    Carollo, C.A.2    Lopes, J.N.C.3    Crotti, A.E.M.4    Lopes, N.P.5    Galembeck, S.E.6
  • 24
    • 84863623202 scopus 로고    scopus 로고
    • ESI-MS studies of the dehydrogenative Heck reaction of furans with acrylates using benzoquinone as the reoxidant and DMSO as the solvent
    • A. Vasseur, D. Harakat, J. Muzart, J. Le Bras,. ESI-MS studies of the dehydrogenative Heck reaction of furans with acrylates using benzoquinone as the reoxidant and DMSO as the solvent. J. Org. Chem. 2012, 77, 5751.
    • (2012) J. Org. Chem. , vol.77 , pp. 5751
    • Vasseur, A.1    Harakat, D.2    Muzart, J.3    Le Bras, J.4
  • 25
    • 77954466059 scopus 로고    scopus 로고
    • Fragmentation studies and electrospray ionization mass spectrometry of lapachol: Protonated, deprotonated and cationized species
    • R. Vessecchi, F. S. Emery, S. E. Galembeck, N. P. Lopes,. Fragmentation studies and electrospray ionization mass spectrometry of lapachol: protonated, deprotonated and cationized species. Rapid Commun. Mass Spectrom. 2010, 24, 2101.
    • (2010) Rapid Commun. Mass Spectrom. , vol.24 , pp. 2101
    • Vessecchi, R.1    Emery, F.S.2    Galembeck, S.E.3    Lopes, N.P.4
  • 26
    • 79957598101 scopus 로고    scopus 로고
    • Generation of Naphthoquinone radical anions by electrospray ionization: Solution, gas-phase, and computational chemistry studies
    • R. Vessecchi, Z. Naal, J. N. C. Lopes, S. E. Galembeck, N. P. Lopes,. Generation of Naphthoquinone radical anions by electrospray ionization: solution, gas-phase, and computational chemistry studies. J. Phys. Chem. A 2011, 115, 5453.
    • (2011) J. Phys. Chem. A , vol.115 , pp. 5453
    • Vessecchi, R.1    Naal, Z.2    Lopes, J.N.C.3    Galembeck, S.E.4    Lopes, N.P.5
  • 27
    • 0000233901 scopus 로고    scopus 로고
    • Computational studies of cyclobutadiene and benzocyclobutene fused to p- and o-quinone
    • M. L. McKee, M. Balci, H. Kilic, E. Yurtsever,. Computational studies of cyclobutadiene and benzocyclobutene fused to p- and o-quinone. J. Phys. Chem A 1998, 102, 2351
    • (1998) J. Phys. Chem A , vol.102 , pp. 2351
    • McKee, M.L.1    Balci, M.2    Kilic, H.3    Yurtsever, E.4
  • 28
    • 0041863981 scopus 로고    scopus 로고
    • Polyhedral boranes with exo multiple bonds: Three-dimensional inorganic analogues of quinones
    • M. M. Balakrishnarajan, R. Hoffmann,. Polyhedral boranes with exo multiple bonds: three-dimensional inorganic analogues of quinones. Angew. Chem. Int. Ed. 2003, 42, 3777.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 3777
    • Balakrishnarajan, M.M.1    Hoffmann, R.2
  • 30
    • 84864408810 scopus 로고    scopus 로고
    • Biomimetic in vitro oxidation of lapachol: A model to predict and analyse the in vivo phase i metabolism of bioactive compounds
    • M. Niehues, V. P. Barros, F. S. Emery, M. Dias-Baruffi, M. D. Assis, N. P. Lopes,. Biomimetic in vitro oxidation of lapachol: a model to predict and analyse the in vivo phase I metabolism of bioactive compounds. Eur. J. Med. Chem. 2012, 54, 804.
    • (2012) Eur. J. Med. Chem. , vol.54 , pp. 804
    • Niehues, M.1    Barros, V.P.2    Emery, F.S.3    Dias-Baruffi, M.4    Assis, M.D.5    Lopes, N.P.6
  • 31
    • 0000118396 scopus 로고
    • Studies in mass pectrometry. I. Mass spectra of substituted naphthoquinones
    • J. H. Bowie, D. W. Cameron, D. H. Williams,. Studies in mass pectrometry. I. Mass spectra of substituted naphthoquinones. J. Am. Chem. Soc. 1965, 81, 5094
    • (1965) J. Am. Chem. Soc. , vol.81 , pp. 5094
    • Bowie, J.H.1    Cameron, D.W.2    Williams, D.H.3
  • 32
    • 9344252886 scopus 로고
    • Mass spectrometry in structural and stereochemical problems. 111. Mass spectrometric fragmentation of substituted naphthoquinones and its application to structural elucidation of echinoderm pigments
    • D. Becher, C. Djerassi, R. E. Moore, H. Singh, P. J. Scheuer,. Mass spectrometry in structural and stereochemical problems. 111. Mass spectrometric fragmentation of substituted naphthoquinones and its application to structural elucidation of echinoderm pigments. J. Org. Chem. 1966, 31, 3650.
    • (1966) J. Org. Chem. , vol.31 , pp. 3650
    • Becher, D.1    Djerassi, C.2    Moore, R.E.3    Singh, H.4    Scheuer, P.J.5
  • 33
    • 0029090886 scopus 로고
    • Structural determination of 1,4-naphthoquinones by mass spectrometry/mass spectrometry
    • W. G. Stensen, E. Jensen,. Structural determination of 1,4-naphthoquinones by mass spectrometry/mass spectrometry. J. Mass Spectrom. 1995, 30, 1126.
    • (1995) J. Mass Spectrom. , vol.30 , pp. 1126
    • Stensen, W.G.1    Jensen, E.2
  • 34
    • 12344278384 scopus 로고    scopus 로고
    • Conversion of lapachol to array of furano and pyranonaphthoquinone congeners
    • V. Krishna, J. Lamba, P. Singh,. Conversion of lapachol to array of furano and pyranonaphthoquinone congeners. J. Ind. Chem. Soc. 2004, 81, 1039.
    • (2004) J. Ind. Chem. Soc. , vol.81 , pp. 1039
    • Krishna, V.1    Lamba, J.2    Singh, P.3
  • 35
    • 46149091762 scopus 로고    scopus 로고
    • Application of computational quantum chemistry to chemical processes involved in mass spectrometry
    • R. Vessecchi, S. E. Galembeck, N. P. Lopes, P. G. B. D. Nascimento, A. E. M. Crotti,. Application of computational quantum chemistry to chemical processes involved in mass spectrometry. Quim. Nova 2008, 31, 840.
    • (2008) Quim. Nova , vol.31 , pp. 840
    • Vessecchi, R.1    Galembeck, S.E.2    Lopes, N.P.3    Nascimento, P.G.B.D.4    Crotti, A.E.M.5
  • 36
    • 0001289595 scopus 로고
    • Richerce sull acido lapachico
    • E. Paternõ,. Richerce sull acido lapachico. Gazz. Chem. Ital. 1882, 12, 337.
    • (1882) Gazz. Chem. Ital. , vol.12 , pp. 337
    • Paternõ, E.1
  • 37
    • 37049177180 scopus 로고
    • The constitution of lapachic acid (lapachol) and its derivatives
    • S. C. Hooker,. The constitution of lapachic acid (lapachol) and its derivatives. J. Chem. Soc. 1892, 61, 611.
    • (1892) J. Chem. Soc. , vol.61 , pp. 611
    • Hooker, S.C.1
  • 38
    • 69549111027 scopus 로고    scopus 로고
    • Quantifying collision induced dissociation energy for small molecule characterization and identification
    • T. M. Kertesz, L. H. Hall, D. W. Hill, D. F. Grant,. Quantifying collision induced dissociation energy for small molecule characterization and identification. J. Am. Soc. Mass Spectrom. 2009, 20, 1759.
    • (2009) J. Am. Soc. Mass Spectrom. , vol.20 , pp. 1759
    • Kertesz, T.M.1    Hall, L.H.2    Hill, D.W.3    Grant, D.F.4
  • 39
    • 34250817103 scopus 로고
    • A new mixing of hartree-fock and local density-functional theories
    • A. D. Becke,. A new mixing of hartree-fock and local density-functional theories. J. Chem. Phys. 1993, 98, 1372.
    • (1993) J. Chem. Phys. , vol.98 , pp. 1372
    • Becke, A.D.1
  • 40
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density
    • C. T. Lee, W. T. Yang, R. G. Parr,. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density. Phys. Rev. B 1988, 37, 785.
    • (1988) Phys. Rev. B , vol.37 , pp. 785
    • Lee, C.T.1    Yang, W.T.2    Parr, R.G.3
  • 41
    • 0000141448 scopus 로고
    • Self-consistent molecular-orbital methods.9. Extended gaussian-type basis for molecular-orbital studies of organic molecules
    • R. Ditchfield, W. J. Hehre, J. A. Pople,. Self-consistent molecular-orbital methods.9. Extended gaussian-type basis for molecular-orbital studies of organic molecules. J. Chem. Phys. 1971, 54, 724.
    • (1971) J. Chem. Phys. , vol.54 , pp. 724
    • Ditchfield, R.1    Hehre, W.J.2    Pople, J.A.3
  • 43
    • 57049136707 scopus 로고    scopus 로고
    • Reactivity and structure of derivatives of 2-hydroxy-1,4-naphthoquinone (lawsone)
    • G. Lamoureux, A. L. Perez, M. Araya, C. Agüero,. Reactivity and structure of derivatives of 2-hydroxy-1,4-naphthoquinone (lawsone). J. Phys. Org. Chem. 2008, 21, 1022.
    • (2008) J. Phys. Org. Chem. , vol.21 , pp. 1022
    • Lamoureux, G.1    Perez, A.L.2    Araya, M.3    Agüero, C.4
  • 44
    • 0001190640 scopus 로고
    • Structure de 1'α-naphthoquinone
    • P. J. Gaultier, C. Hauw,. Structure de 1'α-naphthoquinone. Acta Crystallogr. 1965, 18, 179
    • (1965) Acta Crystallogr. , vol.18 , pp. 179
    • Gaultier, P.J.1    Hauw, C.2
  • 45
    • 0031555717 scopus 로고    scopus 로고
    • Trimethyl-p-benzoquinone provides excellent structural, spectroscopic, and thermochemical models for plastoquinone-1 and its radical anion
    • K. E. Wise, A. K. Grafton, R. A. Wheeler,. Trimethyl-p-benzoquinone provides excellent structural, spectroscopic, and thermochemical models for plastoquinone-1 and its radical anion. J. Phys. Chem A 1997, 101, 1160.
    • (1997) J. Phys. Chem A , vol.101 , pp. 1160
    • Wise, K.E.1    Grafton, A.K.2    Wheeler, R.A.3
  • 46
    • 80855164491 scopus 로고    scopus 로고
    • Application of the atoms in molecules theory and computational chemistry in mass spectrometry analysis of 1,4-naphthoquinone derivatives
    • R. Vessecchi, J. N. C. Lopes, N. P. Lopes, S. E. Galembeck,. Application of the atoms in molecules theory and computational chemistry in mass spectrometry analysis of 1,4-naphthoquinone derivatives. J. Phys. Chem. A 2011, 115, 12780.
    • (2011) J. Phys. Chem. A , vol.115 , pp. 12780
    • Vessecchi, R.1    Lopes, J.N.C.2    Lopes, N.P.3    Galembeck, S.E.4
  • 47
    • 84986468608 scopus 로고
    • An approach to computing electrostatic charges for molecules
    • U. C. Singh, P. A. Kollman,. An approach to computing electrostatic charges for molecules. J. Comp. Chem. 1984, 5, 129.
    • (1984) J. Comp. Chem. , vol.5 , pp. 129
    • Singh, U.C.1    Kollman, P.A.2
  • 48
    • 77954713977 scopus 로고    scopus 로고
    • Definition of molecular structure: By choice or by appeal to observation?
    • R. F. W. Bader,. Definition of molecular structure: by choice or by appeal to observation? J. Phys. Chem. A 2010, 114, 7431
    • (2010) J. Phys. Chem. A , vol.114 , pp. 7431
    • Bader, R.F.W.1
  • 49
    • 0345401784 scopus 로고
    • A quantum-theory of molecular-structure and its applications
    • R. F. W. Bader,. A quantum-theory of molecular-structure and its applications. Chem. Rev. 1991, 91, 893.
    • (1991) Chem. Rev. , vol.91 , pp. 893
    • Bader, R.F.W.1
  • 50
    • 77951728284 scopus 로고    scopus 로고
    • An experimental and computational study on the dissociation behavior of hydroxypyridine N-oxides in atmospheric pressure ionization mass spectrometry
    • M. Butler, P. A. Mañez, G. M. Cabrera,. An experimental and computational study on the dissociation behavior of hydroxypyridine N-oxides in atmospheric pressure ionization mass spectrometry. J. Mass Spectrom. 2010, 45, 536.
    • (2010) J. Mass Spectrom. , vol.45 , pp. 536
    • Butler, M.1    Mañez, P.A.2    Cabrera, G.M.3
  • 51
    • 85153542555 scopus 로고    scopus 로고
    • AIM version 2.0, Copyright 2002
    • AIM 2000, version 2.0, Copyright 2002. AIM2000 Home Page. Available: http://www.aim2000.de
    • (2000) AIM2000 Home Page
  • 53
    • 78651325180 scopus 로고    scopus 로고
    • Swiss National Supercomputing Centre, Manno, Switzerland
    • U. Varetto,. ; Swiss National Supercomputing Centre, Manno, Switzerland.
    • MOLEKEL 5.4
    • Varetto, U.1
  • 54
    • 84871833964 scopus 로고    scopus 로고
    • Gas-phase reactivity of 2-hydroxy-1,4-naphthoquinones: A computational and mass spectrometry study of lapachol congeners
    • R. Vessecchi, F. S. Emery, S. E. Galembeck, N. P. Lopes,. Gas-phase reactivity of 2-hydroxy-1,4-naphthoquinones: a computational and mass spectrometry study of lapachol congeners. J. Mass Spectrom. 2012, 47, 1648.
    • (2012) J. Mass Spectrom. , vol.47 , pp. 1648
    • Vessecchi, R.1    Emery, F.S.2    Galembeck, S.E.3    Lopes, N.P.4
  • 55
    • 0033940964 scopus 로고    scopus 로고
    • Importance of gas-phase proton affinities in determining the electrospray ionization response for analytes and solvents
    • M. H. Amad, N. B. Cech, G. S. Jackson, C. G. Enke,. Importance of gas-phase proton affinities in determining the electrospray ionization response for analytes and solvents. J. Mass Spectrom. 2000, 35, 784.
    • (2000) J. Mass Spectrom. , vol.35 , pp. 784
    • Amad, M.H.1    Cech, N.B.2    Jackson, G.S.3    Enke, C.G.4
  • 56
    • 0004592759 scopus 로고
    • Characterization of C-H-O hydrogen-bonds on the basis of the charge-density
    • U. Koch, P. L. A. Popelier,. Characterization of C-H-O hydrogen-bonds on the basis of the charge-density. J. Phys. Chem. 1995, 99, 9747
    • (1995) J. Phys. Chem. , vol.99 , pp. 9747
    • Koch, U.1    Popelier, P.L.A.2
  • 57
    • 58149171791 scopus 로고    scopus 로고
    • Atoms-in-molecules dual parameter analysis of weak to strong interactions: Behaviors of electronic energy densities versus laplacian of electron densities at bond critical points
    • W. Nakanishi, S. Hayashi, K. Narahara,. Atoms-in-molecules dual parameter analysis of weak to strong interactions: behaviors of electronic energy densities versus laplacian of electron densities at bond critical points. J. Phys. Chem. A 2008, 112, 13595.
    • (2008) J. Phys. Chem. A , vol.112 , pp. 13595
    • Nakanishi, W.1    Hayashi, S.2    Narahara, K.3
  • 58
    • 0034751199 scopus 로고    scopus 로고
    • A study of the effect of pH, solvent system, cone potential and the addition of crown ethers on the formation of the monensin protonated parent ion in electrospray mass spectrometry
    • N. P. Lopes, C. B. W. Stark, H. Hong, P. J. Gates, J. Staunton,. A study of the effect of pH, solvent system, cone potential and the addition of crown ethers on the formation of the monensin protonated parent ion in electrospray mass spectrometry. Analyst 2001, 126, 1630.
    • (2001) Analyst , vol.126 , pp. 1630
    • Lopes, N.P.1    Stark, C.B.W.2    Hong, H.3    Gates, P.J.4    Staunton, J.5
  • 59
    • 0035567362 scopus 로고    scopus 로고
    • Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry
    • N. Fabre, I. Rustan, E. de Hoffmann, J. Quetin-Leclercq,. Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 2001, 12, 707.
    • (2001) J. Am. Soc. Mass Spectrom. , vol.12 , pp. 707
    • Fabre, N.1    Rustan, I.2    De Hoffmann, E.3    Quetin-Leclercq, J.4
  • 60
    • 33750219772 scopus 로고    scopus 로고
    • Density functional theory and atoms-in-molecule study on the role of two-electron stabilizing interactions in retro-Diels-Alder reaction of cycloadducts derived from substituted cyclopentadiene and p-benzoquinone
    • M. P. Patil, R. B. Sunoj,. Density functional theory and atoms-in-molecule study on the role of two-electron stabilizing interactions in retro-Diels-Alder reaction of cycloadducts derived from substituted cyclopentadiene and p-benzoquinone. Org. Biomol. Chem. 2006, 4, 3923.
    • (2006) Org. Biomol. Chem. , vol.4 , pp. 3923
    • Patil, M.P.1    Sunoj, R.B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.