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Volumn 1834, Issue 1, 2013, Pages 454-463

New light on phosphate transfer from triesters

Author keywords

Density Functional Theory; Hydrolysis; LFER; Phosphate transfer

Indexed keywords

ESTER; NUCLEOPHILE; PHOSPHATASE; PHOSPHATE; PHOSPHODIESTERASE; PHOSPHOTRIESTERASE;

EID: 84871721280     PISSN: 15709639     EISSN: 18781454     Source Type: Journal    
DOI: 10.1016/j.bbapap.2012.04.010     Document Type: Review
Times cited : (38)

References (32)
  • 1
    • 33748591572 scopus 로고    scopus 로고
    • Enzymatic mechanisms of phosphate and sulfate transfer
    • W.W. Cleland, and A.C. Hengge Enzymatic mechanisms of phosphate and sulfate transfer Chem. Rev. 106 2006 3252 3278
    • (2006) Chem. Rev. , vol.106 , pp. 3252-3278
    • Cleland, W.W.1    Hengge, A.C.2
  • 2
    • 33749138745 scopus 로고    scopus 로고
    • Mechanistic studies on enzyme-catalyzed phosphoryl transfer
    • J.P. Richard
    • A.C. Hengge Mechanistic studies on enzyme-catalyzed phosphoryl transfer J.P. Richard, Adv. Phys. Org. Chem. vol. 40 2005 49 108
    • (2005) Adv. Phys. Org. Chem. , vol.40 , pp. 49-108
    • Hengge, A.C.1
  • 3
    • 79959432785 scopus 로고    scopus 로고
    • Biological phosphoryl-transfer reactions: Understanding mechanism and catalysis
    • J.K. Lassila, J.G. Zalatan, and D. Herschlag Biological phosphoryl-transfer reactions: understanding mechanism and catalysis Annu. Rev. Biochem. 80 2011 669 702
    • (2011) Annu. Rev. Biochem. , vol.80 , pp. 669-702
    • Lassila, J.K.1    Zalatan, J.G.2    Herschlag, D.3
  • 4
    • 37049057136 scopus 로고
    • The reactions of organic phosphates. Part I. The hydrolysis of methyl dihydrogen phosphate
    • C.A. Bunton, D.R. Llewellyn, K.G. Oldham, and C.A. Vernon The reactions of organic phosphates. Part I. The hydrolysis of methyl dihydrogen phosphate J. Chem. Soc. 1958 3574 3587
    • (1958) J. Chem. Soc. , pp. 3574-3587
    • Bunton, C.A.1    Llewellyn, D.R.2    Oldham, K.G.3    Vernon, C.A.4
  • 5
    • 33947333789 scopus 로고
    • The reactivity of phosphate esters. Monoester hydrolysis
    • A.J. Kirby, and A.G. Varvoglis The reactivity of phosphate esters. Monoester hydrolysis J. Am. Chem. Soc. 89 1967 415 423
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 415-423
    • Kirby, A.J.1    Varvoglis, A.G.2
  • 7
    • 70349380002 scopus 로고    scopus 로고
    • Chemical aspects of pharmacological prophylaxis against nerve agent poisoning
    • J. Bajgar, J. Fusek, J. Kassa, K. Kuca, and D. Jun Chemical aspects of pharmacological prophylaxis against nerve agent poisoning Curr. Med. Chem. 16 2009 2977 2986
    • (2009) Curr. Med. Chem. , vol.16 , pp. 2977-2986
    • Bajgar, J.1    Fusek, J.2    Kassa, J.3    Kuca, K.4    Jun, D.5
  • 8
    • 35548953638 scopus 로고    scopus 로고
    • Metal-catalyzed alcoholysis reactions of carboxylate and organophosphorus esters
    • J.P. Richard
    • R.S. Brown, and A.A. Neverov Metal-catalyzed alcoholysis reactions of carboxylate and organophosphorus esters J.P. Richard, Adv. Phys. Org. Chem vol. 42 2008 271 331
    • (2008) Adv. Phys. Org. Chem , vol.42 , pp. 271-331
    • Brown, R.S.1    Neverov, A.A.2
  • 10
    • 38549163108 scopus 로고    scopus 로고
    • Catalytic methods for the destruction of chemical warfare agents under ambient conditions
    • B.M. Smith Catalytic methods for the destruction of chemical warfare agents under ambient conditions Chem. Soc. Rev. 37 2008 470 478
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 470-478
    • Smith, B.M.1
  • 11
    • 80052814101 scopus 로고    scopus 로고
    • Destruction and detection of chemical warfare agents
    • K. Kim, O.G. Tsay, D.A. Atwood, and D.G. Churchill Destruction and detection of chemical warfare agents Chem. Rev. 111 2011 5345 5403
    • (2011) Chem. Rev. , vol.111 , pp. 5345-5403
    • Kim, K.1    Tsay, O.G.2    Atwood, D.A.3    Churchill, D.G.4
  • 12
    • 0033658178 scopus 로고    scopus 로고
    • Phosphotriesterase: An enzyme in search of its natural substrate
    • F.M. Raushel, and H.M. Holden Phosphotriesterase: an enzyme in search of its natural substrate Adv. Enzymol. Relat. Areas Mol. Biol. 74 2000 51 93
    • (2000) Adv. Enzymol. Relat. Areas Mol. Biol. , vol.74 , pp. 51-93
    • Raushel, F.M.1    Holden, H.M.2
  • 13
    • 33845921520 scopus 로고
    • Reactivity of phosphate esters - Multiple structure-reactivity correlations for reactions of triesters with nucleophiles
    • S.A. Khan, and A.J. Kirby Reactivity of phosphate esters - multiple structure-reactivity correlations for reactions of triesters with nucleophiles J. Chem. Soc. B 1970 1172 1182
    • (1970) J. Chem. Soc. B , pp. 1172-1182
    • Khan, S.A.1    Kirby, A.J.2
  • 14
    • 67849117256 scopus 로고    scopus 로고
    • Efficient intramolecular general-acid catalysis of the reactions of alpha-effect nucleophiles and ammonia oxide with a phosphate triester
    • A.J. Kirby, D.W. Tondo, M. Medeiros, B.S. Souza, J.P. Priebe, M.F. Lima, and F. Nome Efficient intramolecular general-acid catalysis of the reactions of alpha-effect nucleophiles and ammonia oxide with a phosphate triester J. Am. Chem. Soc. 131 2009 2023 2028
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 2023-2028
    • Kirby, A.J.1    Tondo, D.W.2    Medeiros, M.3    Souza, B.S.4    Priebe, J.P.5    Lima, M.F.6    Nome, F.7
  • 15
    • 0001054083 scopus 로고
    • Multiple structure-reactivity correlations in the hydrolysis of epimeric 2-(aryloxy)-2-oxydioxaphosphorinanes. Stereoelectronic effects
    • R. Rowell, and D.G. Gorenstein Multiple structure-reactivity correlations in the hydrolysis of epimeric 2-(aryloxy)-2-oxydioxaphosphorinanes. Stereoelectronic effects J. Am. Chem. Soc. 103 1981 5894 5902
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 5894-5902
    • Rowell, R.1    Gorenstein, D.G.2
  • 16
    • 69249155264 scopus 로고    scopus 로고
    • Activating water: Efficient intramolecular general base catalysis of the hydrolysis of a phosphate triester
    • A.J. Kirby, M. Medeiros, P.S.M. Oliveira, T.A.S. Brandão, and F. Nome Activating water: efficient intramolecular general base catalysis of the hydrolysis of a phosphate triester Chem. Eur. J. 15 2009 8475 8479
    • (2009) Chem. Eur. J. , vol.15 , pp. 8475-8479
    • Kirby, A.J.1    Medeiros, M.2    Oliveira, P.S.M.3    Brandão, T.A.S.4    Nome, F.5
  • 17
    • 0001687582 scopus 로고    scopus 로고
    • Hydrolysis and intramolecular transesterification of ribonucleoside 3′-phosphotriesters: The effect of alkyl groups on the general and specific acid-base-catalyzed reactions of 5′-O-pivaloyluridin-3′-yl dialkyl phosphates
    • M. Kosonen, K. Hakala, and H. Lönnberg Hydrolysis and intramolecular transesterification of ribonucleoside 3′-phosphotriesters: the effect of alkyl groups on the general and specific acid-base-catalyzed reactions of 5′-O-pivaloyluridin-3′-yl dialkyl phosphates J. Chem. Soc., Perkin Trans. 2 1998 663 670
    • (1998) J. Chem. Soc., Perkin Trans. 2 , pp. 663-670
    • Kosonen, M.1    Hakala, K.2    Lönnberg, H.3
  • 18
    • 2842610709 scopus 로고
    • Biomimetic chemistry and artificial enzymes - Catalysis by design
    • R. Breslow Biomimetic chemistry and artificial enzymes - catalysis by design Acc. Chem. Res. 28 1995 146 153
    • (1995) Acc. Chem. Res. , vol.28 , pp. 146-153
    • Breslow, R.1
  • 20
    • 0001631145 scopus 로고
    • Reactions of nucleophilic reagents with phosphoramidate
    • W.P. Jencks, and M. Gilchrist Reactions of nucleophilic reagents with phosphoramidate J. Am. Chem. Soc. 87 1965 3199 3209
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 3199-3209
    • Jencks, W.P.1    Gilchrist, M.2
  • 21
    • 0015119596 scopus 로고
    • Nucleophilic attack by zinc (II)-pyridine-2-carbaldoxime anion on phosphorylimidazole. A model for enzymatic phosphate transfer
    • G.J. Lloyd, and B.S. Cooperman Nucleophilic attack by zinc (II)-pyridine-2-carbaldoxime anion on phosphorylimidazole. A model for enzymatic phosphate transfer J. Am. Chem. Soc. 93 1971 4883 4889
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 4883-4889
    • Lloyd, G.J.1    Cooperman, B.S.2
  • 22
    • 0013872353 scopus 로고
    • Preparation and characterization of 1-phosphohistidine and 3-phosphohistidine
    • D.E. Hultquist, R.W. Moyer, and P.D. Boyer Preparation and characterization of 1-phosphohistidine and 3-phosphohistidine Biochemistry 5 1966 322 331
    • (1966) Biochemistry , vol.5 , pp. 322-331
    • Hultquist, D.E.1    Moyer, R.W.2    Boyer, P.D.3
  • 23
    • 0014411498 scopus 로고
    • Preparation and characterization of phosphorylated derivatives of histidine
    • D.E. Hultquist Preparation and characterization of phosphorylated derivatives of histidine Biochim. Biophys. Acta 153 1968 329 340
    • (1968) Biochim. Biophys. Acta , vol.153 , pp. 329-340
    • Hultquist, D.E.1
  • 25
    • 39749152753 scopus 로고    scopus 로고
    • Intramolecular acid-base catalysis of a phosphate diester: Modeling the ribonuclease mechanism
    • E.S. Orth, T.A.S. Brandao, H.M.S. Milagre, M.N. Eberlin, and F. Nome Intramolecular acid-base catalysis of a phosphate diester: modeling the ribonuclease mechanism J. Am. Chem. Soc. 130 2008 2436 2437
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 2436-2437
    • Orth, E.S.1    Brandao, T.A.S.2    Milagre, H.M.S.3    Eberlin, M.N.4    Nome, F.5
  • 27
    • 37049128042 scopus 로고
    • Intramolecular catalysis of phosphate triester hydrolysis - Nucleophilic catalysis by neighboring carboxy-group of hydrolysis of diaryl 2-carboxyphenyl phosphates
    • R.H. Bromilow, S.A. Khan, and A.J. Kirby Intramolecular catalysis of phosphate triester hydrolysis - nucleophilic catalysis by neighboring carboxy-group of hydrolysis of diaryl 2-carboxyphenyl phosphates J. Chem. Soc., Perkin Trans. 2 1972 911 918
    • (1972) J. Chem. Soc., Perkin Trans. 2 , pp. 911-918
    • Bromilow, R.H.1    Khan, S.A.2    Kirby, A.J.3
  • 29
    • 33845919294 scopus 로고    scopus 로고
    • Efficient intramolecular general acid catalysis of nucleophilic attack on a phosphodiester
    • A.J. Kirby, M.F. Lima, D. Silva, C.D. Roussev, and F. Nome Efficient intramolecular general acid catalysis of nucleophilic attack on a phosphodiester J. Am. Chem. Soc. 128 2006 16944
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 16944
    • Kirby, A.J.1    Lima, M.F.2    Silva, D.3    Roussev, C.D.4    Nome, F.5
  • 30
    • 66349120487 scopus 로고    scopus 로고
    • Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions
    • A.V. Marenich, C.J. Cramer, and D.G. Truhlar Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions J. Phys. Chem. B 113 2009 6378 6396
    • (2009) J. Phys. Chem. B , vol.113 , pp. 6378-6396
    • Marenich, A.V.1    Cramer, C.J.2    Truhlar, D.G.3
  • 31
    • 78650588432 scopus 로고    scopus 로고
    • Comment on the correct use of continuum
    • Junming Ho, Andreas Klamt, and Michelle L. Coote Comment on the correct use of continuum J. Phys. Chem. A 114 2010 13442 13444
    • (2010) J. Phys. Chem. A , vol.114 , pp. 13442-13444
    • Ho, J.1    Klamt, A.2    Coote, M.L.3
  • 32
    • 11544373758 scopus 로고    scopus 로고
    • The hydrolysis of RNA: From theoretical calculations to the hammerhead ribozyme-mediated cleavage of RNA
    • Z. De-Min, and T. Kazunari The hydrolysis of RNA: from theoretical calculations to the hammerhead ribozyme-mediated cleavage of RNA Chem. Rev. 98 1998 991 1026
    • (1998) Chem. Rev. , vol.98 , pp. 991-1026
    • De-Min, Z.1    Kazunari, T.2


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