메뉴 건너뛰기




Volumn 32, Issue 2, 1999, Pages 127-136

Ground state and transition state contributions to the rates of intramolecular and enzymatic reactions

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICHLOROETHANE; ACID ANHYDRIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

EID: 0032931211     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar960131y     Document Type: Review
Times cited : (271)

References (41)
  • 1
    • 0344315216 scopus 로고    scopus 로고
    • Current address: Biology and Biotechnology Research Program, P.O. Box 808, L-452, Lawrence Livermore National Laboratories, Livermore, CA 94550.
    • Current address: Biology and Biotechnology Research Program, P.O. Box 808, L-452, Lawrence Livermore National Laboratories, Livermore, CA 94550.
  • 2
    • 85023100437 scopus 로고
    • The effect of geminal substitution ring size and rotamer distribution on the intramolecular nucleophilic catalysis of the hydrolysis of monophenyl esters of dibasic acids and the solvolysis of the intermediate anhydrides
    • Bruice, T. C.; Pandit, U. K. The Effect of Geminal Substitution Ring Size and Rotamer Distribution on the Intramolecular Nucleophilic Catalysis of the Hydrolysis of Monophenyl Esters of Dibasic Acids and the Solvolysis of the Intermediate Anhydrides. J. Am. Chem. Soc. 1960, 82, 5858-5865.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 5858-5865
    • Bruice, T.C.1    Pandit, U.K.2
  • 3
    • 0000865822 scopus 로고
    • Stereopopulation control. 9. Rate and equilibrium enhancement in the lactonization of (o-Hydroxyphenyl)acetic acids
    • and references therein
    • Hillery, P. S.; Cohen, L. A. Stereopopulation Control. 9. Rate and Equilibrium Enhancement in the Lactonization of (o-Hydroxyphenyl)acetic Acids. J. Org. Chem. 1983, 48, 3465-3471 and references therein.
    • (1983) J. Org. Chem. , vol.48 , pp. 3465-3471
    • Hillery, P.S.1    Cohen, L.A.2
  • 4
    • 77956770660 scopus 로고
    • Effective molarities for intramolecular reactions
    • Kirby, A. J. Effective Molarities for Intramolecular Reactions. Adv. Phys. Org. Chem. 1980, 17, 183-278.
    • (1980) Adv. Phys. Org. Chem. , vol.17 , pp. 183-278
    • Kirby, A.J.1
  • 5
    • 0001617183 scopus 로고
    • On the source of intramolecular and enzymatic reactivity
    • Menger, F. M. On the Source of Intramolecular and Enzymatic Reactivity. Acc. Chem. Res. 1985, 18, 128-134.
    • (1985) Acc. Chem. Res. , vol.18 , pp. 128-134
    • Menger, F.M.1
  • 6
    • 0015101706 scopus 로고
    • Entropic contributions to rate accelerations in enzymic and intramolecular reactions and the chelate effect
    • Page, M. I.; Jencks, W. P. Entropic Contributions to Rate Accelerations in Enzymic and Intramolecular Reactions and the Chelate Effect. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1678-1683.
    • (1971) Proc. Natl. Acad. Sci. U.S.A. , vol.68 , pp. 1678-1683
    • Page, M.I.1    Jencks, W.P.2
  • 7
    • 0000641859 scopus 로고
    • Quantitative modeling of proximity effects on organic reactivity
    • Houk, K. N.; Tucker, J. A.; Dorigo, A. E. Quantitative Modeling of Proximity Effects on Organic Reactivity. Acc. Chem. Res. 1990, 23, 107-113.
    • (1990) Acc. Chem. Res. , vol.23 , pp. 107-113
    • Houk, K.N.1    Tucker, J.A.2    Dorigo, A.E.3
  • 9
    • 0030870598 scopus 로고    scopus 로고
    • Separation of ground state and transition state effects in intramolecular and enzymatic reactions. 2. A theoretical study of the formation of transition states in cyclic anhydride formation
    • Lightstone, F. C.; Bruice, T. C. Separation of Ground State and Transition State Effects in Intramolecular and Enzymatic Reactions. 2. A Theoretical Study of the Formation of Transition States in Cyclic Anhydride Formation. J. Am. Chem. Soc. 1997, 119, 9103-9113.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9103-9113
    • Lightstone, F.C.1    Bruice, T.C.2
  • 10
    • 0032540681 scopus 로고    scopus 로고
    • n2 displacement of Cl-from 1,2-dichloroethane at the active site of xanthobacter autotrophicus haloalkane dehalogenase
    • N2 Displacement of Cl-from 1,2-Dichloroethane at the Active site of Xanthobacter Autotrophicus Haloalkane Dehalogenase. J. Am. Chem. Soc. 1998, 120, 5611-5621.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5611-5621
    • Lightstone, F.C.1    Zheng, Y.-J.2    Bruice, T.C.3
  • 13
    • 11744387198 scopus 로고
    • Stochasitc exploration of molecular mechanics energy surfaces. Hunting for the global minimum
    • Saunders, M. Stochasitc Exploration of Molecular Mechanics Energy Surfaces. Hunting for the Global Minimum. J. Am. Chem. Soc. 1987, 109, 3150-3152.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3150-3152
    • Saunders, M.1
  • 14
    • 84988091759 scopus 로고
    • Stochastic search for the conformations of bicyclic hydrocarbons
    • Saunders, M. Stochastic Search for the Conformations of Bicyclic Hydrocarbons. J. Comput. Chem. 1989, 10, 203-208.
    • (1989) J. Comput. Chem. , vol.10 , pp. 203-208
    • Saunders, M.1
  • 15
    • 0001362186 scopus 로고
    • Molecular mechanics (MM3) studies of carboxylic acids and esters
    • Allinger, N. L.; Zhu, Z.-Q. S.; Chen, K. Molecular Mechanics (MM3) Studies of Carboxylic Acids and Esters. J. Am. Chem. Soc. 1992, 114, 6120-6133.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6120-6133
    • Allinger, N.L.1    Zhu, Z.-Q.S.2    Chen, K.3
  • 16
    • 0002460703 scopus 로고
    • Ring closure reactions of bifunctional chain molecules
    • Illuminati, G.; Mandolini, L. Ring Closure Reactions of Bifunctional Chain Molecules. Acc. Chem. Res. 1981, 14, 95-102.
    • (1981) Acc. Chem. Res. , vol.14 , pp. 95-102
    • Illuminati, G.1    Mandolini, L.2
  • 17
    • 0032582869 scopus 로고    scopus 로고
    • Enthalpy and entropy in ring closure reactions
    • Lightstone, F. C.; Bruice, T. C. Enthalpy and Entropy in Ring Closure Reactions. Bioorg. Chem. 1998, 26, 193-199.
    • (1998) Bioorg. Chem. , vol.26 , pp. 193-199
    • Lightstone, F.C.1    Bruice, T.C.2
  • 18
    • 0000595394 scopus 로고
    • The compensation in △H‡ and △S‡ accompanying the conversion of lower order nucleophilic displacement reactions to higher order catalytic processes. The temperature dependence of the hydrazinolysis and imidazole-catalyzed hydrolysis of substituted phenyl acetates
    • Bruice, T. C.; Benkovic, S. J. The Compensation in △H‡ and △S‡ Accompanying the Conversion of Lower Order Nucleophilic Displacement Reactions to Higher Order Catalytic Processes. The Temperature Dependence of the Hydrazinolysis and Imidazole-Catalyzed Hydrolysis of Substituted Phenyl Acetates. J. Am. Chem. Soc. 1964, 86, 418-426.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 418-426
    • Bruice, T.C.1    Benkovic, S.J.2
  • 19
    • 36549091139 scopus 로고
    • Self-consistent molecular orbital methods 25: Supplementary functions for Gaussian basis sets
    • Frisch, M. J.; Pople, J. A.; Binkley, J. S. Self-Consistent Molecular Orbital Methods 25: Supplementary Functions for Gaussian Basis Sets. J. Chem. Phys. 1984, 80, 3265-3269.
    • (1984) J. Chem. Phys. , vol.80 , pp. 3265-3269
    • Frisch, M.J.1    Pople, J.A.2    Binkley, J.S.3
  • 20
    • 84986468715 scopus 로고
    • Efficient diffuse function-augmented basis set for anion calculations. III. The 3-21+G basis set for first-row elements, Li-F
    • Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Shleyer, P. v. R. Efficient Diffuse Function-Augmented Basis Set for Anion Calculations. III. The 3-21+G Basis Set for First-Row Elements, Li-F. J. Comput. Chem. 1983, 4, 294-301.
    • (1983) J. Comput. Chem. , vol.4 , pp. 294-301
    • Clark, T.1    Chandrasekhar, J.2    Spitznagel, G.W.3    Shleyer, P.V.R.4
  • 23
    • 36549095692 scopus 로고
    • An improved algorithm for reaction path following
    • Gonzalez, C.; Schlegel, H. B. An Improved Algorithm for Reaction Path Following. J. Chem. Phys. 1989, 90, 2154-2161.
    • (1989) J. Chem. Phys. , vol.90 , pp. 2154-2161
    • Gonzalez, C.1    Schlegel, H.B.2
  • 24
    • 33750614386 scopus 로고
    • Reaction path following in mass-weighted internal coordinates
    • Gonzalez, C.; Schlegel, H. B. Reaction Path Following in Mass-Weighted Internal Coordinates. J. Phys. Chem. 1990, 94, 5523-5527.
    • (1990) J. Phys. Chem. , vol.94 , pp. 5523-5527
    • Gonzalez, C.1    Schlegel, H.B.2
  • 25
    • 33751155589 scopus 로고
    • Solvent effects on 1,2-dihaloethane gauche/trans ratios
    • Wiberg, K. B.; Keith, T. A.; Frisch, M. J.; Murcko, M. Solvent Effects on 1,2-Dihaloethane Gauche/Trans Ratios. J. Phys. Chem. 1995, 99, 9072-9079.
    • (1995) J. Phys. Chem. , vol.99 , pp. 9072-9079
    • Wiberg, K.B.1    Keith, T.A.2    Frisch, M.J.3    Murcko, M.4
  • 26
    • 0000978794 scopus 로고
    • Amides. 3. Experimental and theoretical studies of the effect of the medium on the rotational barriers for N, N.-Dimethylforamide and N, N.-Dimethylacetamide
    • Wiberg, K. B.; Rablen, P. R.; Rush, D. J.; Keith, T. A. Amides. 3. Experimental and Theoretical Studies of the Effect of the Medium on the Rotational Barriers for N, N.-Dimethylforamide and N, N.-Dimethylacetamide. J. Am. Chem. Soc. 1995, 117, 42.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 42
    • Wiberg, K.B.1    Rablen, P.R.2    Rush, D.J.3    Keith, T.A.4
  • 27
    • 84962383423 scopus 로고    scopus 로고
    • Solvent effects. 6. A comparison between gas phase and solution acidities
    • Wiberg, K. B.; Castejon, H.; Keith, T. A. Solvent Effects. 6. A Comparison Between Gas Phase and Solution Acidities. J. Comput. Chem. 1996, 17, 185-190.
    • (1996) J. Comput. Chem. , vol.17 , pp. 185-190
    • Wiberg, K.B.1    Castejon, H.2    Keith, T.A.3
  • 28
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys. 1993, 98, 5648-5652.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 29
    • 0032578179 scopus 로고    scopus 로고
    • + and the implications for the catalytic mechanism of formate dehydrogenase
    • + and the Implications for the Catalytic Mechanism of Formate Dehydrogenase. J. Am. Chem. Soc. 1998, 720, 7192-7200.
    • (1998) J. Am. Chem. Soc. , vol.720 , pp. 7192-7200
    • Schiøtt, B.1    Zheng, Y.-J.2    Bruice, T.C.3
  • 30
    • 0030767647 scopus 로고    scopus 로고
    • A theoretical examination of the factors controlling the catalytic efficiency of a transmethylation enzyme: Catechol O-Methyltransferase
    • Zheng, Y. J.; Bruice, T. C. A Theoretical Examination of the Factors Controlling the Catalytic Efficiency of a Transmethylation Enzyme: Catechol O-Methyltransferase. J. Am. Chem. Soc. 1997, 119, 8137-8145.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8137-8145
    • Zheng, Y.J.1    Bruice, T.C.2
  • 32
    • 0027280086 scopus 로고
    • Refinded X-ray structures of haloalkane dehalogenase at pH 6.2 and pH 8.2 and implications for the reaction mechanism
    • Verschueren, K. H. G.; Franken, S. M.; Rozeboom, H. J.; Kalk, K. H.; Dijkstra, B. W. Refinded X-ray Structures of Haloalkane Dehalogenase at pH 6.2 and pH 8.2 and Implications for the Reaction Mechanism. J. Mol. Biol. 1993, 232, 856-872.
    • (1993) J. Mol. Biol. , vol.232 , pp. 856-872
    • Verschueren, K.H.G.1    Franken, S.M.2    Rozeboom, H.J.3    Kalk, K.H.4    Dijkstra, B.W.5
  • 33
    • 0027337615 scopus 로고
    • Crystallographic analysis of the catalytic mechanism of haloalkane dehalogenase
    • Verschueren, K. H. G.; Seljée, F.; Rozeboom, H. J.; Kalk, K. H.; Dijkstra, B. W. Crystallographic Analysis of the Catalytic Mechanism of Haloalkane Dehalogenase. Nature 1993, 363, 693-698.
    • (1993) Nature , vol.363 , pp. 693-698
    • Verschueren, K.H.G.1    Seljée, F.2    Rozeboom, H.J.3    Kalk, K.H.4    Dijkstra, B.W.5
  • 36
    • 84988129057 scopus 로고
    • Optimization of parameters for semiempirical methods. I. Methods
    • Stewart, J. J. P. Optimization of Parameters for Semiempirical Methods. I. Methods. J. Comput. Chem. 1989, 10, 209-220.
    • (1989) J. Comput. Chem. , vol.10 , pp. 209-220
    • Stewart, J.J.P.1
  • 38
    • 0001280101 scopus 로고
    • Kinetic importance of conformations of nicotinamide adenine dinucleotide in the reactions of dehydrogenase enzymes
    • Almarsson, Ö.; Karaman, R.; Bruice, T. C. Kinetic Importance of Conformations of Nicotinamide Adenine Dinucleotide in the Reactions of Dehydrogenase Enzymes. J. Am. Chem. Soc. 1992, 114, 8702-8704.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 8702-8704
    • Almarsson, O.1    Karaman, R.2    Bruice, T.C.3
  • 39
    • 0000500410 scopus 로고
    • Evaluation of the factors influencing reactivity and stereospecificity in NAD(P)H dependent dehydrogenase enzymes
    • Almarsson, Ö.; Bruice, T. C. Evaluation of the Factors Influencing Reactivity and Stereospecificity in NAD(P)H Dependent Dehydrogenase Enzymes. J. Am. Chem. Soc. 1993, 115, 2125-2138.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 2125-2138
    • Almarsson, O.1    Bruice, T.C.2
  • 40
    • 0000286714 scopus 로고
    • Mechanism of one-electron oxidation of NAD(P)H and function of NADPH bound to catalase
    • Almarsson, Ö.; Sinha, A.; Gopinath, E.; Bruice, T. C. Mechanism of One-Electron Oxidation of NAD(P)H and Function of NADPH Bound to Catalase. J. Am. Chem. Soc. 1993, 115, 7093-7102.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7093-7102
    • Almarsson, O.1    Sinha, A.2    Gopinath, E.3    Bruice, T.C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.