1
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Activation of orotidine 5'-monophosphate decarboxylase by phosphite dianion: the whole substrate is the sum of two parts.
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J Am Chem Soc
|
2005
|
2.06
|
2
|
Formation and stability of a vinyl carbanion at the active site of orotidine 5'-monophosphate decarboxylase: pKa of the C-6 proton of enzyme-bound UMP.
|
J Am Chem Soc
|
2008
|
1.85
|
3
|
Enzymatic catalysis of proton transfer at carbon: activation of triosephosphate isomerase by phosphite dianion.
|
Biochemistry
|
2007
|
1.72
|
4
|
A role for flexible loops in enzyme catalysis.
|
Curr Opin Struct Biol
|
2010
|
1.62
|
5
|
Product deuterium isotope effect for orotidine 5'-monophosphate decarboxylase: evidence for the existence of a short-lived carbanion intermediate.
|
J Am Chem Soc
|
2007
|
1.56
|
6
|
A substrate in pieces: allosteric activation of glycerol 3-phosphate dehydrogenase (NAD+) by phosphite dianion.
|
Biochemistry
|
2008
|
1.51
|
7
|
Dissecting the total transition state stabilization provided by amino acid side chains at orotidine 5'-monophosphate decarboxylase: a two-part substrate approach.
|
Biochemistry
|
2008
|
1.45
|
8
|
Substituent effects on carbocation stability: the pK(R) for p-quinone methide.
|
J Am Chem Soc
|
2003
|
1.44
|
9
|
Hydron transfer catalyzed by triosephosphate isomerase. Products of the direct and phosphite-activated isomerization of [1-(13)C]-glycolaldehyde in D(2)O.
|
Biochemistry
|
2009
|
1.33
|
10
|
Hydron transfer catalyzed by triosephosphate isomerase. Products of isomerization of (R)-glyceraldehyde 3-phosphate in D2O.
|
Biochemistry
|
2005
|
1.30
|
11
|
Phosphate binding energy and catalysis by small and large molecules.
|
Acc Chem Res
|
2008
|
1.30
|
12
|
Mechanism of the orotidine 5'-monophosphate decarboxylase-catalyzed reaction: evidence for substrate destabilization.
|
Biochemistry
|
2009
|
1.27
|
13
|
Hydron transfer catalyzed by triosephosphate isomerase. Products of isomerization of dihydroxyacetone phosphate in D2O.
|
Biochemistry
|
2005
|
1.23
|
14
|
Mechanism of the orotidine 5'-monophosphate decarboxylase-catalyzed reaction: effect of solvent viscosity on kinetic constants.
|
Biochemistry
|
2009
|
1.22
|
15
|
Formation and stability of peptide enolates in aqueous solution.
|
J Am Chem Soc
|
2002
|
1.22
|
16
|
Specificity in transition state binding: the Pauling model revisited.
|
Biochemistry
|
2013
|
1.19
|
17
|
An examination of the relationship between active site loop size and thermodynamic activation parameters for orotidine 5'-monophosphate decarboxylase from mesophilic and thermophilic organisms.
|
Biochemistry
|
2009
|
1.18
|
18
|
Role of Lys-12 in catalysis by triosephosphate isomerase: a two-part substrate approach.
|
Biochemistry
|
2010
|
1.18
|
19
|
Activation of R235A mutant orotidine 5'-monophosphate decarboxylase by the guanidinium cation: effective molarity of the cationic side chain of Arg-235.
|
Biochemistry
|
2010
|
1.17
|
20
|
Orotidine 5'-monophosphate decarboxylase: transition state stabilization from remote protein-phosphodianion interactions.
|
Biochemistry
|
2012
|
1.12
|
21
|
Formation and stability of N-heterocyclic carbenes in water: the carbon acid pKa of imidazolium cations in aqueous solution.
|
J Am Chem Soc
|
2004
|
1.10
|
22
|
OMP decarboxylase: phosphodianion binding energy is used to stabilize a vinyl carbanion intermediate.
|
J Am Chem Soc
|
2011
|
1.10
|
23
|
Kinetic and thermodynamic barriers to carbon and oxygen alkylation of phenol and phenoxide ion by the 1-(4-methoxyphenyl)ethyl carbocation.
|
J Am Chem Soc
|
2003
|
1.09
|
24
|
Covalent catalysis by pyridoxal: evaluation of the effect of the cofactor on the carbon acidity of glycine.
|
J Am Chem Soc
|
2007
|
1.05
|
25
|
Scrambling of oxygen-18 during the "borderline" solvolysis of 1-(3-nitrophenyl)ethyl tosylate.
|
Org Lett
|
2004
|
1.05
|
26
|
Product deuterium isotope effects for orotidine 5'-monophosphate decarboxylase: effect of changing substrate and enzyme structure on the partitioning of the vinyl carbanion reaction intermediate.
|
J Am Chem Soc
|
2010
|
1.03
|
27
|
Reactions of ion-pair intermediates of solvolysis.
|
Chem Rec
|
2005
|
1.03
|
28
|
Rescue of K12G triosephosphate isomerase by ammonium cations: the reaction of an enzyme in pieces.
|
J Am Chem Soc
|
2010
|
1.02
|
29
|
Mechanism for activation of triosephosphate isomerase by phosphite dianion: the role of a ligand-driven conformational change.
|
J Am Chem Soc
|
2011
|
1.01
|
30
|
Formation and stability of the enolates of N-protonated proline methyl ester and proline zwitterion in aqueous solution: a nonenzymatic model for the first step in the racemization of proline catalyzed by proline racemase.
|
Biochemistry
|
2003
|
0.99
|
31
|
Proton transfer from C-6 of uridine 5'-monophosphate catalyzed by orotidine 5'-monophosphate decarboxylase: formation and stability of a vinyl carbanion intermediate and the effect of a 5-fluoro substituent.
|
J Am Chem Soc
|
2012
|
0.99
|
32
|
A simple method to determine kinetic deuterium isotope effects provides evidence that proton transfer to carbon proceeds over and not through the reaction barrier.
|
J Am Chem Soc
|
2007
|
0.98
|
33
|
Hydrogen bonding and catalysis of solvolysis of 4-methoxybenzyl fluoride.
|
J Am Chem Soc
|
2002
|
0.97
|
34
|
Mechanism for activation of triosephosphate isomerase by phosphite dianion: the role of a hydrophobic clamp.
|
J Am Chem Soc
|
2012
|
0.97
|
35
|
Direct excitation luminescence spectroscopy of Eu(III) complexes of 1,4,7-tris(carbamoylmethyl)-1,4,7,10- tetraazacyclododecane derivatives and kinetic studies of their catalytic cleavage of an RNA analog.
|
Dalton Trans
|
2007
|
0.96
|
36
|
Glycine enolates: the effect of formation of iminium ions to simple ketones on alpha-amino carbon acidity and a comparison with pyridoxal iminium ions.
|
J Am Chem Soc
|
2008
|
0.96
|
37
|
Wildtype and engineered monomeric triosephosphate isomerase from Trypanosoma brucei: partitioning of reaction intermediates in D2O and activation by phosphite dianion.
|
Biochemistry
|
2011
|
0.95
|
38
|
Physical and kinetic analysis of the cooperative role of metal ions in catalysis of phosphodiester cleavage by a dinuclear Zn(II) complex.
|
J Am Chem Soc
|
2003
|
0.95
|
39
|
When does an intermediate become a transition state? Degenerate isomerization without competing racemization during solvolysis of (S)-1-(3-nitrophenyl)ethyl tosylate.
|
J Am Chem Soc
|
2006
|
0.94
|
40
|
Magnitude and origin of the enhanced basicity of the catalytic glutamate of triosephosphate isomerase.
|
J Am Chem Soc
|
2013
|
0.94
|
41
|
Conformational changes in orotidine 5'-monophosphate decarboxylase: "remote" residues that stabilize the active conformation.
|
Biochemistry
|
2010
|
0.93
|
42
|
Enzyme architecture: remarkably similar transition states for triosephosphate isomerase-catalyzed reactions of the whole substrate and the substrate in pieces.
|
J Am Chem Soc
|
2014
|
0.92
|
43
|
Substituent effects on the thermodynamic stability of imines formed from glycine and aromatic aldehydes: implications for the catalytic activity of pyridoxal-5'-phosphate.
|
J Am Chem Soc
|
2009
|
0.92
|
44
|
Claisen-type addition of glycine to pyridoxal in water.
|
J Am Chem Soc
|
2004
|
0.92
|
45
|
Slow proton transfer from the hydrogen-labelled carboxylic acid side chain (Glu-165) of triosephosphate isomerase to imidazole buffer in D2O.
|
Org Biomol Chem
|
2007
|
0.91
|
46
|
Dynamics for Reactions of Ion Pairs in Aqueous Solution: Reactivity of Tosylate Anion Ion Paired with the Highly Destabilized 1-(4-Methylphenyl)-2,2,2-Trifluoroethyl Carbocation.
|
J Phys Org Chem
|
2010
|
0.91
|
47
|
Formation and stability of the 4-methoxyphenonium ion in aqueous solution.
|
J Org Chem
|
2011
|
0.91
|
48
|
Altered transition state for the reaction of an RNA model catalyzed by a dinuclear zinc(II) catalyst.
|
J Am Chem Soc
|
2008
|
0.90
|
49
|
Structural mutations that probe the interactions between the catalytic and dianion activation sites of triosephosphate isomerase.
|
Biochemistry
|
2013
|
0.90
|
50
|
Role of a guanidinium cation-phosphodianion pair in stabilizing the vinyl carbanion intermediate of orotidine 5'-phosphate decarboxylase-catalyzed reactions.
|
Biochemistry
|
2013
|
0.89
|
51
|
Claisen-type addition of glycine to a pyridoxal iminium ion in water.
|
J Org Chem
|
2006
|
0.89
|
52
|
Conformational changes in orotidine 5'-monophosphate decarboxylase: a structure-based explanation for how the 5'-phosphate group activates the enzyme.
|
Biochemistry
|
2012
|
0.88
|
53
|
Carbon acidity of the alpha-pyridinium carbon of a pyridoxamine analog.
|
Org Biomol Chem
|
2005
|
0.88
|
54
|
Enzyme architecture: deconstruction of the enzyme-activating phosphodianion interactions of orotidine 5'-monophosphate decarboxylase.
|
J Am Chem Soc
|
2014
|
0.87
|
55
|
Structure-reactivity effects on primary deuterium isotope effects on protonation of ring-substituted alpha-methoxystyrenes.
|
J Am Chem Soc
|
2009
|
0.87
|
56
|
The activating oxydianion binding domain for enzyme-catalyzed proton transfer, hydride transfer, and decarboxylation: specificity and enzyme architecture.
|
J Am Chem Soc
|
2015
|
0.86
|
57
|
Cooperativity between metal ions in the cleavage of phosphate diesters and RNA by dinuclear Zn(II) catalysts.
|
Inorg Chem
|
2003
|
0.86
|
58
|
Catalysis by orotidine 5'-monophosphate decarboxylase: effect of 5-fluoro and 4'-substituents on the decarboxylation of two-part substrates.
|
Biochemistry
|
2013
|
0.86
|
59
|
Bovine serum albumin-catalyzed deprotonation of [1-(13)C]glycolaldehyde: protein reactivity toward deprotonation of the alpha-hydroxy alpha-carbonyl carbon.
|
Biochemistry
|
2010
|
0.85
|
60
|
Theoretical analysis of kinetic isotope effects on proton transfer reactions between substituted alpha-methoxystyrenes and substituted acetic acids.
|
J Am Chem Soc
|
2009
|
0.85
|
61
|
Enzyme architecture: the activating oxydianion binding domain for orotidine 5'-monophophate decarboxylase.
|
J Am Chem Soc
|
2013
|
0.84
|
62
|
Substrate specificity of an active dinuclear Zn(II) catalyst for cleavage of RNA analogues and a dinucleoside.
|
J Am Chem Soc
|
2006
|
0.84
|
63
|
Structure-activity studies on the cleavage of an RNA analogue by a potent dinuclear metal ion catalyst: effect of changing the metal ion.
|
Inorg Chem
|
2004
|
0.84
|
64
|
Solvent deuterium isotope effects on phosphodiester cleavage catalyzed by an extraordinarily active Zn(II) complex.
|
J Am Chem Soc
|
2005
|
0.83
|
65
|
A transition state analog for phosphate diester cleavage catalyzed by a small enzyme-like metal ion complex.
|
Bioorg Chem
|
2007
|
0.82
|
66
|
A comparison of the electrophilic reactivities of Zn2+ and acetic acid as catalysts of enolization: imperatives for enzymatic catalysis of proton transfer at carbon.
|
J Am Chem Soc
|
2004
|
0.82
|
67
|
Alanine-dependent reactions of 5'-deoxypyridoxal in water.
|
Bioorg Chem
|
2008
|
0.81
|
68
|
Enhancement of a Lewis acid-base interaction via solvation: ammonia molecules and the benzene radical cation.
|
J Phys Chem A
|
2007
|
0.81
|
69
|
A minimalist approach to understanding the efficiency of mononuclear Zn(II) complexes as catalysts of cleavage of an RNA analog.
|
Dalton Trans
|
2007
|
0.81
|
70
|
Enzyme architecture: the effect of replacement and deletion mutations of loop 6 on catalysis by triosephosphate isomerase.
|
Biochemistry
|
2014
|
0.81
|
71
|
Isopentenyl diphosphate isomerase catalyzed reactions in D2O: product release limits the rate of this sluggish enzyme-catalyzed reaction.
|
J Am Chem Soc
|
2012
|
0.79
|
72
|
Binding energy and catalysis by D-xylose isomerase: kinetic, product, and X-ray crystallographic analysis of enzyme-catalyzed isomerization of (R)-glyceraldehyde.
|
Biochemistry
|
2011
|
0.79
|
73
|
Substituent effects on electrophilic catalysis by the carbonyl group: anatomy of the rate acceleration for PLP-catalyzed deprotonation of glycine.
|
J Am Chem Soc
|
2011
|
0.79
|
74
|
Substrate specificity for catalysis of phosphodiester cleavage by a dinuclear Zn(II) complex.
|
Chem Commun (Camb)
|
2003
|
0.78
|
75
|
Formation and stability of mononuclear and dinuclear Eu(III) complexes and their catalytic reactivity toward cleavage of an RNA analog.
|
Inorg Chem
|
2007
|
0.78
|
76
|
Ketonization of the remarkably strongly acidic elongated enol generated by flash photolytic decarboxylation of p-benzoylphenylacetic acid in aqueous solution.
|
Chem Commun (Camb)
|
2005
|
0.77
|
77
|
Rational design of transition-state analogues as potent enzyme inhibitors with therapeutic applications.
|
ACS Chem Biol
|
2007
|
0.76
|
78
|
Complex biological processes and their central chemical events.
|
Curr Opin Chem Biol
|
2003
|
0.75
|