Bovine serum albumin-catalyzed deprotonation of [1-(13)C]glycolaldehyde: protein reactivity toward deprotonation of the alpha-hydroxy alpha-carbonyl carbon.

PubWeight™: 0.85‹?›

🔗 View Article (PMC 2932853)

Published in Biochemistry on September 07, 2010

Authors

Maybelle K Go1, M Merced Malabanan, Tina L Amyes, John P Richard

Author Affiliations

1: Department of Chemistry, University at Buffalo, State University of New York, Buffalo, New York 14260, USA.

Articles cited by this

How to measure and predict the molar absorption coefficient of a protein. Protein Sci (1995) 18.71

De novo computational design of retro-aldol enzymes. Science (2008) 7.62

Atomic structure and chemistry of human serum albumin. Nature (1992) 6.68

Mechanism of protein modification by glyoxal and glycolaldehyde, reactive intermediates of the Maillard reaction. J Biol Chem (1995) 1.76

pH-dependence of the triose phosphate isomerase reaction. Biochem J (1972) 1.73

Enzymatic catalysis of proton transfer at carbon: activation of triosephosphate isomerase by phosphite dianion. Biochemistry (2007) 1.72

Formation and stability of enolates of acetamide and acetate anion: an Eigen plot for proton transfer at alpha-carbonyl carbon. J Am Chem Soc (2002) 1.50

Contribution of phosphate intrinsic binding energy to the enzymatic rate acceleration for triosephosphate isomerase. J Am Chem Soc (2001) 1.40

Proton transfer at carbon. Curr Opin Chem Biol (2001) 1.36

Active-site labelling of triose phosphate isomerase. The reaction of bromohydroxyacetone phosphate with a unique glutamic acid residue and the migration of the label to tyrosine. Biochem J (1972) 1.35

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

Hydron transfer catalyzed by triosephosphate isomerase. Products of isomerization of (R)-glyceraldehyde 3-phosphate in D2O. Biochemistry (2005) 1.30

Origins of catalysis by computationally designed retroaldolase enzymes. Proc Natl Acad Sci U S A (2010) 1.27

Hydron transfer catalyzed by triosephosphate isomerase. Products of isomerization of dihydroxyacetone phosphate in D2O. Biochemistry (2005) 1.23

Reaction energetics of a mutant triosephosphate isomerase in which the active-site glutamate has been changed to aspartate. Biochemistry (1986) 1.21

Role of Lys-12 in catalysis by triosephosphate isomerase: a two-part substrate approach. Biochemistry (2010) 1.18

Haloacetol phosphates. Characterization of the active site of rabbit muscle triose phosphate isomerase. Biochemistry (1971) 1.17

Nonspecific medium effects versus specific group positioning in the antibody and albumin catalysis of the base-promoted ring-opening reactions of benzisoxazoles. J Am Chem Soc (2004) 1.15

Development of small designer aldolase enzymes: catalytic activity, folding, and substrate specificity. Biochemistry (2005) 1.12

Acetylation of human serum albumin by p-nitrophenyl acetate. Biochemistry (1975) 0.99

Characterization of a small apolar anion binding site of human serum albumin. Arch Biochem Biophys (1979) 0.85

The uncatalyzed rates of enolization of dihydroxyacetone phoshate and of glyceraldehyde 3-phosphate in neutral aqueous solution. The quantitative assessment of the effectiveness of an enzyme catalyst. Biochemistry (1975) 0.85

Articles by these authors

Activation of orotidine 5'-monophosphate decarboxylase by phosphite dianion: the whole substrate is the sum of two parts. J Am Chem Soc (2005) 2.06

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

Enzymatic catalysis of proton transfer at carbon: activation of triosephosphate isomerase by phosphite dianion. Biochemistry (2007) 1.72

A role for flexible loops in enzyme catalysis. Curr Opin Struct Biol (2010) 1.62

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

A substrate in pieces: allosteric activation of glycerol 3-phosphate dehydrogenase (NAD+) by phosphite dianion. Biochemistry (2008) 1.51

Formation and stability of enolates of acetamide and acetate anion: an Eigen plot for proton transfer at alpha-carbonyl carbon. J Am Chem Soc (2002) 1.50

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

Substituent effects on carbocation stability: the pK(R) for p-quinone methide. J Am Chem Soc (2003) 1.44

On the importance of being zwitterionic: enzymatic catalysis of decarboxylation and deprotonation of cationic carbon. Bioorg Chem (2004) 1.36

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

Hydron transfer catalyzed by triosephosphate isomerase. Products of isomerization of (R)-glyceraldehyde 3-phosphate in D2O. Biochemistry (2005) 1.30

Phosphate binding energy and catalysis by small and large molecules. Acc Chem Res (2008) 1.30

Mechanism of the orotidine 5'-monophosphate decarboxylase-catalyzed reaction: evidence for substrate destabilization. Biochemistry (2009) 1.27

Hydron transfer catalyzed by triosephosphate isomerase. Products of isomerization of dihydroxyacetone phosphate in D2O. Biochemistry (2005) 1.23

Mechanism of the orotidine 5'-monophosphate decarboxylase-catalyzed reaction: effect of solvent viscosity on kinetic constants. Biochemistry (2009) 1.22

Formation and stability of peptide enolates in aqueous solution. J Am Chem Soc (2002) 1.22

Specificity in transition state binding: the Pauling model revisited. Biochemistry (2013) 1.19

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

Role of Lys-12 in catalysis by triosephosphate isomerase: a two-part substrate approach. Biochemistry (2010) 1.18

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

Orotidine 5'-monophosphate decarboxylase: transition state stabilization from remote protein-phosphodianion interactions. Biochemistry (2012) 1.12

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

OMP decarboxylase: phosphodianion binding energy is used to stabilize a vinyl carbanion intermediate. J Am Chem Soc (2011) 1.10

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

Scrambling of oxygen-18 during the "borderline" solvolysis of 1-(3-nitrophenyl)ethyl tosylate. Org Lett (2004) 1.05

Covalent catalysis by pyridoxal: evaluation of the effect of the cofactor on the carbon acidity of glycine. J Am Chem Soc (2007) 1.05

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

Reactions of ion-pair intermediates of solvolysis. Chem Rec (2005) 1.03

Pyridoxal 5'-phosphate: electrophilic catalyst extraordinaire. Curr Opin Chem Biol (2009) 1.03

Rescue of K12G triosephosphate isomerase by ammonium cations: the reaction of an enzyme in pieces. J Am Chem Soc (2010) 1.02

Mechanism for activation of triosephosphate isomerase by phosphite dianion: the role of a ligand-driven conformational change. J Am Chem Soc (2011) 1.01

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

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

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

Mechanism for activation of triosephosphate isomerase by phosphite dianion: the role of a hydrophobic clamp. J Am Chem Soc (2012) 0.97

Hydrogen bonding and catalysis of solvolysis of 4-methoxybenzyl fluoride. J Am Chem Soc (2002) 0.97

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

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

Wildtype and engineered monomeric triosephosphate isomerase from Trypanosoma brucei: partitioning of reaction intermediates in D2O and activation by phosphite dianion. Biochemistry (2011) 0.95

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

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

Magnitude and origin of the enhanced basicity of the catalytic glutamate of triosephosphate isomerase. J Am Chem Soc (2013) 0.94

Conformational changes in orotidine 5'-monophosphate decarboxylase: "remote" residues that stabilize the active conformation. Biochemistry (2010) 0.93

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

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

Claisen-type addition of glycine to pyridoxal in water. J Am Chem Soc (2004) 0.92

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

Formation and stability of the 4-methoxyphenonium ion in aqueous solution. J Org Chem (2011) 0.91

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

Altered transition state for the reaction of an RNA model catalyzed by a dinuclear zinc(II) catalyst. J Am Chem Soc (2008) 0.90

Structural mutations that probe the interactions between the catalytic and dianion activation sites of triosephosphate isomerase. Biochemistry (2013) 0.90

Role of a guanidinium cation-phosphodianion pair in stabilizing the vinyl carbanion intermediate of orotidine 5'-phosphate decarboxylase-catalyzed reactions. Biochemistry (2013) 0.89

Claisen-type addition of glycine to a pyridoxal iminium ion in water. J Org Chem (2006) 0.89

Conformational changes in orotidine 5'-monophosphate decarboxylase: a structure-based explanation for how the 5'-phosphate group activates the enzyme. Biochemistry (2012) 0.88

Carbon acidity of the alpha-pyridinium carbon of a pyridoxamine analog. Org Biomol Chem (2005) 0.88

Enzyme architecture: deconstruction of the enzyme-activating phosphodianion interactions of orotidine 5'-monophosphate decarboxylase. J Am Chem Soc (2014) 0.87

Structure-reactivity effects on primary deuterium isotope effects on protonation of ring-substituted alpha-methoxystyrenes. J Am Chem Soc (2009) 0.87

Catalysis by orotidine 5'-monophosphate decarboxylase: effect of 5-fluoro and 4'-substituents on the decarboxylation of two-part substrates. Biochemistry (2013) 0.86

Cooperativity between metal ions in the cleavage of phosphate diesters and RNA by dinuclear Zn(II) catalysts. Inorg Chem (2003) 0.86

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

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

Enzyme architecture: the activating oxydianion binding domain for orotidine 5'-monophophate decarboxylase. J Am Chem Soc (2013) 0.84