Divergence of chemical function in the alkaline phosphatase superfamily: structure and mechanism of the P-C bond cleaving enzyme phosphonoacetate hydrolase.

PubWeight™: 1.03‹?› | Rank: Top 15%

🔗 View Article (PMC 3102601)

Published in Biochemistry on April 08, 2011

Authors

Alexander Kim1, Matthew M Benning, Sang OkLee, John Quinn, Brian M Martin, Hazel M Holden, Debra Dunaway-Mariano

Author Affiliations

1: Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, 87131, USA.

Articles citing this

The treatment-naive microbiome in new-onset Crohn's disease. Cell Host Microbe (2014) 7.43

Cellular function and molecular structure of ecto-nucleotidases. Purinergic Signal (2012) 2.13

The genes and enzymes of phosphonate metabolism by bacteria, and their distribution in the marine environment. Front Microbiol (2012) 1.27

Organophosphonates revealed: new insights into the microbial metabolism of ancient molecules. Nat Rev Microbiol (2013) 1.13

Structural and mechanistic insights into C-P bond hydrolysis by phosphonoacetate hydrolase. Chem Biol (2011) 0.95

Phosphonate biosynthesis and catabolism: a treasure trove of unusual enzymology. Curr Opin Chem Biol (2013) 0.92

Cooperative Electrostatic Interactions Drive Functional Evolution in the Alkaline Phosphatase Superfamily. J Am Chem Soc (2015) 0.82

Answers to the carbon-phosphorus lyase conundrum. Chembiochem (2012) 0.82

Structure and function of phosphonoacetaldehyde dehydrogenase: the missing link in phosphonoacetate formation. Chem Biol (2013) 0.80

Probing the origins of catalytic discrimination between phosphate and sulfate monoester hydrolysis: comparative analysis of alkaline phosphatase and protein tyrosine phosphatases. Biochemistry (2014) 0.79

Site-directed mutagenesis maps interactions that enhance cognate and limit promiscuous catalysis by an alkaline phosphatase superfamily phosphodiesterase. Biochemistry (2013) 0.77

Mechanistic and Evolutionary Insights from Comparative Enzymology of Phosphomonoesterases and Phosphodiesterases across the Alkaline Phosphatase Superfamily. J Am Chem Soc (2016) 0.75

Articles cited by this

Automated MAD and MIR structure solution. Acta Crystallogr D Biol Crystallogr (1999) 41.65

Miscellaneous algorithms for density modification. Acta Crystallogr D Biol Crystallogr (1998) 4.50

Reaction mechanism of alkaline phosphatase based on crystal structures. Two-metal ion catalysis. J Mol Biol (1991) 3.33

Fosfomycin for the treatment of multidrug-resistant, including extended-spectrum beta-lactamase producing, Enterobacteriaceae infections: a systematic review. Lancet Infect Dis (2010) 2.60

Phosphoryl group transfer: evolution of a catalytic scaffold. Trends Biochem Sci (2004) 2.26

Biosynthesis of phosphonic and phosphinic acid natural products. Annu Rev Biochem (2009) 2.19

Divergent evolution in the enolase superfamily: the interplay of mechanism and specificity. Arch Biochem Biophys (2005) 2.18

Acyclic nucleoside phosphonates: a key class of antiviral drugs. Nat Rev Drug Discov (2005) 2.14

Structure and mechanism of alkaline phosphatase. Annu Rev Biophys Biomol Struct (1992) 2.12

Isolation of 2-aminoethane phosphonic acid from rumen protozoa. Nature (1959) 2.05

Alkaline phosphatase revisited: hydrolysis of alkyl phosphates. Biochemistry (2002) 1.61

Structural and functional comparisons of nucleotide pyrophosphatase/phosphodiesterase and alkaline phosphatase: implications for mechanism and evolution. Biochemistry (2006) 1.60

Microbial metabolism of reduced phosphorus compounds. Annu Rev Microbiol (2007) 1.55

A superfamily of metalloenzymes unifies phosphopentomutase and cofactor-independent phosphoglycerate mutase with alkaline phosphatases and sulfatases. Protein Sci (1998) 1.54

New ways to break an old bond: the bacterial carbon-phosphorus hydrolases and their role in biogeochemical phosphorus cycling. Environ Microbiol (2007) 1.48

Autotaxin is an exoenzyme possessing 5'-nucleotide phosphodiesterase/ATP pyrophosphatase and ATPase activities. J Biol Chem (1997) 1.44

A revised mechanism for the alkaline phosphatase reaction involving three metal ions. J Mol Biol (2000) 1.37

Phosphonolipids: localization in surface membranes of Tetrahymena. Science (1970) 1.34

Aminophosphonic acids and derivatives. Synthesis and biological applications. Curr Med Chem (2010) 1.31

Crystallization and structure determination to 2.5-A resolution of the oxidized [2Fe-2S] ferredoxin isolated from Anabaena 7120. Biochemistry (1991) 1.22

Conserved core structure and active site residues in alkaline phosphatase superfamily enzymes. Proteins (2001) 1.19

Comparative enzymology in the alkaline phosphatase superfamily to determine the catalytic role of an active-site metal ion. J Mol Biol (2008) 1.19

Human sulfatases: a structural perspective to catalysis. Cell Mol Life Sci (2007) 1.16

The evolution of microbial phosphonate degradative pathways. J Mol Evol (2005) 1.14

Sulfotransferases, sulfatases and formylglycine-generating enzymes: a sulfation fascination. Curr Opin Chem Biol (2008) 1.13

The purification and properties of phosphonoacetate hydrolase, a novel carbon-phosphorus bond-cleavage enzyme from Pseudomonas fluorescens 23F. Eur J Biochem (1995) 1.10

In vitro characterization of a phosphate starvation-independent carbon-phosphorus bond cleavage activity in Pseudomonas fluorescens 23F. J Bacteriol (1994) 1.02

The 2-aminoethylphosphonate-specific transaminase of the 2-aminoethylphosphonate degradation pathway. J Bacteriol (2002) 1.02

Arginine coordination in enzymatic phosphoryl transfer: evaluation of the effect of Arg166 mutations in Escherichia coli alkaline phosphatase. Biochemistry (2008) 1.02

Insights into the catalytic mechanism of cofactor-independent phosphoglycerate mutase from X-ray crystallography, simulated dynamics and molecular modeling. J Mol Biol (2003) 1.00

Insights into the mechanism of catalysis by the P-C bond-cleaving enzyme phosphonoacetaldehyde hydrolase derived from gene sequence analysis and mutagenesis. Biochemistry (1998) 0.97

Investigation of the Bacillus cereus phosphonoacetaldehyde hydrolase. Evidence for a Schiff base mechanism and sequence analysis of an active-site peptide containing the catalytic lysine residue. Biochemistry (1988) 0.96

Cloning of the phosphonoacetate hydrolase gene from Pseudomonas fluorescens 23F encoding a new type of carbon-phosphorus bond cleaving enzyme and its expression in Escherichia coli and Pseudomonas putida. Gene (1997) 0.95

Detection of a novel carbon-phosphorus bond cleavage activity in cell-free extracts of an environmental Pseudomonas fluorescens isolate. Biochem Biophys Res Commun (1992) 0.94

The phosphonopyruvate decarboxylase from Bacteroides fragilis. J Biol Chem (2003) 0.94

Structural and functional analysis of the phosphonoacetate hydrolase (phnA) gene region in Pseudomonas fluorescens 23F. J Bacteriol (2001) 0.94

Evidence for phosphonate usage in the coral holobiont. ISME J (2009) 0.94

The occurrence of free 2-aminoethylphosphonic acid in the sea anemone, Anthopleura elegantissima. Biochemistry (1962) 0.93

Promiscuous sulfatase activity and thio-effects in a phosphodiesterase of the alkaline phosphatase superfamily. Biochemistry (2008) 0.93

Structure and mechanism of enzymes involved in biosynthesis and breakdown of the phosphonates fosfomycin, dehydrophos, and phosphinothricin. Arch Biochem Biophys (2010) 0.92

Comparison of the binuclear metalloenzymes diphosphoglycerate-independent phosphoglycerate mutase and alkaline phosphatase: their mechanism of catalysis via a phosphoserine intermediate. Chem Rev (2001) 0.89

Detection of phosphonoacetate degradation and phnA genes in soil bacteria from distinct geographical origins suggest its possible biogenic origin. Environ Microbiol (2006) 0.84

Trapping the tetrahedral intermediate in the alkaline phosphatase reaction by substitution of the active site serine with threonine. Protein Sci (2006) 0.81

Alternate modes of binding in two crystal structures of alkaline phosphatase-inhibitor complexes. Protein Sci (2000) 0.81

Crystal structures of 2-methylisocitrate lyase in complex with product and with isocitrate inhibitor provide insight into lyase substrate specificity, catalysis and evolution. Biochemistry (2005) 0.81

The major acidic fibroblast growth factor (aFGF)-stimulated phosphoprotein from bovine liver plasma membranes has aFGF-stimulated kinase, autoadenylylation, and alkaline nucleotide phosphodiesterase activities. J Biol Chem (1993) 0.80

Mutational analysis of wheat (Triticum aestivum L.) nucleotide pyrophosphatase/phosphodiesterase shows the role of six amino acids in the catalytic mechanism. Appl Microbiol Biotechnol (2010) 0.78

Articles by these authors

Acquisition of a natural resistance gene renders a clinical strain of methicillin-resistant Staphylococcus aureus resistant to the synthetic antibiotic linezolid. Mol Microbiol (2007) 3.47

The pentacovalent phosphorus intermediate of a phosphoryl transfer reaction. Science (2003) 3.41

Evolutionary genomics of the HAD superfamily: understanding the structural adaptations and catalytic diversity in a superfamily of phosphoesterases and allied enzymes. J Mol Biol (2006) 3.10

Phosphoryl group transfer: evolution of a catalytic scaffold. Trends Biochem Sci (2004) 2.26

Molecular epidemiological analysis of Escherichia coli sequence type ST131 (O25:H4) and blaCTX-M-15 among extended-spectrum-β-lactamase-producing E. coli from the United States, 2000 to 2009. Antimicrob Agents Chemother (2012) 2.17

The Enzyme Function Initiative. Biochemistry (2011) 1.87

Biochemical subtyping of amyloid in formalin-fixed tissue samples confirms and supplements immunohistologic data. Am J Clin Pathol (2004) 1.77

Structural characterization of a 140 degrees domain movement in the two-step reaction catalyzed by 4-chlorobenzoate:CoA ligase. Biochemistry (2008) 1.68

AdeABC-mediated efflux and tigecycline MICs for epidemic clones of Acinetobacter baumannii. J Antimicrob Chemother (2010) 1.67

Community transmission in the United States of a CTX-M-15-producing sequence type ST131 Escherichia coli strain resulting in death. J Clin Microbiol (2011) 1.66

Prolonged exposure to reduced levels of androgen accelerates prostate cancer progression in Nkx3.1; Pten mutant mice. Cancer Res (2007) 1.51

Glucosylsphingosine accumulation in tissues from patients with Gaucher disease: correlation with phenotype and genotype. Mol Genet Metab (2002) 1.49

The molecular architecture of human N-acetylgalactosamine kinase. J Biol Chem (2005) 1.46

Caught in the act: the structure of phosphorylated beta-phosphoglucomutase from Lactococcus lactis. Biochemistry (2002) 1.43

Molecular structure of the rat vitamin D receptor ligand binding domain complexed with 2-carbon-substituted vitamin D3 hormone analogues and a LXXLL-containing coactivator peptide. Biochemistry (2004) 1.42

The mechanisms of human hotdog-fold thioesterase 2 (hTHEM2) substrate recognition and catalysis illuminated by a structure and function based analysis. Biochemistry (2009) 1.40

The structure of 4-hydroxybenzoyl-CoA thioesterase from arthrobacter sp. strain SU. J Biol Chem (2003) 1.40

A comparison of graphical and textual presentations of time series data to support medical decision making in the neonatal intensive care unit. J Clin Monit Comput (2005) 1.38

Structure, function, and mechanism of the phenylacetate pathway hot dog-fold thioesterase PaaI. J Biol Chem (2006) 1.37

Crystal structure of 4-chlorobenzoate:CoA ligase/synthetase in the unliganded and aryl substrate-bound states. Biochemistry (2004) 1.37

Enrichment of low molecular weight fraction of serum for MS analysis of peptides associated with hepatocellular carcinoma. Proteomics (2006) 1.36

Enzymes with molecular tunnels. Acc Chem Res (2003) 1.35

Diverse range of small peptides associated with high-density lipoprotein. Biochem Biophys Res Commun (2005) 1.34

Mechanism of 4-chlorobenzoate:coenzyme a ligase catalysis. Biochemistry (2008) 1.31

Markers of fitness in a successful enzyme superfamily. Curr Opin Struct Biol (2009) 1.31

Structure and activity analyses of Escherichia coli K-12 NagD provide insight into the evolution of biochemical function in the haloalkanoic acid dehalogenase superfamily. Biochemistry (2006) 1.31

X-ray crystallographic analyses of inhibitor and substrate complexes of wild-type and mutant 4-hydroxybenzoyl-CoA thioesterase. J Biol Chem (2002) 1.30

HAD superfamily phosphotransferase substrate diversification: structure and function analysis of HAD subclass IIB sugar phosphatase BT4131. Biochemistry (2005) 1.29

Divergence of function in the hot dog fold enzyme superfamily: the bacterial thioesterase YciA. Biochemistry (2008) 1.28

The structural determination of an insect sterol carrier protein-2 with a ligand-bound C16 fatty acid at 1.35-A resolution. J Biol Chem (2003) 1.25

Mechanism of the reaction catalyzed by isoaspartyl dipeptidase from Escherichia coli. Biochemistry (2005) 1.24

Molecular structure of human galactokinase: implications for type II galactosemia. J Biol Chem (2004) 1.24

Dysbindin (DTNBP1) and the biogenesis of lysosome-related organelles complex 1 (BLOC-1): main and epistatic gene effects are potential contributors to schizophrenia susceptibility. Biol Psychiatry (2007) 1.23

The X-ray crystal structures of human alpha-phosphomannomutase 1 reveal the structural basis of congenital disorder of glycosylation type 1a. J Biol Chem (2006) 1.22

Confirming RGS4 as a susceptibility gene for schizophrenia. Am J Med Genet B Neuropsychiatr Genet (2004) 1.22

Arginine deiminase uses an active-site cysteine in nucleophilic catalysis of L-arginine hydrolysis. J Am Chem Soc (2004) 1.22

Structural analysis of the Y299C mutant of Escherichia coli UDP-galactose 4-epimerase. Teaching an old dog new tricks. J Biol Chem (2002) 1.21

Analysis of the substrate specificity loop of the HAD superfamily cap domain. Biochemistry (2004) 1.20

The catalytic scaffold of the haloalkanoic acid dehalogenase enzyme superfamily acts as a mold for the trigonal bipyramidal transition state. Proc Natl Acad Sci U S A (2008) 1.19

No evidence for association of the dysbindin gene [DTNBP1] with schizophrenia in an Irish population-based study. Schizophr Res (2003) 1.19

Molecular structure of galactokinase. J Biol Chem (2003) 1.19

Characterization, kinetics, and crystal structures of fructose-1,6-bisphosphate aldolase from the human parasite, Giardia lamblia. J Biol Chem (2006) 1.19

SME-3, a novel member of the Serratia marcescens SME family of carbapenem-hydrolyzing beta-lactamases. Antimicrob Agents Chemother (2006) 1.18

Predicted Relative Metabolomic Turnover (PRMT): determining metabolic turnover from a coastal marine metagenomic dataset. Microb Inform Exp (2011) 1.14

The 2A resolution crystal structure of HetL, a pentapeptide repeat protein involved in regulation of heterocyst differentiation in the cyanobacterium Nostoc sp. strain PCC 7120. J Struct Biol (2008) 1.14

Crystal structures representing the Michaelis complex and the thiouronium reaction intermediate of Pseudomonas aeruginosa arginine deiminase. J Biol Chem (2005) 1.13

Three-dimensional structure of DesVI from Streptomyces venezuelae: a sugar N,N-dimethyltransferase required for dTDP-desosamine biosynthesis. Biochemistry (2008) 1.12

Structure of YciA from Haemophilus influenzae (HI0827), a hexameric broad specificity acyl-coenzyme A thioesterase. Biochemistry (2008) 1.11

Dialysis-dependent renal failure at diagnosis continues to be associated with very poor outcome in multiple myeloma. Br J Haematol (2014) 1.10

Molecular architecture of DesV from Streptomyces venezuelae: a PLP-dependent transaminase involved in the biosynthesis of the unusual sugar desosamine. Protein Sci (2007) 1.09

Kinetic, Raman, NMR, and site-directed mutagenesis studies of the Pseudomonas sp. strain CBS3 4-hydroxybenzoyl-CoA thioesterase active site. Biochemistry (2002) 1.09

The mechanism of domain alternation in the acyl-adenylate forming ligase superfamily member 4-chlorobenzoate: coenzyme A ligase. Biochemistry (2009) 1.07

Molecular architecture of TylM1 from Streptomyces fradiae: an N,N-dimethyltransferase involved in the production of dTDP-D-mycaminose. Biochemistry (2011) 1.07

High resolution X-ray structure of dTDP-glucose 4,6-dehydratase from Streptomyces venezuelae. J Biol Chem (2003) 1.07

Molecular structure of Saccharomyces cerevisiae Gal1p, a bifunctional galactokinase and transcriptional inducer. J Biol Chem (2005) 1.06

Chemical confirmation of a pentavalent phosphorane in complex with beta-phosphoglucomutase. J Am Chem Soc (2005) 1.05

A newly discovered human alpha-globin gene. Blood (2005) 1.05

GDP-perosamine synthase: structural analysis and production of a novel trideoxysugar. Biochemistry (2008) 1.05

Catalytic cycling in beta-phosphoglucomutase: a kinetic and structural analysis. Biochemistry (2005) 1.05

Inflammatory protein profile during systemic high dose interleukin-2 administration. Proteomics (2006) 1.04

Preconditioning-induced protection from oxidative injury is mediated by leukemia inhibitory factor receptor (LIFR) and its ligands in the retina. Neurobiol Dis (2009) 1.04

Analysis of the structural determinants underlying discrimination between substrate and solvent in beta-phosphoglucomutase catalysis. Biochemistry (2009) 1.04

Enhanced degradation of chemical warfare agents through molecular engineering of the phosphotriesterase active site. J Am Chem Soc (2003) 1.04

Molecular architecture of DesI: a key enzyme in the biosynthesis of desosamine. Biochemistry (2007) 1.03

Kinetic analysis of Pseudomonas aeruginosa arginine deiminase mutants and alternate substrates provides insight into structural determinants of function. Biochemistry (2006) 1.02

The x-ray structure of dTDP-4-keto-6-deoxy-D-glucose-3,4-ketoisomerase. J Biol Chem (2007) 1.02

The 2-aminoethylphosphonate-specific transaminase of the 2-aminoethylphosphonate degradation pathway. J Bacteriol (2002) 1.02

True aneurysms of the posterior communicating artery: a systematic review and meta-analysis of individual patient data. World Neurosurg (2011) 1.02

Determinants of function and substrate specificity in human UDP-galactose 4'-epimerase. J Biol Chem (2004) 1.02

Characterization of the 4-hydroxybenzoyl-coenzyme A thioesterase from Arthrobacter sp. strain SU. Appl Environ Microbiol (2003) 1.01

Structural determinants of substrate recognition in the HAD superfamily member D-glycero-D-manno-heptose-1,7-bisphosphate phosphatase (GmhB) . Biochemistry (2010) 1.00

The Akt C-terminal modulator protein is an acyl-CoA thioesterase of the Hotdog-Fold family. Biochemistry (2009) 1.00

Evolution of enzymatic activity in the enolase superfamily: functional studies of the promiscuous o-succinylbenzoate synthase from Amycolatopsis. Biochemistry (2004) 1.00

Structure-function analysis of 2-keto-3-deoxy-D-glycero-D-galactonononate-9-phosphate phosphatase defines specificity elements in type C0 haloalkanoate dehalogenase family members. J Biol Chem (2008) 0.99

Investigation of metal ion binding in phosphonoacetaldehyde hydrolase identifies sequence markers for metal-activated enzymes of the HAD enzyme superfamily. Biochemistry (2004) 0.99

Crystal structure of human thioesterase superfamily member 2. Biochem Biophys Res Commun (2006) 0.99

Nitration and inactivation of IDO by peroxynitrite. J Immunol (2006) 0.99

Structural analysis of the active site geometry of N5-carboxyaminoimidazole ribonucleotide synthetase from Escherichia coli. Biochemistry (2008) 0.99

Oxaloacetate hydrolase, the C-C bond lyase of oxalate secreting fungi. J Biol Chem (2007) 0.99

Sequential univariate gating approach to study the effects of erythropoietin in murine bone marrow. Cytometry A (2008) 0.98

Understanding a transcriptional paradigm at the molecular level. The structure of yeast Gal80p. J Biol Chem (2006) 0.98

Carbamoyl-phosphate synthetase. Creation of an escape route for ammonia. J Biol Chem (2002) 0.98

Structural analysis of QdtB, an aminotransferase required for the biosynthesis of dTDP-3-acetamido-3,6-dideoxy-alpha-D-glucose. Biochemistry (2009) 0.98

A polymorphism associated with depressive disorders differentially regulates brain derived neurotrophic factor promoter IV activity. Biol Psychiatry (2012) 0.97

Three-dimensional structure of a sugar N-formyltransferase from Francisella tularensis. Protein Sci (2014) 0.97

Noncovalent assembly of anti-dendritic cell antibodies and antigens for evoking immune responses in vitro and in vivo. J Immunol (2012) 0.97

Conformational cycling in beta-phosphoglucomutase catalysis: reorientation of the beta-D-glucose 1,6-(Bis)phosphate intermediate. Biochemistry (2006) 0.97

Structure of a sugar N-formyltransferase from Campylobacter jejuni. Biochemistry (2013) 0.97

Structural insights into the substrate binding and stereoselectivity of giardia fructose-1,6-bisphosphate aldolase. Biochemistry (2009) 0.97

Structural and functional studies of QdtC: an N-acetyltransferase required for the biosynthesis of dTDP-3-acetamido-3,6-dideoxy-alpha-D-glucose. Biochemistry (2009) 0.97

X-ray crystal structure of the hypothetical phosphotyrosine phosphatase MDP-1 of the haloacid dehalogenase superfamily. Biochemistry (2004) 0.97

The YbgC protein encoded by the ybgC gene of the tol-pal gene cluster of Haemophilus influenzae catalyzes acyl-coenzyme A thioester hydrolysis. FEBS Lett (2002) 0.97

Vesicle-associated membrane protein (VAMP) cleavage by a new metalloprotease from the Brazilian scorpion Tityus serrulatus. J Biol Chem (2009) 0.96

The structure of GDP-4-keto-6-deoxy-D-mannose-3-dehydratase: a unique coenzyme B6-dependent enzyme. Protein Sci (2006) 0.96