Kinetic analysis of the 4-methylideneimidazole-5-one-containing tyrosine aminomutase in enediyne antitumor antibiotic C-1027 biosynthesis.

PubWeight™: 1.16‹?› | Rank: Top 10%

🔗 View Article (PMID 14580219)

Published in Biochemistry on November 04, 2003

Authors

Steven D Christenson1, Weiming Wu, M Ashley Spies, Ben Shen, Michael D Toney

Author Affiliations

1: Department of Chemistry, University of California-Davis, 95616, USA.

Articles citing this

Characterization of the maduropeptin biosynthetic gene cluster from Actinomadura madurae ATCC 39144 supporting a unifying paradigm for enediyne biosynthesis. J Am Chem Soc (2007) 1.69

Biosynthesis of enediyne antitumor antibiotics. Curr Top Med Chem (2008) 1.39

Explorations of catalytic domains in non-ribosomal peptide synthetase enzymology. Nat Prod Rep (2012) 1.23

Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothrix espanaensis. J Bacteriol (2006) 1.19

Biochemical characterization of a prokaryotic phenylalanine ammonia lyase. J Bacteriol (2005) 1.13

A free-standing condensation enzyme catalyzing ester bond formation in C-1027 biosynthesis. Proc Natl Acad Sci U S A (2009) 1.11

Regiospecific chlorination of (S)-beta-tyrosyl-S-carrier protein catalyzed by SgcC3 in the biosynthesis of the enediyne antitumor antibiotic C-1027. J Am Chem Soc (2007) 1.11

Enantiomeric free radicals and enzymatic control of stereochemistry in a radical mechanism: the case of lysine 2,3-aminomutases. Biochemistry (2006) 1.03

Nonproteinogenic amino acid building blocks for nonribosomal peptide and hybrid polyketide scaffolds. Angew Chem Int Ed Engl (2013) 1.02

Biosynthesis of the enediyne antitumor antibiotic C-1027 involves a new branching point in chorismate metabolism. Proc Natl Acad Sci U S A (2008) 1.01

Cloning and sequencing of the kedarcidin biosynthetic gene cluster from Streptoalloteichus sp. ATCC 53650 revealing new insights into biosynthesis of the enediyne family of antitumor antibiotics. Mol Biosyst (2013) 0.96

Highly Active and Specific Tyrosine Ammonia-Lyases from Diverse Origins Enable Enhanced Production of Aromatic Compounds in Bacteria and Saccharomyces cerevisiae. Appl Environ Microbiol (2015) 0.84

Mutational analysis of substrate interactions with the active site of dialkylglycine decarboxylase. Biochemistry (2010) 0.80

Specificity of the ester bond forming condensation enzyme SgcC5 in C-1027 biosynthesis. Org Lett (2012) 0.79

Analysis of catalytic determinants of diaminopimelate and ornithine decarboxylases using alternate substrates. Biochim Biophys Acta (2011) 0.79

Expression and properties of the highly alkalophilic phenylalanine ammonia-lyase of thermophilic Rubrobacter xylanophilus. PLoS One (2014) 0.78

Probing the active site of MIO-dependent aminomutases, key catalysts in the biosynthesis of beta-amino acids incorporated in secondary metabolites. Biopolymers (2010) 0.77

A new member of the 4-methylideneimidazole-5-one-containing aminomutase family from the enediyne kedarcidin biosynthetic pathway. Proc Natl Acad Sci U S A (2013) 0.76

Articles by these authors

Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature. Nat Prod Rep (2013) 5.38

Inhibition of eukaryotic translation elongation by cycloheximide and lactimidomycin. Nat Chem Biol (2010) 3.44

Decoding human cytomegalovirus. Science (2012) 2.98

Global mapping of translation initiation sites in mammalian cells at single-nucleotide resolution. Proc Natl Acad Sci U S A (2012) 2.79

Biosynthesis of the enediyne antitumor antibiotic C-1027. Science (2002) 2.53

A genomics-guided approach for discovering and expressing cryptic metabolic pathways. Nat Biotechnol (2003) 2.41

Type I polyketide synthase requiring a discrete acyltransferase for polyketide biosynthesis. Proc Natl Acad Sci U S A (2003) 2.40

Convenient oxidation of benzylic and allylic halides to aldehydes and ketones. Tetrahedron Lett (2008) 2.13

Thiopeptide biosynthesis featuring ribosomally synthesized precursor peptides and conserved posttranslational modifications. Chem Biol (2009) 1.93

Antitumor antibiotics: bleomycin, enediynes, and mitomycin. Chem Rev (2005) 1.91

Leinamycin biosynthesis revealing unprecedented architectural complexity for a hybrid polyketide synthase and nonribosomal peptide synthetase. Chem Biol (2004) 1.89

Microbial genomics for the improvement of natural product discovery. Curr Opin Microbiol (2006) 1.87

Surprisingly low aqueous acidity at the alpha-positions of pyridiniums and pyrimidinium: the role of solvation. Org Lett (2008) 1.76

Characterization of the maduropeptin biosynthetic gene cluster from Actinomadura madurae ATCC 39144 supporting a unifying paradigm for enediyne biosynthesis. J Am Chem Soc (2007) 1.69

Excellent correlation between substituent constants and pyridinium N-methyl chemical shifts. Tetrahedron Lett (2009) 1.68

The neocarzinostatin biosynthetic gene cluster from Streptomyces carzinostaticus ATCC 15944 involving two iterative type I polyketide synthases. Chem Biol (2005) 1.61

Nosiheptide biosynthesis featuring a unique indole side ring formation on the characteristic thiopeptide framework. ACS Chem Biol (2009) 1.56

Rapid PCR amplification of minimal enediyne polyketide synthase cassettes leads to a predictive familial classification model. Proc Natl Acad Sci U S A (2003) 1.48

Cloning, sequencing, analysis, and heterologous expression of the fredericamycin biosynthetic gene cluster from Streptomyces griseus. J Am Chem Soc (2005) 1.46

A novel 4-methylideneimidazole-5-one-containing tyrosine aminomutase in enediyne antitumor antibiotic C-1027 biosynthesis. J Am Chem Soc (2003) 1.42

Stability of the 6-carbanion of uracil analogues: mechanistic implications for model reactions of orotidine-5'-monophosphate decarboxylase. Org Lett (2006) 1.39

Biosynthesis of enediyne antitumor antibiotics. Curr Top Med Chem (2008) 1.39

Designer enediynes generate DNA breaks, interstrand cross-links, or both, with concomitant changes in the regulation of DNA damage responses. Proc Natl Acad Sci U S A (2007) 1.38

Identification and localization of the gene cluster encoding biosynthesis of the antitumor macrolactam leinamycin in Streptomyces atroolivaceus S-140. J Bacteriol (2002) 1.38

A phosphopantetheinylating polyketide synthase producing a linear polyene to initiate enediyne antitumor antibiotic biosynthesis. Proc Natl Acad Sci U S A (2008) 1.36

Single chemical modifications of the C-1027 enediyne core, a radiomimetic antitumor drug, affect both drug potency and the role of ataxia-telangiectasia mutated in cellular responses to DNA double-strand breaks. Cancer Res (2007) 1.31

Serine racemase modulates intracellular D-serine levels through an alpha,beta-elimination activity. J Biol Chem (2004) 1.26

Iso-migrastatin congeners from Streptomyces platensis and generation of a glutarimide polyketide library featuring the dorrigocin, lactimidomycin, migrastatin, and NK30424 scaffolds. J Am Chem Soc (2005) 1.25

Migrastatin and dorrigocins are shunt metabolites of iso-migrastatin. J Am Chem Soc (2005) 1.24

C-O bond formation by polyketide synthases. Science (2002) 1.23

Engineered Streptomyces platensis strains that overproduce antibiotics platensimycin and platencin. Antimicrob Agents Chemother (2009) 1.23

Accelerated decarboxylation of 1,3-dimethylorotic acid in ionic liquid. Bioorg Chem (2006) 1.22

The role of tandem acyl carrier protein domains in polyunsaturated fatty acid biosynthesis. J Am Chem Soc (2008) 1.21

The tallysomycin biosynthetic gene cluster from Streptoalloteichus hindustanus E465-94 ATCC 31158 unveiling new insights into the biosynthesis of the bleomycin family of antitumor antibiotics. Mol Biosyst (2006) 1.20

Improvement of secondary metabolite production in Streptomyces by manipulating pathway regulation. Appl Microbiol Biotechnol (2010) 1.19

Bacterial diterpene synthases: new opportunities for mechanistic enzymology and engineered biosynthesis. Curr Opin Chem Biol (2012) 1.15

Oxidase domains in epothilone and bleomycin biosynthesis: thiazoline to thiazole oxidation during chain elongation. Biochemistry (2003) 1.15

Carbanions from decarboxylation of orotate analogs: stability and mechanistic implications. Bioorg Chem (2007) 1.15

Dedicated ent-kaurene and ent-atiserene synthases for platensimycin and platencin biosynthesis. Proc Natl Acad Sci U S A (2011) 1.15

Conservation of mechanism in three chorismate-utilizing enzymes. J Am Chem Soc (2004) 1.14

Biosynthesis of the beta-amino acid moiety of the enediyne antitumor antibiotic C-1027 featuring beta-amino acyl-S-carrier protein intermediates. J Am Chem Soc (2005) 1.14

Modest catalysis of the decarboxylation of orotate by hydrogen bonding: a theoretical model for orotidine- 5' -monophosphate decarboxylase. Bioorg Chem (2004) 1.13

The bifunctional glyceryl transferase/phosphatase OzmB belonging to the HAD superfamily that diverts 1,3-bisphosphoglycerate into polyketide biosynthesis. J Am Chem Soc (2006) 1.13

Polyketide synthase chemistry does not direct biosynthetic divergence between 9- and 10-membered enediynes. Proc Natl Acad Sci U S A (2010) 1.13

Tirandamycins from Streptomyces sp. 17944 inhibiting the parasite Brugia malayi asparagine tRNA synthetase. Org Lett (2011) 1.12

Transcriptome analysis of rice root heterosis by RNA-Seq. BMC Genomics (2013) 1.12

Polyketide chain skipping mechanism in the biosynthesis of the hybrid nonribosomal peptide-polyketide antitumor antibiotic leinamycin in Streptomyces atroolivaceus S-140. J Nat Prod (2006) 1.11

A free-standing condensation enzyme catalyzing ester bond formation in C-1027 biosynthesis. Proc Natl Acad Sci U S A (2009) 1.11

Engineered production of iso-migrastatin in heterologous Streptomyces hosts. Bioorg Med Chem (2008) 1.11

Regiospecific chlorination of (S)-beta-tyrosyl-S-carrier protein catalyzed by SgcC3 in the biosynthesis of the enediyne antitumor antibiotic C-1027. J Am Chem Soc (2007) 1.11

Expression of biosynthetic gene clusters in heterologous hosts for natural product production and combinatorial biosynthesis. Expert Opin Drug Discov (2006) 1.10

Crystal structures of unbound and aminooxyacetate-bound Escherichia coli gamma-aminobutyrate aminotransferase. Biochemistry (2004) 1.10

Radical-mediated enzymatic carbon chain fragmentation-recombination. Nat Chem Biol (2011) 1.09

Biochemical analysis of a beta-D-xylosidase and a bifunctional xylanase-ferulic acid esterase from a xylanolytic gene cluster in Prevotella ruminicola 23. J Bacteriol (2009) 1.08

Evaluation of new migrastatin and dorrigocin congeners unveils cell migration inhibitors with dramatically improved potency. Bioorg Med Chem Lett (2008) 1.08

iso-Migrastatin, migrastatin, and dorrigocin production in Streptomyces platensis NRRL 18993 is governed by a single biosynthetic machinery featuring an acyltransferase-less type I polyketide synthase. J Biol Chem (2009) 1.08

The structure of L-tyrosine 2,3-aminomutase from the C-1027 enediyne antitumor antibiotic biosynthetic pathway. Biochemistry (2007) 1.08

Aminophosphonate inhibitors of dialkylglycine decarboxylase: structural basis for slow binding inhibition. Biochemistry (2002) 1.07

Identification and utility of FdmR1 as a Streptomyces antibiotic regulatory protein activator for fredericamycin production in Streptomyces griseus ATCC 49344 and heterologous hosts. J Bacteriol (2008) 1.07

Accelerated hydrolysis of α-halo and α-cyano pyridinium relative to uracil derivatives: a model for ODCase-catalyzed hydrolysis of 6-cyanoUMP. Tetrahedron Lett (2011) 1.06

Characterization of intact antibody-drug conjugates from plasma/serum in vivo by affinity capture capillary liquid chromatography-mass spectrometry. Anal Biochem (2011) 1.06

Signal mimics derived from a metagenomic analysis of the gypsy moth gut microbiota. Appl Environ Microbiol (2007) 1.06

Kinetic and crystallographic analysis of active site mutants of Escherichia coli gamma-aminobutyrate aminotransferase. Biochemistry (2005) 1.05

Tautomycetin and tautomycin suppress the growth of medullary thyroid cancer cells via inhibition of glycogen synthase kinase-3beta. Mol Cancer Ther (2009) 1.05

Engineering of Streptomyces platensis MA7339 for overproduction of platencin and congeners. Org Lett (2010) 1.05

Lactimidomycin, iso-migrastatin and related glutarimide-containing 12-membered macrolides are extremely potent inhibitors of cell migration. J Am Chem Soc (2009) 1.04

Conversion of (2S)-arginine to (2S,3R)-capreomycidine by VioC and VioD from the viomycin biosynthetic pathway of Streptomyces sp. strain ATCC11861. Chembiochem (2004) 1.04

Strain prioritization for natural product discovery by a high-throughput real-time PCR method. J Nat Prod (2014) 1.03

Alanine racemase free energy profiles from global analyses of progress curves. J Am Chem Soc (2004) 1.03

Coupling of functional hydrogen bonds in pyridoxal-5'-phosphate-enzyme model systems observed by solid-state NMR spectroscopy. J Am Chem Soc (2007) 1.03

The biosynthetic gene cluster of zorbamycin, a member of the bleomycin family of antitumor antibiotics, from Streptomyces flavoviridis ATCC 21892. Mol Biosyst (2008) 1.03

Chain initiation in the leinamycin-producing hybrid nonribosomal peptide/polyketide synthetase from Streptomyces atroolivaceus S-140. Discrete, monofunctional adenylation enzyme and peptidyl carrier protein that directly load D-alanine. J Biol Chem (2007) 1.03

Characterization of the tautomycetin biosynthetic gene cluster from Streptomyces griseochromogenes provides new insight into dialkylmaleic anhydride biosynthesis. J Nat Prod (2009) 1.03

Biosynthetic potential-based strain prioritization for natural product discovery: a showcase for diterpenoid-producing actinomycetes. J Nat Prod (2014) 1.02

Molecular basis for the selectivity and specificity of ligand recognition by the family 16 carbohydrate-binding modules from Thermoanaerobacterium polysaccharolyticum ManA. J Biol Chem (2007) 1.02

C-1027, a radiomimetic enediyne anticancer drug, preferentially targets hypoxic cells. Cancer Res (2009) 1.02

New lactimidomycin congeners shed insight into lactimidomycin biosynthesis in Streptomyces amphibiosporus. Org Lett (2007) 1.02

1,4,7-Trimethyloxatriquinane: S(N)2 reaction at tertiary carbon. J Am Chem Soc (2010) 1.01

Biosynthesis of the enediyne antitumor antibiotic C-1027 involves a new branching point in chorismate metabolism. Proc Natl Acad Sci U S A (2008) 1.01

Actinopolysporins A-C and tubercidin as a Pdcd4 stabilizer from the halophilic actinomycete Actinopolyspora erythraea YIM 90600. J Nat Prod (2011) 1.00

Bafilomycins produced by an endophytic actinomycete Streptomyces sp. YIM56209. J Antibiot (Tokyo) (2010) 1.00

Advances in polyketide synthase structure and function. Curr Opin Drug Discov Devel (2008) 1.00

Substrate specificity of the adenylation enzyme SgcC1 involved in the biosynthesis of the enediyne antitumor antibiotic C-1027. J Biol Chem (2006) 1.00

NMR studies of coupled low- and high-barrier hydrogen bonds in pyridoxal-5'-phosphate model systems in polar solution. J Am Chem Soc (2007) 1.00

Hybrid Steered Molecular Dynamics-Docking: An Efficient Solution to the Problem of Ranking Inhibitor Affinities Against a Flexible Drug Target. Mol Inform (2011) 1.00

Type I polyketide synthases that require discrete acyltransferases. Methods Enzymol (2009) 0.99

Identification and characterization of a novel estrogenic ligand actinopolymorphol A. Biochem Pharmacol (2010) 0.99

BlmIII and BlmIV nonribosomal peptide synthetase-catalyzed biosynthesis of the bleomycin bithiazole moiety involving both in cis and in trans aminoacylation. 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

SHP2 is a target of the immunosuppressant tautomycetin. Chem Biol (2011) 0.98

Characterization of the two-component, FAD-dependent monooxygenase SgcC that requires carrier protein-tethered substrates for the biosynthesis of the enediyne antitumor antibiotic C-1027. J Am Chem Soc (2008) 0.97

Biliverdin reduction by cyanobacterial phycocyanobilin:ferredoxin oxidoreductase (PcyA) proceeds via linear tetrapyrrole radical intermediates. J Am Chem Soc (2004) 0.97

Bifunctional acyltransferase/decarboxylase LnmK as the missing link for beta-alkylation in polyketide biosynthesis. J Am Chem Soc (2009) 0.97

Multiple hydrogen kinetic isotope effects for enzymes catalyzing exchange with solvent: application to alanine racemase. Biochemistry (2003) 0.96

In vivo investigation of the roles of FdmM and FdmM1 in fredericamycin biosynthesis unveiling a new family of oxygenases. J Biol Chem (2009) 0.96

Comparative analysis of the biosynthetic gene clusters and pathways for three structurally related antitumor antibiotics: bleomycin, tallysomycin, and zorbamycin. J Nat Prod (2011) 0.96

Characterization of the tautomycin biosynthetic gene cluster from Streptomyces spiroverticillatus unveiling new insights into dialkylmaleic anhydride and polyketide biosynthesis. J Biol Chem (2008) 0.96

Cloning and sequencing of the kedarcidin biosynthetic gene cluster from Streptoalloteichus sp. ATCC 53650 revealing new insights into biosynthesis of the enediyne family of antitumor antibiotics. Mol Biosyst (2013) 0.96