Structural analysis of an open active site conformation of nonheme iron halogenase CytC3.

PubWeight™: 1.11‹?› | Rank: Top 10%

🔗 View Article (PMC 2663892)

Published in J Am Chem Soc on April 08, 2009

Authors

Cintyu Wong1, Danica Galonić Fujimori, Christopher T Walsh, Catherine L Drennan

Author Affiliations

1: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, Massachusetts 02139, USA.

Articles citing this

Prolyl 4-hydroxylase. Crit Rev Biochem Mol Biol (2010) 1.99

Role of the secondary coordination sphere in metal-mediated dioxygen activation. Inorg Chem (2010) 1.42

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

Conformational switch triggered by alpha-ketoglutarate in a halogenase of curacin A biosynthesis. Proc Natl Acad Sci U S A (2010) 1.08

Kinetic and CD/MCD spectroscopic studies of the atypical, three-His-ligated, non-heme Fe2+ center in diketone dioxygenase: the role of hydrophilic outer shell residues in catalysis. Biochemistry (2010) 0.95

First-principles study of non-heme Fe(II) halogenase SyrB2 reactivity. J Am Chem Soc (2009) 0.91

Catalytic Mechanisms of Fe(II)- and 2-Oxoglutarate-dependent Oxygenases. J Biol Chem (2015) 0.90

Substrate placement influences reactivity in non-heme Fe(II) halogenases and hydroxylases. J Biol Chem (2013) 0.89

Insights from the sea: structural biology of marine polyketide synthases. Nat Prod Rep (2012) 0.83

X-ray absorption spectroscopy structural investigation of early intermediates in the mechanism of DNA repair by human ABH2. Biochemistry (2011) 0.83

Oxidative cyclizations in orthosomycin biosynthesis expand the known chemistry of an oxygenase superfamily. Proc Natl Acad Sci U S A (2015) 0.82

Ab initio structural modeling of and experimental validation for Chlamydia trachomatis protein CT296 reveal structural similarity to Fe(II) 2-oxoglutarate-dependent enzymes. J Bacteriol (2011) 0.82

Protein dynamics control the progression and efficiency of the catalytic reaction cycle of the Escherichia coli DNA-repair enzyme AlkB. J Biol Chem (2014) 0.81

Lessons from Nature: A Bio-Inspired Approach to Molecular Design. Biochemistry (2015) 0.81

Stringency of the 2-His-1-Asp active-site motif in prolyl 4-hydroxylase. PLoS One (2009) 0.81

Crystal structure of the ectoine hydroxylase, a snapshot of the active site. J Biol Chem (2014) 0.80

Structural basis for halogenation by iron- and 2-oxo-glutarate-dependent enzyme WelO5. Nat Chem Biol (2016) 0.79

Structure and function of atypically coordinated enzymatic mononuclear non-heme-Fe(II) centers. Coord Chem Rev (2013) 0.79

The role of chloride in the mechanism of O(2) activation at the mononuclear nonheme Fe(II) center of the halogenase HctB. J Am Chem Soc (2014) 0.78

Distribution and prediction of catalytic domains in 2-oxoglutarate dependent dioxygenases. BMC Res Notes (2012) 0.78

Dioxygen activation by nonheme iron enzymes with the 2-His-1-carboxylate facial triad that generate high-valent oxoiron oxidants. J Biol Inorg Chem (2017) 0.77

Independent Evolution of Six Families of Halogenating Enzymes. PLoS One (2016) 0.76

Insights into enzymatic halogenation from computational studies. Front Chem (2014) 0.75

Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C-H activation. J Biol Inorg Chem (2016) 0.75

Regioselectivity of substrate hydroxylation versus halogenation by a nonheme iron(IV)-oxo complex: possibility of rearrangement pathways. J Biol Inorg Chem (2012) 0.75

Articles cited by this

Coot: model-building tools for molecular graphics. Acta Crystallogr D Biol Crystallogr (2004) 227.01

Crystallography & NMR system: A new software suite for macromolecular structure determination. Acta Crystallogr D Biol Crystallogr (1998) 169.28

Multiple sequence alignment with the Clustal series of programs. Nucleic Acids Res (2003) 38.75

XtalView/Xfit--A versatile program for manipulating atomic coordinates and electron density. J Struct Biol (1999) 17.84

Pushing the boundaries of molecular replacement with maximum likelihood. Acta Crystallogr D Biol Crystallogr (2001) 15.88

X-ray structure of a ClC chloride channel at 3.0 A reveals the molecular basis of anion selectivity. Nature (2002) 9.96

Molecular mechanisms that confer antibacterial drug resistance. Nature (2000) 5.88

Developing a new resource for drug discovery: marine actinomycete bacteria. Nat Chem Biol (2006) 5.78

FeII/alpha-ketoglutarate-dependent hydroxylases and related enzymes. Crit Rev Biochem Mol Biol (2004) 5.61

Structure of the light-driven chloride pump halorhodopsin at 1.8 A resolution. Science (2000) 3.93

Pseudomonas syringae phytotoxins: mode of action, regulation, and biosynthesis by peptide and polyketide synthetases. Microbiol Mol Biol Rev (1999) 3.83

The 2-His-1-carboxylate facial triad--an emerging structural motif in mononuclear non-heme iron(II) enzymes. Eur J Biochem (1997) 3.36

Two interconverting Fe(IV) intermediates in aliphatic chlorination by the halogenase CytC3. Nat Chem Biol (2007) 3.33

Structural studies on 2-oxoglutarate oxygenases and related double-stranded beta-helix fold proteins. J Inorg Biochem (2006) 3.08

Cupins: the most functionally diverse protein superfamily? Phytochemistry (2004) 3.05

Crystal structure of the non-haem iron halogenase SyrB2 in syringomycin biosynthesis. Nature (2006) 2.52

SyrB2 in syringomycin E biosynthesis is a nonheme FeII alpha-ketoglutarate- and O2-dependent halogenase. Proc Natl Acad Sci U S A (2005) 2.12

Evidence for hydrogen abstraction from C1 of taurine by the high-spin Fe(IV) intermediate detected during oxygen activation by taurine:alpha-ketoglutarate dioxygenase (TauD). J Am Chem Soc (2003) 2.11

Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete. Chem Biol (2006) 1.25

A modular approach toward regulating the secondary coordination sphere of metal ions: differential dioxygen activation assisted by intramolecular hydrogen bonds. J Am Chem Soc (2006) 1.14

Variations of the 2-His-1-carboxylate theme in mononuclear non-heme FeII oxygenases. Chembiochem (2006) 1.11

Dichlorination and bromination of a threonyl-S-carrier protein by the non-heme Fe(II) halogenase SyrB2. Chembiochem (2006) 1.01

Metal ligand substitution and evidence for quinone formation in taurine/alpha-ketoglutarate dioxygenase. J Inorg Biochem (2007) 0.99

Relevance of chlorine-substituent for the antifungal activity of syringomycin and syringotoxin, metabolites of the phytopathogenic bacterium Pseudomonas syringae pv. syringae. Experientia (1994) 0.85

Iron(II) complexes of sterically bulky alpha-ketocarboxylates. structural models for alpha-ketoacid-dependent nonheme iron halogenases. Inorg Chem (2008) 0.82

Biological chemistry: just add chlorine. Nature (2005) 0.79

Articles by these authors

Assembly-line enzymology for polyketide and nonribosomal Peptide antibiotics: logic, machinery, and mechanisms. Chem Rev (2006) 7.69

Antibiotics for emerging pathogens. Science (2009) 7.39

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

Genetics and assembly line enzymology of siderophore biosynthesis in bacteria. Microbiol Mol Biol Rev (2002) 5.12

Non-heme Fe(IV)-oxo intermediates. Acc Chem Res (2007) 3.55

Two interconverting Fe(IV) intermediates in aliphatic chlorination by the halogenase CytC3. Nat Chem Biol (2007) 3.33

A Ni-Fe-Cu center in a bifunctional carbon monoxide dehydrogenase/acetyl-CoA synthase. Science (2002) 2.98

Cryptic chlorination by a non-haem iron enzyme during cyclopropyl amino acid biosynthesis. Nature (2005) 2.91

New antibiotics from bacterial natural products. Nat Biotechnol (2006) 2.72

The evolution of gene collectives: How natural selection drives chemical innovation. Proc Natl Acad Sci U S A (2008) 2.71

Crystal structure of biotin synthase, an S-adenosylmethionine-dependent radical enzyme. Science (2004) 2.65

The pathogen-associated iroA gene cluster mediates bacterial evasion of lipocalin 2. Proc Natl Acad Sci U S A (2006) 2.63

BluB cannibalizes flavin to form the lower ligand of vitamin B12. Nature (2007) 2.53

Crystal structure of the non-haem iron halogenase SyrB2 in syringomycin biosynthesis. Nature (2006) 2.52

How pathogenic bacteria evade mammalian sabotage in the battle for iron. Nat Chem Biol (2006) 2.45

Dynamic thiolation-thioesterase structure of a non-ribosomal peptide synthetase. Nature (2008) 2.39

The crystal structure of class II ribonucleotide reductase reveals how an allosterically regulated monomer mimics a dimer. Nat Struct Biol (2002) 2.28

Nature's inventory of halogenation catalysts: oxidative strategies predominate. Chem Rev (2006) 2.24

Thirteen posttranslational modifications convert a 14-residue peptide into the antibiotic thiocillin. Proc Natl Acad Sci U S A (2009) 2.22

Facile detection of acyl and peptidyl intermediates on thiotemplate carrier domains via phosphopantetheinyl elimination reactions during tandem mass spectrometry. Biochemistry (2006) 2.22

The identification of bacillaene, the product of the PksX megacomplex in Bacillus subtilis. Proc Natl Acad Sci U S A (2007) 2.22

SyrB2 in syringomycin E biosynthesis is a nonheme FeII alpha-ketoglutarate- and O2-dependent halogenase. Proc Natl Acad Sci U S A (2005) 2.12

Halogenation strategies in natural product biosynthesis. Chem Biol (2008) 2.08

Selective translocation of intracellular Smoothened to the primary cilium in response to Hedgehog pathway modulation. Proc Natl Acad Sci U S A (2009) 2.04

Genetically encoded short peptide tag for versatile protein labeling by Sfp phosphopantetheinyl transferase. Proc Natl Acad Sci U S A (2005) 2.03

Vancomycin assembly: nature's way. Angew Chem Int Ed Engl (2003) 1.99

AlkB reverses etheno DNA lesions caused by lipid oxidation in vitro and in vivo. Nat Struct Mol Biol (2005) 1.96

Genetically encoded short peptide tags for orthogonal protein labeling by Sfp and AcpS phosphopantetheinyl transferases. ACS Chem Biol (2007) 1.94

Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides. Chem Biol (2002) 1.90

A singular enzymatic megacomplex from Bacillus subtilis. Proc Natl Acad Sci U S A (2006) 1.89

Labeling proteins with small molecules by site-specific posttranslational modification. J Am Chem Soc (2004) 1.84

The structure of VibH represents nonribosomal peptide synthetase condensation, cyclization and epimerization domains. Nat Struct Biol (2002) 1.82

Robust in vitro activity of RebF and RebH, a two-component reductase/halogenase, generating 7-chlorotryptophan during rebeccamycin biosynthesis. Proc Natl Acad Sci U S A (2005) 1.82

Site-specific protein labeling by Sfp phosphopantetheinyl transferase. Nat Protoc (2006) 1.82

Convergence of isoprene and polyketide biosynthetic machinery: isoprenyl-S-carrier proteins in the pksX pathway of Bacillus subtilis. Proc Natl Acad Sci U S A (2006) 1.80

Structural insights into radical generation by the radical SAM superfamily. Chem Rev (2011) 1.77

Yersiniabactin synthetase: a four-protein assembly line producing the nonribosomal peptide/polyketide hybrid siderophore of Yersinia pestis. Chem Biol (2002) 1.75

A transglutaminase homologue as a condensation catalyst in antibiotic assembly lines. Nature (2007) 1.74

Crystal structure of the nickel-responsive transcription factor NikR. Nat Struct Biol (2003) 1.74

Structural basis for glycyl radical formation by pyruvate formate-lyase activating enzyme. Proc Natl Acad Sci U S A (2008) 1.71

Chlorination by a long-lived intermediate in the mechanism of flavin-dependent halogenases. Biochemistry (2007) 1.69

Substrate-triggered formation and remarkable stability of the C-H bond-cleaving chloroferryl intermediate in the aliphatic halogenase, SyrB2. Biochemistry (2009) 1.69

Terrequinone A biosynthesis through L-tryptophan oxidation, dimerization and bisprenylation. Nat Chem Biol (2007) 1.68

Structural basis for the selectivity of the external thioesterase of the surfactin synthetase. Nature (2008) 1.66

Mass spectrometric interrogation of thioester-bound intermediates in the initial stages of epothilone biosynthesis. Chem Biol (2004) 1.61

RlmN and Cfr are radical SAM enzymes involved in methylation of ribosomal RNA. J Am Chem Soc (2010) 1.60

Structural insight into antibiotic fosfomycin biosynthesis by a mononuclear iron enzyme. Nature (2005) 1.59

The genetic and molecular basis for sunscreen biosynthesis in cyanobacteria. Science (2010) 1.59

Dichlorination of a pyrrolyl-S-carrier protein by FADH2-dependent halogenase PltA during pyoluteorin biosynthesis. Proc Natl Acad Sci U S A (2005) 1.58

Assembling the glycopeptide antibiotic scaffold: The biosynthesis of A47934 from Streptomyces toyocaensis NRRL15009. Proc Natl Acad Sci U S A (2002) 1.57

Total biosynthesis: in vitro reconstitution of polyketide and nonribosomal peptide pathways. Nat Prod Rep (2008) 1.56

An unusual role for a mobile flavin in StaC-like indolocarbazole biosynthetic enzymes. Chem Biol (2012) 1.56

Codon randomization for rapid exploration of chemical space in thiopeptide antibiotic variants. Chem Biol (2012) 1.55

Ribbon-helix-helix transcription factors: variations on a theme. Nat Rev Microbiol (2007) 1.54

Halogenation of unactivated carbon centers in natural product biosynthesis: trichlorination of leucine during barbamide biosynthesis. J Am Chem Soc (2006) 1.53

In vitro characterization of IroB, a pathogen-associated C-glycosyltransferase. Proc Natl Acad Sci U S A (2004) 1.52

Manipulation of thiocillin variants by prepeptide gene replacement: structure, conformation, and activity of heterocycle substitution mutants. J Am Chem Soc (2010) 1.51

CloQ, a prenyltransferase involved in clorobiocin biosynthesis. Proc Natl Acad Sci U S A (2003) 1.50

Evidence for a monomeric structure of nonribosomal Peptide synthetases. Chem Biol (2002) 1.49

Structural basis for the cyclization of the lipopeptide antibiotic surfactin by the thioesterase domain SrfTE. Structure (2002) 1.49

Cyclopiazonic acid biosynthesis in Aspergillus sp.: characterization of a reductase-like R* domain in cyclopiazonate synthetase that forms and releases cyclo-acetoacetyl-L-tryptophan. Biochemistry (2009) 1.48

Competencies: a cure for pre-med curriculum. Science (2011) 1.47

Substrate positioning controls the partition between halogenation and hydroxylation in the aliphatic halogenase, SyrB2. Proc Natl Acad Sci U S A (2009) 1.47

In vitro characterization of salmochelin and enterobactin trilactone hydrolases IroD, IroE, and Fes. J Am Chem Soc (2005) 1.47

Crystal structure of vancosaminyltransferase GtfD from the vancomycin biosynthetic pathway: interactions with acceptor and nucleotide ligands. Biochemistry (2004) 1.45

Type II thioesterase restores activity of a NRPS module stalled with an aminoacyl-S-enzyme that cannot be elongated. Chembiochem (2004) 1.45

Structure of the TDP-epi-vancosaminyltransferase GtfA from the chloroeremomycin biosynthetic pathway. Proc Natl Acad Sci U S A (2003) 1.45

Non-uniformly sampled double-TROSY hNcaNH experiments for NMR sequential assignments of large proteins. J Am Chem Soc (2006) 1.45

Characterization of the cereulide NRPS alpha-hydroxy acid specifying modules: activation of alpha-keto acids and chiral reduction on the assembly line. J Am Chem Soc (2006) 1.44

Macrolactamization of glycosylated peptide thioesters by the thioesterase domain of tyrocidine synthetase. Chem Biol (2004) 1.44

Conversion of L-proline to pyrrolyl-2-carboxyl-S-PCP during undecylprodigiosin and pyoluteorin biosynthesis. Chem Biol (2002) 1.44

GliP, a multimodular nonribosomal peptide synthetase in Aspergillus fumigatus, makes the diketopiperazine scaffold of gliotoxin. Biochemistry (2006) 1.42

Identification of the biosynthetic gene cluster for the pacidamycin group of peptidyl nucleoside antibiotics. Proc Natl Acad Sci U S A (2010) 1.42

Fungal indole alkaloid biosynthesis: genetic and biochemical investigation of the tryptoquialanine pathway in Penicillium aethiopicum. J Am Chem Soc (2011) 1.41

Maturation of an Escherichia coli ribosomal peptide antibiotic by ATP-consuming N-P bond formation in microcin C7. J Am Chem Soc (2008) 1.41

Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin. J Am Chem Soc (2008) 1.41

Formation of beta-hydroxy histidine in the biosynthesis of nikkomycin antibiotics. Chem Biol (2002) 1.41

CD and MCD of CytC3 and taurine dioxygenase: role of the facial triad in alpha-KG-dependent oxygenases. J Am Chem Soc (2007) 1.41

Spectroscopic evidence for a high-spin Br-Fe(IV)-oxo intermediate in the alpha-ketoglutarate-dependent halogenase CytC3 from Streptomyces. J Am Chem Soc (2007) 1.40

Structural insights into nonribosomal peptide enzymatic assembly lines. Nat Prod Rep (2009) 1.40

Biomimetic synthesis and optimization of cyclic peptide antibiotics. Nature (2002) 1.39

Staurosporine and rebeccamycin aglycones are assembled by the oxidative action of StaP, StaC, and RebC on chromopyrrolic acid. J Am Chem Soc (2006) 1.39

How the MccB bacterial ancestor of ubiquitin E1 initiates biosynthesis of the microcin C7 antibiotic. EMBO J (2009) 1.38

Creating an interdisciplinary introductory chemistry course without time-intensive curriculum changes. ACS Chem Biol (2009) 1.38

Enzymatic processing of fumiquinazoline F: a tandem oxidative-acylation strategy for the generation of multicyclic scaffolds in fungal indole alkaloid biosynthesis. Biochemistry (2010) 1.33

In vitro biosynthesis of violacein from L-tryptophan by the enzymes VioA-E from Chromobacterium violaceum. Biochemistry (2006) 1.32

Genetic interception and structural characterization of thiopeptide cyclization precursors from Bacillus cereus. J Am Chem Soc (2010) 1.31

Drugs as materials: valuing physical form in drug discovery. Nat Rev Drug Discov (2004) 1.31

Cloning and characterization of the biosynthetic gene cluster for kutznerides. Proc Natl Acad Sci U S A (2007) 1.31

Carrier protein structure and recognition in polyketide and nonribosomal peptide biosynthesis. Biochemistry (2006) 1.29

Generation of thiocillin variants by prepeptide gene replacement and in vivo processing by Bacillus cereus. J Am Chem Soc (2009) 1.28

A protein interaction surface in nonribosomal peptide synthesis mapped by combinatorial mutagenesis and selection. Proc Natl Acad Sci U S A (2006) 1.28

Flavin redox chemistry precedes substrate chlorination during the reaction of the flavin-dependent halogenase RebH. Biochemistry (2006) 1.28

NikR-operator complex structure and the mechanism of repressor activation by metal ions. Proc Natl Acad Sci U S A (2006) 1.26

Anthranilate-activating modules from fungal nonribosomal peptide assembly lines. Biochemistry (2010) 1.25