Two Distinct Mechanisms for C-C Desaturation by Iron(II)- and 2-(Oxo)glutarate-Dependent Oxygenases: Importance of α-Heteroatom Assistance.

No abstract is available for this paper.

• Publication year

  2018

• Venue

  Journal of the American Chemical Society

• Publication date

  2018-04-30

• Fields of study

  Biology, Medicine, Chemistry

• Identifiers
  DOI 10.1021/jacs.8b01933PMID 29708749PMCID PMC5999578
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• A Six-Oxidase Cascade for Tandem C-H Bond Activation Revealed by Reconstitution of Bicyclomycin Biosynthesis.

  2018cited by this paper
• Frontier Molecular Orbital Contributions to Chlorination versus Hydroxylation Selectivity in the Non-Heme Iron Halogenase SyrB2.

  2017cited by this paper
• Vanadyl as a Stable Structural Mimic of Reactive Ferryl Intermediates in Mononuclear Nonheme-Iron Enzymes.

  2017cited by this paper
• Visualizing the Reaction Cycle in an Iron(II)- and 2-(Oxo)-glutarate-Dependent Hydroxylase.

  2017cited by this paper
• Discovery of Key Dioxygenases that Diverged the Paraherquonin and Acetoxydehydroaustin Pathways in Penicillium brasilianum.

  2016cited by this paper
• Structural basis for halogenation by iron- and 2-oxo-glutarate-dependent enzyme WelO5

  2016cited by this paper
• Electronic Structure of the Ferryl Intermediate in the α-Ketoglutarate Dependent Non-Heme Iron Halogenase SyrB2: Contributions to H Atom Abstraction Reactivity.

  2016cited by this paper
• Structure of the Dioxygenase AsqJ: Mechanistic Insights into a One-Pot Multistep Quinolone Antibiotic Biosynthesis.

  2016cited by this paper
• Catalytic Mechanisms of Fe(II)- and 2-Oxoglutarate-dependent Oxygenases*

  2015cited by this paper
• Experimental Correlation of Substrate Position with Reaction Outcome in the Aliphatic Halogenase, SyrB2.

  2015cited by this paper
• Assembly of the unusual oxacycles in the orthosomycin antibiotics

  2015cited by this paper
• Biosynthesis of streptolidine involved two unexpected intermediates produced by a dihydroxylase and a cyclase through unusual mechanisms.

  2014cited by this paper
• Non-heme dioxygenase catalyzes atypical oxidations of 6,7-bicyclic systems to form the 6,6-quinolone core of viridicatin-type fungal alkaloids.

  2014cited by this paper
• Direct nitration and azidation of aliphatic carbons by an iron-dependent halogenase

  2014cited by this paper
• Core assembly mechanism of quinocarcin/SF-1739: bimodular complex nonribosomal peptide synthetases for sequential mannich-type reactions.

  2013cited by this paper
• Elucidation of the Fe(iv)=O intermediate in the catalytic cycle of the halogenase SyrB2

  2013cited by this paper
• Measuring the orientation of taurine in the active site of the non-heme Fe(II)/α-ketoglutarate-dependent taurine hydroxylase (TauD) using electron spin echo envelope modulation (ESEEM) spectroscopy.

  2013cited by this paper
• Electronic structure analysis of the oxygen-activation mechanism by Fe(II)- and α-ketoglutarate (αKG)-dependent dioxygenases.

  2012cited by this paper
• Role of the jelly-roll fold in substrate binding by 2-oxoglutarate oxygenases.

  2012cited by this paper
• Cytochrome P450 Compound I: Capture, Characterization, and C-H Bond Activation Kinetics

  2010cited by this paper
• Substrate-triggered formation and remarkable stability of the C-H bond-cleaving chloroferryl intermediate in the aliphatic halogenase, SyrB2.

  2009cited by this paper
• Substrate positioning controls the partition between halogenation and hydroxylation in the aliphatic halogenase, SyrB2

  2009cited by this paper
• Desaturases: Emerging Models for Understanding Functional Diversification of Diiron-containing Enzymes*

  2009cited by this paper
• Structural basis for the erythro‐stereospecificity of the l‐arginine oxygenase VioC in viomycin biosynthesis

  2009cited by this paper
• Two interconverting Fe(IV) intermediates in aliphatic chlorination by the halogenase CytC3.

  2007cited by this paper
• Spectroscopic evidence for a high-spin Br-Fe(IV)-oxo intermediate in the alpha-ketoglutarate-dependent halogenase CytC3 from Streptomyces.

  2007cited by this paper
• Mechanistic and structural basis of stereospecific Cbeta-hydroxylation in calcium-dependent antibiotic, a daptomycin-type lipopeptide.

  2007cited by this paper
• Non-heme Fe(IV)-oxo intermediates.

  2007cited by this paper
• Probing the iron-substrate orientation for taurine/alpha-ketoglutarate dioxygenase using deuterium electron spin echo envelope modulation spectroscopy.

  2007cited by this paper
• VTVH-MCD and DFT studies of thiolate bonding to [FeNO]7/[FeO2]8 complexes of isopenicillin N synthase: substrate determination of oxidase versus oxygenase activity in nonheme Fe enzymes.

  2007cited by this paper
• Epimerization and desaturation by carbapenem synthase (CarC). A hybrid DFT study

  2006cited by this paper
• Crystal structure of the non-haem iron halogenase SyrB2 in syringomycin biosynthesis

  2006cited by this paper
• Direct spectroscopic detection of a C-H-cleaving high-spin Fe(IV) complex in a prolyl-4-hydroxylase

  2006cited by this paper
• Stalking intermediates in oxygen activation by iron enzymes: motivation and method.

  2006cited by this paper
• Structure and chemistry of cytochrome P450.

  2005cited by this paper
• Kinetic dissection of the catalytic mechanism of taurine:alpha-ketoglutarate dioxygenase (TauD) from Escherichia coli.

  2005cited by this paper
• Oxoiron(IV) in Chloroperoxidase Compound II Is Basic: Implications for P450 Chemistry

  2004cited by this paper
• Conversion of (2S)‐Arginine to (2S,3R)‐Capreomycidine by VioC and VioD from the Viomycin Biosynthetic Pathway of Streptomyces sp. Strain ATCC11861

  2004cited by this paper
• The unusual bifunctional catalysis of epimerization and desaturation by carbapenem synthase.

  2004cited by this paper
• VioC is a Non‐Heme Iron, α‐Ketoglutarate‐Dependent Oxygenase that Catalyzes the Formation of 3S‐Hydroxy‐L‐Arginine during Viomycin Biosynthesis

  2004cited by this paper
• EXAFS spectroscopic evidence for an Fe=O unit in the Fe(IV) intermediate observed during oxygen activation by taurine:alpha-ketoglutarate dioxygenase.

  2004cited by this paper
• 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).

  2003cited by this paper
• The first direct characterization of a high-valent iron intermediate in the reaction of an alpha-ketoglutarate-dependent dioxygenase: a high-spin FeIV complex in taurine/alpha-ketoglutarate dioxygenase (TauD) from Escherichia coli.

  2003cited by this paper
• Crystal structure of a clavaminate synthase–Fe(II)–2‐oxoglutarate–substrate–NO complex: evidence for metal centred rearrangements

  2002cited by this paper
• Spectroscopic studies of substrate interactions with clavaminate synthase 2, a multifunctional alpha-KG-dependent non-heme iron enzyme: correlation with mechanisms and reactivities.

  2001cited by this paper
• Cation-pi interactions in structural biology.

  1999cited by this paper
• An Fe2IVO2 Diamond Core Structure for the Key Intermediate Q of Methane Monooxygenase

  1997cited by this paper
• Transient intermediates of the methane monooxygenase catalytic cycle.

  1993cited by this paper
• Mechanism of assembly of the tyrosyl radical-dinuclear iron cluster cofactor of ribonucleotide reductase.

  1991cited by this paper

• Structural and mechanistic insights into azetidine-associated αKG-NHFe enzyme OkaE with multifunctional catalysis.

  2026cites this paper
• Structural basis of the promiscuity of the unusual Fe(II) and 2-oxoglutarate dependent human aspartate/asparagine-β-hydroxylase.

  2026cites this paper
• Enzymatic formation of endoperoxide by Fe(II)/α-KG-dependent dioxygenase NvfI: Insight into substrate-assisted activation of the distant C–H bond and incorporation of two oxygen molecules

  2026cites this paper
• Deciphering the guanidine code: from core metabolism to biosynthesis of its derivatives.

  2026cites this paper
• Mechanistic Insights into the CC Desaturation Catalyzed by an Fe(II) and αKG‐Dependent Oxygenase AndA

  2025cites this paper
• Demethylation of methylguanidine by a stepwise dioxygenase and lyase reaction

  2025cites this paper
• Unusual O-H Activation-Initiated C-C Bond Cleavage Reaction by a Nonheme Fe Enzyme in Antifungal Nucleoside Biosynthesis.

  2025cites this paper
• Mechanistic insights into the selective oxidation of D-arginine by the nonheme iron-dependent viomycin biosynthesis enzyme VioC

  2025cites this paper
• Guanidine aptamers are present in vertebrate RNAs associated with calcium signaling and neuromuscular function

  2025cites this paper
• Uncovering the Origins of Selectivity in Non-Heme Iron Dioxygenase-Catalyzed Tropolone Biosynthesis.

  2025cites this paper
• Methylene Group Insertion into a C–N Bond: The Mechanism for the Biosynthesis of Dehydrofosmidomycin by a Nonheme Iron Oxygenase

  2025cites this paper
• An Alternative Mechanism for C-C Desaturation Underscores a Dual-Controlled Mechanism for the Fate of Radical Intermediate in Iron(II)- and 2-(Oxo)glutarate-Dependent Oxygenase DfmD.

  2025cites this paper
• From lab reagent to metabolite: the riboswitch ligand guanidine as a relevant compound in bacterial physiology

  2025cites this paper
• Three distinct strategies lead to programmable aliphatic C−H oxidation in bicyclomycin biosynthesis

  2025cites this paper
• Diverging Reaction Pathways and Key Intermediates in Ethylene Forming Enzyme.

  2025cites this paper
• Semirational Design of 4-Hydroxyphenylpyruvate Dioxygenase for Efficient and Regioselective Production of 3-Hydroxy-3-methylbutyrate.

  2025cites this paper
• Characterization of the Biosynthesis of Pimprinine-Type Indolyloxazoles Unravels an Unusual d-Configurational Substrate Metabolic Streamline.

  2025cites this paper
• Heme Oxygenase-Like Metalloenzymes.

  2025cites this paper
• Discovery of Noncanonical Iron and 2-Oxoglutarate Dependent Enzymes Involved in C–C and C–N Bond Formation in Biosynthetic Pathways

  2025cites this paper
• Characterization of an α-ketoglutarate-dependent oxygenase involved in converting 2-(2-phenylethyl)chromones into 2-styrylchromones in agarwood.

  2025cites this paper
• What Factors Determine the Brevione B Desaturation Mechanism in the Nonheme Iron Dioxygenase BrvJ?

  2025cites this paper
• Comparison of a Nonheme Iron Cyclopropanase with a Homologous Hydroxylase Reveals Mechanistic Features Associated with Distinct Reaction Outcomes.

  2025cites this paper
• Beyond Mimicking Enzymes: NewTAML/Peroxide Abstracts sp3 C–H Bonds to Initiate Biotranscendent Water-Purifying Mineralization of Fluoroquinolone Antibiotics

  2025cites this paper
• Discovery and engineering of the biosynthesis of rotenoids

  2025cites this paper
• Metabolic Origin, Role and Fate of the Denaturant Guanidine

  2025cites this paper
• Heterologous Biosynthesis of the Sterol O-Acyltransferase Inhibitor Helvamide Unveils an α-Ketoglutarate-Dependent Cross-Linking Oxygenase.

  2024cites this paper
• Engineering the Reaction Pathway of a Non-heme Iron Oxygenase Using Ancestral Sequence Reconstruction.

  2024cites this paper
• Endoperoxidases in biosynthesis of endoperoxide bonds.

  2024cites this paper
• Fe(II) and 2-oxoglutarate-dependent dioxygenases for natural product synthesis: molecular insights into reaction diversity.

  2024cites this paper
• Dynamic metal coordination controls chemoselectivity in radical halogenases

  2024cites this paper
• Spectroscopic and computational studies of a bifunctional iron- and 2-oxoglutarate dependent enzyme, AsqJ.

  2024cites this paper
• Discovery, Characterization and Synthetic Application of a Promiscuous Nonheme Iron Biocatalyst with Dual Hydroxylase/Desaturase Activity.

  2024cites this paper
• Controllable Multihalogenation of a Non-native Substrate by the SyrB2 Iron Halogenase

  2024cites this paper
• What is the Origin of the Regioselective C3-Hydroxylation of L-Arg by the Nonheme Iron Enzyme Capreomycin C?

  2024cites this paper
• Optimized Substrate Positioning Enables Switches in the C-H Cleavage Site and Reaction Outcome in the Hydroxylation-Epoxidation Sequence Catalyzed by Hyoscyamine 6β-Hydroxylase.

  2024cites this paper
• Growth of complete ammonia oxidizers on guanidine

  2024cites this paper
• Probing Ferryl Reactivity in a Nonheme Iron Oxygenase Using an Expanded Genetic Code

  2024cites this paper
• Coordination dynamics of iron enables the selective C–N coupling but bypasses unwanted C–H hydroxylation in Fe(II)/α-ketoglutarate- dependent non-heme enzymes

  2024cites this paper
• New Frontiers in Nonheme Enzymatic Oxyferryl Species

  2024cites this paper
• An Unusual Ferryl Intermediate and Its Implications for the Mechanism of Oxacyclization by the Loline-Producing Iron(II)- and 2-Oxoglutarate-Dependent Oxygenase, LolO.

  2024cites this paper
• Controllable multi-halogenation of a non-native substrate by SyrB2 iron halogenase

  2024cites this paper
• Substrate-Dependent Mechanism Switch in the Desaturation Reactions of the Mononuclear Nonheme Iron Enzyme PtlD

  2024cites this paper
• How Do Differences in Electronic Structure Affect the Use of Vanadium Intermediates as Mimics in Nonheme Iron Hydroxylases?

  2024cites this paper
• Catalytic divergencies in the mechanism of L-arginine hydroxylating nonheme iron enzymes

  2024cites this paper
• Computational study into the oxidative ring-closure mechanism during the biosynthesis of deoxypodophyllotoxin.

  2024cites this paper
• Guanidine production by plant homoarginine-6-hydroxylases

  2023cites this paper
• Interaction of Vanadium Complexes with Proteins: Revisiting the Reported Structures in the Protein Data Bank (PDB) since 2015

  2023influential citation
• Electronic Structure and Reactivity of Mononuclear Nonheme Iron-Peroxo Complexes as a Biomimetic Model of Rieske Oxygenases: Ring Size Effects of Macrocyclic Ligands.

  2023cites this paper
• LcSAO1, an Unconventional DOXB Clade 2OGD Enzyme from Ligusticum chuanxiong Catalyzes the Biosynthesis of Plant-Derived Natural Medicine Butylphthalide

  2023cites this paper
• Deciphering Deoxynybomycin Biosynthesis Reveals Fe(II)/α-Ketoglutarate-Dependent Dioxygenase-Catalyzed Oxazoline Ring Formation and Decomposition.

  2023cites this paper
• Coordination dynamics of iron center enables the C–H bond activation: QM/MM insight into the catalysis of hydroxyglutarate synthase (HglS)

  2023cites this paper
• A chlorophyll c synthase widely co-opted by phytoplankton

  2023cites this paper
• Enzymatic catalysis favours eight-membered over five-membered ring closure in bicyclomycin biosynthesis

  2023cites this paper
• Synergistic Binding of the Halide and Cationic Prime Substrate of the l-Lysine 4-Chlorinase, BesD, in Both Ferrous and Ferryl States

  2023cites this paper
• Mechanistic Study of Chemoselectivity for Carbon Radical Hydroxylation versus Chlorination with FeIII(OH)(Cl) Complexes.

  2023cites this paper
• Synergistic Binding of the Halide and Cationic Prime Substrate of l-Lysine 4-Chlorinase, BesD, in Both Ferrous and Ferryl States.

  2023cites this paper
• How Does the Nonheme Iron Enzyme NapI React through l-Arginine Desaturation Rather Than Hydroxylation? A Quantum Mechanics/Molecular Mechanics Study

  2023cites this paper
• Poly-γ-glutamylation of biomolecules

  2023cites this paper
• Peroxy Intermediate Drives Carbon Bond Activation in the Dioxygenase AsqJ.

  2022cites this paper
• Properties of the reactants and their interactions within and with the enzyme binding cavity determine reaction selectivities. The case of Fe(II)/2-oxoglutarate dependent enzymes.

  2022cites this paper
• Are Vanadium Intermediates Suitable Mimics in Non-Heme Iron Enzymes? An Electronic Structure Analysis

  2022cites this paper
• Discovery of New Fe(II)/α-Ketoglutarate-Dependent Dioxygenases for Oxidation of l-Proline

  2022cites this paper
• Molecular Basis of the Unusual Seven-Membered Methylenedioxy Bridge Formation Catalyzed by Fe(II)/α-KG-Dependent Oxygenase CTB9

  2022cites this paper
• Engineering Fe(II)/α-Ketoglutarate-Dependent Halogenases and Desaturases.

  2022cites this paper
• Synthesis of 6,6‐ and 7,7‐Difluoro‐1‐acetamidopyrrolizidines and Their Oxidation Catalyzed by the Nonheme Fe Oxygenase LolO

  2022cites this paper
• Mechanism of Methyldehydrofosmidomycin Maturation: Use Olefination to Enable Chain Elongation.

  2022cites this paper
• Using Computational Chemistry To Reveal Nature’s Blueprints for Single-Site Catalysis of C–H Activation

  2022cites this paper
• An artificial pathway for trans-4-hydroxy-L-pipecolic acid production from L-lysine in Escherichia coli.

  2022cites this paper
• Elucidation of divergent desaturation pathways in the formation of vinyl isonitrile and isocyanoacrylate

  2022cites this paper
• Crystal structure of the α-ketoglutarate-dependent non-heme iron oxygenase CmnC in capreomycin biosynthesis and its engineering to catalyze hydroxylation of the substrate enantiomer

  2022cites this paper
• An Iron(IV)-Oxo Intermediate Initiating l-Arginine Oxidation but Not Ethylene Production by the 2-Oxoglutarate-Dependent Oxygenase, Ethylene-Forming Enzyme.

  2021cites this paper
• Fermentative Production of l-2-Hydroxyglutarate by Engineered Corynebacterium glutamicum via Pathway Extension of l-Lysine Biosynthesis

  2021cites this paper
• C─H Bond Cleavage by Bioinspired Non-Heme Metal Complexes

  2021cites this paper
• Metabolic engineering of Corynebacterium glutamicum for de novo production of 3-hydroxycadaverine

  2021cites this paper
• Biosynthesis of Guatrypmethine C Implies Two Different Oxidases for exo Double Bond Installation at the Diketopiperazine Ring

  2021cites this paper
• Stereochemical Assignment and Absolute Abundance of Nonproteinogenic Amino Acid Homoarginine in Marine Sponges

  2021cites this paper
• C-H Bond Cleavage by Bioinspired Nonheme Metal Complexes.

  2021cites this paper
• Modulating Chemoselectivity in a Fe(II)/α-Ketoglutarate-Dependent Dioxygenase for the Oxidative Modification of a Nonproteinogenic Amino Acid

  2021cites this paper
• Harnessing the Substrate Promiscuity of Dioxygenase AsqJ and Developing Efficient Chemoenzymatic Synthesis for Quinolones.

  2021cites this paper
• Mechanisms of O2 Activation by Mononuclear Non-Heme Iron Enzymes.

  2021cites this paper
• Density Functional Theory Study into the Reaction Mechanism of Isonitrile Biosynthesis by the Nonheme Iron Enzyme ScoE

  2021cites this paper
• A metabolic regulon reveals early and late acting enzymes in neuroactive Lycopodium alkaloid biosynthesis

  2021cites this paper
• Negative catalysis / non-Bell-Evans-Polanyi reactivity by metalloenzymes: Examples from mononuclear heme and non-heme iron oxygenases

  2021cites this paper
• N-Nitrosation Mechanism Catalyzed by Non-heme Iron-Containing Enzyme SznF Involving Intramolecular Oxidative Rearrangement.

  2021cites this paper
• Cytochrome P450 Enzyme Mechanisms

  2021cites this paper
• Advances in Fe(II)/2-ketoglutarate-dependent dioxygenase-mediated C–H bond oxidation for regioselective and stereoselective hydroxyl amino acid synthesis: from structural insights into practical applications

  2021cites this paper
• Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine

  2021cites this paper
• Glutarate Hydroxylation by the Carbon Starvation-Induced Protein D: A Computational Study into the Stereo- and Regioselectivities of the Reaction.

  2021cites this paper
• Activation modes in biocatalytic radical cyclization reactions

  2021cites this paper
• How Do Electrostatic Perturbations of the Protein Affect the Bifurcation Pathways of Substrate Hydroxylation versus Desaturation in the Nonheme Iron-Dependent Viomycin Biosynthesis Enzyme?

  2021cites this paper
• Reinvigorating the Chiral Pool: Chemoenzymatic Approaches to Complex Peptides and Terpenoids.

  2021cites this paper
• What determines the selectivity of arginine dihydroxylation by the nonheme iron enzyme OrfP?

  2020cites this paper
• NRVS Definition of the Facial Triad FeIV=O Intermediate in Taurine Dioxygenase: Evaluation of Structural Contributions to Hydrogen Atom Abstraction

  2020cites this paper
• Enzyme multifunctionality via control of substrate positioning within the catalytic cycle - a QM/MM study for clavaminic acid synthase.

  2020cites this paper
• QM/MM Calculations Reveal the Important Role of α-Heteroatom Substituents in Controlling Selectivity of Mononuclear Nonheme HppE-Catalyzed Reactions

  2020cites this paper
• Nuclear Resonance Vibrational Spectroscopic Definition of the Facial Triad FeIV═O Intermediate in Taurine Dioxygenase: Evaluation of Structural Contributions to Hydrogen Atom Abstraction.

  2020cites this paper
• Nature's Machinery, Repurposed: Expanding the Repertoire of Iron-Dependent Oxygenases.

  2020cites this paper
• Olefin, Nitrile and Isonitrile Installation Catalyzed by Metalloenzymes

  2020cites this paper
• Evaluation of a concerted vs. sequential oxygen activation mechanism in α-ketoglutarate–dependent nonheme ferrous enzymes

  2020cites this paper
• Pathway from N-alkylglycine to alkylisonitrile catalyzed by iron(II) and 2-oxoglutarate dependent oxygenases.

  2020cites this paper