Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center

York, Nicholas J.; Lockart, Molly M.; Sardar, Sinjinee; Khadka, Nimesh; Shi, Wuxian; Stenkamp, Ronald E.; Zhang, Jianye; Kiser, Philip D.; Pierce, Brad S.

doi:10.1016/j.jbc.2021.100492

Title: Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center

Abstract

Thiol dioxygenases are a subset of nonheme iron oxygenases that catalyze the formation of sulfinic acids from sulfhydryl-containing substrates and dioxygen. Among this class, cysteine dioxygenases (CDOs) and 3-mercaptopropionic acid dioxygenases (3MDOs) are the best characterized, and the mode of substrate binding for CDOs is well understood. However, the manner in which 3-mercaptopropionic acid (3MPA) coordinates to the nonheme iron site in 3MDO remains a matter of debate. A model for bidentate 3MPA coordination at the 3MDO Fe-site has been proposed on the basis of computational docking, whereas steady-state kinetics and EPR spectroscopic measurements suggest a thiolate-only coordination of the substrate. To address this gap in knowledge, we determined the structure of Azobacter vinelandii 3MDO (Av3MDO) in complex with the substrate analog and competitive inhibitor, 3-hydroxypropionic acid (3HPA). The structure together with DFT computational modeling demonstrates that 3HPA and 3MPA associate with iron as chelate complexes with the substrate-carboxylate group forming an additional interaction with Arg168 and the thiol bound at the same position as in CDO. A chloride ligand was bound to iron in the coordination site assigned as the O₂-binding site. Supporting HYSCORE spectroscopic experiments were performed on the (3MPA/NO)-bound Av3MDO iron nitrosyl (S = 3/2) site. Inmore »« less

Authors:

^[1]; Lockart, Molly M. ^[1]; Sardar, Sinjinee ^[2]; Khadka, Nimesh ^[3]; Shi, Wuxian ^[4];

^[5]; Zhang, Jianye ^[6];

^[7];

^[1]

Univ. of Alabama, Birmingham, AL (United States). Dept. of Chemistry and Biochemistry
Univ. of Texas, Arlington, TX (United States). Dept. of Chemistry and Biochemistry
Case Western Reserve Univ., Cleveland, OH (United States). Dept. of Pharmacology
Brookhaven National Lab. (BNL), Upton, NY (United States). National Synchrotron Light Source II (NSLS-II)
Univ. of Washington, Seattle, WA (United States). Depts. of Biological Structure and Biochemistry
Univ. of California, Irvine, CA (United States). School of Medicine, Dept. of Ophthalmology
Univ. of California, Irvine, CA (United States). School of Medicine, Dept. of Ophthalmology; Univ. of California, Irvine, CA (United States). School of Medicine, Dept. of Physiology and Biophysics; VA Long Beach Healthcare System, CA (United States). Research Service

Publication Date:: Fri Jan 01 00:00:00 EST 2021

Research Org.:: Brookhaven National Lab. (BNL), Upton, NY (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1778798

Report Number(s):: BNL-221309-2021-JAAM
Journal ID: ISSN 0021-9258

Grant/Contract Number:: SC0012704

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Biological Chemistry

Additional Journal Information:: Journal Volume: 296; Journal ID: ISSN 0021-9258

Publisher:: American Society for Biochemistry and Molecular Biology

Country of Publication:: United States

Language:: English

Subject:: 36 MATERIALS SCIENCE

Citation Formats


                    York, Nicholas J., Lockart, Molly M., Sardar, Sinjinee, Khadka, Nimesh, Shi, Wuxian, Stenkamp, Ronald E., Zhang, Jianye, Kiser, Philip D., and Pierce, Brad S. Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center.  United States: N. p., 2021. 
Web.  doi:10.1016/j.jbc.2021.100492.

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                    York, Nicholas J., Lockart, Molly M., Sardar, Sinjinee, Khadka, Nimesh, Shi, Wuxian, Stenkamp, Ronald E., Zhang, Jianye, Kiser, Philip D., & Pierce, Brad S. Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center.  United States.  https://doi.org/10.1016/j.jbc.2021.100492

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                    York, Nicholas J., Lockart, Molly M., Sardar, Sinjinee, Khadka, Nimesh, Shi, Wuxian, Stenkamp, Ronald E., Zhang, Jianye, Kiser, Philip D., and Pierce, Brad S. Fri .  
"Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center".  United States.  https://doi.org/10.1016/j.jbc.2021.100492.  https://www.osti.gov/servlets/purl/1778798.

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@article{osti_1778798,

  title        = {Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center},

  author       = {York, Nicholas J. and Lockart, Molly M. and Sardar, Sinjinee and Khadka, Nimesh and Shi, Wuxian and Stenkamp, Ronald E. and Zhang, Jianye and Kiser, Philip D. and Pierce, Brad S.},

  abstractNote = {Thiol dioxygenases are a subset of nonheme iron oxygenases that catalyze the formation of sulfinic acids from sulfhydryl-containing substrates and dioxygen. Among this class, cysteine dioxygenases (CDOs) and 3-mercaptopropionic acid dioxygenases (3MDOs) are the best characterized, and the mode of substrate binding for CDOs is well understood. However, the manner in which 3-mercaptopropionic acid (3MPA) coordinates to the nonheme iron site in 3MDO remains a matter of debate. A model for bidentate 3MPA coordination at the 3MDO Fe-site has been proposed on the basis of computational docking, whereas steady-state kinetics and EPR spectroscopic measurements suggest a thiolate-only coordination of the substrate. To address this gap in knowledge, we determined the structure of Azobacter vinelandii 3MDO (Av3MDO) in complex with the substrate analog and competitive inhibitor, 3-hydroxypropionic acid (3HPA). The structure together with DFT computational modeling demonstrates that 3HPA and 3MPA associate with iron as chelate complexes with the substrate-carboxylate group forming an additional interaction with Arg168 and the thiol bound at the same position as in CDO. A chloride ligand was bound to iron in the coordination site assigned as the O2-binding site. Supporting HYSCORE spectroscopic experiments were performed on the (3MPA/NO)-bound Av3MDO iron nitrosyl (S = 3/2) site. In combination with spectroscopic simulations and optimized DFT models, this work provides an experimentally verified model of the Av3MDO enzyme–substrate complex, effectively resolving a debate in the literature regarding the preferred substrate-binding denticity. These results elegantly explain the observed 3MDO substrate specificity, but leave unanswered questions regarding the mechanism of substrate-gated reactivity with dioxygen.},

  doi          = {10.1016/j.jbc.2021.100492},

  journal      = {Journal of Biological Chemistry},

  number       = ,

  volume       = 296,

  place        = {United States},

  year         = {Fri Jan 01 00:00:00 EST 2021},

  month        = {Fri Jan 01 00:00:00 EST 2021}

}

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Structure, Vol. 19, Issue 10
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EasySpin, a comprehensive software package for spectral simulation and analysis in EPR
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Stoll, Stefan; Schweiger, Arthur
Journal of Magnetic Resonance, Vol. 178, Issue 1, p. 42-55
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UCSF Chimera?A visualization system for exploratory research and analysis
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Pettersen, Eric F.; Goddard, Thomas D.; Huang, Conrad C.
Journal of Computational Chemistry, Vol. 25, Issue 13
DOI: 10.1002/jcc.20084

Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy
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Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305
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The Journal of Chemical Physics, Vol. 84, Issue 8
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Density-functional approximation for the correlation energy of the inhomogeneous electron gas
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Physical Review B, Vol. 33, Issue 12
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Geometries of Transition-Metal Complexes from Density-Functional Theory
journal, June 2006

Bühl, Michael; Kabrede, Hendrik
Journal of Chemical Theory and Computation, Vol. 2, Issue 5
DOI: 10.1021/ct6001187

Cryoreduction of the NO-Adduct of Taurine:α-Ketoglutarate Dioxygenase (TauD) Yields an Elusive {FeNO} ⁸ Species
journal, March 2010

Ye, Shengfa; Price, John C.; Barr, Eric W.
Journal of the American Chemical Society, Vol. 132, Issue 13
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Integral approximations for LCAO-SCF calculations
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Vahtras, O.; Almlöf, J.; Feyereisen, M. W.
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The impact of the resolution of the identity approximate integral method on modern ab initio algorithm development
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Kendall, Rick A.; Früchtl, Herbert A.
Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta), Vol. 97, Issue 1-4
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Neese, Frank; Wennmohs, Frank; Hansen, Andreas
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Inorganic Chemistry, Vol. 48, Issue 3
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Driggers, Camden M.; Cooley, Richard B.; Sankaran, Banumathi
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In some bacteria, cysteine is converted to cysteine sulfinic acid by cysteine dioxygenases (CDO) that are only ~15–30% identical in sequence to mammalian CDOs. Among bacterial proteins having this range of sequence similarity to mammalian CDO are some that conserve an active site Arg residue (“Arg-type” enzymes) and some having a Gln substituted for this Arg (“Gln-type” enzymes). Here, we describe a structure from each of these enzyme types by analyzing structures originally solved by structural genomics groups but not published: a Bacillus subtilis “Arg-type” enzyme that has cysteine dioxygenase activity (BsCDO), and a Ralstonia eutropha “Gln-type” CDO homolog ofmore »« less
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Title: Structure of 3-mercaptopropionic acid dioxygenase with a substrate analog reveals bidentate substrate binding at the iron center

Abstract

Citation Formats

SULFUR AMINO ACID METABOLISM: Pathways for Production and Removal of Homocysteine and Cysteine journal, July 2004

Characteristics of the cysteinesulfinate-forming enzyme system in rat liver journal, November 1966

The enzymatic oxidation of cysteine to cysteinesulfinate in rat liver journal, February 1965

Cysteine Oxygenase journal, March 1969

Identification and Characterization of Bacterial Cysteine Dioxygenases: a New Route of Cysteine Degradation for Eubacteria journal, August 2006

Spectroscopic Investigation of Cysteamine Dioxygenase journal, June 2020

Discovery and Characterization of a Second Mammalian Thiol Dioxygenase, Cysteamine Dioxygenase journal, August 2007

Mercaptosuccinate Dioxygenase, a Cysteine Dioxygenase Homologue, from Variovorax paradoxus Strain B4 Is the Key Enzyme of Mercaptosuccinate Degradation journal, October 2014

Substrate Specificity in Thiol Dioxygenases journal, April 2019

Substrate and pH-Dependent Kinetic Profile of 3-Mercaptopropionate Dioxygenase from Pseudomonas aeruginosa journal, February 2016

The Cysteine Dioxygenase Homologue from Pseudomonas aeruginosa Is a 3-Mercaptopropionate Dioxygenase journal, October 2015

Outer-Sphere Tyrosine 159 within the 3-Mercaptopropionic Acid Dioxygenase S-H-Y Motif Gates Substrate-Coordination Denticity at the Non-Heme Iron Active Site journal, November 2019

Non-chemical proton-dependent steps prior to O2-activation limit Azotobacter vinelandii 3-mercaptopropionic acid dioxygenase (MDO) catalysis journal, August 2016

The “Gln-Type” Thiol Dioxygenase from Azotobacter vinelandii Is a 3-Mercaptopropionic Acid Dioxygenase journal, December 2015

Plant cysteine oxidases control the oxygen-dependent branch of the N-end-rule pathway journal, March 2014

Plant cysteine oxidases are dioxygenases that directly enable arginyl transferase-catalysed arginylation of N-end rule targets journal, March 2017

Conserved N-terminal cysteine dioxygenases transduce responses to hypoxia in animals and plants journal, July 2019

Abnormal sulphur oxidation in systemic lupus erythematosus journal, January 1992

Plasma cysteine and sulphate levels in patients with motor neurone, Parkinson's and Alzheimer's disease journal, March 1990

Metabolic biomarkers of increased oxidative stress and impaired methylation capacity in children with autism journal, December 2004

How environmental and genetic factors combine to cause autism: A redox/methylation hypothesis journal, January 2008

Expanding the functional diversity of proteins through cysteine oxidation journal, December 2008

Oxidative activation of antioxidant defence journal, August 2005

Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach? journal, May 2009

Structures of Arg- and Gln-type bacterial cysteine dioxygenase homologs: Arg- and Gln-type Bacterial CDO Homologs journal, November 2014

Structure-Based Insights into the Role of the Cys–Tyr Crosslink and Inhibitor Recognition by Mammalian Cysteine Dioxygenase journal, October 2016

Crystal Structure of Mammalian Cysteine Dioxygenase: A NOVEL MONONUCLEAR IRON CENTER FOR CYSTEINE THIOL OXIDATION journal, April 2006

The Cys-Tyr Cross-Link of Cysteine Dioxygenase Changes the Optimal pH of the Reaction without a Structural Change journal, December 2014

Spectroscopic and Computational Investigation of the H155A Variant of Cysteine Dioxygenase: Geometric and Electronic Consequences of a Third-Sphere Amino Acid Substitution journal, April 2015

Second-Sphere Interactions between the C93–Y157 Cross-Link and the Substrate-Bound Fe Site Influence the O 2 Coupling Efficiency in Mouse Cysteine Dioxygenase journal, November 2013

An Insight into the Mechanism of Human Cysteine Dioxygenase: KEY ROLES OF THE THIOETHER-BONDED TYROSINE-CYSTEINE COFACTOR journal, November 2006

Synthesis of Amino Acid Cofactor in Cysteine Dioxygenase Is Regulated by Substrate and Represents a Novel Post-translational Regulation of Activity journal, February 2008

Shifting redox states of the iron center partitions CDO between crosslink formation or cysteine oxidation journal, September 2014

Steady-state substrate specificity and O2-coupling efficiency of mouse cysteine dioxygenase journal, January 2015

Studies on the relationship between chemical constitution and physiological action journal, January 1933

Structure and mechanism of mouse cysteine dioxygenase journal, February 2006

Characterization of the Nitrosyl Adduct of Substrate-Bound Mouse Cysteine Dioxygenase by Electron Paramagnetic Resonance: Electronic Structure of the Active Site and Mechanistic Implications † journal, July 2007

Inference of Macromolecular Assemblies from Crystalline State journal, September 2007

Influence of cysteine 164 on active site structure in rat cysteine dioxygenase journal, May 2016

Mononuclear and dinuclear iron thiocyanate and selenocyanate complexes of tris-pyrazolylmethane ligands journal, August 2008

Determination of the pKa value of the hydroxyl group in the α-hydroxycarboxylates citrate, malate and lactate by 13C NMR: implications for metal coordination in biological systems journal, March 2009

Water-Soluble Fe(II)–H 2 O Complex with a Weak O–H Bond Transfers a Hydrogen Atom via an Observable Monomeric Fe(III)–OH journal, February 2015

Modulation of the p K a of Metal-Bound Water via Oxidation of Thiolato Sulfur in Model Complexes of Co(III) Containing Nitrile Hydratase: Insight into Possible Effect of Cysteine Oxidation in Co−Nitrile Hydratase journal, September 2003

Principles of structure, bonding, and reactivity for metal nitrosyl complexes journal, September 1974

Direct evidence that an extended hydrogen-bonding network influences activation of pyridoxal 5′-phosphate in aspartate aminotransferase journal, February 2017

Heme-bound nitroxyl, hydroxylamine, and ammonia ligands as intermediates in the reaction cycle of cytochrome c nitrite reductase: a theoretical study journal, November 2013

Computational study of the electronic structure and magnetic properties of the Ni–C state in [NiFe] hydrogenases including the second coordination sphere journal, October 2012

VTVH-MCD and DFT Studies of Thiolate Bonding to {FeNO} 7 /{FeO 2 } 8 Complexes of Isopenicillin N Synthase: Substrate Determination of Oxidase versus Oxygenase Activity in Nonheme Fe Enzymes journal, June 2007

EPR and Mössbauer studies of protocatechuate 4,5-dioxygenase. Characterization of a new Fe2+ environment. journal, December 1983

1H-HYSCORE Reveals Structural Details at the Fe(II) Active Site of Taurine:2-Oxoglutarate Dioxygenase journal, October 2020

HYSCORE Analysis of the Effects of Substrates on Coordination of Water to the Active Site Iron in Tyrosine Hydroxylase journal, June 2015

Experimental Correlation of Substrate Position with Reaction Outcome in the Aliphatic Halogenase, SyrB2 journal, May 2015

Visualizing the Reaction Cycle in an Iron(II)- and 2-(Oxo)-glutarate-Dependent Hydroxylase journal, September 2017

Elucidating the Reaction Pathway of Decarboxylation-Assisted Olefination Catalyzed by a Mononuclear Non-Heme Iron Enzyme journal, October 2018

Two-Dimensional ESEEM Spectroscopy of Nitrogen Hyperfine Couplings in Methemerythrin and Azidomethemerythrin journal, July 1998

Ligation of the diiron site of the hydroxylase component of methane monooxygenase. An electron nuclear double resonance study. journal, January 1992

Plasticity of enzyme active sites journal, August 2002

Thiol dioxygenase turnover yields benzothiazole products from 2-mercaptoaniline and O2-dependent oxidation of primary alcohols journal, October 2017

Structures, Spectroscopic Properties, and Dioxygen Reactivity of 5- and 6-Coordinate Nonheme Iron(II) Complexes: A Combined Enzyme/Model Study of Thiol Dioxygenases journal, October 2018

Oxidative Uncoupling in Cysteine Dioxygenase Is Gated by a Proton-Sensitive Intermediate journal, November 2014

XDS journal, January 2010

A statistic for local intensity differences: robustness to anisotropy and pseudo-centering and utility for detecting twinning journal, June 2003

Surprises and pitfalls arising from (pseudo)symmetry journal, December 2007

Phaser crystallographic software journal, July 2007

Features and development of Coot journal, March 2010

REFMAC 5 for the refinement of macromolecular crystal structures journal, March 2011

Intensity statistics in twinned crystals with examples from the PDB journal, December 2005

Space-group and origin ambiguity in macromolecular structures with pseudo-symmetry and its treatment with the program Zanuda journal, August 2014

Detection and correction of underassigned rotational symmetry prior to structure deposition journal, April 2010

Recent advances in biological production of 3-hydroxypropionic acid journal, November 2013

Production of 3-Hydroxypropanoic Acid From Glycerol by Metabolically Engineered Bacteria journal, May 2019

MolProbity: More and better reference data for improved all-atom structure validation: PROTEIN SCIENCE.ORG journal, November 2017

A New Generation of Crystallographic Validation Tools for the Protein Data Bank journal, October 2011

EasySpin, a comprehensive software package for spectral simulation and analysis in EPR journal, January 2006

UCSF Chimera?A visualization system for exploratory research and analysis journal, January 2004

Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy journal, January 2005

Density functional calculations of molecular bond energies journal, April 1986

SULFUR AMINO ACID METABOLISM: Pathways for Production and Removal of Homocysteine and Cysteine
journal, July 2004

Characteristics of the cysteinesulfinate-forming enzyme system in rat liver
journal, November 1966

The enzymatic oxidation of cysteine to cysteinesulfinate in rat liver
journal, February 1965

Cysteine Oxygenase
journal, March 1969

Identification and Characterization of Bacterial Cysteine Dioxygenases: a New Route of Cysteine Degradation for Eubacteria
journal, August 2006

Spectroscopic Investigation of Cysteamine Dioxygenase
journal, June 2020

Discovery and Characterization of a Second Mammalian Thiol Dioxygenase, Cysteamine Dioxygenase
journal, August 2007

Mercaptosuccinate Dioxygenase, a Cysteine Dioxygenase Homologue, from Variovorax paradoxus Strain B4 Is the Key Enzyme of Mercaptosuccinate Degradation
journal, October 2014

Substrate Specificity in Thiol Dioxygenases
journal, April 2019

Substrate and pH-Dependent Kinetic Profile of 3-Mercaptopropionate Dioxygenase from Pseudomonas aeruginosa
journal, February 2016

The Cysteine Dioxygenase Homologue from Pseudomonas aeruginosa Is a 3-Mercaptopropionate Dioxygenase
journal, October 2015

Outer-Sphere Tyrosine 159 within the 3-Mercaptopropionic Acid Dioxygenase S-H-Y Motif Gates Substrate-Coordination Denticity at the Non-Heme Iron Active Site
journal, November 2019

Non-chemical proton-dependent steps prior to O2-activation limit Azotobacter vinelandii 3-mercaptopropionic acid dioxygenase (MDO) catalysis
journal, August 2016

The “Gln-Type” Thiol Dioxygenase from Azotobacter vinelandii Is a 3-Mercaptopropionic Acid Dioxygenase
journal, December 2015

Plant cysteine oxidases control the oxygen-dependent branch of the N-end-rule pathway
journal, March 2014

Plant cysteine oxidases are dioxygenases that directly enable arginyl transferase-catalysed arginylation of N-end rule targets
journal, March 2017

Conserved N-terminal cysteine dioxygenases transduce responses to hypoxia in animals and plants
journal, July 2019

Abnormal sulphur oxidation in systemic lupus erythematosus
journal, January 1992

Plasma cysteine and sulphate levels in patients with motor neurone, Parkinson's and Alzheimer's disease
journal, March 1990

Metabolic biomarkers of increased oxidative stress and impaired methylation capacity in children with autism
journal, December 2004

How environmental and genetic factors combine to cause autism: A redox/methylation hypothesis
journal, January 2008

Expanding the functional diversity of proteins through cysteine oxidation
journal, December 2008

Oxidative activation of antioxidant defence
journal, August 2005

Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach?
journal, May 2009

Structures of Arg- and Gln-type bacterial cysteine dioxygenase homologs: Arg- and Gln-type Bacterial CDO Homologs
journal, November 2014

Structure-Based Insights into the Role of the Cys–Tyr Crosslink and Inhibitor Recognition by Mammalian Cysteine Dioxygenase
journal, October 2016

Crystal Structure of Mammalian Cysteine Dioxygenase: A NOVEL MONONUCLEAR IRON CENTER FOR CYSTEINE THIOL OXIDATION
journal, April 2006

The Cys-Tyr Cross-Link of Cysteine Dioxygenase Changes the Optimal pH of the Reaction without a Structural Change
journal, December 2014

Spectroscopic and Computational Investigation of the H155A Variant of Cysteine Dioxygenase: Geometric and Electronic Consequences of a Third-Sphere Amino Acid Substitution
journal, April 2015

Second-Sphere Interactions between the C93–Y157 Cross-Link and the Substrate-Bound Fe Site Influence the O ₂ Coupling Efficiency in Mouse Cysteine Dioxygenase
journal, November 2013

An Insight into the Mechanism of Human Cysteine Dioxygenase: KEY ROLES OF THE THIOETHER-BONDED TYROSINE-CYSTEINE COFACTOR
journal, November 2006

Synthesis of Amino Acid Cofactor in Cysteine Dioxygenase Is Regulated by Substrate and Represents a Novel Post-translational Regulation of Activity
journal, February 2008

Shifting redox states of the iron center partitions CDO between crosslink formation or cysteine oxidation
journal, September 2014

Steady-state substrate specificity and O2-coupling efficiency of mouse cysteine dioxygenase
journal, January 2015

Studies on the relationship between chemical constitution and physiological action
journal, January 1933

Structure and mechanism of mouse cysteine dioxygenase
journal, February 2006

Characterization of the Nitrosyl Adduct of Substrate-Bound Mouse Cysteine Dioxygenase by Electron Paramagnetic Resonance: Electronic Structure of the Active Site and Mechanistic Implications ^†
journal, July 2007

Inference of Macromolecular Assemblies from Crystalline State
journal, September 2007

Influence of cysteine 164 on active site structure in rat cysteine dioxygenase
journal, May 2016

Mononuclear and dinuclear iron thiocyanate and selenocyanate complexes of tris-pyrazolylmethane ligands
journal, August 2008

Determination of the pKa value of the hydroxyl group in the α-hydroxycarboxylates citrate, malate and lactate by 13C NMR: implications for metal coordination in biological systems
journal, March 2009

Water-Soluble Fe(II)–H ₂ O Complex with a Weak O–H Bond Transfers a Hydrogen Atom via an Observable Monomeric Fe(III)–OH
journal, February 2015

Modulation of the p K _a of Metal-Bound Water via Oxidation of Thiolato Sulfur in Model Complexes of Co(III) Containing Nitrile Hydratase: Insight into Possible Effect of Cysteine Oxidation in Co−Nitrile Hydratase
journal, September 2003

Principles of structure, bonding, and reactivity for metal nitrosyl complexes
journal, September 1974

Direct evidence that an extended hydrogen-bonding network influences activation of pyridoxal 5′-phosphate in aspartate aminotransferase
journal, February 2017

Heme-bound nitroxyl, hydroxylamine, and ammonia ligands as intermediates in the reaction cycle of cytochrome c nitrite reductase: a theoretical study
journal, November 2013

Computational study of the electronic structure and magnetic properties of the Ni–C state in [NiFe] hydrogenases including the second coordination sphere
journal, October 2012

VTVH-MCD and DFT Studies of Thiolate Bonding to {FeNO} ⁷ /{FeO ₂ } ⁸ Complexes of Isopenicillin N Synthase: Substrate Determination of Oxidase versus Oxygenase Activity in Nonheme Fe Enzymes
journal, June 2007

EPR and Mössbauer studies of protocatechuate 4,5-dioxygenase. Characterization of a new Fe2+ environment.
journal, December 1983

1H-HYSCORE Reveals Structural Details at the Fe(II) Active Site of Taurine:2-Oxoglutarate Dioxygenase
journal, October 2020

HYSCORE Analysis of the Effects of Substrates on Coordination of Water to the Active Site Iron in Tyrosine Hydroxylase
journal, June 2015

Experimental Correlation of Substrate Position with Reaction Outcome in the Aliphatic Halogenase, SyrB2
journal, May 2015

Visualizing the Reaction Cycle in an Iron(II)- and 2-(Oxo)-glutarate-Dependent Hydroxylase
journal, September 2017

Elucidating the Reaction Pathway of Decarboxylation-Assisted Olefination Catalyzed by a Mononuclear Non-Heme Iron Enzyme
journal, October 2018

Two-Dimensional ESEEM Spectroscopy of Nitrogen Hyperfine Couplings in Methemerythrin and Azidomethemerythrin
journal, July 1998

Ligation of the diiron site of the hydroxylase component of methane monooxygenase. An electron nuclear double resonance study.
journal, January 1992

Plasticity of enzyme active sites
journal, August 2002

Thiol dioxygenase turnover yields benzothiazole products from 2-mercaptoaniline and O2-dependent oxidation of primary alcohols
journal, October 2017

Structures, Spectroscopic Properties, and Dioxygen Reactivity of 5- and 6-Coordinate Nonheme Iron(II) Complexes: A Combined Enzyme/Model Study of Thiol Dioxygenases
journal, October 2018

Oxidative Uncoupling in Cysteine Dioxygenase Is Gated by a Proton-Sensitive Intermediate
journal, November 2014

XDS
journal, January 2010

A statistic for local intensity differences: robustness to anisotropy and pseudo-centering and utility for detecting twinning
journal, June 2003

Surprises and pitfalls arising from (pseudo)symmetry
journal, December 2007

Phaser crystallographic software
journal, July 2007

Features and development of Coot
journal, March 2010

REFMAC 5 for the refinement of macromolecular crystal structures
journal, March 2011

Intensity statistics in twinned crystals with examples from the PDB
journal, December 2005

Space-group and origin ambiguity in macromolecular structures with pseudo-symmetry and its treatment with the program Zanuda
journal, August 2014

Detection and correction of underassigned rotational symmetry prior to structure deposition
journal, April 2010

Recent advances in biological production of 3-hydroxypropionic acid
journal, November 2013

Production of 3-Hydroxypropanoic Acid From Glycerol by Metabolically Engineered Bacteria
journal, May 2019

MolProbity: More and better reference data for improved all-atom structure validation: PROTEIN SCIENCE.ORG
journal, November 2017

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journal, October 2011

EasySpin, a comprehensive software package for spectral simulation and analysis in EPR
journal, January 2006

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journal, January 2004

Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy
journal, January 2005

Density functional calculations of molecular bond energies
journal, April 1986

Density-functional approximation for the correlation energy of the inhomogeneous electron gas
journal, June 1986

Geometries of Transition-Metal Complexes from Density-Functional Theory
journal, June 2006

Cryoreduction of the NO-Adduct of Taurine:α-Ketoglutarate Dioxygenase (TauD) Yields an Elusive {FeNO} ⁸ Species
journal, March 2010