Works (63)

Updated: April 8th, 2024 08:24

2024 journal article

Poly-γ-glutamylation of biomolecules

NATURE COMMUNICATIONS, 15(1).

By: G. Bashiri*, E. Bulloch*, W. Bramley*, M. Davidson n, S. Stuteley*, P. Young*, P. Harris*, M. Naqvi* ...

TL;DR: It is discovered that folylpolyglutamate synthase and γ-glutamyl ligase enzymes add successive L -glutamates to the termini of the growing γ-glutamyl chain in a processive mechanism. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: March 25, 2024

2024 article

Variation in Biosynthesis and Metal-Binding Properties of Isonitrile-Containing Peptides Produced by Mycobacteria versus Streptomyces

Chen, T.-Y., Chen, J., Ruszczycky, M. W., Hilovsky, D., Hostetler, T., Liu, X., … Chang, W.-chen. (2024, March 19). ACS CATALYSIS, Vol. 3.

By: T. Chen n, J. Chen*, M. Ruszczycky*, D. Hilovsky n, T. Hostetler n, X. Liu n, J. Zhou*, W. Chang n

author keywords: isonitriles; Fe/2OG enzymes; metallophores; Mycobacterium; natural products
Sources: Web Of Science, ORCID
Added: April 1, 2024

2023 journal article

A Ferric-Superoxide Intermediate Initiates P450-Catalyzed Cyclic Dipeptide Dimerization

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 8.

By: H. Gering n, X. Li n, H. Tang n, P. Swartz n, W. Chang n & T. Makris n

Sources: Web Of Science, ORCID
Added: September 11, 2023

2023 article

An <i>S</i>=1 Iron(IV) Intermediate Revealed in a Non-Heme Iron Enzyme-Catalyzed Oxidative C-S Bond Formation

Paris, J. C., Hu, S., Wen, A., Weitz, A. C., Cheng, R., Gee, L. B., … Guo, Y. (2023, September 13). ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, Vol. 9.

By: J. Paris*, S. Hu*, A. Wen*, A. Weitz*, R. Cheng*, L. Gee*, Y. Tang*, H. Kim* ...

author keywords: Ergothioneine; Ferryl Intermediates; High-Valent Iron; Ovothiol A; Oxidative C-S Bond Formation
TL;DR: The identification and characterization of a kinetically competent S = 1 iron(IV) intermediate supported by a four-histidine ligand environment in enabling C-S bond formation in OvoA from Methyloversatilis thermotoleran, which represents the first experimentally observed intermediate spin iron( IV) species in non-heme iron enzymes. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: October 10, 2023

2023 review

Current understanding of lignan biosynthesis

[Review of ]. ARKIVOC.

By: N. Canty* & W. Chang*

author keywords: Lignin; biosynthesis; podophyllotoxin; enzyme transformation
TL;DR: This review covers the current understanding of lignan biosynthesis and aims to highlight key biosynthetic transformations responsible for their structural and biological diversity. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: February 19, 2024

2023 journal article

Excision of a Protein-Derived Amine for <i>p</i>-Aminobenzoate Assembly by the Self-Sacrificial Heterobimetallic Protein CADD

BIOCHEMISTRY, 62(22), 3276–3282.

By: H. Phan n, O. Manley n, S. Skirboll n, L. Cha n, D. Hilovsky n, W. Chang n, P. Thompson n, X. Liu n, T. Makris n

TL;DR: Turnover studies using limiting O2 have identified a para-aminobenzaldehyde metabolic intermediate that is formed on the path to pABA formation and use of pABCHO and other probe substrates shows that the heterobimetallic Fe/Mn form of the enzyme is capable of oxygen insertion to generate the pA BA-carboxylate. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: December 12, 2023

2023 journal article

Mechanistic Analysis of Stereodivergent Nitroalkane Cyclopropanation Catalyzed by Nonheme Iron Enzymes

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 145(44), 24210–24217.

By: R. Ushimaru*, L. Cha n, S. Shimo*, X. Li n, J. Paris*, T. Mori*, K. Miyamoto*, L. Coffer n ...

TL;DR: The results suggest that the nitroalkane moiety of the substrate is first deprotonated to produce the nitronate form, and Sequence and structure comparisons of these cyclopropanases enable us to determine the amino acid residues critical for controlling the stereoselectivity of cycloprostanation. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: December 11, 2023

2023 article

Mechanistic Studies of Aziridine Formation Catalyzed by Mononuclear Non-Heme Iron Enzymes

Cha, L., Paris, J. C., Zanella, B., Spletzer, M., Yao, A., Guo, Y., & Chang, W.-chen. (2023, March 13). JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol. 3.

By: L. Cha n, J. Paris*, B. Zanella n, M. Spletzer*, A. Yao n, Y. Guo*, W. Chang n

MeSH headings : Iron / chemistry; Aziridines; Hydroxylation; Catalysis
TL;DR: The use of in silico methods to identify enzymes with potential aziridine-installing (aziridinase) functionality are reported and reconstitute enzymatic activity in vitro and demonstrate that an iron(IV)-oxo species initiates aziridine ring closure by the C-H bond cleavage. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: April 4, 2023

2023 article

Repurposing Iron- and 2-Oxoglutarate-Dependent Oxygenases to Catalyze Olefin Hydration

Wang, B., Lu, Y., Cha, L., Chen, T.-Y., Palacios, P. M., Li, L., … Chen, C. (2023, September 6). ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, Vol. 9.

By: B. Wang*, Y. Lu*, L. Cha n, T. Chen n, P. Palacios*, L. Li*, Y. Guo*, W. Chang n, C. Chen*

author keywords: Biocatalysis; Hydrogen Atom Transfer; Mukaiyama Hydration; Nonheme Fe/2OG-Dependent Oxygenase
TL;DR: It is shown that various enzymes of this family, when reconstituted with Fe(II) or Fe(III), can catalyze Mukaiyama hydration-a redox neutral transformation and demonstrates that Fe/2OG enzymes have utility in catalysis beyond the current scope of catalytic oxidation. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: September 11, 2023

2022 journal article

Deciphering the Reaction Pathway of Mononuclear Iron Enzyme-Catalyzed N C Triple Bond Formation in Isocyanide Lipopeptide and Polyketide Biosynthesis

ACS CATALYSIS, 12(4), 2270–2279.

By: T. Chen n, Z. Zheng*, X. Zhang*, J. Chen*, L. Cha n, Y. Tang*, Y. Guo*, J. Zhou* ...

author keywords: isocyanide; oxygenase; natural product; reaction mechanism; desaturation; C-N bond formation
TL;DR: The results indicate that isocyanide formation likely entails a two-step sequence involving an imine intermediate that undergoes decarboxylation-assisted desaturation to yield the isOCyanide product. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, ORCID
Added: March 28, 2022

2022 journal article

Elucidation of divergent desaturation pathways in the formation of vinyl isonitrile and isocyanoacrylate

NATURE COMMUNICATIONS, 13(1).

By: W. Kim*, T. Chen n, L. Cha n, G. Zhou*, K. Xing*, N. Canty n, Y. Zhang*, W. Chang n

MeSH headings : Iron / metabolism; Ketoglutaric Acids / metabolism; Tyrosine
TL;DR: It is suggested that a carbocation might be deployed to enable chemically divergent desaturations through decarboxylation and deprotonation and hints at substrate promiscuity of these enzymes. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: September 26, 2022

2022 journal article

Mechanism of Methyldehydrofosmidomycin Maturation: Use Olefination to Enable Chain Elongation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 144(18), 8257–8266.

By: X. Li n, S. Xue*, Y. Guo* & W. Chang n

MeSH headings : Alkenes / chemistry; Catalysis; Hydroxylation; Iron / chemistry; Ketoglutaric Acids / metabolism
TL;DR: This work characterized the reactive species, revealed the structure of the reaction intermediate, and used mechanistic probes to investigate the reaction pathway and mechanism, leading to the elucidation of a two-step process in which the first reaction employs a long-lived Fe(IV)-oxo species to trigger C═C bond installation. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: June 6, 2022

2022 journal article

Mechanistic analysis of carbon-carbon bond formation by deoxypodophyllotoxin synthase

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 119(1).

By: H. Tang n, M. Wu*, H. Lin*, M. Han*, Y. Tu*, Z. Yang*, T. Chien*, N. Chan*, W. Chang n

author keywords: C-C coupling; cyclization; oxygenase; natural product; reaction mechanism
MeSH headings : Berberidaceae / enzymology; Drugs, Chinese Herbal / chemistry; Ligases / chemistry; Oxidation-Reduction; Plant Proteins / chemistry; Podophyllotoxin / analogs & derivatives; Podophyllotoxin / chemistry
TL;DR: This study reports two structures of DPS in complex with 2OG and (±)-yatein, in vitro analysis of enzymatic reactivity with substrate analogs, and model reactions addressing DPS’s catalytic mechanism, and suggests what types of substrate modification are likely tolerable in DPS-catalyzed production of deoxypodophyllotoxin analogs. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: February 21, 2022

2022 journal article

Self-sacrificial tyrosine cleavage by an Fe:Mn oxygenase for the biosynthesis of para-aminobenzoate in Chlamydia trachomatis

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 119(39).

By: O. Manley n, H. Phan n, A. Stewart n, D. Mosley n, S. Xue*, L. Cha n, H. Bai n, V. Lightfoot* ...

Contributors: T. Williams n

author keywords: folate biosynthesis; radical transfer; spectroscopy; heterobinuclear cluster
MeSH headings : Bacterial Proteins / metabolism; Chlamydia trachomatis / enzymology; Folic Acid; Iron / metabolism; Manganese / metabolism; Oxygen / metabolism; Oxygenases / metabolism; Tyrosine / metabolism; para-Aminobenzoates / metabolism
TL;DR: High in vitro activity relies on the stoichiometric addition of both Fe and Mn, and CADD is shown to activate O2 to self-sacrificially produce pABA from Tyr27. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: September 21, 2022

2021 article

A postreplicative C5-cytosine hypermodification triggered by bacteriophage methyltransferase and hydroxylase

Chen, T.-Y., & Chang, W.-chen. (2021, July 13). PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, Vol. 118.

By: T. Chen n & W. Chang n

MeSH headings : Bacteriophages / enzymology; Cytosine / metabolism; DNA Replication; Glycosylation; Glycosyltransferases / metabolism; Methyltransferases / metabolism; Mixed Function Oxygenases / metabolism; Substrate Specificity; Viral Proteins / metabolism
TL;DR: Through bioinfor-matic screening, the authors identify and characterize tailoring enzymes, such as glycosyltransferases, that collaborate with phage C5-MT and TET to further elaborate DNA at 5hmC site. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 23, 2021

2021 article

BesC Initiates C-C Cleavage through a Substrate-Triggered and Reactive Diferric-Peroxo Intermediate

Manley, O. M., Tang, H., Xue, S., Guo, Y., Chang, W.-chen, & Makris, T. M. (2021, December 13). JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol. 12.

By: O. Manley n, H. Tang n, S. Xue*, Y. Guo*, W. Chang n & T. Makris n

MeSH headings : Carbon / chemistry; Carbon / metabolism; Ferric Compounds / chemistry; Oxidoreductases / metabolism; Oxygen / chemistry; Spectroscopy, Mossbauer; Streptomyces / enzymology; Substrate Specificity
TL;DR: The observed reactivity of BesC represents the first example of a dinuclear-iron enzyme that utilizes a diferric-peroxo intermediate to capably cleave a C-H bond as part of its native function, thus circumventing the formation of a high-valent intermediate more commonly associated with substrate monooxygenations. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: January 3, 2022

2021 journal article

Current Understanding toward Isonitrile Group Biosynthesis and Mechanism

CHINESE JOURNAL OF CHEMISTRY, 39(2), 463–472.

author keywords: Biosynthesis; Enzymes; Natural products; Reaction mechanisms; Biotransformations
TL;DR: The current biosynthetic pathways and the corresponding enzymes that are responsible for isonitrile-containing natural product generation are summarized and two fundamentally distinctive approaches are discussed. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: March 1, 2021

2021 journal article

Deciphering Pyrrolidine and Olefin Formation Mechanism in Kainic Acid Biosynthesis

ACS CATALYSIS, 11(1), 278–282.

By: T. Chen n, S. Xue*, W. Tsai*, T. Chien*, Y. Guo* & W. Chang n

author keywords: metalloenzyme; C-H activation; cyclization; desaturation; enzyme mechanism
TL;DR: A comparison of C–H bond activation and cyclization in the isodomoic acid and kainic acid biosynthesis experiments shows that the former is superior to the latter in terms of both molecular complexity and physical properties. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: January 11, 2021

2021 journal article

Harnessing the Substrate Promiscuity of Dioxygenase AsqJ and Developing Efficient Chemoenzymatic Synthesis for Quinolones

ACS CATALYSIS, 11(12), 7186–7192.

author keywords: Fe/2OG enzyme; AsqJ; chemoenzymatic synthesis; rearrangement; quinolone
TL;DR: By leveraging the power of chemo-enzymatic synthesis, a library of quinolone alkaloids is effectively prepared through chemoenzymatic cascades, and the robustness of this method in gram-scale reactions is evaluated. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: July 19, 2021

2021 article

Identification of Cyclopropane Formation in the Biosyntheses of Hormaomycins and Belactosins: Sequential Nitration and Cyclopropanation by Metalloenzymes

Li, X., Shimaya, R., Dairi, T., Chang, W.-chen, & Ogasawara, Y. (2021, December 27). ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, Vol. 12.

By: X. Li n, R. Shimaya*, T. Dairi*, W. Chang n & Y. Ogasawara

author keywords: Biosynthesis; Cyclopropane; Metalloenzymes; Natural products; Peptides
MeSH headings : Catalysis; Cyclopropanes / chemistry; Cyclopropanes / metabolism; Depsipeptides / chemistry; Depsipeptides / metabolism; Intercellular Signaling Peptides and Proteins / chemistry; Intercellular Signaling Peptides and Proteins / metabolism; Metalloproteins / chemistry; Metalloproteins / metabolism; Molecular Structure
TL;DR: Observations disclose a novel pathway of cyclopropane ring construction and exemplify the new chemistry involving metalloenzymes in natural product biosynthesis. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: January 10, 2022

2020 journal article

Alternative Reactivity of Leucine 5-Hydroxylase Using an Olefin-Containing Substrate to Construct a Substituted Piperidine Ring

BIOCHEMISTRY, 59(21), 1961–1965.

Contributors: L. Cha n, S. Milikisiyants n, M. Davidson n, S. Xue*, T. Smirnova n, A. Smirnov n, Y. Guo*, W. Chang n

MeSH headings : Alkenes / chemistry; Alkenes / metabolism; Leucine / chemistry; Leucine / metabolism; Mixed Function Oxygenases / chemistry; Mixed Function Oxygenases / metabolism; Molecular Conformation; Nostoc / enzymology; Substrate Specificity
TL;DR: It is demonstrated that the activity of an Fe/2OG enzyme can be redirected when changing the targeted carbon hybridization from sp3 to sp2 and the resulting epoxide subsequently undergoes intramolecular cyclization to form the substituted piperidine, 2S,5S-hydroxypipecolic acid. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: June 22, 2020

2020 article

An Effective Strategy to Introduce Carbon Isotopes by Simple Swaps of CO2

Cha, L., & Chang, W.-chen. (2020, December). TRENDS IN CHEMISTRY, Vol. 2, pp. 1040–1042.

By: L. Cha n & W. Chang n

Contributors: L. Cha n & W. Chang n

Sources: Web Of Science, ORCID
Added: January 4, 2021

2020 journal article

Epoxidation Catalyzed by the Nonheme Iron(II)- and 2-Oxoglutarate-Dependent Oxygenase, AsqJ: Mechanistic Elucidation of Oxygen Atom Transfer by a Ferryl Intermediate

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 142(13), 6268–6284.

By: J. Li*, H. Liao*, Y. Tang*, J. Huang n, L. Cha n, T. Lin*, J. Lee*, I. Kurnikov* ...

Contributors: J. Li*, H. Liao*, Y. Tang*, J. Huang n, L. Cha n, T. Lin*, J. Lee*, I. Kurnikov* ...

MeSH headings : Aspergillus nidulans / chemistry; Aspergillus nidulans / enzymology; Aspergillus nidulans / metabolism; Crystallography, X-Ray; Epoxy Compounds / chemistry; Epoxy Compounds / metabolism; Fungal Proteins / chemistry; Fungal Proteins / metabolism; Iron / chemistry; Iron / metabolism; Ketoglutaric Acids / metabolism; Models, Molecular; Oxygen / chemistry; Oxygen / metabolism; Oxygenases / chemistry; Oxygenases / metabolism
TL;DR: A detailed study on epoxidation catalyzed by the non-heme iron- and 2-oxoglutarate-dependent (Fe/2OG) oxygenase, AsqJ, with mechanistic insights on the nature of the para substituents of the substrate during the OAT step. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: May 26, 2020

2020 journal article

Pathway from N-Alkylglycine to Alkylisonitrile Catalyzed by Iron(II) and 2-Oxoglutarate-Dependent Oxygenases

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 59(19), 7367–7371.

Contributors: T. Chen n, J. Chen*, Y. Tang*, J. Zhou*, Y. Guo* & W. Chang n

author keywords: catalysis; decarboxylation; enzymes; iron; reaction mechanisms
MeSH headings : Catalysis; Glycine / analogs & derivatives; Glycine / chemical synthesis; Hydroxylation; Iron / chemistry; Models, Molecular; Nitriles / chemical synthesis; Nuclear Magnetic Resonance, Biomolecular; Oxidation-Reduction; Procollagen-Lysine, 2-Oxoglutarate 5-Dioxygenase / chemistry; X-Ray Diffraction
TL;DR: The plausible mechanism of three Fe/2OG enzymes, Sav607, ScoE and SfaA, catalyzed isonitrile formation is reported, and the X-ray structures of iron loaded ScoE in complex with its substrate and the intermediate, along with biochemical and biophysical data reveal that -N≡C bond formation involves two cycles of Fe/ 2OG enzyme catalysis. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, ORCID
Added: May 8, 2020

2019 journal article

A New Microbial Pathway for Organophosphonate Degradation Catalyzed by Two Previously Misannotated Non-Heme-Iron Oxygenases

BIOCHEMISTRY, 58(12), 1627–1647.

By: L. Rajkovich, M. Pandelia*, A. Mitchell*, W. Chang*, B. Zhang*, A. Boal*, C. Krebs*, J. Bollinger*

Contributors: L. Rajakovich*, M. Pandelia*, A. Mitchell*, W. Chang*, B. Zhang*, A. Boal*, C. Krebs*, J. Bollinger*

MeSH headings : Aminoethylphosphonic Acid / analogs & derivatives; Aminoethylphosphonic Acid / chemistry; Bacterial Proteins / chemistry; Bacterial Proteins / genetics; Escherichia coli / genetics; Humans; Iron / chemistry; Ketoglutaric Acids / chemistry; Organophosphonates; Organophosphorus Compounds / chemistry; Oxidation-Reduction; Oxygenases / chemistry; Oxygenases / genetics; Pseudomonas / enzymology; Rhodobacteraceae / enzymology; Substrate Specificity
TL;DR: The structural and functional characterization of two non-heme-iron oxygenases, TmpA and TmpB, which are encoded by a genomically clustered pair of genes found in more than 350 species of bacteria are described, suggesting that they have evolved specifically to degrade TMAEP, which was not previously known to be subject to microbial catabolism. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: April 15, 2019

2019 journal article

Reaction Mechanism of a Nonheme Iron Enzyme Catalyzed Oxidative Cyclization via C-C Bond Formation

ORGANIC LETTERS, 21(1), 228–232.

By: W. Chang n, Z. Yang*, Y. Tu* & T. Chien*

Contributors: W. Chang n, Z. Yang*, Y. Tu* & T. Chien*

MeSH headings : Biocatalysis; Cyclization; Molecular Conformation; Nonheme Iron Proteins / metabolism; Oxidation-Reduction; Podophyllotoxin / biosynthesis; Podophyllotoxin / chemistry; Stereoisomerism
TL;DR: The results indicate that the originally proposed hydroxylated intermediate is unlikely to be involved in this reaction, and the formation of benzylic radical/carbocation intermediate can be utilized to trigger the C-C bond formation to construct theC-ring of (-)-podophyllotoxin. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, ORCID
Added: January 28, 2019

2019 journal article

Repurposing Nonheme Iron Hydroxylases To Enable Catalytic Nitrile Installation through an Azido Group Assistance

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 141(8), 3419–3423.

By: M. Davidson n, M. McNamee n, R. Fan*, Y. Guo* & W. Chang n

Contributors: M. Davidson n, M. McNamee n, R. Fan*, Y. Guo* & W. Chang n

TL;DR: It is demonstrated that these enzymes can accommodate leucine isomers and catalyze regiospecific hydroxylation and can catalyze non-native nitrile group installation when an azido group is introduced. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: March 25, 2019

2019 article

Unraveling flavoenzyme reaction mechanisms using flavin analogues and linear free energy relationships

NEW APPROACHES FOR FLAVIN CATALYSIS, Vol. 620, pp. 167–188.

By: C. Thibodeaux*, W. Chang n & H. Liu*

Contributors: C. Thibodeaux*, W. Chang n & H. Liu*

MeSH headings : Enzyme Assays / methods; Enzymes / chemistry; Flavins / chemistry; Flavoproteins / chemistry; Kinetics; Oxidation-Reduction; Thermodynamics
TL;DR: Methods for the chemoenzymatic preparation and purification of flavin analogs, the reconstitution of apo-flavoenzymes with these analogues, and the use of linear free energy relationships (LFERs) to correlate the perturbations induced by the altered substituents are detailed. (via Semantic Scholar)
UN Sustainable Development Goal Categories
2. Zero Hunger (Web of Science)
7. Affordable and Clean Energy (OpenAlex)
13. Climate Action (Web of Science)
Sources: Web Of Science, ORCID
Added: December 30, 2019

2018 journal article

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

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 140(45), 15190–15193.

Contributors: C. Yu n, Y. Tang*, L. Cha n, S. Milikisiyants n, T. Smirnova n, A. Smirnov n, Y. Guo*, W. Chang n

MeSH headings : Alkenes / chemistry; Alkenes / metabolism; Biocatalysis; Decarboxylation; Molecular Structure; Nonheme Iron Proteins / metabolism
TL;DR: Experimental observations imply that a pathway involving an initial C-H activation followed by a benzylic carbocation species or by electron transfer coupled β-scission is likely utilized to complete C═C bond formation. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: December 10, 2018

2018 journal article

Insights into the Desaturation of Cyclopeptin and its C3 Epimer Catalyzed by a non-Heme Iron Enzyme: Structural Characterization and Mechanism Elucidation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 57(7), 1831–1835.

By: H. Liao*, J. Li*, J. Huang n, M. Davidson n, I. Kurnikov*, T. Lin*, J. Lee*, M. Kurnikova* ...

Contributors: H. Liao*, J. Li*, J. Huang n, M. Davidson n, I. Kurnikov*, T. Lin*, J. Lee*, M. Kurnikova* ...

author keywords: carbocations; C-C bond formation; desaturation; enzyme mechanisms; viridicatin
MeSH headings : Aspergillus nidulans / enzymology; Biocatalysis; Catalytic Domain; Cytochrome P-450 Enzyme System / metabolism; Epoxy Compounds / chemistry; Epoxy Compounds / metabolism; Ferric Compounds / chemistry; Fungal Proteins / chemistry; Fungal Proteins / metabolism; Ketoglutaric Acids / chemistry; Ketoglutaric Acids / metabolism; Molecular Dynamics Simulation; Peptides / chemistry; Peptides / metabolism; Quantum Theory; Stereoisomerism
TL;DR: Findings suggest that a pathway involving hydrogen atom abstraction at the C10 position of the substrate by a short-lived FeIV -oxo species and the subsequent formation of a carbocation or a hydroxylated intermediate is preferred during AsqJ-catalyzed desaturation. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2018 journal article

Installation of the Ether Bridge of Lolines by the Iron- and 2-Oxoglutarate-Dependent Oxygenase, LolO: Regio- and Stereochemistry of Sequential Hydroxylation and Oxacyclization Reactions

Biochemistry, 57(14), 2074–2083.

By: J. Pan*, M. Bhardwaj*, B. Zhang*, W. Chang*, C. Schardl*, C. Krebs*, R. Grossman*, J. Bollinger*

Contributors: J. Pan*, M. Bhardwaj*, B. Zhang*, W. Chang*, C. Schardl*, C. Krebs*, R. Grossman*, J. Martin Bollinger*

MeSH headings : Alkaloids / chemistry; Epichloe / enzymology; Fungal Proteins / chemistry; Iron / chemistry; Ketoglutaric Acids / chemistry; Oxygenases / chemistry
TL;DR: The findings delineate the pathway to an important class of natural insecticides and lay the foundation for mechanistic dissection of the chemically challenging oxacyclization reaction. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Crossref, ORCID
Added: December 11, 2020

2018 journal article

Mechanistic Elucidation of Two Catalytically Versatile Iron(II)- and -Ketoglutarate-Dependent Enzymes: Cases Beyond Hydroxylation

COMMENTS ON INORGANIC CHEMISTRY, 38(4), 127–165.

By: W. Chang n, P. Liu* & Y. Guo*

Contributors: W. Chang n, P. Liu* & Y. Guo*

author keywords: alpha-ketoglutarate-dependentenzyme; Ferryl intermediate; Endoperoxidation; Epoxidation; Desaturation
TL;DR: The mechanisms of two newly discovered Fe/αKG enzymes are studied, revealing their strategies in controlling reactivity, namely the effect of redox/polar residues near the iron center, the electronic properties of the substrate, and the intrinsic reactivity of the ferryl intermediate. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, ORCID
Added: October 29, 2018

2018 journal article

Mechanistic Investigation of Oxidative Decarboxylation Catalyzed by Two Iron(II)- and 2-Oxoglutarate-Dependent Enzymes

BIOCHEMISTRY, 57(12), 1838–1841.

By: J. Huang n, Y. Tang*, C. Yu n, D. Sanyal n, X. Jia n, X. Liu*, Y. Guo*, W. Chang n

Contributors: J. Huang n, Y. Tang*, C. Yu n, D. Sanyal n, X. Jia n, X. Liu*, Y. Guo*, W. Chang n

MeSH headings : Carboxy-Lyases / chemistry; Catalysis; Iron / chemistry; Ketoglutaric Acids / chemistry
TL;DR: It is proposed that both IsnB and AmbI3 initiate stereoselective olefination via a benzylic C-H bond activation by an Fe(IV)-oxo intermediate, and the reaction likely proceeds through a radical- or carbocation-induced decarboxylation to complete C═C bond installation. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2018 journal article

Structural Basis for Superoxide Activation of Flavobacterium johnsoniae Class i Ribonucleotide Reductase and for Radical Initiation by Its Dimanganese Cofactor

Biochemistry, 57(18), 2679–2693.

By: H. Rose*, M. Ghosh*, A. Maggiolo*, C. Pollock*, E. Blaesi*, V. Hajj*, Y. Wei*, L. Rajakovich* ...

Contributors: H. Rose*, M. Ghosh*, A. Maggiolo*, C. Pollock*, E. Blaesi*, V. Hajj*, Y. Wei*, L. Rajakovich* ...

MeSH headings : Catalysis; Catalytic Domain; Flavobacterium / chemistry; Flavobacterium / enzymology; Flavoproteins / chemistry; Flavoproteins / metabolism; Iron / chemistry; Manganese / chemistry; Oxidation-Reduction; Oxygen / chemistry; Ribonucleotide Reductases / chemistry; Ribonucleotide Reductases / classification; Ribonucleotide Reductases / metabolism; Superoxides / chemistry; Tyrosine / chemistry
TL;DR: Structural comparisons suggest that the Id protein might most closely resemble the primordial RNR-β, as the structure of the protein rationalizes its distinctive traits. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: NC State University Libraries, ORCID
Added: August 6, 2018

2018 journal article

Substrate Conformation Correlates with the Outcome of Hyoscyamine 6β-Hydroxylase Catalyzed Oxidation Reactions

Journal of the American Chemical Society, 140(24), 7433–7436.

By: R. Ushimaru*, M. Ruszczycky*, W. Chang*, F. Yan*, Y. Liu* & H. Liu*

Contributors: R. Ushimaru*, M. Ruszczycky*, W. Chang*, F. Yan*, Y. Liu* & H. Liu*

MeSH headings : Atropine Derivatives / chemistry; Catalysis; Cyclization; Hydroxylation; Mixed Function Oxygenases / chemistry; Models, Chemical; Molecular Conformation; Oxidation-Reduction
TL;DR: Results indicate that hydroxyl rebound is unlikely to take place during the cyclization reaction and that the hydroxyase versus oxidative cyclase activity of H6H is correlated with the presence of an exo-hydroxy group having syn-periplanar geometry with respect to the adjacent H atom to be abstracted. (via Semantic Scholar)
Sources: Crossref, ORCID
Added: December 11, 2020

2018 journal article

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

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 140(23), 7116–7126.

By: N. Dunham*, W. Chang*, A. Mitchell*, R. Martinie*, B. Zhang*, J. Bergman*, L. Rajakovich*, B. Wang* ...

Contributors: N. Dunham*, W. Chang*, A. Mitchell*, R. Martinie*, B. Zhang*, J. Bergman*, L. Rajakovich*, B. Wang* ...

MeSH headings : Binding Sites; Deuterium / chemistry; Homoarginine / chemistry; Hydroxylation; Iron / chemistry; Ketoglutaric Acids / chemistry; Kinetics; Mixed Function Oxygenases / chemistry; Models, Chemical; Oxidation-Reduction; Stereoisomerism
TL;DR: The results suggest that, although the sequential-HAT mechanism is feasible, its geometric requirements may make competing hydroxylation unavoidable, thus explaining the presence of α-heteroatoms in nearly all native substrates for Fe/2OG desaturases. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2017 journal article

In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate

ORGANIC LETTERS, 19(5), 1208–1211.

By: W. Chang n, D. Sanyal n, J. Huang n, K. Ittiamornkui, Q. Zhu* & X. Liu*

Contributors: W. Chang n, D. Sanyal n, J. Huang n, K. Ittiamornkul*, Q. Zhu* & X. Liu*

MeSH headings : Amino Acids; Cyanides / chemistry; Molecular Structure
TL;DR: Establishment of a tractable isonitrile synthase system (AmbI1 and AmbI2) paves the way to elucidate the enigmatic enzyme mechanism for isocyanide formation. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2017 journal article

Structure-Guided Reprogramming of a Hydroxylase To Halogenate Its Small Molecule Substrate

BIOCHEMISTRY, 56(3), 441–444.

By: A. Mitchell, N. Dunham, J. Bergman, B. Wang, Q. Zhu*, W. Chang*, X. Liu*, A. Boal

Contributors: A. Mitchell, N. Dunham, J. Bergman, B. Wang, Q. Zhu*, W. Chang*, X. Liu*, A. Boal

MeSH headings : Bacterial Proteins / chemistry; Bacterial Proteins / genetics; Bacterial Proteins / metabolism; Biocatalysis; Burkholderia / enzymology; Burkholderia / genetics; Gene Expression; Green Chemistry Technology; Halogenation; Halogens / chemistry; Halogens / metabolism; Iron / chemistry; Iron / metabolism; Ketoglutaric Acids / chemistry; Ketoglutaric Acids / metabolism; Mixed Function Oxygenases / chemistry; Mixed Function Oxygenases / genetics; Mixed Function Oxygenases / metabolism; Oxidoreductases / chemistry; Oxidoreductases / genetics; Oxidoreductases / metabolism; Protein Engineering; Structural Homology, Protein; Substrate Specificity; Succinic Acid / chemistry; Succinic Acid / metabolism
TL;DR: This work identified a similar N-acyl amino acid hydroxylase and reprogrammed it to halogenate its substrate, thereby generating a new chiral haloalkyl center and highlights the potential of FeII/2OG enzymes as platforms for development of novel stereospecific catalysts for late-stage C-H functionalization. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2017 journal article

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

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 139(39), 13830–13836.

By: A. Mitchell*, N. Dipham, R. Martinie*, J. Bergman*, C. Pollock*, K. Hu*, B. Allen*, W. Chang* ...

Contributors: A. Mitchell*, N. Dunham*, R. Martinie*, J. Bergman*, C. Pollock*, K. Hu*, B. Allen*, W. Chang* ...

MeSH headings : Biocatalysis; Crystallography, X-Ray; Ferrous Compounds / chemistry; Ferrous Compounds / metabolism; Glutarates / chemistry; Glutarates / metabolism; Mixed Function Oxygenases / chemistry; Mixed Function Oxygenases / metabolism; Models, Molecular
TL;DR: Comparison of high-resolution X-ray crystal structures of the substrate complex, an Fe(II)-peroxysuccinate ferryl precursor, and a vanadium(IV)-oxo mimic of the ferryl intermediate in the l-arginine 3-hydroxylase, VioC, reveals coordinated motions of active site residues that appear to control the intermediate geometries to determine reaction outcome. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2016 journal article

Mechanistic Investigation of a Non-Heme Iron Enzyme Catalyzed Epoxidation in (-)-4 '-Methoxycyclopenin Biosynthesis

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 138(33), 10390–10393.

By: W. Chang n, J. Li*, J. Lee*, A. Cronican* & Y. Guo*

Contributors: W. Chang n, J. Li*, J. Lee*, A. Cronican* & Y. Guo*

MeSH headings : Alkenes / chemistry; Aspergillus nidulans / enzymology; Benzodiazepinones / chemistry; Benzodiazepinones / metabolism; Biocatalysis; Enzymes / metabolism; Epoxy Compounds / chemistry; Iron; Kinetics; Oxygen / chemistry
TL;DR: Using a combination of methods including transient kinetics, Mössbauer spectroscopy, and mass spectrometry, it is demonstrated that AsqJ-catalyzed (-)-4'-methoxycyclopenin formation uses a high-spin Fe(IV)-oxo intermediate to carry out epoxidation. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2016 journal article

Spectroscopic Evidence for the Two C–H-Cleaving Intermediates of Aspergillus nidulans Isopenicillin N Synthase

Journal of the American Chemical Society, 138(28), 8862–8874.

By: E. Tamanaha*, B. Zhang*, Y. Guo*, W. Chang*, E. Barr*, G. Xing*, J. St. Clair*, S. Ye* ...

Contributors: E. Tamanaha*, B. Zhang*, Y. Guo*, W. Chang*, E. Barr*, G. Xing*, J. St Clair*, S. Ye* ...

MeSH headings : Aspergillus nidulans / enzymology; Kinetics; Oxidoreductases / chemistry; Oxidoreductases / metabolism; Oxygen / metabolism; Quantum Theory; Spectrum Analysis
TL;DR: A combination of transient-state-kinetic and spectroscopic methods, together with the specifically deuterium-labeled substrates, are employed, to identify both C-H-cleaving intermediates, and the results show that they are high-spin Fe(III)-superoxo and high- spin Fe(IV)-oxo complexes, respectively, in agreement with published mechanistic proposals derived computationally from Baldwin's founding work. (via Semantic Scholar)
Sources: ORCID, Crossref
Added: January 11, 2021

2015 journal article

Assembly of the unusual oxacycles in the orthosomycin antibiotics

Proceedings of the National Academy of Sciences, 112(39), 11989–11990.

By: A. Boal*, J. Bollinger* & W. Chang*

Contributors: A. Boal*, J. Bollinger* & W. Chang*

MeSH headings : Aminoglycosides / chemistry; Anti-Bacterial Agents / chemistry; Oxygen / chemistry; Oxygenases / chemistry
TL;DR: Evidence is provided for two new reaction types by Fe/2OG oxygenases that would explain how two unusual structures, orthoester and dioxymethylene, are installed into the oligosaccharide antibiotics known as orthosomycins. (via Semantic Scholar)
Sources: ORCID, Crossref
Added: January 11, 2021

2015 journal article

Experimental correlation of substrate position with reaction outcome in the aliphatic halogenase, SyrB2

Journal of the American Chemical Society, 137(21), 6912–6919.

Contributors: R. Martinie*, J. Livada*, W. Chang*, M. Green*, C. Krebs*, J. Bollinger*, A. Silakov*

MeSH headings : Bacterial Proteins / chemistry; Bacterial Proteins / metabolism; Molecular Conformation; Pseudomonas syringae / enzymology; Substrate Specificity
TL;DR: The hypothesis that positioning of the targeted carbon dictates the outcome is tested, and an experimental correlation of position to outcome should aid in judging from structural data on other Fe/2OG enzymes whether they suppress hydroxylation or form Hydroxylated intermediates on the pathways to other outcomes. (via Semantic Scholar)
Source: ORCID
Added: January 11, 2021

2015 chapter

Mechanisms of 2-oxoglutarate-dependent oxygenases: The hydroxylation paradigm and beyond

In RSC Metallobiology: Vol. 2015-January (pp. 95–122).

TL;DR: The understanding of hydroxylation reactions mediated by Fe/2OG hydoxylases is summarized and recent advances in the elucidation of two of the ‘alternative’ reactivities (halogenation and stereoinversion) are reviewed. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: January 11, 2021

2015 journal article

Rapid Reduction of the Diferric-Peroxyhemiacetal Intermediate in Aldehyde-Deformylating Oxygenase by a Cyanobacterial Ferredoxin: Evidence for a Free-Radical Mechanism

Journal of the American Chemical Society, 137(36), 11695–11709.

MeSH headings : Acetals / chemistry; Aldehydes / chemistry; Cyanobacteria / chemistry; Electron Spin Resonance Spectroscopy; Ferredoxins / chemistry; Ferric Compounds / chemistry; Free Radicals / chemistry; Oxidation-Reduction; Oxygenases / chemistry; Spectroscopy, Mossbauer
TL;DR: The detection of these radicals under turnover conditions provides the most direct evidence to date for a free-radical mechanism in aldehyde-deformylating oxygenase, exposing an inefficiency of the enzyme in processing its radical intermediate. (via Semantic Scholar)
Sources: ORCID, Crossref
Added: January 11, 2021

2014 journal article

Direct nitration and azidation of aliphatic carbons by an iron-dependent halogenase

Nature Chemical Biology, 10(3), 209–215.

By: M. Matthews*, W. Chang*, A. Layne*, L. Miles*, C. Krebs* & J. Bollinger*

Contributors: M. Matthews*, W. Chang*, A. Layne*, L. Miles*, C. Krebs* & J. Bollinger*

MeSH headings : Azides / chemistry; Chromatography, Liquid; Coordination Complexes / chemistry; Enzymes / metabolism; Iron / chemistry; Ketoglutaric Acids / chemistry; Mass Spectrometry; Mutation; Nitrates / chemistry; Pseudomonas syringae / enzymology; Pseudomonas syringae / genetics
TL;DR: It is shown that the wild-type halogenase SyrB2 can indeed direct aliphatic nitration and azidation reactions by the same chemical logic and suggests unrecognized or untapped versatility in ferryl-mediated enzymatic C–H-bond activation. (via Semantic Scholar)
Sources: ORCID, Crossref
Added: January 11, 2021

2014 journal article

Mechanism of the C5 stereoinversion reaction in the biosynthesis of carbapenem antibiotics

Science, 343(6175), 1140–1144.

Contributors: W. Chang*, Y. Guo*, C. Wang*, S. Butch*, A. Rosenzweig*, A. Boal*, C. Krebs*, J. Bollinger Jr.

MeSH headings : Carbapenems / biosynthesis; Carbapenems / chemistry; Catalysis; Crystallography, X-Ray; Enzymes / chemistry; Enzymes / genetics; Escherichia coli; Hydrogen / chemistry; Oxidation-Reduction; Pectobacterium carotovorum / enzymology; Stereoisomerism; Tyrosine / chemistry
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: January 11, 2021

2014 journal article

Mechanistic Consequences of Chiral Radical Clock Probes: Analysis of the Mononuclear Non-Heme Iron Enzyme HppE with 2-Hydroxy-3-methylenecyclopropyl Radical Clock Substrates

Journal of the American Chemical Society, 136(8), 2944–2947.

By: H. Huang*, W. Chang*, G. Lin*, A. Romo*, P. Pai*, W. Russell*, D. Russell*, H. Liu*

Contributors: H. Huang*, W. Chang*, G. Lin*, A. Romo*, P. Pai*, W. Russell*, D. Russell*, H. Liu*

MeSH headings : Fosfomycin / biosynthesis; Organophosphonates / chemistry; Oxidoreductases / chemistry; Stereoisomerism
TL;DR: The results strongly suggest that an internal electron transfer to the iron center subsequent to C–H homolysis competes with ring-opening in the processing of the C2 radical intermediate of HppE-catalyzed reaction. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: ORCID, Crossref
Added: January 11, 2021

2013 journal article

Current development in isoprenoid precursor biosynthesis and regulation

Current Opinion in Chemical Biology, 17(4), 571–579.

By: W. Chang*, H. Song*, H. Liu* & P. Liu*

Contributors: W. Chang*, H. Song*, H. Liu* & P. Liu*

MeSH headings : Animals; Biosynthetic Pathways; Hemiterpenes / biosynthesis; Hemiterpenes / chemistry; Humans; Mevalonic Acid / metabolism; Organophosphorus Compounds / chemistry; Terpenes / chemistry; Terpenes / metabolism
TL;DR: This review summarizes the newly discovered IPP and DMAPP production pathways since late 1990s, their distribution among different kingdoms, and their roles in secondary metabolite production. (via Semantic Scholar)
Sources: ORCID, Crossref
Added: January 11, 2021

2013 journal article

Evidence that the fosfomycin-producing epoxidase, HppE, is a non-heme-iron peroxidase

Science, 342(6161), 991–995.

Contributors: C. Wang*, W. Chang*, Y. Guo*, H. Huang*, S. Peck*, M. Pandelia*, G. Lin*, H. Liu*, C. Krebs*, J. Bollinger Jr.

MeSH headings : Anti-Bacterial Agents / biosynthesis; Fosfomycin / biosynthesis; Hydrogen Peroxide / chemistry; Nonheme Iron Proteins / chemistry; Nonheme Iron Proteins / classification; Oxidoreductases / chemistry; Oxidoreductases / classification; Peroxidases / chemistry; Peroxidases / classification; Yersinia pseudotuberculosis / enzymology
TL;DR: It is shown here that the preferred cosubstrate is actually H2O2 and that HppE therefore almost certainly uses an iron(IV)-oxo complex as the H• abstractor, which expands the structural scope of iron-bearing peroxidase enzymes beyond heme motifs. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Source: ORCID
Added: January 11, 2021

2013 journal article

Mechanistic studies of an unprecedented enzyme-catalysed 1,2-phosphono-migration reaction

Nature, 496(7443), 114–118.

By: W. Chang*, M. Dey*, P. Liu*, S. Mansoorabadi*, S. Moon*, Z. Zhao*, C. Drennan*, H. Liu*

Contributors: W. Chang*, M. Dey*, P. Liu*, S. Mansoorabadi*, S. Moon*, Z. Zhao*, C. Drennan*, H. Liu*

MeSH headings : Biocatalysis; Biological Products / chemistry; Biological Products / metabolism; Crystallography, X-Ray; Fosfomycin / biosynthesis; Fosfomycin / chemistry; Fosfomycin / metabolism; Hydrogenation; Iron; Magnetic Resonance Spectroscopy; Models, Molecular; Nonheme Iron Proteins / chemistry; Nonheme Iron Proteins / metabolism; Organophosphonates / chemistry; Organophosphonates / metabolism; Oxidoreductases / chemistry; Oxidoreductases / metabolism; Substrate Specificity; Time Factors
TL;DR: It is shown that HppE also catalyses a biologically unprecedented 1,2-phosphono migration with the alternative substrate (R)-1-HPP, providing compelling evidence for the formation of a substrate-derived cation intermediate in the catalytic cycle of a mononuclear non-haem-iron-dependent enzyme. (via Semantic Scholar)
Sources: ORCID, Crossref
Added: January 11, 2021

2013 book

Methylerythritol phosphate pathway of isoprenoid biosynthesis

In Annual Review of Biochemistry (Vol. 82, pp. 497–530).

By: L. Zhao*, W. Chang*, Y. Xiao*, H. Liu* & P. Liu*

Contributors: L. Zhao*, W. Chang*, Y. Xiao*, H. Liu* & P. Liu*

author keywords: isoprenoids; biosynthesis; enzyme mechanism; metabolic engineering; synthetic biology; methylerythritol phosphate pathway; mevalonic acid pathway; MVA; MEP
MeSH headings : Biosynthetic Pathways / physiology; Catalysis; Erythritol / metabolism; Hemiterpenes / biosynthesis; Humans; Organophosphorus Compounds; Terpenes / metabolism
TL;DR: This review summarizes mechanistic insights on the MEP pathway enzymes and discusses recent advances in both MVA and MEP pathway-based synthetic biology, illustrated by reviewing the landmark work of artemisinic acid and taxadien-5α-ol production through microbial fermentations. (via Semantic Scholar)
Source: ORCID
Added: January 11, 2021

2013 journal article

Reaction of HppE with Substrate Analogues: Evidence for Carbon–Phosphorus Bond Cleavage by a Carbocation Rearrangement

Journal of the American Chemical Society, 135(22), 8153–8156.

By: W. Chang*, S. Mansoorabadi* & H. Liu*

Contributors: W. Chang*, S. Mansoorabadi* & H. Liu*

MeSH headings : Biocatalysis; Carbon / chemistry; Carbon / metabolism; Ketones / chemistry; Ketones / metabolism; Molecular Structure; Oxidoreductases / chemistry; Oxidoreductases / metabolism; Phosphorus / chemistry; Phosphorus / metabolism; Substrate Specificity
TL;DR: A series of substrate analogues were designed, synthesized, and used as mechanistic probes to study this novel enzymatic transformation and are consistent with a mechanism of HppE-catalyzed phosphono group migration that involves the formation of a carbocation intermediate. (via Semantic Scholar)
Sources: ORCID, Crossref
Added: January 11, 2021

2013 journal article

Substrate-Triggered Addition of Dioxygen to the Diferrous Cofactor of Aldehyde-Deformylating Oxygenase to Form a Diferric-Peroxide Intermediate

Journal of the American Chemical Society, 135(42), 15801–15812.

MeSH headings : Aldehyde-Lyases / chemistry; Aldehyde-Lyases / metabolism; Aldehydes / chemistry; Aldehydes / metabolism; Formates / chemistry; Formates / metabolism; Molecular Conformation; Nostoc / enzymology; Oxygen / chemistry; Oxygen / metabolism; Peroxides / chemistry; Peroxides / metabolism; Spectroscopy, Mossbauer; Substrate Specificity
TL;DR: The results represent the most definitive evidence to date that ADO can use a diiron cofactor (rather than a homo- or heterodinuclear cluster involving another transition metal) and provide support for a mechanism involving attack on the carbonyl of the bound substrate by the reduced O2 moiety to form a Fe2(III/III) complex with a bound peroxide. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: ORCID, Crossref
Added: January 11, 2021

2012 journal article

Enzymatic Chemistry of Cyclopropane, Epoxide, and Aziridine Biosynthesis

Chemical Reviews, 112(3), 1681–1709.

By: C. Thibodeaux*, W. Chang* & H. Liu*

Contributors: C. Thibodeaux*, W. Chang* & H. Liu*

MeSH headings : Animals; Aziridines / chemistry; Aziridines / metabolism; Cyclopropanes / chemistry; Cyclopropanes / metabolism; Enzymes / metabolism; Epoxy Compounds / chemistry; Epoxy Compounds / metabolism; Humans
TL;DR: In this review, the established biosynthetic strategies for construction of cyclopropane, epoxide, and aziridine rings are illustrated, focusing primarily on studies that were performed in the last decade. (via Semantic Scholar)
Sources: ORCID, Crossref
Added: January 11, 2021

2012 journal article

Evidence for Only Oxygenative Cleavage of Aldehydes to Alk(a/e)nes and Formate by Cyanobacterial Aldehyde Decarbonylases

Biochemistry, 51(40), 7908–7916.

Contributors: N. Li*, W. Chang*, D. Warui*, S. Booker*, C. Krebs* & J. Bollinger Jr.

MeSH headings : Aldehyde-Lyases / genetics; Aldehyde-Lyases / metabolism; Aldehydes / chemistry; Aldehydes / metabolism; Chromatography, Liquid; Cyanobacteria / enzymology; Formates / metabolism; Hexanes / chemistry; Hexanes / metabolism; Hydrolysis; Mass Spectrometry; Oxygen / chemistry; Oxygen / metabolism; Oxygen Isotopes / chemistry; Oxygen Isotopes / metabolism
TL;DR: For multiple combinations of the AD orthologue (Np and Pm), reducing system (protein-based and chemical), and substrate (n-heptanal and n-octadecanal), the preparations strictly require O(2) for activity and do not support detectable hydrolytic formate production, despite having catalytic activities similar to or greater than those reported by Marsh and co-workers. (via Semantic Scholar)
UN Sustainable Development Goal Categories
14. Life Below Water (OpenAlex)
Sources: ORCID, Crossref
Added: January 11, 2021

2012 journal article

Evidence for Radical-Mediated Catalysis by HppE: A Study Using Cyclopropyl and Methylenecyclopropyl Substrate Analogues

Journal of the American Chemical Society, 134(39), 16171–16174.

By: H. Huang*, W. Chang*, P. Pai*, A. Romo*, S. Mansoorabadi*, D. Russell*, H. Liu*

Contributors: H. Huang*, W. Chang*, P. Pai*, A. Romo*, S. Mansoorabadi*, D. Russell*, H. Liu*

MeSH headings : Biocatalysis; Cyclopropanes / chemistry; Cyclopropanes / metabolism; Enzyme Activation; Free Radicals / chemistry; Free Radicals / metabolism; Oxidation-Reduction; Oxidoreductases / metabolism; Phosphorous Acids / chemistry; Phosphorous Acids / metabolism
TL;DR: These findings provide, for the first time, experimental evidence for the involvement of a C2-centered radical intermediate with a lifetime on the order of nanoseconds in the HppE-catalyzed oxidation of (R)-HPP. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: ORCID, Crossref
Added: January 11, 2021

2012 journal article

Nucleophilic Participation of Reduced Flavin Coenzyme in Mechanism of UDP-galactopyranose Mutase

Journal of Biological Chemistry, 287(7), 4602–4608.

By: H. Sun*, M. Ruszczycky*, W. Chang*, C. Thibodeaux* & H. Liu*

Contributors: H. Sun*, M. Ruszczycky*, W. Chang*, C. Thibodeaux* & H. Liu*

MeSH headings : Catalysis; Escherichia coli / enzymology; Escherichia coli / genetics; Escherichia coli Proteins / chemistry; Escherichia coli Proteins / genetics; Escherichia coli Proteins / metabolism; Flavin-Adenine Dinucleotide / analogs & derivatives; Flavin-Adenine Dinucleotide / chemistry; Flavin-Adenine Dinucleotide / genetics; Flavin-Adenine Dinucleotide / metabolism; Intramolecular Transferases / chemistry; Intramolecular Transferases / genetics; Intramolecular Transferases / metabolism; Kinetics
TL;DR: A variety of F AD analogues were employed to characterize the role of FADred in the UGM catalytic cycle using positional isotope exchange (PIX) and linear free energy relationship studies, finding that these findings are most consistent with a chemical mechanism for UGM involving an SN2-type displacement of UDP from UDP-Galf/p by N5 of Fadred. (via Semantic Scholar)
UN Sustainable Development Goal Categories
7. Affordable and Clean Energy (OpenAlex)
Sources: ORCID, Crossref
Added: January 11, 2021

2011 journal article

Mechanistic Studies of an IspH-Catalyzed Reaction: Implications for Substrate Binding and Protonation in the Biosynthesis of Isoprenoids

Angewandte Chemie International Edition, 50(51), 12304–12307.

By: W. Chang*, Y. Xiao*, H. Liu* & P. Liu*

Contributors: W. Chang*, Y. Xiao*, H. Liu* & P. Liu*

author keywords: deoxyxylulose phosphate pathway; enzyme catalysis; isoprenoid biosynthesis; IspH enzyme; reaction mechanisms
MeSH headings : Binding Sites; Catalysis; Kinetics; Models, Molecular; Molecular Structure; Oxidoreductases / metabolism; Substrate Specificity; Terpenes / metabolism
TL;DR: Isoprenoids are found widely in nature and have remarkably diverse structures, including serving as structural components of cell membranes, key constituents of electron transport chains, and hormones to regulate various physiological processes. (via Semantic Scholar)
Sources: ORCID, Crossref
Added: January 11, 2021

2011 journal article

Study of IspH, a Key Enzyme in the Methylerythritol Phosphate Pathway Using Fluoro-Substituted Substrate Analogues

Organic Letters, 13(21), 5912–5915.

By: Y. Xiao*, W. Chang*, H. Liu* & P. Liu*

Contributors: Y. Xiao*, W. Chang*, H. Liu* & P. Liu*

MeSH headings : Alkyl and Aryl Transferases / metabolism; Biocatalysis; Erythritol / chemistry; Erythritol / metabolism; Fluorine Compounds / chemistry; Fluorine Compounds / metabolism; Models, Molecular; Molecular Structure; Oxidation-Reduction; Substrate Specificity; Sugar Phosphates / chemistry; Sugar Phosphates / metabolism
TL;DR: Studying of IspH using fluoro-substituted substrate analogues to dissect the contributions of several factors to IsPH catalysis, including the coordination of the HMBPP C(4)-OH group to the iron-sulfur cluster, the H-bonding network in the active site, and the electronic properties of the substrates, are reported. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: ORCID, Crossref
Added: January 11, 2021

2010 journal article

Linear Free Energy Relationships Demonstrate a Catalytic Role for the Flavin Mononucleotide Coenzyme of the Type II Isopentenyl Diphosphate:Dimethylallyl Diphosphate Isomerase

Journal of the American Chemical Society, 132(29), 9994–9996.

By: C. Thibodeaux*, W. Chang* & H. Liu*

Contributors: C. Thibodeaux*, W. Chang* & H. Liu*

MeSH headings : Biocatalysis; Carbon-Carbon Double Bond Isomerases / chemistry; Carbon-Carbon Double Bond Isomerases / metabolism; Electrons; Flavin Mononucleotide / chemistry; Flavin Mononucleotide / metabolism; Hemiterpenes; Kinetics; Linear Models; Oxidation-Reduction; Staphylococcus aureus / enzymology; Thermodynamics
TL;DR: The data presented in this work suggest that the reduced FMN coenzyme of IDI-2 functions as an acid/base catalyst, with the N5 atom of the flavin likely playing a critical role in the deprotonation of IPP en route to DMAPP formation. (via Semantic Scholar)
UN Sustainable Development Goal Categories
7. Affordable and Clean Energy (OpenAlex)
Sources: ORCID, Crossref
Added: January 11, 2021

2008 journal article

Evidence for the Involvement of Acid/Base Chemistry in the Reaction Catalyzed by the Type II Isopentenyl Diphosphate/Dimethylallyl Diphosphate Isomerase fromStaphylococcus aureus

Biochemistry, 47(8), 2547–2558.

By: C. Thibodeaux*, S. Mansoorabadi*, W. Kittleman*, W. Chang* & H. Liu*

Contributors: C. Thibodeaux*, S. Mansoorabadi*, W. Kittleman*, W. Chang* & H. Liu*

MeSH headings : Acids / chemistry; Amines / chemistry; Carbon-Carbon Double Bond Isomerases / chemistry; Carbon-Carbon Double Bond Isomerases / metabolism; Catalysis; Flavin Mononucleotide / metabolism; Hemiterpenes; Hydrogen-Ion Concentration; Isoenzymes / chemistry; Isoenzymes / metabolism; Models, Biological; Spectrophotometry, Ultraviolet; Staphylococcus aureus / enzymology
TL;DR: UV-vis spectral analysis of the IDI-2 reaction revealed the accumulation of a reduced neutral dihydroflavin intermediate when the reduced enzyme was incubated with IPP or DMAPP, suggesting that the C2-H bond of IPP is cleaved in the rate determining step and that general acid/base catalysis may be involved during turnover. (via Semantic Scholar)
Sources: ORCID, Crossref
Added: January 11, 2021

2008 journal article

Purification and Characterization of the Epoxidase Catalyzing the Formation of Fosfomycin from Pseudomonas syringae

Biochemistry, 47(33), 8726–8735.

By: J. Munos*, S. Moon*, S. Mansoorabadi*, W. Chang*, L. Hong*, F. Yan*, A. Liu*, H. Liu*

Contributors: J. Munos*, S. Moon*, S. Mansoorabadi*, W. Chang*, L. Hong*, F. Yan*, A. Liu*, H. Liu*

MeSH headings : Amino Acid Sequence; Cloning, Molecular; Flavin Mononucleotide / chemistry; Flavin Mononucleotide / metabolism; Fosfomycin / biosynthesis; Gene Expression Regulation, Bacterial / physiology; Iron / chemistry; Iron / metabolism; Molecular Sequence Data; NAD / chemistry; NAD / metabolism; Oxidoreductases / chemistry; Oxidoreductases / isolation & purification; Oxidoreductases / metabolism; Oxygen / chemistry; Oxygen / metabolism; Pseudomonas syringae / enzymology
Sources: ORCID, Crossref
Added: January 11, 2021

Employment

Updated: September 1st, 2018 12:54

2016 - present

North Carolina State University Raleigh, NC, US
Chemistry

2011 - 2015

Pennsylvania State University University Park, PA, US

2003 - 2005

mandatory Military Service Kinmen , TW

Education

Updated: October 11th, 2019 13:50

2005 - 2011

University of Texas at Austin Austin, TX, US

1999 - 2003

National Taiwan University Taipei, TW

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