Front Cover

2024

Wenger, E. S.; Martinie, R. J.; Ushimaru, R.; Pollock, C. J.; Sil, D.; Li, A.; Hoang, N. H.; Palowitch, G, M.’ Graham, B. P.; Schaperdoth, I.; Burke, E. J.; Maggiolo, A.; Chang, W.-c; Allen, B. D.; Krebs, C.; Silakov, A.; Boal, A. K.; Bollinger, J. M.. “Optimized Substrate Positioning Enables Switches in the C−H Cleavage Site and Reaction Outcome in the Hydroxylation−Epoxidation Sequence Catalyzed by Hyoscyamine 6β-Hydroxylase” J. Am. Chem. Soc. 2024, 146, 24271-24287.

Paris, J. C.; Cheng, Y. H.; Zhang, T.; *Chang, W.-c.; Liu, P.; Guo, Y. “New Frontiers in Nonheme Enzymatic Oxyferryl Species” ChemBioChem, 2024, e202400307.

Bashira, G.; Bulloch, E. M. M.; Bramley, W. R.; Davison, M.; Stuteley, S. M.; Youn, P. G.; Harris, P. W. R.; Naqvi, M. S. H.; Middledditch, M. J.; Schimitz, M. Chang,. W.-c.; Baker, E. N.; Squitr, C. J. “Poly-γ-glutamylation of biomolecules” Nat. Commun. 2024, 15, 1310.

Chen, T.-Y.; Chen, J.; Ruszczycky, M. W.; Hilovsky, D.; Hostetler, T.; Liu, X.; Zhou, J, *Chang, W.-c. “Variation in Biosynthesis and Metal-Binding Properties of Isonitrile-Containing Peptides Produced by Mycobacteria versus Streptomyces” ACS Catal. 2024, 14, 4975-4983. (selected as the journal cover)

Micheal, C; *Chang, W.-c. “A survey of C–C bond formation strategies and mechanism deployed by iron-containing enzymes in natural products” Tetrahedron, 2024, 161, 134084

Chen, T.-Y.; Cha, L.; Paris, J.C.; Guo, Y;  *Chang, W.-c. “Cyclopropanation and aziridination catalyzed by non-heme iron and 2-oxoglutarate dependent enzymes” Methods in Enzymology 2024

Xue, S.; Tang, Y.; Kumikov, I. V.; Li, J.; Laio, H.-J.; Chen, N.-L.; Kurnkova, M. G.; *Chang, W.-c.; Guo, Y. “Spectroscopic and Computational Studies of a Bifunctional Iron- and 2-Oxoglutarate Dependent Enzymes, AsqJ” Methods in Enzymology 2024

2023

Canty, N. K.; *Chang, W.-c. “Current understanding of lignan biosynthesis” Arkivoc 2023, 202312006 (TL-12006OR)

Phan, H. N; Manley, O. M.; Skirboll, S. S.; Cha, L.; Hilovsky, D.; Chang,. W.-c.; Thompson, P. M.; Liu, X.; Makris, T. M. “Excision of a Protein-Derived Amine for p-Aminobenzoate Assembly by the Self-Sacrificial Heterobimetallic Protein CADD” Biochemistry 2023, 62, 3267-3282.

Ushimaru, R.; Cha, L.; Shimo, S.; Li, X.; Paris, J. C.; Mori, T.; Miyamoto, K.; Coffer, L.; Uchiyama, M.; Guo, Y.; *Chang, W.-c.; Abe, I. “Mechanistic Analysis of Stereodivergent Nitroalkane Cyclopropanation Catalyzed by Nonheme Iron Enzymes” J. Am. Chem. Soc. 2023, 145, 24210-24217.

Cha, L.; Yao, A.; *Chang, W.-c. “Detailed Computational Analysis Reveals the Molecular Basis of FTO Catalysis” Chem. Catalysis 2023, 3, 100763.

Paris, J. C.; Hu, S.; Wen, A.; Weitz, A. C.; Cheng, R.; Gee, L. B.; Tang, Y.; Kim, H.; Vegas, A.; *Chang, W.-c.; Elliott, S. J.; Liu, P.; Gao, Y. “An S=1 Iron(IV) Intermediate Revealed in a Non-Heme Iron Enzyme-Catalyzed Oxidative C−S Bond Formation” Angew. Chem. Int. Ed. 2023, e202309362.

Wang, B.; Lu, Y.; Cha, L.; Chen, T.-Y.; Palacios, P. M.; Guo, Y.; *Chang, W.-c.; Chen, C. “Repurposing Iron‐and 2‐Oxoglutarate‐Dependent Oxygenases to Catalyze Olefin Hydration” Angew. Chem. Int. Ed. 2023, e202311099.

Gering, H. E.; Li, X.; Tang, H.; Swartz, P. D.; Chang, W.-c.; Makris, T. M. “A Ferric-Superoxide Intermediate Initiates P450-Catalyzed Cyclic Dipeptide Dimerization” J. Am. Chem. Soc. 2023, 145, 19256-19264.

Chen, T.-Y.; Guo, Y; *Chang, W.-c. “Iron and 2-Oxoglutarate-Dependent Isonitrile-Forming Enzymes” Encyclopedia of Inorganic and Bioinorganic Chemistry 2023, eibc2838.

Cha, L.; Paris, J. C.; Zanella, B.; Spletzer. M.; Yao, A. Guo, Y.; *Chang, W.-c. “Mechanistic Studies of Aziridine Formation Catalyzed by Mononuclear Non-Heme Iron Enzymes” J. Am. Chem. Soc. 2023, 145, 3240-6246

2022

W Kim, TY Chen, L Cha, G Zhou, K Xing, NK Canty, Y Zhang, *W.-c. Chang “Elucidation of divergent desaturation pathways in the formation of vinyl isonitrile and isocyanoacrylate.” Nat. Commun. 2022, 13: 5343.

X Li, S Xue, Y Guo, *W.-c. Chang “Mechanism of Methyldehydrofosmidomycin Maturation: Use Olefination to Enable Chain Elongation.” J. Am. Chem. Soc. 2022,144, 8257-8266.

TY Chen, Z Zheng, X Zhang, J Chen, L Cha, Y Tang, Y Guo, J Zhou, B Wang, H-w Liu, *W.-c. Chang “Deciphering the Reaction Pathway of Mononuclear Iron Enzyme-Catalyzed N≡C Triple Bond Formation in Isocyanide Lipopeptide and Polyketide Biosynthesis.” ACS Catal. 2022,12, 2270–2279.

X Li, R Shimaya, T Dairi, *W.-c. Chang, Y Ogasawara. “Identification of Cyclopropane Formation in the Biosyntheses of Hormaomycins and Belactosins: Sequential Nitration and Cyclopropanation by Metalloenzymes.” Angew. Chem. Int. Ed. 2022, 61, e202113189

H Tang, MH Wu, HY Lin, MR Han, YH Tu, ZI Yang, TC Chien, NL Chan, *W.-c. Chang “Mechanistic analysis of carbon-carbon bond formation by deoxypodophyllotoxin synthase.” PNAS. 2022, 119, e2113770119.

2021

OM Manley, H Tang, S Xue, Y Guo, *W.-c. Chang, TM Makris. “BesC Initiates C-C Cleavage through a Substrate-Triggered and Reactive Diferric-Peroxo Intermediate.” J. Am. Chem. Soc. 2021,143, 21416-21424.

TY Chen, *W.-c. Chang “A postreplicative C5-cytosine hypermodification triggered by bacteriophage methyltransferase and hydroxylase.” PNAS. 2021, 118, e2109992118

H Tang,  Y Tang, IV Kurnikov, H-J Liao, N-L Chan, MG Kurnikova, Y Guo, *W.-c. Chang “Harnessing the Substrate Promiscuity of Dioxygenase AsqJ and Developing Efficient Chemoenzymatic Synthesis for Quinolones.” ACS Catal. 2021,11, 7186–7192 (Editor’s choice; Front cover)

TY Chen, S Xue, WC Tsai, TC Chien, Y Guo, *W.-c. Chang “Deciphering Pyrrolidine and Olefin Formation Mechanism in Kainic Acid Biosynthesis” ACS Catal. 2021, 11, 278-282 (Front Cover)

2020

L Cha, *W.-c. Chang “An Effective Strategy to Introduce Carbon Isotopes by Simple Swaps of CO2.” Trends in Chemistry 2020,  2, 1040-1042

L Cha, S Milikisiyants, M Davidson, S Xue, T Smirnova, AI Smirnov, Y Guo, *W.-c. Chang “Alternative reactivity of leucine 5-hydroxylase using an olefin-containing substrate to construct substituted piperidine ring.”  Biochemistry. 2020, 59, 1961-1965 (Front cover)

TY Chen, J Chen, Y Tang, J Zhou, Y Guo, *W.-c. Chang “Pathway from N‐Alkylglycine to Alkylisonitrile Catalyzed by Iron (II) and 2‐Oxoglutarate‐Dependent Oxygenases.” Angew. Chem. Int. Ed. 2020,132, 7437-7441

J Li, H-j Liao, Y Tang, J-l Huang, L Cha, T-s Lin, J L Lee, IV Kurnikov, MG Kurnikova, *W.-c. Chang, N-l Chan, Y Guo. “Epoxidation catalyzed by the nonheme iron (II)-and 2-oxoglutarate-dependent oxygenase, AsqJ: Mechanistic elucidation of oxygen atom transfer by a ferryl intermediate.” J. Am. Chem. Soc. 2020, 142, 6268-6284 (Front cover)

L Cha, Y Tang, Y Guo, *W.-c. Chang “Olefin, Nitrile and Isonitrile Installation Catalyzed by Metalloenzymes.” Elsevier 2020

Y Guo, *W.-c. Chang, J Li, M Davidson. “Non-Heme Mono-Iron Enzymes: Co-Substrate-Dependent Dioxygen Activation.” Elsevier 2020

2019

LJ Rajakovich, M-E Pandelia, AJ Mitchell, W-c Chang, B Zhang, AK Boal, C Krebs, JM Bollinger Jr. 2019. A new microbial pathway for organophosphonate degradation catalyzed by two previously misannotated non-heme-iron oxygenases. Biochemistry 58 (12), 1627-1647

M Davidson, M McNamee, R Fan, Y Guo, W-c Chang. 2019. Repurposing Nonheme Iron Hydroxylases To Enable Catalytic Nitrile Installation through an Azido Group Assistance. Journal of the American Chemical Society 141 (8), 3419-3423

J Zhang, PH Fan, GM Lin, W-c Chang, H Liu. 2019. Recent Progress in Unusual Carbohydrate-Containing Natural Products Biosynthesis. Elsevier

CJ Thibodeaux, W-c Chang, H Liu. 2019. Unraveling flavoenzyme reaction mechanisms using flavin analogues and linear free energy relationships. Methods in enzymology 620, 167-188

 

2018

W-c Chang, ZJ Yang, YH Tu, TC Chien. 2018. Reaction mechanism of a nonheme iron enzyme catalyzed oxidative cyclization via C–C bond formation. Organic letters 21 (1), 228-232

C-p Yu, Y Tang, L Cha, S Milikisiyants, TI Smirnova, AI Smirnov, Y Guo, W-c Chang. 2018. 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

W-c Chang, P Liu, Y Guo. 2018. Mechanistic elucidation of two catalytically versatile iron (II)-and α-ketoglutarate-dependent enzymes: cases beyond hydroxylation. Comments on Inorganic Chemistry 38 (4), 127-165

R Ushimaru, MW Ruszczycky, W-c Chang, F Yan, Y Liu, H Liu. 2018. Substrate conformation correlates with the outcome of hyoscyamine 6β-hydroxylase catalyzed oxidation reactions. Journal of the American Chemical Society 140 (24), 7433-7436

NP Dunham, W-c Chang, AJ Mitchell, RJ Martinie, B Zhang, JA Bergman, LJ Rajakovich, B Wang, A Silakov, C Krebs, AK Boal, JM Bollinger Jr. 2018. Two distinct mechanisms for C–C desaturation by iron (II)-and 2-(oxo) glutarate-dependent oxygenases: Importance of α-heteroatom assistance. Journal of the American Chemical Society 140 (23), 7116-7126

HR Rose, MK Ghosh, AO Maggiolo, CJ Pollock, EJ Blaesi, V Hajj, Y Wei, LJ Rajakovich, W-c Chang, Y Han, M Hajj, C Krebs, A Silakov, M-E Pandelia, JM Bollinger Jr, AK Boal. 2018. 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

J Pan, M Bhardwaj, B Zhang, W-c Chang, CL Schardl, C Krebs, RB Grossman, JM Bollinger Jr. 2018. 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

JL Huang, Y Tang, CP Yu, D Sanyal, X Jia, X Liu, Y Guo, W-c Chang. 2018. Mechanistic investigation of oxidative decarboxylation catalyzed by two iron (II)-and 2-oxoglutarate-dependent enzymes. Biochemistry 57 (12), 1838-1841

H‐j Liao, J Li, J‐l Huang, M Davidson, I Kurnikov, T‐s Lin, JL Lee, M Kurnikova, Y Guo, N‐l Chan, W-c Chang. 2018. 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

 

2017

AJ Mitchell, NP Dunham, RJ Martinie, JA Bergman, CJ Pollock, K Hu, BD Allen, W-c Chang, A Silakov, JM Bollinger Jr, C Krebs, Amie K Boal. 2017. Visualizing the reaction cycle in an iron (II)-and 2-(oxo)-glutarate-dependent hydroxylase. Journal of the American Chemical Society 139 (39), 13830-13836

W-c Chang, D Sanyal, JL Huang, K Ittiamornkul, Q Zhu, X Liu. 2017. In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate. Organic letters 19 (5), 1208-1211

AJ Mitchell, NP Dunham, JA Bergman, B Wang, Q Zhu, W-c Chang, X Liu, AK Boal. 2017. Structure-guided reprogramming of a hydroxylase to halogenate its small molecule substrate. Biochemistry 56 (3), 441-444

 

2016

W-c Chang, J Li, JL Lee, AA Cronican, Y Guo. 2016. Mechanistic investigation of a non-heme iron enzyme catalyzed epoxidation in (−)-4′-methoxycyclopenin biosynthesis. Journal of the American Chemical Society 138 (33), 10390-10393

E Tamanaha, B Zhang, Y Guo, W-c Chang, EW Barr, G Xing, J St. Clair, S Ye, F Neese, JM Bollinger Jr, C Krebs. 2016. 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

 

2015

AK Boal, JM Bollinger, W-c Chang. 2015. Assembly of the unusual oxacycles in the orthosomycin antibiotics. Proceedings of the National Academy of Sciences 112 (39), 11989-11990

LJ Rajakovich, H Nørgaard, DM Warui, W-c Chang, N Li, SJ Booker, C Krebs, JM Bollinger Jr, M-E Pandelia. 2015. 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

RJ Martinie, J Livada, W-c Chang, MT Green, C Krebs, JM Bollinger Jr, A Silakov. 2015. Experimental correlation of substrate position with reaction outcome in the aliphatic halogenase, SyrB2. Journal of the American Chemical Society 137 (21), 6912-6919

JM Bollinger Jr, W-c Chang, ML Matthews, RJ Martinie, AK Boal, C Krebs. 2015. Mechanisms of 2-oxoglutarate-dependent oxygenases: the hydroxylation paradigm and beyond. 2-Oxoglutarate-dependent oxygenases, 95-122

 

2014

W-c Chang, Y Guo, C Wang, SE Butch, AC Rosenzweig, AK Boal, C Krebs, JM Bollinger. 2014. Mechanism of the C5 stereoinversion reaction in the biosynthesis of carbapenem antibiotics. Science 343 (6175), 1140-1144

ML Matthews, W-c Chang, AP Layne, LA Miles, C Krebs, JM Bollinger. 2014. Direct nitration and azidation of aliphatic carbons by an iron-dependent halogenase. Nature chemical biology 10 (3), 209-215

H Huang, W-c Chang, G-M Lin, A Romo, P-J Pai, WK Russell, DH Russell, H-W Liu. 2014. 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

 

2013

C Wang, W-c Chang, Y Guo, H Huang, SC Peck, ME Pandelia, G-m Lin, H-w Liu, C Krebs, JM Bollinger. 2013. Evidence that the fosfomycin-producing epoxidase, HppE, is a non–heme-iron peroxidase. Science 342 (6161), 991-995

ME Pandelia, N Li, H Nørgaard, DM Warui, LJ Rajakovich, W-c Chang, SJ Booker, C Krebs, JM Bollinger Jr. 2013. 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

W-c Chang, H Song, H Liu, P Liu. 2013. Current development in isoprenoid precursor biosynthesis and regulation. Current opinion in chemical biology 17 (4), 571-579

W-c Chang, SO Mansoorabadi, H Liu. 2013. 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

W-c Chang, M Dey, P Liu, SO Mansoorabadi, S-j Moon, ZK Zhao, CL Drennan, H-w Liu. 2013. Mechanistic studies of an unprecedented enzyme-catalysed 1, 2-phosphono-migration reaction. Nature 496 (7443), 114-118

L Zhao, W-c Chang, Y Xiao, H Liu, P Liu. 2013. Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annual review of biochemistry 82, 497

 

2012

N Li, W-c Chang, DM Warui, SJ Booker, C Krebs, JM Bollinger Jr. 2012. Evidence for only oxygenative cleavage of aldehydes to alk (a/e) nes and formate by cyanobacterial aldehyde decarbonylases. Biochemistry 51 (40), 7908-7916

H Huang, W-c Chang, P-J Pai, A Romo, SO Mansoorabadi, DH Russell, H-w Liu. 2012. 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

CJ Thibodeaux, W-c Chang, H Liu. 2012. Enzymatic chemistry of cyclopropane, epoxide, and aziridine biosynthesis. Chemical reviews 112 (3), 1681-1709

HG Sun, MW Ruszczycky, W-c Chang, CJ Thibodeaux, H Liu. 2012. Nucleophilic participation of reduced flavin coenzyme in mechanism of UDP-galactopyranose mutase. Journal of Biological Chemistry 287 (7), 4602-4608

 

2011

W-c Chang, Y Xiao, H Liu, P Liu. 2011. Mechanistic Studies of IspH-catalyzed Reaction Using Substrate Analogue: Implications for Substrate Binding and Protonation. Angewandte Chemie (International ed. in English) 50 (51), 12304

W-c Chang, Y Xiao, H Liu, P Liu. 2011. 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

Y Xiao, W-c Chang, H Liu, P Liu. 2011. Study of IspH, a key enzyme in the methylerythritol phosphate pathway using fluoro-substituted substrate analogues. Organic letters 13 (21), 5912-5915

 

2010

CJ Thibodeaux, W-c Chang, H Liu. 2010. 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

 

2008

JW Munos, S-J Moon, SO Mansoorabadi, W-c Chang, L Hong, F Yan, A Liu, H-w Liu. 2008. Purification and Characterization of the Epoxidase Catalyzing the Formation of Fosfomycin from Pseudomonas syringae. Biochemistry 47 (33), 8726-8735

CJ Thibodeaux, SO Mansoorabadi, W Kittleman, W-c Chang, H Liu. 2008. Evidence for the involvement of acid/base chemistry in the reaction catalyzed by the type II isopentenyl diphosphate/dimethylallyl diphosphate isomerase from Staphylococcus aureus. Biochemistry 47 (8), 2547-2558