ArticleJournal of the American Chemical Society2018
Elucidating the Reaction Pathway of Decarboxylation-Assisted Olefination Catalyzed by a Mononuclear Non-Heme Iron Enzyme.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed.
- Heme oxygenase-like dimetal oxidases and oxygenases.Biochemical Society transactions · 2026Review
- Biosynthesis of 14-Membered Cyclopeptide Alkaloids via Nonheme Iron- and 2-Oxoglutarate-Dependent Oxidative Decarboxylation.Journal of the American Chemical Society · 2026Article
- Biosynthesis of 14-membered cyclopeptide alkaloids via non-heme-iron- and 2-oxoglutarate-dependent oxidative decarboxylation.bioRxiv : the preprint server for biology · 2026Article
- Electronic Structure Contributions to the Reactivity of Mononuclear FeAccounts of chemical research · 2026Article
- Studies of Isonitrile Synthases Help Elucidate the Mechanism of Isonitrile Installation.ACS catalysis · 2025Article
- New Frontiers in Nonheme Enzymatic Oxyferryl Species.Chembiochem : a European journal of chemical biology · 2024Review
- Decarboxylation in Natural Products Biosynthesis.JACS Au · 2024Review
- Multinuclear non-heme iron dependent oxidative enzymes (MNIOs) involved in unusual peptide modifications.Current opinion in chemical biology · 2024Review
- Discovery and Characterization of Pyridoxal 5'-Phosphate-Dependent Cycloleucine Synthases.Journal of the American Chemical Society · 2024Article
- Biosynthesis of Macrocyclic Peptides with C-Terminal β-Amino-α-keto Acid Groups by Three Different Metalloenzymes.ACS central science · 2024Article
- 1,5-Disubstituted tetrazoles as PD-1/PD-L1 antagonists.RSC medicinal chemistry · 2024Article
- Biosynthesis of macrocyclic peptides with C-terminal β-amino-α-keto acid groups by three different metalloenzymes.bioRxiv : the preprint server for biology · 2024Article
- Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes.The Journal of organic chemistry · 2023Article
- Elucidation of divergent desaturation pathways in the formation of vinyl isonitrile and isocyanoacrylate.Nature communications · 2022Article
- Mechanism of Methyldehydrofosmidomycin Maturation: Use Olefination to Enable Chain Elongation.Journal of the American Chemical Society · 2022Article
- Probing the Mechanism of Isonitrile Formation by a Non-Heme Iron(II)-Dependent Oxidase/Decarboxylase.Journal of the American Chemical Society · 2022Article
- Mechanistic analysis of carbon-carbon bond formation by deoxypodophyllotoxin synthase.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- BesC Initiates C-C Cleavage through a Substrate-Triggered and Reactive Diferric-Peroxo Intermediate.Journal of the American Chemical Society · 2021Article
- C-H Bond Cleavage by Bioinspired Nonheme Metal Complexes.Inorganic chemistry · 2021Review
- A metabolic regulon reveals early and late acting enzymes in neuroactive Lycopodium alkaloid biosynthesis.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
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8 authors.
Funding
Abstract
Installation of olefins into molecules is a key transformation in organic synthesis. The recently discovered decarboxylation-assisted olefination in the biosynthesis of rhabduscin by a mononuclear non-heme iron enzyme ( P.IsnB) represents a novel approach in olefin construction. This method is commonly employed in natural product biosynthesis. Herein, we demonstrate that a ferryl intermediate is used for C-H activation at the benzylic position of the substrate. We further establish that P.IsnB reactivity can be switched from olefination to hydroxylation using electron-withdrawing groups appended on the phenyl moiety of the analogues. These 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.
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