ArticleJournal of the American Chemical Society2011
The mechanism of formation of N-formylkynurenine by heme dioxygenases.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 38 papers.
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Who cites it
38 citing papers in PubMed, 91 citations in OpenAlex.
- Compensatory pathways in tryptophan metabolism and immune regulation following IDO inhibition.Molecular biology reports · 2026Review
- Evidence for the Formation of an Iron(III)-Indolenylperoxo Intermediate During Indole Dioxygenation: Similarities with Heme Dioxygenases.Inorganic chemistry · 2026Article
- Monooxygenase Activity of Indoleamine 2,3-Dioxygenase.Journal of the American Chemical Society · 2026Article
- Substrate Analogs Implicate a Free Radical Pathway in Tyrosine Hydroxylase Catalysis.ACS catalysis · 2025Article
- Engineering auxin degradation into root-associated bacteria promotes plant growth.bioRxiv : the preprint server for biology · 2025Article
- Deciphering Tryptophan Oxygenation: Key Modulators of 2-Oxindole Formation in MarE.Angewandte Chemie (International ed. in English) · 2025Article
- Diverse Physiological Roles of Kynurenine Pathway Metabolites: Updated Implications for Health and Disease.Metabolites · 2025Review
- Non-targeted LC-MS metabolomics reveals serum metabolites for high-altitude adaptation in Tibetan donkeys.Scientific reports · 2025Article
- Heme-based dioxygenases: Structure, function and dynamics.Journal of inorganic biochemistry · 2024Review
- Hydroxytryptophan biosynthesis by a family of heme-dependent enzymes in bacteria.Nature chemical biology · 2023Article
- A Ferric-Superoxide Intermediate Initiates P450-Catalyzed Cyclic Dipeptide Dimerization.Journal of the American Chemical Society · 2023Article
- Indoleamine 2,3-Dioxygenase as a Therapeutic Target for Alzheimer's Disease and Geriatric Depression.Brain sciences · 2023Review
- In Vitro Antiglycation Potential of Erva-Baleeira (Antioxidants (Basel, Switzerland) · 2023Article
- Metabolism-Guided Optimization of Tryptophanol-Derived Isoindolinone p53 Activators.Pharmaceuticals (Basel, Switzerland) · 2023Article
- Combined spectroscopic and structural approaches to explore the mechanism of histidine-ligated heme-dependent aromatic oxygenases.Methods in enzymology · 2023Article
- Article
- A biosynthetic pathway to aromatic amines that uses glycyl-tRNA as nitrogen donor.Nature chemistry · 2022Article
- Design, synthesis and evaluation of tryptophan analogues as tool compounds to study IDO1 activity.RSC chemical biology · 2021Article
- A new regime of heme-dependent aromatic oxygenase superfamily.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
- Molecular Rationale for Partitioning between C-H and C-F Bond Activation in Heme-Dependent Tyrosine Hydroxylase.Journal of the American Chemical Society · 2021Article
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
Abstract
Heme dioxygenases catalyze the oxidation of L-tryptophan to N-formylkynurenine (NFK), the first and rate-limiting step in tryptophan catabolism. Although recent progress has been made on early stages in the mechanism, there is currently no experimental data on the mechanism of product (NFK) formation. In this work, we have used mass spectrometry to examine product formation in a number of dioxygenases. In addition to NFK formation (m/z = 237), the data identify a species (m/z = 221) that is consistent with insertion of a single atom of oxygen into the substrate during O(2)-driven turnover. The fragmentation pattern for this m/z = 221 species is consistent with a cyclic amino acetal structure; independent chemical synthesis of the 3a-hydroxypyrroloindole-2-carboxylic acid compound is in agreement with this assignment. Labeling experiments with (18)O(2) confirm the origin of the oxygen atom as arising from O(2)-dependent turnover. These data suggest that the dioxygenases use a ring-opening mechanism during NFK formation, rather than Criegee or dioxetane mechanisms as previously proposed.
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