ArticleCell chemical biology2018
Snapshots of C-S Cleavage in Egt2 Reveals Substrate Specificity and Reaction Mechanism.
Article in Cell chemical biology, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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22 citing papers in PubMed, 46 citations in OpenAlex.
- Metabolic engineering ofSynthetic and systems biotechnology · 2026Article
- Natural Histidine Derivatives-From Basic Research to Potential Applications in Cosmetics and Nutricosmetics.Antioxidants (Basel, Switzerland) · 2026Review
- Biosynthesis of 6-thioguanine: characterizing two intermediates involved in its thioamide formation reaction.ACS catalysis · 2026Article
- The mechanism of thioamide formation by the YcfA-YcfC system in 6-thioguanine biosynthesis.Nature communications · 2025Article
- Molecular basis for the diversification of lincosamide biosynthesis by pyridoxal phosphate-dependent enzymes.Nature chemistry · 2025Article
- Ergothioneine biosynthesis: The present state and future prospect.Synthetic and systems biotechnology · 2025Review
- The Catalytic Mechanism of Key Enzymes Involved in the Synthesis of Ergothioneine inMolecules (Basel, Switzerland) · 2024Article
- Edible mycelium bioengineered for enhanced nutritional value and sensory appeal using a modular synthetic biology toolkit.Nature communications · 2024Article
- Structure of mycobacterial ergothioneine-biosynthesis C-S lyase EgtE.The Journal of biological chemistry · 2024Article
- Biochemical and Structural Characterization of OvoAACS catalysis · 2023Article
- HAntioxidants & redox signaling · 2023Article
- Enhancement of ergothioneine production by discovering and regulating its metabolic pathway in Cordyceps militaris.Microbial cell factories · 2022Article
- Ergothioneine: A Stress Vitamin with Antiaging, Vascular, and Neuroprotective Roles?Antioxidants & redox signaling · 2022Review
- Ergothioneine, Ovothiol A, and Selenoneine-Histidine-Derived, Biologically Significant, Trace Global Alkaloids.Molecules (Basel, Switzerland) · 2022Review
- Metabolic Adaptations to Marine Environments: Molecular Diversity and Evolution of Ovothiol Biosynthesis in Bacteria.Genome biology and evolution · 2021Article
- Implications for an imidazol-2-yl carbene intermediate in the rhodanase-catalyzed C-S bond formation reaction of anaerobic ergothioneine biosynthesis.ACS catalysis · 2021Article
- Chemical modifications of proteins and their applications in metalloenzyme studies.Synthetic and systems biotechnology · 2021Review
- The biology of ergothioneine, an antioxidant nutraceutical.Nutrition research reviews · 2020Review
- Successful biosynthesis of natural antioxidant ergothioneine in Saccharomyces cerevisiae required only two genes from Grifola frondosa.Microbial cell factories · 2020Article
- The complex evolutionary history of sulfoxide synthase in ovothiol biosynthesis.Proceedings. Biological sciences · 2019Article
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Authors and funding
12 authors at 2 institutions in 1 country.
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Abstract
Sulfur incorporation in the biosynthesis of ergothioneine, a histidine thiol derivative, differs from other well-characterized transsulfurations. A combination of a mononuclear non-heme iron enzyme-catalyzed oxidative C-S bond formation and a subsequent pyridoxal 5'-phosphate (PLP)-mediated C-S lyase reaction leads to the net transfer of a sulfur atom from a cysteine to a histidine. In this study, we structurally and mechanistically characterized a PLP-dependent C-S lyase Egt2, which mediates the sulfoxide C-S bond cleavage in ergothioneine biosynthesis. A cation-π interaction between substrate and enzyme accounts for Egt2's preference of sulfoxide over thioether as a substrate. Using mutagenesis and structural biology, we captured three distinct states of the Egt2 C-S lyase reaction cycle, including a labile sulfenic intermediate captured in Egt2 crystals. Chemical trapping and high-resolution mass spectrometry were used to confirm the involvement of the sulfenic acid intermediate in Egt2 catalysis.
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