ArticleJournal of the American Chemical Society2018
C-H Hydroxylation in Paralytic Shellfish Toxin Biosynthesis.
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 41 papers.
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Who cites it
41 citing papers in PubMed, 77 citations in OpenAlex.
- Hemolymph-Mediated Dynamics of Paralytic Shellfish Toxins and Tetrodotoxin in Scallops.Marine drugs · 2026Article
- Pyrazofurin Biosynthesis Involves Nonenzymatic Ring Contraction of a Pyridazine Intermediate Triggered by a Rieske Enzyme-Catalyzed Oxygenation.Journal of the American Chemical Society · 2025Article
- Article
- The Chemistry and Biology of the Tetrodotoxin Natural Product Family.Angewandte Chemie (International ed. in English) · 2025Review
- Temperature-Driven Intraspecific Diversity in Paralytic Shellfish Toxin Profiles of the Dinoflagellate Alexandrium pacificum and Intragenic Variation in the Saxitoxin Biosynthetic Gene, sxtA4.Microbial ecology · 2025Article
- Impact of Induced Fitting and Secondary Noncovalent Interactions on Site-Selective and Enantioselective C-H Functionalization of Arylcyclohexanes.Journal of the American Chemical Society · 2025Article
- A Fresh Perspective on Cyanobacterial Paralytic Shellfish Poisoning Toxins: History, Methodology, and Toxicology.Marine drugs · 2025Review
- Iridium porphyrin-catalysed asymmetric carbene insertion into primary N-adjacent C-H bonds with TON over 1000000.Nature communications · 2025Article
- Advanced Technologies for Large Scale Supply of Marine Drugs.Marine drugs · 2025Review
- Biosynthesis of guanidine-containing natural products in cyanobacteria.Journal of industrial microbiology & biotechnology · 2024Review
- Synthesis of Saxitoxin Biosynthetic Intermediates: Reveal the Mechanism for Formation of its Tricyclic Skeleton in Biosynthesis.Chemistry, an Asian journal · 2024Article
- Radical-Mediated Regiodivergent C(Chem catalysis · 2024Article
- Elucidating the Role of OACS environmental Au · 2024Article
- Purification and characterization of a Rieske oxygenase and its NADH-regenerating partner proteins.Methods in enzymology · 2024Article
- Custom tuning of Rieske oxygenase reactivity.Nature communications · 2023Article
- Non-Native Site-Selective Enzyme Catalysis.Chemical reviews · 2023Review
- Leveraging a Structural Blueprint to Rationally Engineer the Rieske Oxygenase TsaM.Biochemistry · 2023Article
- Engineering Rieske oxygenase activity one piece at a time.Current opinion in chemical biology · 2023Review
- Chemodivergent C(spNature catalysis · 2023Article
- Contrasting Mechanisms of Aromatic and Aryl-Methyl Substituent Hydroxylation by the Rieske Monooxygenase Salicylate 5-Hydroxylase.Biochemistry · 2023Article
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Authors and funding
7 authors at 3 institutions in 1 country.
Funding
Abstract
The remarkable degree of synthetic selectivity found in Nature is exemplified by the biosynthesis of paralytic shellfish toxins such as saxitoxin. The polycyclic core shared by saxitoxin and its relatives is assembled and subsequently elaborated through the installation of hydroxyl groups with exquisite precision that is not possible to replicate with traditional synthetic methods. Here, we report the identification of the enzymes that carry out a subset of C-H functionalizations involved in paralytic shellfish toxin biosynthesis. We have shown that three Rieske oxygenases mediate hydroxylation reactions with perfect site- and stereoselectivity. Specifically, the Rieske oxygenase SxtT is responsible for selective hydroxylation of a tricyclic precursor to the famous natural product saxitoxin, and a second Rieske oxygenase, GxtA, selectively hydroxylates saxitoxin to access the oxidation pattern present in gonyautoxin natural products. Unexpectedly, a third Rieske oxygenase, SxtH, does not hydroxylate tricyclic intermediates, but rather a linear substrate prior to tricycle formation, rewriting the biosynthetic route to paralytic shellfish toxins. Characterization of SxtT, SxtH, and GxtA is the first demonstration of enzymes carrying out C-H hydroxylation reactions in paralytic shellfish toxin biosynthesis. Additionally, the reactions of these oxygenases with a suite of saxitoxin-related molecules are reported, highlighting the substrate promiscuity of these catalysts and the potential for their application in the synthesis of natural and unnatural saxitoxin congeners.
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