ArticleJournal of the American Chemical Society2024
Optimized Substrate Positioning Enables Switches in the C-H Cleavage Site and Reaction Outcome in the Hydroxylation-Epoxidation Sequence Catalyzed by Hyoscyamine 6β-Hydroxylase.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Experimental and Computational Elucidation of C(sp3)-H Fluorination Barriers in an Iron(II)- and 2-Oxoglutarate-Dependent Halogenase.Journal of the American Chemical Society · 2026Article
- Total Synthesis of (+)-12-The Journal of organic chemistry · 2026Article
- Rational Design of Hyoscyamine 6β-Hydroxylase for the Efficient Production of Scopolamine.Plant biotechnology journal · 2026Article
- Dynamic metal coordination controls chemoselectivity in a radical halogenase.Nature chemical biology · 2026Article
- 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
- Regio- and Stereoselective Halogenation by an Iron(II)- and 2-Oxoglutarate-Dependent Halogenase in the Biosynthesis of Halogenated Nucleosides.Journal of the American Chemical Society · 2025Article
- Refining the Substrate-Cofactor Disposition Model of Hyoscyamine 6β-Hydroxylase Catalysis Using Hyoscyamine Analogs.Journal of the American Chemical Society · 2025Article
- Unusual O-H Activation-Initiated C-C Bond Cleavage Reaction by a Nonheme Fe Enzyme in Antifungal Nucleoside Biosynthesis.Journal of the American Chemical Society · 2025Article
- Three distinct strategies lead to programmable aliphatic C-H oxidation in bicyclomycin biosynthesis.Nature communications · 2025Article
- Discovery of Noncanonical Iron and 2-Oxoglutarate Dependent Enzymes Involved in C-C and C-N Bond Formation in Biosynthetic Pathways.ACS bio & med chem Au · 2025Review
- Comparison of a Nonheme Iron Cyclopropanase with a Homologous Hydroxylase Reveals Mechanistic Features Associated with Distinct Reaction Outcomes.Journal of the American Chemical Society · 2025Article
- Sequential oxidation of L-lysine by a non-heme iron hydroxylase.bioRxiv : the preprint server for biology · 2025Article
- An Unusual Ferryl Intermediate and Its Implications for the Mechanism of Oxacyclization by the Loline-Producing Iron(II)- and 2-Oxoglutarate-Dependent Oxygenase, LolO.Biochemistry · 2024Article
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18 authors.
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Abstract
Hyoscyamine 6β-hydroxylase (H6H) is an iron(II)- and 2-oxoglutarate-dependent (Fe/2OG) oxygenase that produces the prolifically administered antinausea drug, scopolamine. After its namesake hydroxylation reaction, H6H then couples the newly installed C6 oxygen to C7 to produce the drug's epoxide functionality. Oxoiron(IV) (ferryl) intermediates initiate both reactions by cleaving C-H bonds, but it remains unclear how the enzyme switches the target site and promotes (C6)O-C7 coupling in preference to C7 hydroxylation in the second step. In one possible epoxidation mechanism, the C6 oxygen would─analogously to mechanisms proposed for the Fe/2OG halogenases and, in our more recent study,
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