ArticleJournal of the American Chemical Society2022
Recycling Upstream Redox Enzymes Expands the Regioselectivity of Cycloaddition in Pseudo-Aspidosperma Alkaloid Biosynthesis.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 28 citations in OpenAlex.
- Seasonal variation affects the accumulation of alkaloids in Amsonia elliptica.Journal of plant research · 2026Article
- Discovery of a Plant Pictet-Spenglerase With R-Stereoselectivity.Angewandte Chemie (International ed. in English) · 2026Article
- Protein-Protein Interactions Modulate a Key Branch Point in Monoterpene Indole Alkaloid Biosynthesis.ACS chemical biology · 2026Article
- Ipecac alkaloid biosynthesis in two evolutionarily distant plants.Nature chemical biology · 2025Article
- Stereochemical insights into sarpagan and akuammiline alkaloid biosynthesis.The New phytologist · 2025Article
- A Tight-Knit Family: The Medium-Chain Dehydrogenase/Reductases of Monoterpene Indole Alkaloid Biosynthesis.Biochemistry · 2025Review
- Reverse prenylation in plants by non-canonical aromatic prenyltransferases.The Plant journal : for cell and molecular biology · 2025Article
- Oxidation of four monoterpenoid indole alkaloid classes by three cytochrome P450 monooxygenases from Tabernaemontana litoralis.The Plant journal : for cell and molecular biology · 2024Article
- Regiodivergent biosynthesis of bridged bicyclononanes.Nature communications · 2024Article
- Evolution and diversification of carboxylesterase-like [4+2] cyclases in aspidosperma and iboga alkaloid biosynthesis.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Emerging functions within the enzyme families of plant alkaloid biosynthesis.Phytochemistry reviews : proceedings of the Phytochemical Society of Europe · 2023Article
- Reinventing metabolic pathways: Independent evolution of benzoxazinoids in flowering plants.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Photoexcited Ru single-atomic sites for efficient biomimetic redox catalysis.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
Corrections and comments
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Authors and funding
9 authors at 2 institutions in 2 countries.
Funding
Abstract
Nature uses cycloaddition reactions to generate complex natural product scaffolds. Dehydrosecodine is a highly reactive biosynthetic intermediate that undergoes cycloaddition to generate several alkaloid scaffolds that are the precursors to pharmacologically important compounds such as vinblastine and ibogaine. Here we report how dehydrosecodine can be subjected to redox chemistry, which in turn allows cycloaddition reactions with alternative regioselectivity. By incubating dehydrosecodine with reductase and oxidase biosynthetic enzymes that act upstream in the pathway, we can access the rare pseudoaspidosperma alkaloids pseudo-tabersonine and pseudo-vincadifformine, both
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Registered trials
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