ArticleAngewandte Chemie (International ed. in English)2023
Biomimetic Approach to Diverse Coral Diterpenes from a Biosynthetic Scaffold.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Combining biocatalytic and radical retrosynthesis for efficient chemoenzymatic synthesis of natural products.Chemical Society reviews · 2025Review
- Pseudopterosin Biosynthesis: Unravelling a Decades Old Problem in Animal Specialized Metabolism.Journal of the American Chemical Society · 2025Article
- Discovery of a terpene synthase synthesizing a nearly non-flexible eunicellane reveals the basis of flexibility.Nature communications · 2024Article
- Brewing coral terpenes-A yeast based approach to soft coral terpene cyclases.Methods in enzymology · 2024Article
- Computation-guided scaffold exploration of 2Beilstein journal of organic chemistry · 2024Article
- Cytochrome P450 Mediated Cyclization in Eunicellane Derived Diterpenoid Biosynthesis.Angewandte Chemie (International ed. in English) · 2023Article
- Biosynthesis, enzymology, and future of eunicellane diterpenoids.Journal of industrial microbiology & biotechnology · 2023Review
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2 authors.
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Abstract
Thousands of coral terpenes originate from simple scaffolds that undergo oxidative tailoring. While corals are excellent sources of drug leads, the challenge of supplying structurally complex drug leads from marine organisms has sometimes slowed their development. Making this even more challenging, in comparison to other organisms, such as plants and microbes, for which the terpene literature is substantial, very little is known about how the unique coral terpenes are biosynthesized and elaborated in nature. In this study, we used a semisynthetic strategy to produce at gram scale in yeast the eunicellane scaffold that underlies >200 coral compounds. Synthetic oxidation reactions were explored, generating key scaffolds that reflect three of the four structural classes derived from eunicellane and enabling the first asymmetric syntheses of the natural products solenopodin C and klysimplexin Q. Biomimetic methods and detailed mechanistic studies of synthetic reactions shed light on potential enzymological reactivity, including the role of epoxide rearrangement in eunicellane biosynthesis.
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