ArticleJournal of the American Chemical Society2022
Intramolecular C-C Bond Formation Links Anthraquinone and Enediyne Scaffolds in Tiancimycin 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 9 papers.
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Who cites it
9 citing papers in PubMed.
- Mechanistic Perspective on C-N and C-S Bond Construction Catalyzed by Cytochrome P450 Enzymes.ACS bio & med chem Au · 2025Review
- Advances in the Study of Halogenated Natural Products.Current topics in medicinal chemistry · 2025Review
- Enediyne natural product biosynthesis unified by a diiodotetrayne intermediate.Nature chemical biology · 2024Article
- Article
- Cofactorless oxygenases guide anthraquinone-fused enediyne biosynthesis.Nature chemical biology · 2024Article
- Dynemicin A Derivatives as Potential Cancer Chemotherapeutics by Mutasynthesis.Helvetica chimica acta · 2023Article
- Normal and Aberrant Methyltransferase Activities Give Insights into the Final Steps of Dynemicin A Biosynthesis.Journal of the American Chemical Society · 2023Article
- A discrete intermediate for the biosynthesis of both the enediyne core and the anthraquinone moiety of enediyne natural products.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Examining Heterodimerization by Aryl C-N Coupling in Dynemicin Biosynthesis.ACS chemical biology · 2023Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
First discovered in 1989, the anthraquinone-fused enediynes are a class of DNA-cleaving bacterial natural products composed of a DNA-intercalating anthraquinone moiety and a 10-membered enediyne warhead. However, until recently, there has been a lack of genetically amenable hosts and sequenced biosynthetic gene clusters available for solving the biosynthetic questions surrounding these molecules. Herein, we have identified and biochemically and structurally characterized TnmK1, a member of the α/β-hydrolase fold superfamily responsible for the C-C bond formation linking the anthraquinone moiety and enediyne core together in tiancimycin (TNM) biosynthesis. In doing so, two intermediates, TNM H and TNM I, in anthraquinone-fused enediyne biosynthesis, containing an unprecedented cryptic C16 aldehyde group, were identified. This aldehyde plays a key role in the TnmK1-catalyzed C-C bond formation via a Michael addition, representing the first example of this chemistry for the α/β-hydrolase fold superfamily. Additionally, TNM I shows sub-nanomolar cytotoxicity against selected cancer cell lines, indicating a new mechanism of action compared to previously known anthraquinone-fused enediynes. Together, the findings from this study are expected to impact enzymology, natural product biosynthesis, and future efforts at enediyne discovery and drug development.
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