ArticleNature chemical biology2013
Distinct mechanisms for spiro-carbon formation reveal biosynthetic pathway crosstalk.
Article in Nature chemical biology, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 56 papers.
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56 citing papers in PubMed, 153 citations in OpenAlex.
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- A unique mechanism involving cocatalysis of enzyme and nonenzyme to form β-carboline and spirotryprostatins inScience advances · 2025Article
- Whole-chromosome duplications drive antimicrobial resistance inbioRxiv : the preprint server for biology · 2025Article
- Mechanistic Perspective on C-N and C-S Bond Construction Catalyzed by Cytochrome P450 Enzymes.ACS bio & med chem Au · 2025Review
- Transcriptomic insights into the interplay between polyketide biosynthesis and other secondary metabolite biosynthetic clusters and biological pathways in entomopathogenFrontiers in microbiology · 2025Article
- Next-generation AMA1-based plasmids for enhanced heterologous expression in filamentous fungi.Microbial biotechnology · 2024Article
- Critical analysis of polycyclic tetramate macrolactam biosynthetic gene cluster phylogeny and functional diversity.Applied and environmental microbiology · 2024Article
- Elucidation of genes enhancing natural product biosynthesis through co-evolution analysis.Nature metabolism · 2024Article
- Novel anti-inflammatory diketopiperazine alkaloids from the marine-derived fungus Penicillium brasilianum.Applied microbiology and biotechnology · 2024Article
- Hydroxytryptophan biosynthesis by a family of heme-dependent enzymes in bacteria.Nature chemical biology · 2023Article
- Molecular Dynamics Simulations Guide Chimeragenesis and Engineered Control of Chemoselectivity in Diketopiperazine Dimerases.Angewandte Chemie (International ed. in English) · 2023Article
- Discovery of a cytochrome P450 enzyme catalyzing the formation of spirooxindole alkaloid scaffold.Frontiers in plant science · 2023Article
- Unexpected assembly machinery for 4(3H)-quinazolinone scaffold synthesis.Nature communications · 2022Article
- Total Heterologous Biosynthesis of Fungal Natural Products inJournal of natural products · 2022Review
- Data Science-Driven Analysis of Substrate-Permissive Diketopiperazine Reverse Prenyltransferase NotF: Applications in Protein Engineering and Cascade Biocatalytic Synthesis of (-)-Eurotiumin A.Journal of the American Chemical Society · 2022Article
- Molecular basis for coordinating secondary metabolite production by bacterial and plant signaling molecules.The Journal of biological chemistry · 2022Article
Corrections and comments
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Authors and funding
8 authors at 4 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Spirotryprostatins, an indole alkaloid class of nonribosomal peptides isolated from Aspergillus fumigatus, are known for their antimitotic activity in tumor cells. Because spirotryprostatins and many other chemically complex spiro-carbon-bearing natural products exhibit useful biological activities, identifying and understanding the mechanism of spiro-carbon biosynthesis is of great interest. Here we report a detailed study of spiro-ring formation in spirotryprostatins from tryprostatins derived from the fumitremorgin biosynthetic pathway, using reactants and products prepared with engineered yeast and fungal strains. Unexpectedly, FqzB, an FAD-dependent monooxygenase from the unrelated fumiquinazoline biosynthetic pathway, catalyzed spiro-carbon formation in spirotryprostatin A via an epoxidation route. Furthermore, FtmG, a cytochrome P450 from the fumitremorgin biosynthetic pathway, was determined to catalyze the spiro-ring formation in spirotryprostatin B. Our results highlight the versatile role of oxygenating enzymes in the biosynthesis of structurally complex natural products and indicate that cross-talk of different biosynthetic pathways allows product diversification in natural product biosynthesis.
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