ArticleJournal of the American Chemical Society2014
Generation of complexity in fungal terpene biosynthesis: discovery of a multifunctional cytochrome P450 in the fumagillin pathway.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 105 citations in OpenAlex.
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- Self-Resistance as a Functional Beacon: Target-Directed Microbial Genome Mining from Classical Discovery to Automated Pipelines.Microorganisms · 2026Review
- Discovery of a dimeric isopimarane derivative by reexploring a labdane-related diterpenoid biosynthetic gene cluster in Aspergillus nidulans.Microbial cell factories · 2026Article
- Expression of a strain-specific non-ribosomal peptide synthetase from Aspergillus lentulus lead to the discovery of a new fungal alkaloid lentoquinazoline.The Journal of antibiotics · 2026Article
- Engineering terpene synthases and their substrates for the biocatalytic production of terpene natural products and analogues.Chemical communications (Cambridge, England) · 2025Review
- Uncovering the genetic basis of antiviral polyketide limocrocin biosynthesis through heterologous expression.Microbial cell factories · 2025Article
- Research Progress in Mutagenesis Techniques forMini reviews in medicinal chemistry · 2025Review
- Combinatorial biosynthesis for the engineering of novel fungal natural products.Communications chemistry · 2024Review
- Prokaryotic expression and characterization of artificial self-sufficient CYP120A monooxygenases.Applied microbiology and biotechnology · 2023Article
- Fungal P450 Deconstructs the 2,5-Diazabicyclo[2.2.2]octane RingJournal of the American Chemical Society · 2023Article
- Late-stage cascade of oxidation reactions during the biosynthesis of oxalicine B inActa pharmaceutica Sinica. B · 2023Article
- Combinatorial Biosynthesis of Terpenoids through Mixing-and-Matching Sesquiterpene Cyclase and Cytochrome P450 Pairs.Organic letters · 2022Article
- Peculiarities of meroterpenoids and their bioproduction.Applied microbiology and biotechnology · 2021Review
- Recent developments in self-resistance gene directed natural product discovery.Natural product reports · 2020Review
- Fumagillin, a Mycotoxin ofToxins · 2019Review
- Detecting and prioritizing biosynthetic gene clusters for bioactive compounds in bacteria and fungi.Applied microbiology and biotechnology · 2019Review
- Bortezomib-induced new bergamotene derivatives xylariterpenoids H-K from sponge-derived fungusRSC advances · 2019Article
- Formation and Cleavage of C-C Bonds by Enzymatic Oxidation-Reduction Reactions.Chemical reviews · 2018Review
- Sesquiterpene Synthase-3-Hydroxy-3-Methylglutaryl Coenzyme A Synthase Fusion Protein Responsible for Hirsutene Biosynthesis in Stereum hirsutum.Applied and environmental microbiology · 2018Article
- Activation of an unconventional meroterpenoid gene cluster inActa pharmaceutica Sinica. B · 2018Article
Corrections and comments
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Authors and funding
10 authors at 4 institutions in 3 countries.
Funding
Abstract
Fumagillin (1), a meroterpenoid from Aspergillus fumigatus, is known for its antiangiogenic activity due to binding to human methionine aminopeptidase 2. 1 has a highly oxygenated structure containing a penta-substituted cyclohexane that is generated by oxidative cleavage of the bicyclic sesquiterpene β-trans-bergamotene. The chemical nature, order, and biochemical mechanism of all the oxygenative tailoring reactions has remained enigmatic despite the identification of the biosynthetic gene cluster and the use of targeted-gene deletion experiments. Here, we report the identification and characterization of three oxygenases from the fumagillin biosynthetic pathway, including a multifunctional cytochrome P450 monooxygenase, a hydroxylating nonheme-iron-dependent dioxygenase, and an ABM family monooxygenase for oxidative cleavage of the polyketide moiety. Most significantly, the P450 monooxygenase is shown to catalyze successive hydroxylation, bicyclic ring-opening, and two epoxidations that generate the sesquiterpenoid core skeleton of 1. We also characterized a truncated polyketide synthase with a ketoreductase function that controls the configuration at C-5 of hydroxylated intermediates.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.