ArticleNature chemistry2011
Tirandamycin biosynthesis is mediated by co-dependent oxidative enzymes.
Article in Nature chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 41 papers.
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Who cites it
41 citing papers in PubMed, 94 citations in OpenAlex.
- Studies on Secondary Metabolites ofPolish journal of microbiology · 2025Article
- Evaluation of tirandamycins with selective activity against Enterococci in the silkworm infection model.The Journal of antibiotics · 2025Article
- Exploring extreme environments in Türkiye for novel P450s through metagenomic analysis.PloS one · 2025Article
- Biosynthetic Strategies of Berberine Bridge Enzyme-like Flavoprotein Oxidases toward Structural Diversification in Natural Product Biosynthesis.Biochemistry · 2024Review
- Endowing homodimeric carbamoyltransferase GdmN with iterative functions through structural characterization and mechanistic studies.Nature communications · 2022Article
- Discovery and characterization of a terpene biosynthetic pathway featuring a norbornene-forming Diels-Alderase.Nature communications · 2022Article
- Engineering sequence and selectivity of late-stage C-H oxidation in the MycG iterative cytochrome P450.Journal of industrial microbiology & biotechnology · 2022Article
- Engineering P450 TamI as an Iterative Biocatalyst for Selective Late-Stage C-H Functionalization and Epoxidation of Tirandamycin Antibiotics.ACS catalysis · 2021Article
- An overview of the cytochrome P450 enzymes that catalyze the same-site multistep oxidation reactions in biotechnologically relevant selected actinomycete strains.Applied microbiology and biotechnology · 2021Review
- Discovery and Biosynthesis of Tetrachlorizine Reveals Enzymatic Benzylic Dehydrogenation via anJournal of the American Chemical Society · 2021Article
- Bioactivity Potential of Marine Natural Products from Scleractinia-Associated Microbes and In Silico Anti-SARS-COV-2 Evaluation.Marine drugs · 2020Review
- Molecular Basis of Iterative C─H Oxidation by TamI, a Multifunctional P450 monooxygenase from the Tirandamycin Biosynthetic Pathway.ACS catalysis · 2020Article
- Structure and Function of NzeB, a Versatile C-C and C-N Bond-Forming Diketopiperazine Dimerase.Journal of the American Chemical Society · 2020Article
- More P450s Are Involved in Secondary Metabolite Biosynthesis inInternational journal of molecular sciences · 2020Article
- Short-Chain Dehydrogenase NcmD Is Responsible for the C-10 Oxidation of Nocamycin F in Nocamycin Biosynthesis.Frontiers in microbiology · 2020Article
- Mechanism of the Flavoprotein d-6-Hydroxynicotine Oxidase: Substrate Specificity, pH and Solvent Isotope Effects, and Roles of Key Active-Site Residues.Biochemistry · 2019Article
- A Promiscuous Cytochrome P450 Hydroxylates Aliphatic and Aromatic C-H Bonds of Aromatic 2,5-Diketopiperazines.Chembiochem : a European journal of chemical biology · 2019Article
- Cytochrome P450 oxidase SlgO1 catalyzes the biotransformation of tirandamycin C to a new tirandamycin derivative.3 Biotech · 2019Article
- Cytotoxic anthracycline and antibacterial tirandamycin analogues from a marine-derived Streptomyces sp. SCSIO 41399.The Journal of antibiotics · 2019Article
- Extracellularly oxidative activation and inactivation of matured prodrug for cryptic self-resistance in naphthyridinomycin biosynthesis.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Elucidation of natural product biosynthetic pathways provides important insights into the assembly of potent bioactive molecules, and expands access to unique enzymes able to selectively modify complex substrates. Here, we show full reconstitution, in vitro, of an unusual multi-step oxidative cascade for post-assembly-line tailoring of tirandamycin antibiotics. This pathway involves a remarkably versatile and iterative cytochrome P450 monooxygenase (TamI) and a flavin adenine dinucleotide-dependent oxidase (TamL), which act co-dependently through the repeated exchange of substrates. TamI hydroxylates tirandamycin C (TirC) to generate tirandamycin E (TirE), a previously unidentified tirandamycin intermediate. TirE is subsequently oxidized by TamL, giving rise to the ketone of tirandamycin D (TirD), after which a unique exchange back to TamI enables successive epoxidation and hydroxylation to afford, respectively, the final products tirandamycin A (TirA) and tirandamycin B (TirB). Ligand-free, substrate- and product-bound crystal structures of bicovalently flavinylated TamL oxidase reveal a likely mechanism for the C10 oxidation of TirE.
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Registered trials
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.