ArticleJournal of the American Chemical Society2019
Cryptic and Stereospecific Hydroxylation, Oxidation, and Reduction in Platensimycin and Platencin Biosynthesis.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 38 citations in OpenAlex.
- Discovery and engineering of bacterial P450s for C-14 hydroxylation in ent-kaurane diterpenoids.Nature communications · 2026Article
- Complete biosynthesis of phenylspirodrimanes with unclustered genes inActa pharmaceutica Sinica. B · 2026Article
- Coenzyme A Tethering Mediates Dehydratase Substrate Promiscuity and Reaction Specificity in Platensimycin, Platencin, and Platensilin Biosynthesis.Biochemistry · 2025Article
- Divergent multifunctional P450s-empowered biosynthesis of bioactive tripterifordin and cryptic atiserenoids in Aconitum implies convergent evolution.Nature communications · 2025Article
- Biocatalytic diversification of abietic acid in Streptomyces.Journal of industrial microbiology & biotechnology · 2024Article
- Biotransformation of selected secondary metabolites by Alternaria species and the pharmaceutical, food and agricultural application of biotransformation products.Natural products and bioprospecting · 2024Review
- Development of platensimycin, platencin, and platensilin overproducers by biosynthetic pathway engineering and fermentation medium optimization.Journal of industrial microbiology & biotechnology · 2024Article
- Cytochrome P450 Mediated Cyclization in Eunicellane Derived Diterpenoid Biosynthesis.Angewandte Chemie (International ed. in English) · 2023Article
- Strategic application of C-H oxidation in natural product total synthesis.Nature reviews. Chemistry · 2023Review
- Charting the Evolution of Chemoenzymatic Strategies in the Syntheses of Complex Natural Products.Journal of the American Chemical Society · 2023Review
- Bioinspired Synthesis of Platensimycin from NaturalOrganic letters · 2023Article
- Engineering Catalytically Self-Sufficient P450s.Biochemistry · 2023Review
- Synthetic utility of oxygenases in site-selective terpenoid functionalization.Journal of industrial microbiology & biotechnology · 2021Review
- Bacterial terpenome.Natural product reports · 2021Review
- Reinvigorating the Chiral Pool: Chemoenzymatic Approaches to Complex Peptides and Terpenoids.Accounts of chemical research · 2021Review
- Divergent synthesis of complex diterpenes through a hybrid oxidative approach.Science (New York, N.Y.) · 2020Article
- Linking Genes to Molecules in Eukaryotic Sources: An Endeavor to Expand Our Biosynthetic Repertoire.Molecules (Basel, Switzerland) · 2020Review
- Characterization and Crystal Structure of a Nonheme Diiron Monooxygenase Involved in Platensimycin and Platencin Biosynthesis.Journal of the American Chemical Society · 2019Article
- Late-Stage Functionalization of Platensimycin Leading to Multiple Analogues with Improved Antibacterial Activity in Vitro and in Vivo.Journal of medicinal chemistry · 2019Article
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Authors and funding
8 authors at 1 institution in 1 country.
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Abstract
Platensimycin (PTM) and platencin (PTN) are highly functionalized bacterial diterpenoids of ent-kauranol and ent-atiserene biosynthetic origin. C7 oxidation in the B-ring plays a key biosynthetic role in generating structural complexity known for ent-kaurane and ent-atisane derived diterpenoids. While all three oxidation patterns, α-hydroxyl, β-hydroxyl, and ketone, at C7 are seen in both the ent-kaurane and ent-atisane derived diterpenoids, their biosynthetic origins remain largely unknown. We previously established that PTM and PTN are produced by a single biosynthetic machinery, featuring cryptic C7 oxidations at the B-rings that transform the ent-kauranol and ent-atiserene derived precursors into the characteristic PTM and PTN scaffolds. Here, we report a three-enzyme cascade affording C7 α-hydroxylation in PTM and PTN biosynthesis. Combining in vitro and in vivo studies, we show that PtmO3 and PtmO6 are two functionally redundant α-ketoglutarate-dependent dioxygenases that generate a cryptic C7 β-hydroxyl on each of the ent-kauranol and ent-atiserene scaffolds, and PtmO8 and PtmO1, a pair of NAD
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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.