ArticleJournal of the American Chemical Society2018
Cytochrome P450-Catalyzed Hydroxylation Initiating Ether Formation in Platensimycin Biosynthesis.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- A Revised Model for Muscarine Biosynthesis Involving Lysine Trimethylation.Angewandte Chemie (International ed. in English) · 2026Article
- Discovery and engineering of bacterial P450s for C-14 hydroxylation in ent-kaurane diterpenoids.Nature communications · 2026Article
- Total Synthesis FacilitatesJournal of the American Chemical Society · 2024Article
- Strategic application of C-H oxidation in natural product total synthesis.Nature reviews. Chemistry · 2023Review
- Melatonin Activation by Human Cytochrome P450 Enzymes: A Comparison between Different Isozymes.Molecules (Basel, Switzerland) · 2023Article
- 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
- The important role of P450 monooxygenase for the biosynthesis of new benzophenones from Cytospora rhizophorae.Applied microbiology and biotechnology · 2021Article
- 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
- 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
- Cryptic and Stereospecific Hydroxylation, Oxidation, and Reduction in Platensimycin and Platencin Biosynthesis.Journal of the American Chemical Society · 2019Article
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5 authors.
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Abstract
Platensimycin (PTM) and platencin (PTN) are potent and selective inhibitors of bacterial and mammalian fatty acid synthases. The regio- and stereospecificity of the ether oxygen atom in PTM, which PTN does not have, strongly contribute to the selectivity and potency of PTM. We previously reported the biosynthetic origin of the 11 S,16 S-ether moiety by characterizing the diterpene synthase PtmT3 as a (16 R)- ent-kauran-16-ol synthase and isolating 11-deoxy-16 R-hydroxylated congeners of PTM from the Δ ptmO5 mutant. PtmO5, a cytochrome P450, was proposed to catalyze formation of the ether moiety in PTM. Here we report the in vitro characterization of PtmO5, revealing that PtmO5 stereoselectively hydroxylates the C-11 position of the ent-kaurane scaffold resulting in an 11 S,16 R-diol intermediate. The ether moiety, the oxygen of which originates from the P450-catalyzed hydroxylation at C-11, is formed via cyclization of the diol intermediate. This study provides mechanistic insight into ether formation in natural product biosynthetic pathways.
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