ArticleChemistry & biology2010
Structure of cytochrome P450 PimD suggests epoxidation of the polyene macrolide pimaricin occurs via a hydroperoxoferric intermediate.
Article in Chemistry & biology, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 58 citations in OpenAlex.
- Genome-guided discovery of tropansamycins: antimicrobial pentaketide ansamycins.Engineering microbiology · 2026Article
- The Octadecanoids: Synthesis and Bioactivity of 18-Carbon Oxygenated Fatty Acids in Mammals, Bacteria, and Fungi.Chemical reviews · 2025Review
- Investigating the Active Oxidants Involved in Cytochrome P450 Catalyzed Sulfoxidation Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Exploring optimal Taxol® CYP725A4 activity in Saccharomyces cerevisiae.Microbial cell factories · 2022Article
- New Glycosylated Polyene Macrolides: Refining the Ore from Genome Mining.Antibiotics (Basel, Switzerland) · 2022Review
- The important role of P450 monooxygenase for the biosynthesis of new benzophenones from Cytospora rhizophorae.Applied microbiology and biotechnology · 2021Article
- Cytochromes P450 for natural product biosynthesis in Streptomyces: sequence, structure, and function.Natural product reports · 2017Review
- The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems.Angewandte Chemie (International ed. in English) · 2017Review
- Carboxyl-terminal domain characterization of polyene-specific P450 hydroxylase in Pseudonocardia autotrophica.Journal of industrial microbiology & biotechnology · 2016Article
- Discovery of a regioselectivity switch in nitrating P450s guided by molecular dynamics simulations and Markov models.Nature chemistry · 2016Article
- Biotechnological production and application of the antibiotic pimaricin: biosynthesis and its regulation.Applied microbiology and biotechnology · 2016Review
- New reactions and products resulting from alternative interactions between the P450 enzyme and redox partners.Journal of the American Chemical Society · 2014Article
- Biosynthesis and pathway engineering of antifungal polyene macrolides in actinomycetes.Journal of industrial microbiology & biotechnology · 2013Review
- Substrate recognition by the multifunctional cytochrome P450 MycG in mycinamicin hydroxylation and epoxidation reactions.The Journal of biological chemistry · 2012Article
- Diversity of P450 enzymes in the biosynthesis of natural products.Natural product reports · 2012Review
- Proximal ligand electron donation and reactivity of the cytochrome P450 ferric-peroxo anion.Journal of the American Chemical Society · 2012Article
- Enzymatic chemistry of cyclopropane, epoxide, and aziridine biosynthesis.Chemical reviews · 2012Review
- Article
- A new structural form in the SAM/metal-dependent o‑methyltransferase family: MycE from the mycinamicin biosynthetic pathway.Journal of molecular biology · 2011Article
- Molecular control of polyene macrolide biosynthesis: direct binding of the regulator PimM to eight promoters of pimaricin genes and identification of binding boxes.The Journal of biological chemistry · 2011Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 2 countries.
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Abstract
We present the X-ray structure of PimD, both substrate-free and in complex with 4,5-desepoxypimaricin. PimD is a cytochrome P450 monooxygenase with native epoxidase activity that is critical in the biosynthesis of the polyene macrolide antibiotic pimaricin. Intervention in this secondary metabolic pathway could advance the development of drugs with improved pharmacologic properties. Epoxidation by P450 typically includes formation of a charge-transfer complex between an oxoferryl pi-cation radical species (Compound I) and the olefin pi-bond as the initial intermediate. Catalytic and structural evidence presented here suggest that epoxidation of 4,5-desepoxypimaricin proceeds via a hydroperoxoferric intermediate (Compound 0). The oxygen atom of Compound 0 distal to the heme iron may insert into the double bond of the substrate to make an epoxide ring. Stereoelectronic features of the putative transition state suggest substrate-assisted proton delivery.
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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.