ArticleAngewandte Chemie (International ed. in English)2021
Molecular Basis for Two Stereoselective Diels-Alderases that Produce Decalin Skeletons*.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 23 citations in OpenAlex.
- Zopfiellamides C and D, New Decalin-Type Tetramic Acid Derivatives from the Marine-Derived FungusMolecules (Basel, Switzerland) · 2025Article
- Discovery, Biosynthesis, Total Synthesis, and Biological Activities of Solanapyrones: [4 + 2] Cycloaddition-Derived Polyketides of Fungal Origin.Journal of natural products · 2024Review
- Approach to the Core Structure of Signermycin B.ChemistryOpen · 2024Article
- Iron-sulphur protein catalysed [4+2] cycloadditions in natural product biosynthesis.Nature communications · 2024Article
- Discovery of fungal onoceroid triterpenoids through domainless enzyme-targeted global genome mining.Nature communications · 2024Article
- Elucidation of the stereocontrol mechanisms of the chemical and biosynthetic intramolecular Diels-Alder cycloaddition for the formation of bioactive decalins.RSC advances · 2023Article
- Peroxidase-induced C-N bond formationGreen chemistry : an international journal and green chemistry resource : GC · 2023Article
- EnzymaticJournal of the American Chemical Society · 2023Article
- β-Lactams from the Ocean.Marine drugs · 2023Review
- cis-Decalin-containing tetramic acids as inhibitors of insect steroidogenic glutathione S-transferase Noppera-bo.PloS one · 2023Article
- Recent advances in the chemo-biological characterization of decalin natural products and unraveling of the workings of Diels-Alderases.Fungal biology and biotechnology · 2022Review
- Mechanism of the Stereoselective Catalysis of Diels-Alderase PyrE3 Involved in Pyrroindomycin Biosynthesis.Journal of the American Chemical Society · 2022Article
- Molecular Basis for Two Stereoselective Diels-Alderases that Produce Decalin Skeletons*.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
12 authors at 6 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Enzymes catalyzing [4+2] cycloaddition have attracted increasing attention because of their key roles in natural product biosynthesis. Here, we solved the X-ray crystal structures of a pair of decalin synthases, Fsa2 and Phm7, that catalyze intramolecular [4+2] cycloadditions to form enantiomeric decalin scaffolds during biosynthesis of the HIV-1 integrase inhibitor equisetin and its stereochemical opposite, phomasetin. Computational modeling, using molecular dynamics simulations as well as quantum chemical calculations, demonstrates that the reactions proceed through synergetic conformational constraints assuring transition state-like substrates folds and their stabilization by specific protein-substrate interactions. Site-directed mutagenesis experiments verified the binding models. Intriguingly, the flexibility of bound substrates is largely different in two enzymes, suggesting the distinctive mechanism of dynamics regulation behind these stereoselective reactions. The proposed reaction mechanism herein deepens the basic understanding how these enzymes work but also provides a guiding principle to create artificial enzymes.
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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.