ArticleACS catalysis2017
Chemical Control in the Battle against Fidelity in Promiscuous Natural Product Biosynthesis: The Case of Trichodiene Synthase.
Article in ACS catalysis, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 75 citations in OpenAlex.
- Reprogramming product selectivity and activity in promiscuous terpene synthases via substrate conformation engineering.Nature communications · 2026Article
- A methionine-lined active site governs carbocation stabilization and product specificity in a bacterial terpene synthase.FEBS letters · 2026Article
- Dock & design: engineering specificity for an alternative pimaradiene outcome with theChemical science · 2026Article
- Biosynthesis of sydonol reveals a new bisabolene cyclase and an unusual P450 aromatase.RSC chemical biology · 2025Article
- Mechanistic Characterisation of a Diterpene Synthase for Chryseojoostenes A-E from Chryseobacterium Joostei.Angewandte Chemie (International ed. in English) · 2025Article
- The initial dynamics of product release in terpene synthases-The case of CotB2.Protein science : a publication of the Protein Society · 2025Article
- Avoidance of Secondary Carbocations, Unusual Deprotonation, and Nonstatistical Dynamic Effects in the Cyclization Mechanism of Tetraisoquinane.Journal of the American Chemical Society · 2025Article
- Engineering terpene synthases and their substrates for the biocatalytic production of terpene natural products and analogues.Chemical communications (Cambridge, England) · 2025Review
- Article
- Differential Substrate Sensing in Terpene Synthases from Plants and Microorganisms: Insight from Structural, Bioinformatic, and EnzyDock Analyses.Angewandte Chemie (International ed. in English) · 2024Article
- Perspectives on Computational Enzyme Modeling: From Mechanisms to Design and Drug Development.ACS omega · 2024Review
- Stability trends in carbocation intermediates stemming from germacrene A and hedycaryol.Beilstein journal of organic chemistry · 2024Article
- Mechanistic docking in terpene synthases using EnzyDock.Methods in enzymology · 2024Review
- Decoding Catalysis by Terpene Synthases.ACS catalysis · 2023Review
- Article
- Unraveling the role of prenyl side-chain interactions in stabilizing the secondary carbocation in the biosynthesis of variexenol B.Beilstein journal of organic chemistry · 2023Article
- Biotechnological potential and initial characterization of two novel sesquiterpene synthases from Basidiomycota Coniophora puteana for heterologous production of δ-cadinol.Microbial cell factories · 2022Article
- Unusual (2iScience · 2022Article
- Towards an understanding of oleate hydratases and their application in industrial processes.Microbial cell factories · 2022Review
- Molecular Determinants of Carbocation Cyclisation in Bacterial Monoterpene Synthases.Chembiochem : a European journal of chemical biology · 2022Article
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Authors and funding
4 authors at 2 institutions in 3 countries.
Funding
Abstract
Terpene cyclases catalyze the highly stereospecific molding of polyisoprenes into terpenes, which are precursors to most known natural compounds. The isoprenoids are formed via intricate chemical cascades employing rich, yet highly erratic, carbocation chemistry. It is currently not well understood how these biocatalysts achieve chemical control. Here, we illustrate the catalytic control exerted by trichodiene synthase, and in particular, we discover two features that could be general catalytic tools adopted by other terpenoid cyclases. First, to avoid formation of byproducts, the enzyme raises the energy of bisabolyl carbocation, which is a general mechanistic branching point in many sesquiterpene cyclases, resulting in an essentially concerted cyclization cascade. Second, we identify a sulfur-carbocation dative bonding interaction that anchors the bisabolyl cation in a reactive conformation, avoiding tumbling and premature deprotonation. Specifically, Met73 acts as a chameleon, shifting from an initial sulfur-
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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.