ArticleACS chemical biology2010
Structural elucidation of cisoid and transoid cyclization pathways of a sesquiterpene synthase using 2-fluorofarnesyl diphosphates.
Article in ACS chemical biology, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Highly efficient production ofSynthetic and systems biotechnology · 2027Article
- Divergent Lineage of Terpene Synthases Establishes Terpenoid Biosynthesis in Brown Macroalgae.Journal of the American Chemical Society · 2026Article
- Genetic blueprint of herbaceous peony floral scent: evidence from terpene synthase, Nudix hydrolase, and prenyltransferase.Horticulture research · 2026Article
- Simulation-Guided Engineering Enables a Functional Switch in Selinadiene Synthase toward Hydroxylation.ACS catalysis · 2024Article
- Insights into the functional mechanisms of three terpene synthases fromFrontiers in plant science · 2024Article
- Decoding Catalysis by Terpene Synthases.ACS catalysis · 2023Review
- Heterocyclic and Alkyne Terpenoids by Terpene Synthase-Mediated Biotransformation of Non-Natural Prenyl Diphosphates: Access to New Fragrances and Probes.Chembiochem : a European journal of chemical biology · 2022Article
- Nerylneryl diphosphate is the precursor of serrulatane, viscidane and cembrane-type diterpenoids in Eremophila species.BMC plant biology · 2020Article
- Exploring the catalytic cascade of cembranoid biosynthesis by combination of genetic engineering and molecular simulations.Computational and structural biotechnology journal · 2020Article
- Sesquiterpene Synthase-Catalysed Formation of a New Medium-Sized Cyclic Terpenoid Ether from Farnesyl Diphosphate Analogues.Chembiochem : a European journal of chemical biology · 2018Article
- Catalysis of amorpha-4,11-diene synthase unraveled and improved by mutability landscape guided engineering.Scientific reports · 2018Article
- Structural and Chemical Biology of Terpenoid Cyclases.Chemical reviews · 2017Review
- An in-silico insight into the substrate binding characteristics of the active site of amorpha-4, 11-diene synthase, a key enzyme in artemisinin biosynthesis.Journal of molecular modeling · 2017Article
- Article
- Mechanistically informed predictions of binding modes for carbocation intermediates of a sesquiterpene synthase reaction.Chemical science · 2016Article
- Identification, Functional Characterization, and Evolution of Terpene Synthases from a Basal Dicot.Plant physiology · 2015Article
- Formation of a Novel Macrocyclic Alkaloid from the Unnatural Farnesyl Diphosphate Analogue Anilinogeranyl Diphosphate by 5-Epi-Aristolochene Synthase.ACS chemical biology · 2015Article
- Modulation of inherent dynamical tendencies of the bisabolyl cationChemical science · 2015Article
- Emergence of terpene cyclization in Artemisia annua.Nature communications · 2015Article
- Predicting the functions and specificity of triterpenoid synthases: a mechanism-based multi-intermediate docking approach.PLoS computational biology · 2014Article
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8 authors.
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Abstract
Sesquiterpene skeletal complexity in nature originates from the enzyme-catalyzed ionization of (trans,trans)-farnesyl diphosphate (FPP) (1a) and subsequent cyclization along either 2,3-transoid or 2,3-cisoid farnesyl cation pathways. Tobacco 5-epi-aristolochene synthase (TEAS), a transoid synthase, produces cisoid products as a component of its minor product spectrum. To investigate the cryptic cisoid cyclization pathway in TEAS, we employed (cis,trans)-FPP (1b) as an alternative substrate. Strikingly, TEAS was catalytically robust in the enzymatic conversion of (cis,trans)-FPP (1b) to exclusively (>/=99.5%) cisoid products. Further, crystallographic characterization of wild-type TEAS and a catalytically promiscuous mutant (M4 TEAS) with 2-fluoro analogues of both all-trans FPP (1a) and (cis,trans)-FPP (1b) revealed binding modes consistent with preorganization of the farnesyl chain. These results provide a structural glimpse into both cisoid and transoid cyclization pathways efficiently templated by a single enzyme active site, consistent with the recently elucidated stereochemistry of the cisoid products. Further, computational studies using density functional theory calculations reveal concerted, highly asynchronous cyclization pathways leading to the major cisoid cyclization products. The implications of these discoveries for expanded sesquiterpene diversity in nature are discussed.
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