ArticleChembiochem : a European journal of chemical biology2007
Interception of the enzymatic conversion of farnesyl diphosphate to 5-epi-aristolochene by using a fluoro substrate analogue: 1-fluorogermacrene A from (2E,6Z)-6-fluorofarnesyl diphosphate.
Article in Chembiochem : a European journal of chemical biology, 2007. 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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13 citing papers in PubMed, 46 citations in OpenAlex.
- Engineering terpene synthases and their substrates for the biocatalytic production of terpene natural products and analogues.Chemical communications (Cambridge, England) · 2025Review
- 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
- Enzymatic Synthesis of Methylated Terpene Analogues Using the Plasticity of Bacterial Terpene Synthases.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Silent catalytic promiscuity in the high-fidelity terpene cyclase δ-cadinene synthase.Organic & biomolecular chemistry · 2019Article
- Harnessing enzyme plasticity for the synthesis of oxygenated sesquiterpenoids.Beilstein journal of organic chemistry · 2019Article
- Sesquiterpene Synthase-Catalysed Formation of a New Medium-Sized Cyclic Terpenoid Ether from Farnesyl Diphosphate Analogues.Chembiochem : a European journal of chemical biology · 2018Article
- Concise synthesis of artemisinin from a farnesyl diphosphate analogue.Bioorganic & medicinal chemistry · 2018Article
- Structural and Chemical Biology of Terpenoid Cyclases.Chemical reviews · 2017Review
- An Efficient Chemoenzymatic Synthesis of Dihydroartemisinic Aldehyde.Angewandte Chemie (International ed. in English) · 2017Article
- High-throughput screening for terpene-synthase-cyclization activity and directed evolution of a terpene synthase.Angewandte Chemie (International ed. in English) · 2013Article
- Structural elucidation of cisoid and transoid cyclization pathways of a sesquiterpene synthase using 2-fluorofarnesyl diphosphates.ACS chemical biology · 2010Article
- Total (bio)synthesis: strategies of nature and of chemists.Topics in current chemistry · 2010Review
- Identification of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain PCC 7120.Journal of bacteriology · 2008Article
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5 authors at 3 institutions in 1 country.
Funding
Abstract
Tobacco 5-epi-aristolochene synthase (TEAS) catalyzes the Mg(II)-dependent cyclizations and rearrangements of (E,E)-farnesyl diphosphate (PP) to the bicyclic sesquiterpene hydrocarbon via a tightly bound (+)-germacrene A as a deprotonated intermediate. With the native enzyme, only a few percent of the putative germacrene A intermediate is released from the active site during the catalytic cycle. 6-Fluorofarnesyl PP was designed and synthesized with the aim of arresting the cyclization-rearrangement mechanism en route to 5-epi-aristolochene. Indeed, incubation of (2E,6Z)-6-fluorofarnesyl PP with recombinant TEAS afforded (-)-1-fluorogermacrene A as the sole product in 58% yield. Steady-state kinetic experiments with farnesyl PP and the 6-fluoro analogue showed that the overall catalytic efficiencies (k(cat)/K(m)) are essentially the same for both substrates. 1-Fluorogermacrene A was characterized by chromatographic properties (TLC, GC), MS, optical rotation, UV, IR and (1)H NMR data, and by heat-induced Cope rearrangement to (+)-1-fluoro-beta-elemene. (1)H NMR spectra at room temperature revealed that this (E,E)-configured fluorocyclodecadiene exists in solution as a 7:3 mixture of UU and UD conformers. 1-Fluorogermacrene A underwent trifluoroacetic acid-catalyzed cyclization to give three 1alpha-fluoroselinene isomers at a rate estimated to be about 1000 times slower than that of the similar cyclization of (+)-germacrene A to the parent selinenes.
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