ArticleChembiochem : a European journal of chemical biology2010
Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers.
Article in Chembiochem : a European journal of chemical biology, 2010. 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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34 citing papers in PubMed.
- Specific and Multi-Product Clade I and Clade IV Sesquiterpene Synthases Contribute to the Psilocybe cubensis Volatilome.Chembiochem : a European journal of chemical biology · 2026Article
- Introducing Small Rings into Farnesyl Pyrophosphates Paves the Way for the Enzymatic Generation of Unnatural Sesquiterpene Scaffolds.Journal of the American Chemical Society · 2026Article
- Chemoenzymatic Synthesis of Structurally Diverse Terpenoids from Farnesyl Pyrophosphates Modified at the Central Alkene Unit.Journal of the American Chemical Society · 2026Article
- Homoterpene Biosynthesis in Fungi.Angewandte Chemie (International ed. in English) · 2025Article
- Biosynthesis of sydonol reveals a new bisabolene cyclase and an unusual P450 aromatase.RSC chemical biology · 2025Article
- Characterization of the Cubamyces Menziesii Terpenome.Chembiochem : a European journal of chemical biology · 2025Article
- Chemoenzymatic Generation of Thio-analogues of δ-Cadinene, δ-Cadinol, and a Thio-diquinane Using 8-Thio-farnesylpyrophosphate.Journal of natural products · 2025Article
- Clade III Synthases Add Cyclic and Linear Terpenoids to the Psilocybe Metabolome.Chembiochem : a European journal of chemical biology · 2025Article
- Chemoenzymatic Formation of Oxa-Terpenoids by Sesqui- and Diterpene Synthase-Mediated Biotransformations with 9-Oxy-FPP Ether Derivatives.Biochemistry · 2025Article
- Characterization of a sesquiterpene synthase and a short-chain dehydrogenase in zerumbone biosynthesis and the applications in engineeredFrontiers in plant science · 2025Article
- Bifunctional Sesquiterpene/Diterpene Synthase Agr2 fromACS chemical biology · 2024Article
- Genome Mining of Fungal Unique Trichodiene Synthase-like Sesquiterpene Synthases.Journal of fungi (Basel, Switzerland) · 2024Article
- Sesquiterpenes of the ectomycorrhizal fungus Pisolithus microcarpus alter root growth and promote host colonization.Mycorrhiza · 2024Article
- Whole-Genome Resequencing Reveals the Diversity of Patchouli Germplasm.International journal of molecular sciences · 2023Article
- Dual RNA-Seq Profiling Unveils Mycoparasitic Activities ofMicrobiology spectrum · 2023Article
- Overview of fungal terpene synthases and their regulation.World journal of microbiology & biotechnology · 2023Review
- Genome mining of cryptic bisabolenes that were biosynthesized by intramembrane terpene synthases fromPhilosophical transactions of the Royal Society of London. Series B, Biological sciences · 2023Article
- Biosynthesis of Sesquiterpenes in Basidiomycetes: A Review.Journal of fungi (Basel, Switzerland) · 2022Review
- 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
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Abstract
Sesquiterpene synthases catalyze with different catalytic fidelity the cyclization of farnesyl pyrophosphate (FPP) into hundreds of known compounds with diverse structures and stereochemistries. Two sesquiterpene synthases, Cop4 and Cop6, were previously isolated from Coprinus cinereus as part of a fungal genome survey. This study investigates the reaction mechanism and catalytic fidelity of the two enzymes. Cyclization of all-trans-FPP ((E,E)-FPP) was compared to the cyclization of the cis-trans isomer of FPP ((Z,E)-FPP) as a surrogate for the secondary cisoid neryl cation intermediate generated by sesquiterpene synthases, which are capable of isomerizing the C2--C3 pi bond of all-trans-FPP. Cop6 is a "high-fidelity" alpha-cuprenene synthase that retains its fidelity under various conditions tested. Cop4 is a catalytically promiscuous enzyme that cyclizes (E,E)-FPP into multiple products, including (-)-germacrene D and cubebol. Changing the pH of the reaction drastically alters the fidelity of Cop4 and makes it a highly selective enzyme. Cyclization of (Z,E)-FPP by Cop4 and Cop6 yields products that are very different from those obtained with (E,E)-FPP. Conversion of (E,E)-FPP proceeds via a (6R)-beta-bisabolyl carbocation in the case of Cop6 and an (E,E)-germacradienyl carbocation in the case of Cop4. However, (Z,E)-FPP is cyclized via a (6S)-beta-bisabolene carbocation by both enzymes. Structural modeling suggests that differences in the active site and the loop that covers the active site of the two enzymes might explain their different catalytic fidelities.
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