ArticleChembiochem : a European journal of chemical biology2022
Heterocyclic and Alkyne Terpenoids by Terpene Synthase-Mediated Biotransformation of Non-Natural Prenyl Diphosphates: Access to New Fragrances and Probes.
Article in Chembiochem : a European journal of chemical biology, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- 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
- Chemoenzymatic Generation of Thio-analogues of δ-Cadinene, δ-Cadinol, and a Thio-diquinane Using 8-Thio-farnesylpyrophosphate.Journal of natural products · 2025Article
- Engineering terpene synthases and their substrates for the biocatalytic production of terpene natural products and analogues.Chemical communications (Cambridge, England) · 2025Review
- The utility of Streptococcus mutans undecaprenol kinase for the chemoenzymatic synthesis of diverse non-natural isoprenoids.Bioorganic chemistry · 2024Article
- Sesquiterpene Cyclase BcBOT2 Promotes the Unprecedented Wagner-Meerwein Rearrangement of the Methoxy Group.Journal of the American Chemical Society · 2024Article
- Enhancing structural diversity of terpenoids by multisubstrate terpene synthases.Beilstein journal of organic chemistry · 2024Review
- Sesquiterpene Backbones Generated by Sesquiterpene Cyclases: Formation ofOrganic letters · 2023Article
- 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
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9 authors.
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Abstract
Two terpene cyclases were used as biocatalytic tool, namely, limonene synthase from Cannabis sativa (CLS) and 5-epi-aristolochene synthase (TEAS) from Nicotiana tabacum. They showed significant substrate flexibility towards non-natural prenyl diphosphates to form novel terpenoids, including core oxa- and thia-heterocycles and alkyne-modified terpenoids. We elucidated the structures of five novel monoterpene-analogues and a known sesquiterpene-analogue. These results reflected the terpene synthases' ability and promiscuity to broaden the pool of terpenoids with structurally complex analogues. Docking studies highlight an on-off conversion of the unnatural substrates.
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