ArticleNature chemistry2023
Fragmentation and [4 + 3] cycloaddition in sodorifen biosynthesis.
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed, 43 citations in OpenAlex.
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- A Wagner-Meerwein-Like Rearrangement Generates a Vinyl Group in the Biosynthesis of the Polychlorinated Lipopeptides Fischerazoles.Angewandte Chemie (International ed. in English) · 2026Article
- Discovery and Biosynthesis of Farnesyl Pyrophosphate-Derived Noncanonical CJournal of the American Chemical Society · 2026Article
- Structural Revision of the CAngewandte Chemie (International ed. in English) · 2026Article
- All Nanozyme-Based Cascade Reactions for Biomedical Applications: from Self-Cascading Nanozyme to Immobilized Cascade Nanozyme.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Review
- Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis.Beilstein journal of organic chemistry · 2026Review
- Homoterpene Biosynthesis in Fungi.Angewandte Chemie (International ed. in English) · 2025Article
- Vinigrol Tricyclic Scaffold Biosynthesis Employs an Atypical Terpene Cyclase and a Multipotent Cyclization Cascade.Journal of the American Chemical Society · 2025Article
- Mechanistic Characterisation of a Diterpene Synthase for Chryseojoostenes A-E from Chryseobacterium Joostei.Angewandte Chemie (International ed. in English) · 2025Article
- Telescoping a Prenyltransferase and a Diterpene Synthase to Transform Unnatural FPP Derivatives to Diterpenoids.Organic letters · 2024Article
- Mining the noncanonical terpenome.Nature chemical biology · 2023Article
- Genome Mining from Agriculturally Relevant Fungi Led to a d-Glucose Esterified Polyketide with a Terpene-like Core Structure.Journal of the American Chemical Society · 2023Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Terpenes constitute the largest class of natural products. Their skeletons are formed by terpene cyclases (TCs) from acyclic oligoprenyl diphosphates through sophisticated enzymatic conversions. These enzyme reactions start with substrate ionization through diphosphate abstraction, followed by a cascade reaction via cationic intermediates. Based on isotopic-labelling experiments in combination with a computational study, the cyclization mechanism for sodorifen, a highly methylated sesquiterpene from the soil bacterium Serratia plymuthica, was resolved. A peculiar problem in its biosynthesis lies in the formation of several methyl groups from chain methylene carbons. The underlying mechanism involves a methyltransferase-mediated cyclization and unprecedented ring contraction with carbon extrusion from the chain to form a methyl group. A terpene cyclase subsequently catalyses a fragmentation into two reactive intermediates, followed by hydrogen transfers between them and recombination of the fragments by [4 + 3] cycloaddition. This study solves the intricate mechanistic problem of extra methyl group formation in sodorifen biosynthesis.
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