ArticleAngewandte Chemie (International ed. in English)2016
Blocking Deprotonation with Retention of Aromaticity in a Plant ent-Copalyl Diphosphate Synthase Leads to Product Rearrangement.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 42 papers.
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Who cites it
42 citing papers in PubMed.
- Comprehensive genomic analysis reveals the class II diterpene cyclases in Dodonaea viscosa.Phytochemistry · 2026Article
- Peeking behind the carbocation: identification of (alternative) catalytic bases in the class II active site of conifer resin acid diterpene synthases.The Biochemical journal · 2026Article
- Comparative genome analysis provides a foundation for defining salvinorin A biosynthesis in Salvia divinorum.Nature communications · 2026Article
- A Single Residue Switch Controls Isomer Selectivity in the Myxobacterial Isobonnadiene Synthase.Organic letters · 2026Article
- Basic importance: mechanistic molecular modeling of theOrganic & biomolecular chemistry · 2026Article
- Investigating conserved aromatic residues in ent-copalyl pyrophosphate synthases required for gibberellin phytohormone biosynthesis.Phytochemistry · 2025Article
- Cryo-EM Structure of the Cyclase Domain and Evaluation of Substrate Channeling in a Bifunctional Class II Terpene Synthase.Biochemistry · 2025Article
- Cryo-EM Structure of the Cyclase Domain and Evaluation of Substrate Channeling in a Bifunctional Class II Terpene Synthase.bioRxiv : the preprint server for biology · 2025Article
- A high-quality genome assembly of the tetraploid Teucrium chamaedrys unveils a recent whole-genome duplication and a large biosynthetic gene cluster for diterpenoid metabolism.Plant communications · 2025Article
- Exploring evolutionary use of single residue switches for alternative product outcome in class II diterpene cyclases.Phytochemistry · 2025Article
- Molecular Dynamics Simulation Reveal the Structure-Activity Relationships of Kainoid Synthases.Marine drugs · 2024Article
- Expanding catalytic promiscuity of a bifunctional terpene synthase through a single mutation-induced change in hydrogen-bond network within the catalytic pocket.Synthetic and systems biotechnology · 2024Article
- Class II terpene cyclases: structures, mechanisms, and engineering.Natural product reports · 2024Review
- Sequence-Structure Analysis Unlocking the Potential Functional Application of the Local 3D Motifs of Plant-Derived Diterpene Synthases.Biomolecules · 2024Article
- Structural and functional investigations of syn-copalyl diphosphate synthase from Oryza sativa.Communications chemistry · 2023Article
- Decoding Catalysis by Terpene Synthases.ACS catalysis · 2023Review
- Plant (di)terpenoid evolution: from pigments to hormones and beyond.Natural product reports · 2023Review
- Structure-guided product determination of the bacterial type II diterpene synthase Tpn2.Communications chemistry · 2022Article
- Investigation of Acid-Base Catalysis in Halimadienyl Diphosphate Synthase Involved inACS bio & med chem Au · 2022Article
- Novel Aporphine- and Proaporphine-Clerodane Hybrids Identified from the Barks of TaiwanesePharmaceuticals (Basel, Switzerland) · 2022Article
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Authors and funding
7 authors.
Funding
Abstract
Substitution of a histidine, comprising part of the catalytic base group in the ent-copalyl diphosphate synthases found in all seed plants for gibberellin phytohormone metabolism, by a larger aromatic residue leads to rearrangements. Through a series of 1,2-hydride and methyl shifts of the initially formed bicycle predominant formation of (-)-kolavenyl diphosphate is observed. Further mutational analysis and quantum chemical calculations provide mechanistic insight into the basis for this profound effect on product outcome.
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