ArticleAngewandte Chemie (International ed. in English)2023
Cytochrome P450 Mediated Cyclization in Eunicellane Derived Diterpenoid Biosynthesis.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
16 citing papers in PubMed, 22 citations in OpenAlex.
- Chromosome-scale genome assembly of Artabotrys hexapetalus provides insights into its evolution and terpenoid biosynthesis.BMC plant biology · 2026Article
- Biosynthetic formation of the 6/7/5-odyverdiene diterpenes via a 6/10-ACS catalysis · 2026Article
- Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis.Beilstein journal of organic chemistry · 2026Review
- Discovery of UbiA-Type Cyathane Synthases in Bacteria.ACS catalysis · 2025Article
- Crystal Structure and Catalytic Mechanism of the cis-Eunicellane Cyclase AriE.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Three distinct strategies lead to programmable aliphatic C-H oxidation in bicyclomycin biosynthesis.Nature communications · 2025Article
- Dihydroartemisinic acid dehydrogenase-mediated alternative route for artemisinin biosynthesis.Nature communications · 2025Article
- Exploring and expanding the natural chemical space of bacterial diterpenes.Nature communications · 2025Article
- Discovery of bacterial terpenoids by genome mining.Methods in enzymology · 2025Article
- Functional Redundancy and Dual Function of a Hypothetical Protein in the Biosynthesis of Eunicellane-Type Diterpenoids.ACS chemical biology · 2024Article
- Mechanism of the Oxidative Ring-Closure Reaction during Gliotoxin Biosynthesis by Cytochrome P450 GliF.International journal of molecular sciences · 2024Article
- Discovery of a terpene synthase synthesizing a nearly non-flexible eunicellane reveals the basis of flexibility.Nature communications · 2024Article
- Computation-guided scaffold exploration of 2Beilstein journal of organic chemistry · 2024Article
- Discovery and biosynthesis of bacterial drimane-type sesquiterpenoids fromBeilstein journal of organic chemistry · 2024Article
- Cryptic Isomerization in Diterpene Biosynthesis and the Restoration of an Evolutionarily Defunct P450.Journal of the American Chemical Society · 2023Article
- Biosynthesis, enzymology, and future of eunicellane diterpenoids.Journal of industrial microbiology & biotechnology · 2023Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
10 authors at 3 institutions in 2 countries.
Funding
Abstract
Terpene cyclization, one of the most complex chemical reactions in nature, is generally catalyzed by two classes of terpene cyclases (TCs). Cytochrome P450s that act as unexpected TC-like enzymes are known but are very rare. In this study, we genome-mined a cryptic bacterial terpenoid gene cluster, named ari, from the thermophilic actinomycete strain Amycolatopsis arida. By employing a heterologous production system, we isolated and characterized three highly oxidized eunicellane derived diterpenoids, aridacins A-C (1-3), that possess a 6/7/5-fused tricyclic scaffold. In vivo and in vitro experiments systematically established a noncanonical two-step biosynthetic pathway for diterpene skeleton formation. First, a class I TC (AriE) cyclizes geranylgeranyl diphosphate (GGPP) into a 6/10-fused bicyclic cis-eunicellane skeleton. Next, a cytochrome P450 (AriF) catalyzes cyclization of the eunicellane skeleton into the 6/7/5-fused tricyclic scaffold through C2-C6 bond formation. Based on the results of quantum chemical computations, hydrogen abstraction followed by electron transfer coupled to barrierless carbocation ring closure is shown to be a viable mechanism for AriF-mediated cyclization. The biosynthetic logic of skeleton construction in the aridacins is unprecedented, expanding the catalytic capacity and diversity of P450s and setting the stage to investigate the inherent principles of carbocation generation by P450s in the biosynthesis of terpenoids.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.