ArticleACS chemical biology2015
Formation of a Novel Macrocyclic Alkaloid from the Unnatural Farnesyl Diphosphate Analogue Anilinogeranyl Diphosphate by 5-Epi-Aristolochene Synthase.
Article in ACS chemical biology, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 40 citations in OpenAlex.
- Formal Chemoenzymatic Skeletal Editing of Fusicoccane Core to Access 6‑Aza-Fusicoccanes.JACS Au · 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
- Isolation and characterisation of sesquiterpene synthase from aromatic orchid Phalaenopsis bellina (Rchb.f.) Christenson.Molecular biology reports · 2024Article
- Expanding the terpene biosynthetic code with non-canonical 16 carbon atom building blocks.Nature communications · 2022Article
- Alternative metabolic pathways and strategies to high-titre terpenoid production inNatural product reports · 2022Review
- Genome-wide detection and classification of terpene synthase genes inPhysiology and molecular biology of plants : an international journal of functional plant biology · 2021Article
- Mining methods and typical structural mechanisms of terpene cyclases.Bioresources and bioprocessing · 2021Review
- Synthetic biology, combinatorial biosynthesis, and chemo‑enzymatic synthesis of isoprenoids.Journal of industrial microbiology & biotechnology · 2020Review
- Accelerating Biphasic Biocatalysis through New Process Windows.Angewandte Chemie (International ed. in English) · 2020Article
- Probing Enzymatic Structure and Function in the Dihydroxylating Sesquiterpene Synthase ZmEDS.Biochemistry · 2020Article
- Direct Evidence of an Enzyme-Generated LPP Intermediate in (+)-Limonene Synthase Using a Fluorinated GPP Substrate Analog.ACS chemical biology · 2019Article
- Harnessing enzyme plasticity for the synthesis of oxygenated sesquiterpenoids.Beilstein journal of organic chemistry · 2019Article
- Synthesis of 11-carbon terpenoids in yeast using protein and metabolic engineering.Nature chemical biology · 2018Article
- Sesquiterpene Synthase-Catalysed Formation of a New Medium-Sized Cyclic Terpenoid Ether from Farnesyl Diphosphate Analogues.Chembiochem : a European journal of chemical biology · 2018Article
- Concise synthesis of artemisinin from a farnesyl diphosphate analogue.Bioorganic & medicinal chemistry · 2018Article
- Structural and Chemical Biology of Terpenoid Cyclases.Chemical reviews · 2017Review
- An Efficient Chemoenzymatic Synthesis of Dihydroartemisinic Aldehyde.Angewandte Chemie (International ed. in English) · 2017Article
- Accessing Nature's diversity through metabolic engineering and synthetic biology.F1000Research · 2016Review
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Authors and funding
11 authors at 4 institutions in 1 country.
Funding
Abstract
As part of an effort to identify substrate analogs suitable for helping to resolve structural features important for terpene synthases, the inhibition of 5-epi-aristolochene biosynthesis from farnesyl diphosphate (FPP) by the tobacco 5-epi-aristolochene synthase incubated with anilinogeranyl diphosphate (AGPP) was examined. The apparent noncompetitive nature of the inhibition supported further assessment of how AGPP might be bound to crystallographic forms of the enzyme. Surprisingly, the bound form of the inhibitor appeared to have undergone a cyclization event consistent with the native mechanism associated with FPP catalysis. Biocatalytic formation of a novel 13-membered macrocyclic paracyclophane alkaloid was confirmed by high-resolution GC-MS and NMR analysis. This work provides insights into new biosynthetic means for generating novel, functionally diversified, medium-sized terpene alkaloids.
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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.