ArticleJournal of the American Chemical Society2009
Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor. Mechanism and stereochemistry of the enzymatic formation of epi-isozizaene.
Article in Journal of the American Chemical Society, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.
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40 citing papers in PubMed, 90 citations in OpenAlex.
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- Actinomycetes as Producers of Biologically Active Terpenoids: Current Trends and Patents.Pharmaceuticals (Basel, Switzerland) · 2023Review
- New Trends and Future Opportunities in the Enzymatic Formation of C-C, C-N, and C-O bonds.Chembiochem : a European journal of chemical biology · 2022Review
- Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of anMolecules (Basel, Switzerland) · 2021Article
- Complete Genome Analysis of Undecylprodigiosin Pigment Biosynthesizing MarineMicroorganisms · 2021Article
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- Production of Plant-Associated Volatiles by Select Model and Industrially ImportantMicroorganisms · 2020Article
- Mechanism Underlying Anti-Markovnikov Addition in the Reaction of Pentalenene Synthase.Biochemistry · 2020Article
- Complete genome sequence of high-yield strainSynthetic and systems biotechnology · 2020Article
- The Chemistry, Pharmacology and Therapeutic Potential of the Edible MushroomBiomedicines · 2019Review
- Comparative Genomic Insights into Secondary Metabolism Biosynthetic Gene Cluster Distributions of MarineMarine drugs · 2019Article
- Crystal structure of F95Q epi-isozizaene synthase, an engineered sesquiterpene cyclase that generates biofuel precursors β- and γ-curcumene.Journal of structural biology · 2019Article
- Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering.Beilstein journal of organic chemistry · 2019Review
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Epi-isozizaene synthase from Streptomyces coelicolor catalyzes the multistep cyclization of farnesyl diphosphate (2, FPP) to the tricyclic sesquiterpene hydrocarbon (+)-epi-isozizaene (3), which is converted in turn to the antibiotic albaflavenone (1) in a two-step, cytochrome P450-catalyzed oxidation. Competitive incubation of deuterated and nondeuterated samples of (3S)-NPP and (3RS)-NPP followed by GC-MS analysis of the degree of deuteration in the resulting labeled epi-isozizaene established that (3R)-NPP is the natural cyclization intermediate. Incubation of (3RS)-(Z)-[1-(2)H]NPP (4b) with epi-isozizaene synthase gave [11(anti)-(2)H]epi-isozizaene (3b), indicating that the S(N)' cyclization of 4 involves the predicted anti stereochemistry, consistent with the inference from earlier experiments with chirally deuterated FPP. Incubation of separate samples of [12,12,12-(2)H(3)]FPP (2d) and [13,13,13-(2)H(3)]FPP (2e) gave epi-isozizaenes 3d and 3e, thereby establishing the stereochemical course of the cyclization of the proposed intermediate acorenyl cation 6, as well as the stereochemistry of the successive 1,2-methyl migration and deprotonation that generate the final product. Further insights into the mechanism and the role of the enzyme came from site-directed mutagenesis of active site residues in two universally conserved Mg(2+)-binding domains and the identification of six minor sesquiterpene products 9-13 and 15 produced by the wild-type and mutant proteins. The aberrant products are believed to result from derailment and premature quenching of the normal intermediates of the cationic cyclization cascade.
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