ArticleBiochemistry2012
Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate.
Article in Biochemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- Encapsulins in Terpene Biosynthesis: Enzyme Nanoreactors in Bacterial Secondary Metabolism.Biochemistry · 2026Review
- Homoterpene Biosynthesis in Fungi.Angewandte Chemie (International ed. in English) · 2025Article
- The biosynthesis of the odorant 2-methylisoborneol is compartmentalized inside a protein shell.Nature communications · 2024Article
- The biosynthesis of the odorant 2-methylisoborneol is compartmentalized inside a protein shell.bioRxiv : the preprint server for biology · 2024Article
- The microbial biosynthesis of noncanonical terpenoids.Applied microbiology and biotechnology · 2024Review
- Decoding Catalysis by Terpene Synthases.ACS catalysis · 2023Review
- Actinomycetes as Producers of Biologically Active Terpenoids: Current Trends and Patents.Pharmaceuticals (Basel, Switzerland) · 2023Review
- Functions of enzyme domains in 2-methylisoborneol biosynthesis and enzymatic synthesis of non-natural analogs.Beilstein journal of organic chemistry · 2023Article
- The stereochemical course of 2-methylisoborneol biosynthesis.Beilstein journal of organic chemistry · 2022Article
- A monodomain class II terpene cyclase assembles complex isoprenoid scaffolds.Nature chemistry · 2020Article
- Phylogenomic analyses and distribution of terpene synthases amongBeilstein journal of organic chemistry · 2019Article
- Synthesis of 11-carbon terpenoids in yeast using protein and metabolic engineering.Nature chemical biology · 2018Article
- Heterologous expression of 2-methylisoborneol / 2 methylenebornane biosynthesis genes in Escherichia coli yields novel C11-terpenes.PloS one · 2018Article
- Substitution of Aromatic Residues with Polar Residues in the Active Site Pocket of epi-Isozizaene Synthase Leads to the Generation of New Cyclic Sesquiterpenes.Biochemistry · 2017Article
- Structural and Chemical Biology of Terpenoid Cyclases.Chemical reviews · 2017Review
- Structural Basis of Catalysis in the Bacterial Monoterpene Synthases Linalool Synthase and 1,8-Cineole Synthase.ACS catalysis · 2017Article
- Incubation of 2-methylisoborneol synthase with the intermediate analog 2-methylneryl diphosphate.The Journal of antibiotics · 2017Article
- Structural Characterization of Early Michaelis Complexes in the Reaction Catalyzed by (+)-Limonene Synthase from Citrus sinensis Using Fluorinated Substrate Analogues.Biochemistry · 2017Article
- Multi-domain terpenoid cyclase architecture and prospects for proximity in bifunctional catalysis.Current opinion in structural biology · 2016Review
- Nature as organic chemist.The Journal of antibiotics · 2016Article
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Abstract
The crystal structure of 2-methylisoborneol synthase (MIBS) from Streptomyces coelicolor A3(2) has been determined in complex with substrate analogues geranyl-S-thiolodiphosphate and 2-fluorogeranyl diphosphate at 1.80 and 1.95 Å resolution, respectively. This terpenoid cyclase catalyzes the cyclization of the naturally occurring, noncanonical C-methylated isoprenoid substrate, 2-methylgeranyl diphosphate, to form the bicyclic product 2-methylisoborneol, a volatile C(11) homoterpene alcohol with an earthy, musty odor. While MIBS adopts the tertiary structure of a class I terpenoid cyclase, its dimeric quaternary structure differs from that previously observed in dimeric terpenoid cyclases from plants and fungi. The quaternary structure of MIBS is nonetheless similar in some respects to that of dimeric farnesyl diphosphate synthase, which is not a cyclase. The structures of MIBS complexed with substrate analogues provide insights regarding differences in the catalytic mechanism of MIBS and the mechanisms of (+)-bornyl diphosphate synthase and endo-fenchol synthase, plant cyclases that convert geranyl diphosphate into products with closely related bicyclic bornyl skeletons, but distinct structures and stereochemistries.
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