ArticleBiochemistry2012
Structure of geranyl diphosphate C-methyltransferase from Streptomyces coelicolor and implications for the mechanism of isoprenoid modification.
Article in Biochemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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21 citing papers in PubMed, 57 citations in OpenAlex.
- Structural Revision of the CAngewandte Chemie (International ed. in English) · 2026Article
- 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
- Unusual vitamin E profile in the oil of a wild African oil palm tree (Frontiers in plant science · 2024Article
- Tryptophan Stabilization of a Biochemical Carbocation Evaluated by Analysis of π Complexes of 3-Ethylindole with theACS omega · 2023Article
- Engineered geranyl diphosphate methyltransferase produces 2-methyl-dimethylallyl diphosphate as a noncanonical CSynthetic and systems biotechnology · 2023Article
- Functions of enzyme domains in 2-methylisoborneol biosynthesis and enzymatic synthesis of non-natural analogs.Beilstein journal of organic chemistry · 2023Article
- Expanding the terpene biosynthetic code with non-canonical 16 carbon atom building blocks.Nature communications · 2022Article
- Catalytic trajectory of a dimeric nonribosomal peptide synthetase subunit with an inserted epimerase domain.Nature communications · 2022Article
- The stereochemical course of 2-methylisoborneol biosynthesis.Beilstein journal of organic chemistry · 2022Article
- Reaction mechanism of the farnesyl pyrophosphate C-methyltransferase towards the biosynthesis of pre-sodorifen pyrophosphate by Serratia plymuthica 4Rx13.Scientific reports · 2021Article
- Structural Basis of Polyketide Synthase O-Methylation.ACS chemical biology · 2018Article
- Heterologous expression of 2-methylisoborneol / 2 methylenebornane biosynthesis genes in Escherichia coli yields novel C11-terpenes.PloS one · 2018Article
- Microbial Platform for Terpenoid Production:Frontiers in microbiology · 2018Article
- Structural and Chemical Biology of Terpenoid Cyclases.Chemical reviews · 2017Review
- A Terpene Synthase Is Involved in the Synthesis of the Volatile Organic Compound Sodorifen of Serratia plymuthica 4Rx13.Frontiers in microbiology · 2016Article
- Structure and mechanism of an antibiotics-synthesizing 3-hydroxykynurenine C-methyltransferase.Scientific reports · 2015Article
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
Geranyl diphosphate C-methyltransferase (GPPMT) from Streptomyces coelicolor A3(2) is the first methyltransferase discovered that modifies an acyclic isoprenoid diphosphate, geranyl diphosphate (GPP), to yield a noncanonical acyclic allylic diphosphate product, 2-methylgeranyl diphosphate, which serves as the substrate for a subsequent cyclization reaction catalyzed by a terpenoid cyclase, methylisoborneol synthase. Here, we report the crystal structures of GPPMT in complex with GPP or the substrate analogue geranyl S-thiolodiphosphate (GSPP) along with S-adenosyl-L-homocysteine in the cofactor binding site, resulting from in situ demethylation of S-adenosyl-L-methionine, at 2.05 or 1.82 Å resolution, respectively. These structures suggest that both GPP and GSPP can undergo catalytic methylation in crystalline GPPMT, followed by dissociation of the isoprenoid product. S-Adenosyl-L-homocysteine remains bound in the active site, however, and does not exchange with a fresh molecule of cofactor S-adenosyl-L-methionine. These structures provide important clues about the molecular mechanism of the reaction, especially with regard to the face of the 2,3 double bond of GPP that is methylated as well as the stabilization of the resulting carbocation intermediate through cation-π interactions.
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