ArticlePloS one2018
Heterologous expression of 2-methylisoborneol / 2 methylenebornane biosynthesis genes in Escherichia coli yields novel C11-terpenes.
Article in PloS one, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed, 36 citations in OpenAlex.
- Systematic biotechnological production of isoprenoid analogs with bespoke carbon skeletons.Nature communications · 2025Article
- The microbial biosynthesis of noncanonical terpenoids.Applied microbiology and biotechnology · 2024Review
- Enhancing structural diversity of terpenoids by multisubstrate terpene synthases.Beilstein journal of organic chemistry · 2024Review
- Heterologous expression ofMicrobiology spectrum · 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
- High Versatility of IPP and DMAPP Methyltransferases Enables Synthesis of CChembiochem : a European journal of chemical biology · 2022Article
- Odor Characteristics of Novel Non-Canonical Terpenes.Molecules (Basel, Switzerland) · 2022Article
- Alternative metabolic pathways and strategies to high-titre terpenoid production inNatural product reports · 2022Review
- The stereochemical course of 2-methylisoborneol biosynthesis.Beilstein journal of organic chemistry · 2022Article
- Plasticity engineering of plant monoterpene synthases and application for microbial production of monoterpenoids.Biotechnology for biofuels · 2021Review
- Reaction mechanism of the farnesyl pyrophosphate C-methyltransferase towards the biosynthesis of pre-sodorifen pyrophosphate by Serratia plymuthica 4Rx13.Scientific reports · 2021Article
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5 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The structural diversity of terpenoids is limited by the isoprene rule which states that all primary terpene synthase products derive from methyl-branched building blocks with five carbon atoms. With this study we discover a broad spectrum of novel terpenoids with eleven carbon atoms as byproducts of bacterial 2-methylisoborneol or 2-methylenebornane synthases. Both enzymes use 2-methyl-GPP as substrate, which is synthesized from GPP by the action of a methyltransferase. We used E. coli strains that heterologously produce different C11-terpene synthases together with the GPP methyltransferase and the mevalonate pathway enzymes. With this de novo approach, 35 different C11-terpenes could be produced. In addition to eleven known compounds, it was possible to detect 24 novel C11-terpenes which have not yet been described as terpene synthase products. Four of them, 3,4-dimethylcumene, 2-methylborneol and the two diastereomers of 2-methylcitronellol could be identified. Furthermore, we showed that an E. coli strain expressing the GPP-methyltransferase can produce the C16-terpene 6-methylfarnesol which indicates the condensation of 2-methyl-GPP and IPP to 6-methyl-FPP by the E. coli FPP-synthase. Our study demonstrates the broad range of unusual terpenes accessible by expression of GPP-methyltransferases and C11-terpene synthases in E. coli and provides an extended mechanism for C11-terpene synthases.
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