Enzymes
UniProtKB help_outline | 2 proteins |
GO Molecular Function help_outline |
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Reaction participants Show >> << Hide
- Name help_outline (2E,6E)-farnesyl diphosphate Identifier CHEBI:175763 Charge -3 Formula C15H25O7P2 InChIKeyhelp_outline VWFJDQUYCIWHTN-YFVJMOTDSA-K SMILEShelp_outline CC(C)=CCC\C(C)=C\CC\C(C)=C\COP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 180 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (−)-β-barbatene Identifier CHEBI:193072 Charge 0 Formula C15H24 InChIKeyhelp_outline RTONMYLSQISFQA-XQLPTFJDSA-N SMILEShelp_outline C[C@]12CCC(=C)[C@H](C1)[C@@]3([C@]2(CCC3)C)C 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline diphosphate Identifier CHEBI:33019 (Beilstein: 185088) help_outline Charge -3 Formula HO7P2 InChIKeyhelp_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILEShelp_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,146 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:73983 | RHEA:73984 | RHEA:73985 | RHEA:73986 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Gene Ontology help_outline |
Publications
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Terpene synthase genes in eukaryotes beyond plants and fungi: Occurrence in social amoebae.
Chen X., Koellner T.G., Jia Q., Norris A., Santhanam B., Rabe P., Dickschat J.S., Shaulsky G., Gershenzon J., Chen F.
Terpenes are structurally diverse natural products involved in many ecological interactions. The pivotal enzymes for terpene biosynthesis, terpene synthases (TPSs), had been described only in plants and fungi in the eukaryotic domain. In this report, we systematically analyzed the genome sequences ... >> More
Terpenes are structurally diverse natural products involved in many ecological interactions. The pivotal enzymes for terpene biosynthesis, terpene synthases (TPSs), had been described only in plants and fungi in the eukaryotic domain. In this report, we systematically analyzed the genome sequences of a broad range of nonplant/nonfungus eukaryotes and identified putative TPS genes in six species of amoebae, five of which are multicellular social amoebae from the order of Dictyosteliida. A phylogenetic analysis revealed that amoebal TPSs are evolutionarily more closely related to fungal TPSs than to bacterial TPSs. The social amoeba Dictyostelium discoideum was selected for functional study of the identified TPSs. D. discoideum grows as a unicellular organism when food is abundant and switches from vegetative growth to multicellular development upon starvation. We found that expression of most D. discoideum TPS genes was induced during development. Upon heterologous expression, all nine TPSs from D. discoideum showed sesquiterpene synthase activities. Some also exhibited monoterpene and/or diterpene synthase activities. Direct measurement of volatile terpenes in cultures of D. discoideum revealed essentially no emission at an early stage of development. In contrast, a bouquet of terpenes, dominated by sesquiterpenes including β-barbatene and (E,E)-α-farnesene, was detected at the middle and late stages of development, suggesting a development-specific function of volatile terpenes in D. discoideum. The patchy distribution of TPS genes in the eukaryotic domain and the evidence for TPS function in D. discoideum indicate that the TPS genes mediate lineage-specific adaptations. << Less
Proc. Natl. Acad. Sci. U.S.A. 113:12132-12137(2016) [PubMed] [EuropePMC]
This publication is cited by 10 other entries.
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Characterisation of three terpene synthases for beta-barbatene, beta-araneosene and nephthenol from social amoebae.
Rinkel J., Koellner T.G., Chen F., Dickschat J.S.
The products of three terpene synthases from two social amoebae, Dictyostelium discoideum and Dictyostelium purpureum, were identified, showing sesquiterpene synthase activity for one and diterpene synthase activity for the other two enzymes. Site-directed mutagenesis experiments revealed the impo ... >> More
The products of three terpene synthases from two social amoebae, Dictyostelium discoideum and Dictyostelium purpureum, were identified, showing sesquiterpene synthase activity for one and diterpene synthase activity for the other two enzymes. Site-directed mutagenesis experiments revealed the importance of a newly identfied highly conserved residue for catalytic activity. For one of the enzyme products, β-araneosene, a bromonium ion induced transannular cyclisation was investigated, yielding the first brominated derivatives of this diterpene. << Less
Chem. Commun. (Camb.) 55:13255-13258(2019) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.