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- Name help_outline all-trans-hexaprenyl diphosphate Identifier CHEBI:58179 Charge -3 Formula C30H49O7P2 InChIKeyhelp_outline NGFSMHKFTZROKJ-MMSZMYIBSA-K SMILEShelp_outline CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\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 10 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline talaropentaene Identifier CHEBI:192978 Charge 0 Formula C30H48 InChIKeyhelp_outline VVHPNQSUMLARNW-NGCRBCODSA-N SMILEShelp_outline [H]C12CC\C(C)=C\CC\C(C)=C\CC1(C)CC=C2C(C)CC\C=C(/C)CCC=C(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 1,188 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:77971 | RHEA:77972 | RHEA:77973 | RHEA:77974 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Discovery of non-squalene triterpenes.
Tao H., Lauterbach L., Bian G., Chen R., Hou A., Mori T., Cheng S., Hu B., Lu L., Mu X., Li M., Adachi N., Kawasaki M., Moriya T., Senda T., Wang X., Deng Z., Abe I., Dickschat J.S., Liu T.
All known triterpenes are generated by triterpene synthases (TrTSs) from squalene or oxidosqualene<sup>1</sup>. This approach is fundamentally different from the biosynthesis of short-chain (C<sub>10</sub>-C<sub>25</sub>) terpenes that are formed from polyisoprenyl diphosphates<sup>2-4</sup>. In t ... >> More
All known triterpenes are generated by triterpene synthases (TrTSs) from squalene or oxidosqualene<sup>1</sup>. This approach is fundamentally different from the biosynthesis of short-chain (C<sub>10</sub>-C<sub>25</sub>) terpenes that are formed from polyisoprenyl diphosphates<sup>2-4</sup>. In this study, two fungal chimeric class I TrTSs, Talaromyces verruculosus talaropentaene synthase (TvTS) and Macrophomina phaseolina macrophomene synthase (MpMS), were characterized. Both enzymes use dimethylallyl diphosphate and isopentenyl diphosphate or hexaprenyl diphosphate as substrates, representing the first examples, to our knowledge, of non-squalene-dependent triterpene biosynthesis. The cyclization mechanisms of TvTS and MpMS and the absolute configurations of their products were investigated in isotopic labelling experiments. Structural analyses of the terpene cyclase domain of TvTS and full-length MpMS provide detailed insights into their catalytic mechanisms. An AlphaFold2-based screening platform was developed to mine a third TrTS, Colletotrichum gloeosporioides colleterpenol synthase (CgCS). Our findings identify a new enzymatic mechanism for the biosynthesis of triterpenes and enhance understanding of terpene biosynthesis in nature. << Less
Nature 606:414-419(2022) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.