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- Name help_outline (2E,6E,10E,14E)-geranylfarnesyl diphosphate Identifier CHEBI:57907 Charge -3 Formula C25H41O7P2 InChIKeyhelp_outline JMVSBFJBMXQNJW-GIXZANJISA-K SMILEShelp_outline CC(C)=CCC\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 23 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 1,129 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline quiannulatene Identifier CHEBI:167518 Charge 0 Formula C25H40 InChIKeyhelp_outline KZVSASHATZZHHJ-SBISLLLRSA-N SMILEShelp_outline [H][C@@]12CC[C@@]3(C)C(C)=C4C[C@]5(C)CC[C@@H](C(C)C)[C@@]5([H])C[C@]4([H])[C@@]13CC[C@H]2C 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:66864 | RHEA:66865 | RHEA:66866 | RHEA:66867 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Genome-based Discovery of an unprecedented cyclization mode in fungal sesterterpenoid biosynthesis.
Okada M., Matsuda Y., Mitsuhashi T., Hoshino S., Mori T., Nakagawa K., Quan Z., Qin B., Zhang H., Hayashi F., Kawaide H., Abe I.
Sesterterpenoids are a group of terpenoid natural products that are primarily biosynthesized via cyclization of the C25 linear substrate geranylfarnesyl pyrophosphate (GFPP). Although the long carbon chain of GFPP in theory allows for many different cyclization patterns, sesterterpenoids are relat ... >> More
Sesterterpenoids are a group of terpenoid natural products that are primarily biosynthesized via cyclization of the C25 linear substrate geranylfarnesyl pyrophosphate (GFPP). Although the long carbon chain of GFPP in theory allows for many different cyclization patterns, sesterterpenoids are relatively rare species among terpenoids, suggesting that many intriguing sesterterpenoid scaffolds have been overlooked. Meanwhile, the recent identification of the first sesterterpene synthase has allowed the discovery of new sesterterpenoids by the genome mining approach. In this study, we characterized the unusual fungal sesterterpene synthase EvQS and successfully obtained the sesterterpene quiannulatene (1) with a novel and unique highly congested carbon skeleton, which is further oxidized to quiannulatic acid (2) by the cytochrome P450 Qnn-P450. A mechanistic study of its cyclization from GFPP indicated that the biosynthesis employs an unprecedented cyclization mode, which involves three rounds of hydride shifts and two successive C-C bond migrations to construct the 5-6-5-5-5 fused ring system of 1. << Less
J. Am. Chem. Soc. 138:10011-10018(2016) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.