Reaction participants Show >> << Hide
- Name help_outline 9α-copalyl diphosphate Identifier CHEBI:58622 Charge -3 Formula C20H33O7P2 InChIKeyhelp_outline JCAIWDXKLCEQEO-HZEYQZKKSA-K SMILEShelp_outline [H][C@@]12CCC(=C)[C@@H](CC\C(C)=C\COP([O-])(=O)OP([O-])([O-])=O)[C@@]1(C)CCCC2(C)C 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 (12E)-9α-labda-8(17),12,14-triene Identifier CHEBI:63707 Charge 0 Formula C20H32 InChIKeyhelp_outline VJVMMXUPZGOBSN-URKRXPPWSA-N SMILEShelp_outline C\C(C=C)=C/C[C@@H]1C(=C)CC[C@H]2C(C)(C)CCC[C@]12C 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 1,085 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:32151 | RHEA:32152 | RHEA:32153 | RHEA:32154 | |
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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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Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals.
Morrone D., Hillwig M.L., Mead M.E., Lowry L., Fulton D.B., Peters R.J.
The evolution of natural product biosynthetic pathways can be envisioned to occur via a number of mechanisms. In the present study we provide evidence that latent plasticity plays a role in such metabolic evolution. In particular, rice (Oryza sativa) produces both ent- and syn-CPP (copalyl diphosp ... >> More
The evolution of natural product biosynthetic pathways can be envisioned to occur via a number of mechanisms. In the present study we provide evidence that latent plasticity plays a role in such metabolic evolution. In particular, rice (Oryza sativa) produces both ent- and syn-CPP (copalyl diphosphate), which are substrates for downstream diterpene synthases. In the present paper we report that several members of this enzymatic family exhibit dual reactivity with some pairing of ent-, syn- or normal CPP stereochemistry. Evident plasticity was observed, as a previously reported ent-sandaracopimaradiene synthase also converts syn-CPP into syn-labda-8(17),12E,14-triene, which can be found in planta. Notably, normal CPP is not naturally found in rice. Thus the presence of diterpene synthases that react with this non-native metabolite reveals latent enzymatic/metabolic plasticity, providing biochemical capacity for utilization of such a novel substrate (i.e. normal CPP) which may arise during evolution, the implications of which are discussed. << Less
Biochem. J. 435:589-595(2011) [PubMed] [EuropePMC]
This publication is cited by 4 other entries.