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Literature summary extracted from
- Herbivore-induced and floral homoterpene volatiles are biosynthesized by a single P450 enzyme (CYP82G1) in Arabidopsis (2010), Proc. Natl. Acad. Sci. USA, 107, 21205-21210.
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 1.14.14.58 | cloned into the yeast expression vector YEp352 under the control of the constitutive alcohol dehydrogenase 1 promoter, expression in yeast | Arabidopsis thaliana |
| 1.14.14.58 | expression in yeast WAT11 cells | Arabidopsis thaliana |
Crystallization (Commentary)
| EC Number | Crystallization (Comment) | Organism |
|---|---|---|
| 1.14.14.58 | molecular docking of (E,E)-geranyllinalool and (E)-nerolidol shows that both substrates occupiy the same position in the enzyme binding site with the hydroxyl group at C-3, forming a strong hydrogen bond to the carbonyl oxygen of Thr313. The position of the allylic hydrogen atoms at C-5 of (E,E)-geranyllinalool and (E)-nerolidol and the hydroxyl group at C-3 relative to the reactive iron-oxo heme moiety supports an oxidative-bond cleavage reaction proceeding by a syn-elimination mechanism | Arabidopsis thaliana |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.14.58 | 0.00184 | - |
(3S,6E)-nerolidol | pH and temperature not specified in the publication | Arabidopsis thaliana |  |
| 1.14.14.58 | 0.00184 | - |
(3S)-(E)-nerolidol | pH not specified in the publication, temperature not specified in the publication | Arabidopsis thaliana | |
| 1.14.14.58 | 0.00268 | - |
(E,E)-geranyllinalool | pH and temperature not specified in the publication | Arabidopsis thaliana | |
| 1.14.14.58 | 0.00268 | - |
(3S)-(E,E)-geranyllinalool | pH not specified in the publication, temperature not specified in the publication | Arabidopsis thaliana | |
Localization
| EC Number | Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|---|
| 1.14.14.58 | microsome | - |
Arabidopsis thaliana | - |
- |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.58 | (3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2 | Arabidopsis thaliana | - |
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O | - |
? | |
| 1.14.14.58 | (3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2 | Arabidopsis thaliana | biosynthesis of the volatile organic compound (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene | (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O | - |
? | |
| 1.14.14.58 | (3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2 | Arabidopsis thaliana | in vitro activity is 5.3fold higher than with (E,E)-geranyllinalool. (3E)-4,8-dimethylnona-1,3,7-triene is not emitted from Arabidopsis leaves (or only in negligible amounts according to our analysis) because of the absence of a prominent (E)-nerolidol synthase activity in this tissue | (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.14.58 | Arabidopsis thaliana | Q9LSF8 | - |
- |
| 1.14.14.58 | Arabidopsis thaliana | Q9LSF8 | ecotype Columbia | - |
| 4.2.3.144 | Arabidopsis thaliana | Q93YV0 | - |
- |
Reaction
| EC Number | Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|---|
| 1.14.14.58 | (6E,10E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2 = (3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + [oxidized NADPH-hemoprotein reductase] + but-3-en-2-one + 2 H2O | the exact mechanism of enzyme is not yet determined. It is possible that CYP82G1 may promote the direct transformation of (E,E)-geranyllinalool and (3R,6E)-nerolidol to (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene and (3E)-4,8-dimethylnona-1,3,7-triene, respectively, with the concomitant release of but-1-en-3-one. But it is also possible that a two-step conversion occurs that includes the formation of intermediate compounds C18 (E,E)-farnesylacetone (from (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene) and C13 (E)-geranylacetone (from (3E)-4,8-dimethylnona-1,3,7-triene). A C4-cleavage product (but-1-en-3-one) resulting from the breakdown of (E,E)-geranyllinalool or (E)-nerolidol is not observed, neither in vitro nor in vivo, and none of the previously proposed ketone intermediates, C18-farnesylacetone and C13-geranylacetone, are detected | Arabidopsis thaliana |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 1.14.14.58 | inflorescence | constitutive expression | Arabidopsis thaliana | - |
| 1.14.14.58 | inflorescence | constitutively expressed | Arabidopsis thaliana | - |
| 1.14.14.58 | leaf | highly coordinated herbivore-induced expression with geranyllinalool synthase in leaves depending on the F-box protein COI-1 | Arabidopsis thaliana | - |
| 1.14.14.58 | stem | constitutive expression | Arabidopsis thaliana | - |
| 1.14.14.58 | stem | constitutively expressed | Arabidopsis thaliana | - |
| 4.2.3.144 | leaf | - |
Arabidopsis thaliana | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.58 | (3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2 | - |
Arabidopsis thaliana | (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O | - |
? | |
| 1.14.14.58 | (3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2 | biosynthesis of the volatile organic compound (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene | Arabidopsis thaliana | (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O | - |
? | |
| 1.14.14.58 | (3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2 | - |
Arabidopsis thaliana | (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O | - |
? | |
| 1.14.14.58 | (3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2 | in vitro activity is 5.3fold higher than with (E,E)-geranyllinalool. (3E)-4,8-dimethylnona-1,3,7-triene is not emitted from Arabidopsis leaves (or only in negligible amounts according to our analysis) because of the absence of a prominent (E)-nerolidol synthase activity in this tissue | Arabidopsis thaliana | (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O | - |
? | |
| 1.14.14.58 | additional information | no activity with isophytol, (E)-geraniol, linalool, 3,7,11-trimethyl-3-dodecanol, (Z)-nerolidol. Less than 1% of the activity with (3S,6E)-nerolidol: (E,E,E)-geranylgeraniol, (E,E)-farnesylacetone, (E,E)-farnesol, (E)-geranylacetone. Construction of a protein model based on multiple mammalian P450 templates with closest sequence similarity. Subsequent molecular docking confirms a position of (E)-nerolidol and (E,E)-geranyllinalool in the active site cavity that allows the suggested oxidative bond cleavage reaction to proceed by a syn-elimination (beta-elimination) mechanism. In particular, the carbonyl oxygen of Thr313 in one of the substrate recognition sites appears to be essential for anchoring the substrates by forming a strong hydrogen bond with the hydroxyl group at C3. The model supported the observed differences in substrate specificities | Arabidopsis thaliana | ? | - |
? | |
| 1.14.14.58 | additional information | cytochrome P450 monooxygenase with narrow substrate specificity for (E,E)-geranyllinalool and (E)-nerolidol. Mechanism follows oxidative bond cleavage of the alcohol substrate via syn-elimination of the polar head, together with an allylic C-5 hydrogen atom. No substrate: racemic linalool or (R)-(-)-linalool | Arabidopsis thaliana | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.14.58 | At3g25180 | - |
Arabidopsis thaliana |
| 1.14.14.58 | CYP82G1 | - |
Arabidopsis thaliana |
| 1.14.14.58 | cytochrome P450 82G1 | - |
Arabidopsis thaliana |
| 1.14.14.58 | DMNT homoterpene synthase | - |
Arabidopsis thaliana |
| 1.14.14.58 | DMNT synthase | - |
Arabidopsis thaliana |
| 1.14.14.58 | DMNT/TMTT homoterpene synthase | - |
Arabidopsis thaliana |
| 1.14.14.58 | TMTT homoterpene synthase | - |
Arabidopsis thaliana |
| 1.14.14.58 | TMTT synthase | - |
Arabidopsis thaliana |
Turnover Number [1/s]
| EC Number | Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.14.58 | 0.11 | - |
(E,E)-geranyllinalool | pH and temperature not specified in the publication | Arabidopsis thaliana | |
| 1.14.14.58 | 0.11 | - |
(3S)-(E,E)-geranyllinalool | pH not specified in the publication, temperature not specified in the publication | Arabidopsis thaliana | |
| 1.14.14.58 | 0.2 | - |
(3S,6E)-nerolidol | pH and temperature not specified in the publication | Arabidopsis thaliana | |
| 1.14.14.58 | 0.2 | - |
(3S)-(E)-nerolidol | pH not specified in the publication, temperature not specified in the publication | Arabidopsis thaliana | |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.14.58 | cytochrome P450 | a cytochrome P450 monooxygenase | Arabidopsis thaliana |
Expression
| EC Number | Organism | Comment | Expression |
|---|---|---|---|
| 1.14.14.58 | Arabidopsis thaliana | constitutively expressed in Arabidopsis stems and inflorescences | additional information |
| 1.14.14.58 | Arabidopsis thaliana | highly coordinated herbivore-induced expression with geranyllinalool synthase in leaves depending on the F-box protein COI-1. Induction of CYP82G1 in response to feeding by Pseudomonas xylostella larvae and upon infection with Pseudomonas syringae DC3000 | up |
| 4.2.3.144 | Arabidopsis thaliana | highly coordinated herbivore-induced expression of geranyllinalool synthase with CYP82G1 (At3g25180, a cytochrome P450 monooxygenase of the Arabidopsis CYP82 family, is responsible for the breakdown of the C20-precursor (E,E)-geranyllinalool to the insect-induced C16-homoterpene (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene (TMTT)) in leaves depending on the F-box protein COI-1 | up |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 1.14.14.58 | malfunction | CYP82G1 gene knockout plants do not produce (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene and their phenotype is complemented by the constitutive expression of CYP82G1 | Arabidopsis thaliana |
kcat/KM [mM/s]
| EC Number | kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.14.58 | 41 | - |
(E,E)-geranyllinalool | pH and temperature not specified in the publication | Arabidopsis thaliana | |
| 1.14.14.58 | 109 | - |
(3S,6E)-nerolidol | pH and temperature not specified in the publication | Arabidopsis thaliana | |
| 1.14.21.B1 | 0.05 | - |
(3S)-(E,E)-geranyllinalool | pH not specified in the publication, temperature not specified in the publication | Arabidopsis thaliana | |
| 1.14.21.B1 | 0.11 | - |
(3S)-(E)-nerolidol | pH not specified in the publication, temperature not specified in the publication | Arabidopsis thaliana | |
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