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Enzyme Nomenclature
Information on EC 1.14.13.B14 - (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene synthase
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The expected taxonomic range for this enzyme is: Arabidopsis thaliana
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EC NUMBER 
COMMENTARY 
1.14.13.B14
preliminary BRENDA-supplied EC number
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RECOMMENDED NAME
GeneOntology No.
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(3S)-(E,E)-geranyllinalool + NADPH + H+ + O2 = (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + 2 H2O
(3S)-(E,E)-geranyllinalool + NADPH + H+ + O2 = (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + 2 H2O
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(3S)-(E,E)-geranyllinalool + NADPH + H+ + O2 = (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + 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
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SYSTEMATIC NAME
IUBMB Comments
(E,E)-geranyllinalool,NADPH:oxygen oxidoreductase
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(3S)-(E,E)-geranyllinalool + NADPH + H+ + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + 2 H2O
(3S,6E)-nerolidol + NADPH + H+ + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + 2 H2O
(E)-nerolidol + NADPH + H+ + O2
4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O
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?
(E,E)-geranyllinalool + NADPH + H+ + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + H2O
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?
(3S)-(E,E)-geranyllinalool + NADPH + H+ + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + 2 H2O
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-
-
?
(3S)-(E,E)-geranyllinalool + NADPH + H+ + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + 2 H2O
biosynthesis of the volatile organic compound (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene
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?
(3S,6E)-nerolidol + NADPH + H+ + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + 2 H2O
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?
(3S,6E)-nerolidol + NADPH + H+ + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + 2 H2O
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
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?
additional information
?
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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
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additional information
?
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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
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additional information
?
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linalool, (Z)-nerolidol, the primary terpene alcohols (E,E,E)-geranylgeraniol, (E,E)-farnesol, and (E)-geraniol, or fully saturated analogs of (E)-nerolidol and (E,E)-geranyllinalool (3,7,11-trimethyl-3-dodecanol, isophytol) are no functional substrates of the CYP82G1 enzyme
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(3S)-(E,E)-geranyllinalool + NADPH + H+ + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + 2 H2O
(3S,6E)-nerolidol + NADPH + H+ + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + 2 H2O
Q9LSF8
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
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?
(E)-nerolidol + NADPH + H+ + O2
4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O
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?
(E,E)-geranyllinalool + NADPH + H+ + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + H2O
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?
additional information
?
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linalool, (Z)-nerolidol, the primary terpene alcohols (E,E,E)-geranylgeraniol, (E,E)-farnesol, and (E)-geraniol, or fully saturated analogs of (E)-nerolidol and (E,E)-geranyllinalool (3,7,11-trimethyl-3-dodecanol, isophytol) are no functional substrates of the CYP82G1 enzyme
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(3S)-(E,E)-geranyllinalool + NADPH + H+ + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + 2 H2O
Q9LSF8
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?
(3S)-(E,E)-geranyllinalool + NADPH + H+ + O2
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + NADP+ + 2 H2O
Q9LSF8
biosynthesis of the volatile organic compound (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene
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?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00184
(3S)-(E)-nerolidol
pH not specified in the publication, temperature not specified in the publication
0.00268
(3S)-(E,E)-geranyllinalool
pH not specified in the publication, temperature not specified in the publication
0.00184
(3S,6E)-nerolidol
pH and temperature not specified in the publication
0.00268
(E,E)-geranyllinalool
pH and temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.2
(3S)-(E)-nerolidol
Arabidopsis thaliana
Q9LSF8
pH not specified in the publication, temperature not specified in the publication
0.11
(3S)-(E,E)-geranyllinalool
Arabidopsis thaliana
Q9LSF8
pH not specified in the publication, temperature not specified in the publication
0.2
(3S,6E)-nerolidol
Arabidopsis thaliana
Q9LSF8
pH and temperature not specified in the publication
0.11
(E,E)-geranyllinalool
Arabidopsis thaliana
Q9LSF8
pH and temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
109
(3S,6E)-nerolidol
Arabidopsis thaliana
Q9LSF8
pH and temperature not specified in the publication
19192
41
(E,E)-geranyllinalool
Arabidopsis thaliana
Q9LSF8
pH and temperature not specified in the publication
15125
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
highly coordinated herbivore-induced expression with geranyllinalool synthase in leaves depending on the F-box protein COI-1
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloned into the yeast expression vector YEp352 under the control of the constitutive alcohol dehydrogenase 1 promoter, expression in yeast; expression in yeast WAT11 cells
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression of CYP82G1 is induced by treatment with alamethicin, coronalon and at sites of feeding damage by larvae of P. xylostella
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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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.B14)
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