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

EC NUMBER
COMMENTARY hide
1.14.13.B14
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
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
show the reaction diagram
SYSTEMATIC NAME
IUBMB Comments
(E,E)-geranyllinalool,NADPH:oxygen oxidoreductase
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
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
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
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
show the reaction diagram
(3S,6E)-nerolidol + NADPH + H+ + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + 2 H2O
show the reaction diagram
(E)-nerolidol + NADPH + H+ + O2
4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + H2O
show the reaction diagram
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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
show the reaction diagram
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
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
show the reaction diagram
(3S,6E)-nerolidol + NADPH + H+ + O2
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + 2 H2O
show the reaction diagram
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
show the reaction diagram
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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
show the reaction diagram
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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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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
a cytochrome P450 monooxygenase
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
constitutive expression; constitutively expressed
Manually annotated by BRENDA team
highly coordinated herbivore-induced expression with geranyllinalool synthase in leaves depending on the F-box protein COI-1
Manually annotated by BRENDA team
constitutive expression; constitutively expressed
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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
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
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
constitutively expressed in Arabidopsis stems and inflorescences
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