Information on EC 1.14.13.B14 - (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene synthase

for references in articles please use BRENDA:EC1.14.13.B14
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The enzyme appears in viruses and cellular organisms

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
evolution
malfunction
metabolism
physiological function
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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-
-
-
?
arabidiol + NADPH + H+ + O2
(3E)-4,8-dimethylnona-1,3,7-triene + ? + NADP+ + 2 H2O
show the reaction diagram
Q0LSF8
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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
(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
-
-
-
-
?
arabidiol + NADPH + H+ + O2
(3E)-4,8-dimethylnona-1,3,7-triene + ? + NADP+ + 2 H2O
show the reaction diagram
Q0LSF8
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-
-
?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
clotrimazole
Q0LSF8
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miconazole
Q0LSF8
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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 - 0.0104
(3S)-(E,E)-geranyllinalool
0.00184 - 0.0142
(3S,6E)-nerolidol
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
pH not specified in the publication, temperature not specified in the publication
0.11
(3S)-(E,E)-geranyllinalool
pH not specified in the publication, temperature not specified in the publication
0.2
(3S,6E)-nerolidol
pH and temperature not specified in the publication
0.11
(E,E)-geranyllinalool
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
pH and temperature not specified in the publication
41
(E,E)-geranyllinalool
pH and temperature not specified in the publication
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
constitutive expression; constitutively expressed
Manually annotated by BRENDA team
Q0LSF8
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Manually annotated by BRENDA team
constitutive expression; constitutively expressed
Manually annotated by BRENDA team
additional information
Q0LSF8
CYP705A1 clusters with the arabidiol synthase gene ABDS, and both genes are coexpressed constitutively in the root stele and meristematic tissue; CYP82G1 is not expressed in roots
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
gene CYP705A1, the full-length CYP705A1 transcript is fused to the CaMV 35S promoter for ectopic expression in the cyp705a1-1 mutant background
Q0LSF8
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
constitutively expressed in Arabidopsis stems and inflorescences
CYP705A1 is transiently induced in a jasmonate-dependent manner by infection with the root rot oomycete pathogen Pythium irregulare. DMNT is emitted from Arabidopsis thaliana roots upon infection with Pythium irregulare or treatment with jasmonic acid. ProCYP705A1:CYP705A1-eYFP lines, accumulation of the full-length CYP705A1 transcript is detected upon JA treatment, while only basal transcript levels of the gene are observed in ProCaMV35S-CYP705A1 lines with no jasmonate-dependent increase of transcript abundance; CYP82G1 is induced in Arabidopsis thaliana leaves upon insect feeding damage
Q0LSF8
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
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
Q0LSF8
construction of the cyp705a1-1 null mutant, the mutant is complemented with a full-length CYP705A1 cDNA in C-terminal fusion to enhanced yellow fluorescent protein (eYFP)