BRENDA - Enzyme Database show
show all sequences of 1.14.14.58

Herbivore-induced and floral homoterpene volatiles are biosynthesized by a single P450 enzyme (CYP82G1) in Arabidopsis

Lee, S.; Badieyan, S.; Bevan, D.R.; Herde, M.; Gatz, C.; Tholl, D.; Proc. Natl. Acad. Sci. USA 107, 21205-21210 (2010)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
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
Arabidopsis thaliana
Crystallization (Commentary)
Crystallization
Organism
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]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.00184
-
(3S,6E)-nerolidol
pH and temperature not specified in the publication
Arabidopsis thaliana
0.00184
-
(3S)-(E)-nerolidol
pH not specified in the publication, temperature not specified in the publication
Arabidopsis thaliana
0.00268
-
(3S)-(E,E)-geranyllinalool
pH not specified in the publication, temperature not specified in the publication
Arabidopsis thaliana
0.00268
-
(E,E)-geranyllinalool
pH and temperature not specified in the publication
Arabidopsis thaliana
Localization
Localization
Commentary
Organism
GeneOntology No.
Textmining
microsome
-
Arabidopsis thaliana
-
-
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(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
-
-
?
(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
-
-
?
(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
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Arabidopsis thaliana
Q9LSF8
; ecotype Columbia
-
Reaction
Reaction
Commentary
Organism
(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
Source Tissue
Commentary
Organism
Textmining
inflorescence
constitutive expression; constitutively expressed
Arabidopsis thaliana
-
leaf
highly coordinated herbivore-induced expression with geranyllinalool synthase in leaves depending on the F-box protein COI-1
Arabidopsis thaliana
-
stem
constitutive expression; constitutively expressed
Arabidopsis thaliana
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
-
713423
Arabidopsis thaliana
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(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
713423
Arabidopsis thaliana
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2
-
713423
Arabidopsis thaliana
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(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
713423
Arabidopsis thaliana
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
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
713423
Arabidopsis thaliana
?
-
-
-
-
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
713423
Arabidopsis thaliana
?
-
-
-
-
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.11
-
(3S)-(E,E)-geranyllinalool
pH not specified in the publication, temperature not specified in the publication
Arabidopsis thaliana
0.11
-
(E,E)-geranyllinalool
pH and temperature not specified in the publication
Arabidopsis thaliana
0.2
-
(3S,6E)-nerolidol
pH and temperature not specified in the publication
Arabidopsis thaliana
0.2
-
(3S)-(E)-nerolidol
pH not specified in the publication, temperature not specified in the publication
Arabidopsis thaliana
Cofactor
Cofactor
Commentary
Organism
Structure
cytochrome P450
a cytochrome P450 monooxygenase
Arabidopsis thaliana
Cloned(Commentary) (protein specific)
Commentary
Organism
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
Arabidopsis thaliana
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
cytochrome P450
a cytochrome P450 monooxygenase
Arabidopsis thaliana
Crystallization (Commentary) (protein specific)
Crystallization
Organism
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] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.00184
-
(3S,6E)-nerolidol
pH and temperature not specified in the publication
Arabidopsis thaliana
0.00184
-
(3S)-(E)-nerolidol
pH not specified in the publication, temperature not specified in the publication
Arabidopsis thaliana
0.00268
-
(3S)-(E,E)-geranyllinalool
pH not specified in the publication, temperature not specified in the publication
Arabidopsis thaliana
0.00268
-
(E,E)-geranyllinalool
pH and temperature not specified in the publication
Arabidopsis thaliana
Localization (protein specific)
Localization
Commentary
Organism
GeneOntology No.
Textmining
microsome
-
Arabidopsis thaliana
-
-
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
(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
-
-
?
(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
-
-
?
(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
-
-
?
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
inflorescence
constitutive expression; constitutively expressed
Arabidopsis thaliana
-
leaf
highly coordinated herbivore-induced expression with geranyllinalool synthase in leaves depending on the F-box protein COI-1
Arabidopsis thaliana
-
stem
constitutive expression; constitutively expressed
Arabidopsis thaliana
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(3S)-(E,E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
-
713423
Arabidopsis thaliana
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(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
713423
Arabidopsis thaliana
(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(3S,6E)-nerolidol + [reduced NADPH-hemoprotein reductase] + O2
-
713423
Arabidopsis thaliana
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(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
713423
Arabidopsis thaliana
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
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
713423
Arabidopsis thaliana
?
-
-
-
-
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
713423
Arabidopsis thaliana
?
-
-
-
-
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
0.11
-
(3S)-(E,E)-geranyllinalool
pH not specified in the publication, temperature not specified in the publication
Arabidopsis thaliana
0.11
-
(E,E)-geranyllinalool
pH and temperature not specified in the publication
Arabidopsis thaliana
0.2
-
(3S,6E)-nerolidol
pH and temperature not specified in the publication
Arabidopsis thaliana
0.2
-
(3S)-(E)-nerolidol
pH not specified in the publication, temperature not specified in the publication
Arabidopsis thaliana
Expression
Organism
Commentary
Expression
Arabidopsis thaliana
constitutively expressed in Arabidopsis stems and inflorescences
additional information
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
General Information
General Information
Commentary
Organism
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
General Information (protein specific)
General Information
Commentary
Organism
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
Expression (protein specific)
Organism
Commentary
Expression
Arabidopsis thaliana
constitutively expressed in Arabidopsis stems and inflorescences
additional information
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
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
41
-
(E,E)-geranyllinalool
pH and temperature not specified in the publication
Arabidopsis thaliana
109
-
(3S,6E)-nerolidol
pH and temperature not specified in the publication
Arabidopsis thaliana
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
41
-
(E,E)-geranyllinalool
pH and temperature not specified in the publication
Arabidopsis thaliana
109
-
(3S,6E)-nerolidol
pH and temperature not specified in the publication
Arabidopsis thaliana
Other publictions for EC 1.14.14.58
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
746032
Richter
Characterization of biosynthe ...
Zea mays
Plant Cell
28
2651-2665
2016
-
-
1
-
-
-
-
5
-
-
-
2
-
3
-
-
-
-
-
1
-
-
8
-
-
-
-
-
-
-
-
1
-
-
-
-
-
2
2
-
-
-
-
-
-
5
-
-
-
2
-
-
-
-
-
2
-
-
8
-
-
-
-
-
-
-
-
-
1
3
6
2
-
-
746029
Sohrabi
In planta variation of volati ...
Arabidopsis thaliana
Plant Cell
27
874-890
2015
-
-
1
-
1
-
2
-
1
-
-
4
-
2
-
-
-
-
-
5
-
-
6
-
-
-
-
-
-
-
-
1
-
-
-
-
-
1
2
-
1
-
-
2
-
-
1
-
-
4
-
-
-
-
-
6
-
-
6
-
-
-
-
-
-
-
-
-
1
4
5
2
-
-
728442
Tholl
The biochemistry of homoterpen ...
Arabidopsis thaliana
Phytochemistry
72
1635-1646
2011
-
-
-
-
-
-
-
-
-
-
-
3
-
1
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
713423
Lee
Herbivore-induced and floral h ...
Arabidopsis thaliana
Proc. Natl. Acad. Sci. USA
107
21205-21210
2010
-
-
1
1
-
-
-
4
1
-
-
3
-
1
-
-
-
1
-
3
-
-
6
-
-
-
-
4
-
-
-
1
-
-
-
-
-
1
1
1
-
-
-
-
-
4
1
-
-
3
-
-
-
-
-
3
-
-
6
-
-
-
-
4
-
-
-
-
2
1
1
2
2
2
746284
Lee
Herbivore-induced and floral ...
Arabidopsis thaliana
Proc. Natl. Acad. Sci. USA
107
21205-21210
2010
-
-
-
1
-
-
-
1
-
-
-
-
-
1
-
-
-
-
-
2
-
-
1
-
-
-
-
1
-
-
-
1
-
-
-
-
-
-
1
1
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
2
-
-
1
-
-
-
-
1
-
-
-
-
-
-
-
-
1
1