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show all sequences of 1.14.14.58

Characterization of biosynthetic pathways for the production of the volatile homoterpenes DMNT and TMTT in Zea mays

Richter, A.; Schaff, C.; Zhang, Z.; Lipka, A.; Tian, F.; Koellner, T.; Schnee, C.; Preiss, S.; Irmisch, S.; Jander, G.; Boland, W.; Gershenzon, J.; Buckler, E.; Degenhardt, J.; Plant Cell 28, 2651-2665 (2016)

Data extracted from this reference:

Cloned(Commentary)
Commentary
Organism
expression in Saccharomyces cerevisiae; expression in Saccharomyces cerevisiae
Zea mays
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0056
-
(3S)-(E,E)-geranyllinalool
pH and temperature not specified in the publication
Zea mays
0.0056
-
(6E,10E)-geranyllinalool
pH 6.8, 30°C
Zea mays
0.0104
-
(3S)-(E,E)-geranyllinalool
pH and temperature not specified in the publication
Zea mays
0.0104
-
(6E,10E)-geranyllinalool
pH 6.8, 30°C
Zea mays
0.0142
-
(3S,6E)-nerolidol
pH and temperature not specified in the publication
Zea mays
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
Zea mays
-
(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
Zea mays
-
(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
Zea mays
B6ST66
26 Zea mays inbred lines; enzyme catalyzes reactions of EC 1.14.14.58 and of EC 1.14.14.59
-
Zea mays
B8A110
-
-
Zea mays
-
26 Zea mays inbred lines
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
leaf
;
Zea mays
-
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
-
746032
Zea mays
(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
-
746032
Zea mays
(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
major substrate
746032
Zea mays
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(6E,10E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
-
746032
Zea mays
(3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + [oxidized NADPH-hemoprotein reductase] + but-3-en-2-one + 2 H2O
-
-
-
?
additional information
no substrate: linalool
746032
Zea mays
?
-
-
-
-
Cofactor
Cofactor
Commentary
Organism
Structure
cytochrome P450
;
Zea mays
Cloned(Commentary) (protein specific)
Commentary
Organism
expression in Saccharomyces cerevisiae
Zea mays
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
cytochrome P450
-
Zea mays
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0056
-
(3S)-(E,E)-geranyllinalool
pH and temperature not specified in the publication
Zea mays
0.0056
-
(6E,10E)-geranyllinalool
pH 6.8, 30°C
Zea mays
0.0104
-
(3S)-(E,E)-geranyllinalool
pH and temperature not specified in the publication
Zea mays
0.0104
-
(6E,10E)-geranyllinalool
pH 6.8, 30°C
Zea mays
0.0142
-
(3S,6E)-nerolidol
pH and temperature not specified in the publication
Zea mays
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
Zea mays
-
(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
Zea mays
-
(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
leaf
-
Zea mays
-
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
-
746032
Zea mays
(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
-
746032
Zea mays
(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
major substrate
746032
Zea mays
(3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
(6E,10E)-geranyllinalool + [reduced NADPH-hemoprotein reductase] + O2
-
746032
Zea mays
(3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene + [oxidized NADPH-hemoprotein reductase] + but-3-en-2-one + 2 H2O
-
-
-
?
additional information
no substrate: linalool
746032
Zea mays
?
-
-
-
-
Expression
Organism
Commentary
Expression
Zea mays
low transcript levels in undamaged leaves, expression is strongly induced in response to simulated herbivory; low transcript levels in undamaged leaves, expression is strongly induced in response to simulated herbivory
additional information
General Information
General Information
Commentary
Organism
evolution
the DMNT biosynthetic pathway and both (DMNT and TMTT) monooxygenases are distinct from those previously characterized for (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, synthesis in Arabidopsis thaliana, suggesting independent evolution of these enzymatic activities. The amino acid identity between the maize and Arabidopsis enzymes is below 30%; the DMNT biosynthetic pathway and both (DMNT and TMTT) monooxygenases are distinct from those previously characterized for (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, synthesis in Arabidopsis thaliana, suggesting independent evolution of these enzymatic activities. The amino acid identity between the maize and Arabidopsis enzymes is below 30%
Zea mays
metabolism
the C11 homoterpene (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) is formed by the oxidative degradation of (E)-nerolidol. (E,E)-4,8,12-Trimethyltrideca-1,3,7,11-tetraene (TMTT) is produced via oxidative degradation of (E,E)-geranyllinalool. The first step of both pathways, the formation of the tertiary terpene alcohols (E,E)-geranyllinalool and (E)-nerolidol, is catalyzed by the terpene synthase, TPS2, whereas the subsequent oxidative degradation to DMNT and TMTT is catalyzed by two specific P450 monooxygenases, CYP92C5 and CYP92C6. Pathway mapping of 26 parent lines of US-NAM population for pathways and enzymes contributing to volatile terpene biosynthesis in maize leaves. TPS2 is the regulatory key enzyme; the C11 homoterpene (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) is formed by the oxidative degradation of (E)-nerolidol. (E,E)-4,8,12-Trimethyltrideca-1,3,7,11-tetraene (TMTT) is produced via oxidative degradation of (E,E)-geranyllinalool. The first step of both pathways, the formation of the tertiary terpene alcohols (E,E)-geranyllinalool and (E)-nerolidol, is catalyzed by the terpene synthase, TPS2, whereas the subsequent oxidative degradation to DMNT and TMTT is catalyzed by two specific P450 monooxygenases, CYP92C5 and CYP92C6. Pathway mapping of 26 parent lines of US-NAM population for pathways and enzymes contributing to volatile terpene biosynthesis in maize leaves. TPS2 is the regulatory key enzyme
Zea mays
physiological function
gene disruption of CYP92C5 results in loss of (3E)-4,8-dimethylnona-1,3,7-triene production and reduced levels of (3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene after simulated herbivory. In planta (3E)-4,8-dimethylnona-1,3,7-triene is primarily produced by isoform CYP92C5, whereas the majority of (3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene is produced by cytochrome P450 monooxygenase, CYP92C6; while enzyme CYP92C5 converts (E)-nerolidol and (E,E)-geranyllinalool to (3E)-4,8-dimethyl-1,3,7,-nonatriene (DMNT) and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, respectively, enzyme CYP92C6 only converts (E,E)-geranyllinalool to (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT. (E)-4,8-Dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, are volatile homoterpenes. Many such volatiles are assigned functions in the defense against pathogens like lepidopteran larvae, aphids, fungi,and bacteria. Maize volatiles released after herbivore damage display high levels of quantitative and qualitative variation. In planta, DMNT is primarily produced by CYP92C5, whereas the majority of TMTT is produced by a related cytochrome P450 monooxygenase, CYP92C6, which is specific for the conversion of (E,E)-geranyllinalool to TMTT; while enzyme CYP92C5 converts (E)-nerolidol and (E,E)-geranyllinalool to DMNT and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, respectively, enzyme CYP92C6 only converts (E,E)-geranyllinalool to (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT. (E)-4,8-Dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, are volatile homoterpenes. Many such volatiles are assigned functions in the defense against pathogens like lepidopteran larvae, aphids, fungi,and bacteria. Maize volatiles released after herbivore damage display high levels of quantitative and qualitative variation. In planta, DMNT is primarily produced by CYP92C5, whereas the majority of TMTT is produced by a related cytochrome P450 monooxygenase, CYP92C6, which is specific for the conversion of (E,E)-geranyllinalool to TMTT
Zea mays
General Information (protein specific)
General Information
Commentary
Organism
evolution
the DMNT biosynthetic pathway and both (DMNT and TMTT) monooxygenases are distinct from those previously characterized for (E)-4,8-dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, synthesis in Arabidopsis thaliana, suggesting independent evolution of these enzymatic activities. The amino acid identity between the maize and Arabidopsis enzymes is below 30%
Zea mays
metabolism
the C11 homoterpene (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) is formed by the oxidative degradation of (E)-nerolidol. (E,E)-4,8,12-Trimethyltrideca-1,3,7,11-tetraene (TMTT) is produced via oxidative degradation of (E,E)-geranyllinalool. The first step of both pathways, the formation of the tertiary terpene alcohols (E,E)-geranyllinalool and (E)-nerolidol, is catalyzed by the terpene synthase, TPS2, whereas the subsequent oxidative degradation to DMNT and TMTT is catalyzed by two specific P450 monooxygenases, CYP92C5 and CYP92C6. Pathway mapping of 26 parent lines of US-NAM population for pathways and enzymes contributing to volatile terpene biosynthesis in maize leaves. TPS2 is the regulatory key enzyme
Zea mays
physiological function
while enzyme CYP92C5 converts (E)-nerolidol and (E,E)-geranyllinalool to (3E)-4,8-dimethyl-1,3,7,-nonatriene (DMNT) and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, respectively, enzyme CYP92C6 only converts (E,E)-geranyllinalool to (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT. (E)-4,8-Dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, are volatile homoterpenes. Many such volatiles are assigned functions in the defense against pathogens like lepidopteran larvae, aphids, fungi,and bacteria. Maize volatiles released after herbivore damage display high levels of quantitative and qualitative variation. In planta, DMNT is primarily produced by CYP92C5, whereas the majority of TMTT is produced by a related cytochrome P450 monooxygenase, CYP92C6, which is specific for the conversion of (E,E)-geranyllinalool to TMTT
Zea mays
physiological function
gene disruption of CYP92C5 results in loss of (3E)-4,8-dimethylnona-1,3,7-triene production and reduced levels of (3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene after simulated herbivory. In planta (3E)-4,8-dimethylnona-1,3,7-triene is primarily produced by isoform CYP92C5, whereas the majority of (3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene is produced by cytochrome P450 monooxygenase, CYP92C6; while enzyme CYP92C5 converts (E)-nerolidol and (E,E)-geranyllinalool to DMNT and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, respectively, enzyme CYP92C6 only converts (E,E)-geranyllinalool to (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT. (E)-4,8-Dimethyl-1,3,7-nonatriene, DMNT, and (E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene, TMTT, are volatile homoterpenes. Many such volatiles are assigned functions in the defense against pathogens like lepidopteran larvae, aphids, fungi,and bacteria. Maize volatiles released after herbivore damage display high levels of quantitative and qualitative variation. In planta, DMNT is primarily produced by CYP92C5, whereas the majority of TMTT is produced by a related cytochrome P450 monooxygenase, CYP92C6, which is specific for the conversion of (E,E)-geranyllinalool to TMTT
Zea mays
Expression (protein specific)
Organism
Commentary
Expression
Zea mays
low transcript levels in undamaged leaves, expression is strongly induced in response to simulated herbivory
additional information
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
-
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-
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-
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-
-
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-
-
-
3
-
-
-
-
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-
-
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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
-
-
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-
-
2
-
-
1
-
-
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1
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1
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1
1
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1
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-
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2
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1
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1
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-
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1
1