BRENDA - Enzyme Database show
show all sequences of 1.14.14.114

Artemisia annua mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism

Czechowski, T.; Larson, T.R.; Catania, T.M.; Harvey, D.; Brown, G.D.; Graham, I.A.; Proc. Natl. Acad. Sci. USA 113, 15150-15155 (2016)

Data extracted from this reference:

Engineering
Amino acid exchange
Commentary
Organism
additional information
construction of enzyme knockout mutant cyp71av1-1, phenotype, overview
Artemisia annua
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
amorpha-4,11-diene + 3 O2 + [reduced NADPH-hemoprotein reductase]
Artemisia annua
overall reactionvia artemsinic alcohol and artemsinic aldehyde, multistep process
artemisinate + [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
amorpha-4,11-diene + O2 + [reduced NADPH-hemoprotein reductase]
Artemisia annua
-
artemisinic alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
artemisinic alcohol + O2 + [reduced NADPH-hemoprotein reductase]
Artemisia annua
-
artemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
?
artemisinic aldehyde + O2 + [reduced NADPH-hemoprotein reductase]
Artemisia annua
-
artemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Artemisia annua
Q1PS23
-
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
inflorescence
-
Artemisia annua
-
leaf
-
Artemisia annua
-
secretory trichome
the production of artemisinin occurs in specialized 10-cell biseriate glandular trichomes present on the leaves, stems, and inflorescences of Artemisia annua
Artemisia annua
-
stem
-
Artemisia annua
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
amorpha-4,11-diene + 3 O2 + [reduced NADPH-hemoprotein reductase]
overall reactionvia artemsinic alcohol and artemsinic aldehyde, multistep process
746309
Artemisia annua
artemisinate + [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
amorpha-4,11-diene + O2 + [reduced NADPH-hemoprotein reductase]
-
746309
Artemisia annua
artemisinic alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
artemisinic alcohol + O2 + [reduced NADPH-hemoprotein reductase]
-
746309
Artemisia annua
artemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
artemisinic aldehyde + O2 + [reduced NADPH-hemoprotein reductase]
-
746309
Artemisia annua
artemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
additional information
conversion of dihydroartemsinic aldehyde to artemisinate is nonenzymatic in trichomes by nonenzymatic autoxidation of dihydroartemsinic aldehyde to dihydroartemsinic acid tertiary hydroperoxide and subsequent nonenzymatic rearrangement to artemisinin
746309
Artemisia annua
?
-
-
-
-
Cofactor
Cofactor
Commentary
Organism
Structure
cytochrome P450
-
Artemisia annua
NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
Artemisia annua
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
cytochrome P450
-
Artemisia annua
NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
Artemisia annua
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
additional information
construction of enzyme knockout mutant cyp71av1-1, phenotype, overview
Artemisia annua
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
amorpha-4,11-diene + 3 O2 + [reduced NADPH-hemoprotein reductase]
Artemisia annua
overall reactionvia artemsinic alcohol and artemsinic aldehyde, multistep process
artemisinate + [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
?
amorpha-4,11-diene + O2 + [reduced NADPH-hemoprotein reductase]
Artemisia annua
-
artemisinic alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
artemisinic alcohol + O2 + [reduced NADPH-hemoprotein reductase]
Artemisia annua
-
artemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
?
artemisinic aldehyde + O2 + [reduced NADPH-hemoprotein reductase]
Artemisia annua
-
artemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
?
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
inflorescence
-
Artemisia annua
-
leaf
-
Artemisia annua
-
secretory trichome
the production of artemisinin occurs in specialized 10-cell biseriate glandular trichomes present on the leaves, stems, and inflorescences of Artemisia annua
Artemisia annua
-
stem
-
Artemisia annua
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
amorpha-4,11-diene + 3 O2 + [reduced NADPH-hemoprotein reductase]
overall reactionvia artemsinic alcohol and artemsinic aldehyde, multistep process
746309
Artemisia annua
artemisinate + [oxidized NADPH-hemoprotein reductase] + 4 H2O
-
-
-
?
amorpha-4,11-diene + O2 + [reduced NADPH-hemoprotein reductase]
-
746309
Artemisia annua
artemisinic alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
artemisinic alcohol + O2 + [reduced NADPH-hemoprotein reductase]
-
746309
Artemisia annua
artemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
-
-
-
?
artemisinic aldehyde + O2 + [reduced NADPH-hemoprotein reductase]
-
746309
Artemisia annua
artemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
additional information
conversion of dihydroartemsinic aldehyde to artemisinate is nonenzymatic in trichomes by nonenzymatic autoxidation of dihydroartemsinic aldehyde to dihydroartemsinic acid tertiary hydroperoxide and subsequent nonenzymatic rearrangement to artemisinin
746309
Artemisia annua
?
-
-
-
-
General Information
General Information
Commentary
Organism
malfunction
the enzyme knockout mutant cyp71av1-1 reveals that the consequence of blocking the artemisinin biosynthetic pathway is the redirection of sesquiterpene metabolism to a sesquiterpene epoxide, termed arteannuin X. Disruption of CYP71AV1 results in the accumulation of a sesquiterpene epoxide at the expense of artemisinin
Artemisia annua
metabolism
the amorpha-4,11-diene C-12 oxidase (CYP71AV1) enzyme, responsible for a series of oxidation reactions in the artemisinin biosynthetic pathway, overview
Artemisia annua
physiological function
the antimalarial artemisinin is a sesquiterpene lactone produced by glandular secretory trichomes on the leaves, stems, and inflorescences of Artemisia annua. Glandular secretory trichomes are able to redirect flux into a sesquiterpene epoxide. The amorpha-4,11-diene C-12 oxidase (CYP71AV1) enzyme, responsible for a series of oxidation reactions in the artemisinin biosynthetic pathway
Artemisia annua
General Information (protein specific)
General Information
Commentary
Organism
malfunction
the enzyme knockout mutant cyp71av1-1 reveals that the consequence of blocking the artemisinin biosynthetic pathway is the redirection of sesquiterpene metabolism to a sesquiterpene epoxide, termed arteannuin X. Disruption of CYP71AV1 results in the accumulation of a sesquiterpene epoxide at the expense of artemisinin
Artemisia annua
metabolism
the amorpha-4,11-diene C-12 oxidase (CYP71AV1) enzyme, responsible for a series of oxidation reactions in the artemisinin biosynthetic pathway, overview
Artemisia annua
physiological function
the antimalarial artemisinin is a sesquiterpene lactone produced by glandular secretory trichomes on the leaves, stems, and inflorescences of Artemisia annua. Glandular secretory trichomes are able to redirect flux into a sesquiterpene epoxide. The amorpha-4,11-diene C-12 oxidase (CYP71AV1) enzyme, responsible for a series of oxidation reactions in the artemisinin biosynthetic pathway
Artemisia annua
Other publictions for EC 1.14.14.114
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)
745821
Chen
Multienzyme biosynthesis of d ...
Artemisia annua
Molecules
22
1422-1433
2017
-
1
1
-
1
-
-
-
-
-
-
4
-
1
-
-
-
-
-
-
-
-
4
-
-
-
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-
1
-
-
3
-
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1
1
3
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1
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-
-
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4
-
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-
-
-
4
-
-
-
-
-
1
-
-
-
-
2
2
-
-
-
745905
Chen
Glandular trichome-specific W ...
Artemisia annua
New Phytol.
214
304-316
2017
-
-
1
-
-
-
-
-
-
-
-
4
-
2
-
-
-
-
-
1
-
-
4
-
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-
-
-
-
2
-
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1
2
-
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-
4
-
-
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-
1
-
-
4
-
-
-
-
-
-
-
-
-
1
1
1
1
-
-
746043
Muangphrom
Functional analysis of amorph ...
Artemisia absinthium, Artemisia afra, Artemisia annua, Artemisia kurramensis
Plant Cell Physiol.
57
1678-1688
2016
-
-
3
-
-
-
-
-
-
-
-
4
-
9
-
-
-
-
-
3
-
-
4
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8
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3
8
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4
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3
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4
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8
8
-
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-
746069
Zheng
-
The influence of endophytic P ...
Artemisia annua
Plant Growth Regul.
80
93-102
2016
-
-
-
-
-
-
-
-
-
-
-
1
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1
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3
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1
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1
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1
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1
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1
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3
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1
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-
1
-
-
-
1
-
-
1
-
-
746309
Czechowski
Artemisia annua mutant impair ...
Artemisia annua
Proc. Natl. Acad. Sci. USA
113
15150-15155
2016
-
-
-
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1
-
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-
4
-
2
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4
-
-
5
-
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-
-
-
-
-
2
-
-
-
-
-
-
2
-
1
-
-
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-
4
-
-
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4
-
-
5
-
-
-
-
-
-
-
-
-
-
3
3
-
-
-
746035
Ji
Cloning and characterization ...
Artemisia annua
Plant Cell Physiol.
55
1592-1604
2014
-
-
1
-
-
-
-
-
-
-
-
4
-
3
-
-
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-
-
1
-
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4
-
-
-
-
-
-
-
-
1
-
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-
1
1
-
-
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-
4
-
-
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-
1
-
-
4
-
-
-
-
-
-
-
-
-
1
2
2
1
-
-
716656
Alejos-Gonzalez
Characterization of developmen ...
Artemisia annua
Planta
234
685-697
2011
-
1
-
-
-
-
-
-
-
-
-
-
-
2
-
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-
2
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1
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2
-
-
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-
-
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-
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-
-
-
-
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-
718205
Zhang
The production of artemisinin ...
Artemisia annua
Plant Biotechnol. J.
9
445-454
2011
-
1
-
-
-
-
-
-
-
-
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3
-
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1
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706125
Olsson
Localization of enzymes of art ...
Artemisia annua
Phytochemistry
70
1123-1128
2009
-
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-
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1
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1
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1
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-
1
1
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-
717445
Teoh
-
Molecular cloning of an aldehy ...
Artemisia annua
Botany
87
635-642
2009
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1
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2
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1
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2
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1
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13
1
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2
1
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1
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2
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1
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1
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13
1
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2
1
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2
2
717601
Teoh
Artemisia annua L. (Asteraceae ...
Artemisia annua
FEBS Lett.
580
1411-1416
2006
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-
1
-
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4
-
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4
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4
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1
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