Information on EC 1.14.14.114 - amorpha-4,11-diene 12-monooxygenase

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The expected taxonomic range for this enzyme is: Artemisia

EC NUMBER
COMMENTARY hide
1.14.14.114
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RECOMMENDED NAME
GeneOntology No.
amorpha-4,11-diene 12-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
amorpha-4,11-diene + 3 O2 + 3 [reduced NADPH-hemoprotein reductase] = artemisinate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
show the reaction diagram
overall reaction
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amorpha-4,11-diene + O2 + [reduced NADPH-hemoprotein reductase] = artemisinic alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1a)
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artemisinic alcohol + O2 + [reduced NADPH-hemoprotein reductase] = artemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(1b)
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artemisinic aldehyde + O2 + [reduced NADPH-hemoprotein reductase] = artemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1c)
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SYSTEMATIC NAME
IUBMB Comments
amorpha-4,11-diene,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (12-hydroxylating)
A heme-thiolate protein (P-450). Cloned from the plant Artemisia annua (sweet wormwood). Part of the biosynthetic pathway of artemisinin.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
2-nonenal + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
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amorpha-4,11-diene + 3 O2 + [reduced NADPH-hemoprotein reductase]
artemisinate + [oxidized NADPH-hemoprotein reductase] + 4 H2O
show the reaction diagram
amorpha-4,11-diene + O2 + [reduced NADPH-hemoprotein reductase]
artemisinic alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
amorpha-4,11-diene + [reduced NADPH-hemoprotein reductase] + O2
artemisinic alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
artemisinic alcohol + O2 + [reduced NADPH-hemoprotein reductase]
artemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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-
-
-
?
artemisinic alcohol + [reduced NADPH-hemoprotein reductase] + O2
artemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
artemisinic aldehyde + O2 + [reduced NADPH-hemoprotein reductase]
artemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
-
?
artemisinic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
artemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
dihydroartemisinic alcohol + [reduced NADPH-hemoprotein reductase] + O2
dihydroartemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
dihydroartemisinic aldehyde + [reduced NADPH-hemoprotein reductase] + O2
dihydroartemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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octanal + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + 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
amorpha-4,11-diene + 3 O2 + [reduced NADPH-hemoprotein reductase]
artemisinate + [oxidized NADPH-hemoprotein reductase] + 4 H2O
show the reaction diagram
amorpha-4,11-diene + O2 + [reduced NADPH-hemoprotein reductase]
artemisinic alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
artemisinic alcohol + O2 + [reduced NADPH-hemoprotein reductase]
artemisinic aldehyde + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
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-
-
?
artemisinic aldehyde + O2 + [reduced NADPH-hemoprotein reductase]
artemisinate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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heme
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a heme catalytic site situated at the C-terminal domain
NADPH-hemoprotein reductase
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0026
artemisinic aldehyde
pH 8.5, 30°C
0.0088
dihydroartemisinic aldehyde
pH 8.5, 30°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.53
artemisinic aldehyde
pH 8.5, 30°C
7.74
dihydroartemisinic aldehyde
pH 8.5, 30°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
593
artemisinic aldehyde
pH 8.5, 30°C
881
dihydroartemisinic aldehyde
pH 8.5, 30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8
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recombinant enzyme
8.5
substrate dihydroartemisinic aldehyde
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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expression of farnesyl diphosphate synthase takes place in apical and sub-apical cells as well as in mesophyl cells while the three enzymes involved in artemisinin biosynthesis, i.e. amorpha-4,11-diene synthase, amorpha-4,11-diene hydroxylase, a cytochrome P450 monooxygenase, and artemisinic aldehyde DELTA11(13) reductase are expressed only in the apical cells
Manually annotated by BRENDA team
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moderate expression
Manually annotated by BRENDA team
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low expression
Manually annotated by BRENDA team
regenerated plantlets
Manually annotated by BRENDA team
additional information
callus cannot produce artemisinin
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
53800
x * 53800, calculated
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 53800, calculated
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
expression in Escherichia coli
expression in Saccharomyces cerevisiae
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gene CYP71AV1, quantitative real-time PCR enzyme expression analysis
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gene cyp71av1, recombinant expression of cytochrome P450 CYP71AV1 in Saccharomyces cerevisiae, coexpression with artemisinic aldehyde D11(13) reductase (DBR2), and artemisinic aldehyde dehydrogenase (ALDH1), which recycles NADPH
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gene CYP71AV1, semi-quantitative RT-PCR enzyme expression analysis, the expression level of CYP71AV1 significantly increases with the overexpression of AabHLH1
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
endophyte Penicillium oxalicum strain B4 induces the enzyme and leads to enhanced growth and artemisinin content of host plant in an in vitro dual culture of endophyte with regenerated plantlets via generation of reactive oxygen species (ROS) including superoxide ions and H2O2
the expression level of CYP71AV1 significantly increases with the overexpression of transcription factor AabHLH1. The promoters of ADS and CYP71AV1 contain E-box elements, which are putative binding sites for basic helix-loop-helix (bHLH) transcription factors. The E-box is important for the CYP71AV1 promoter activity. AabHLH1 can positively regulate the biosynthesis of artemisinin. AabHLH1 protein is capable of binding to the E-box cis-elements, present in both ADS and CYP71AV1 promoters, and possesses transactivation activity in yeast. Transient expression of AabHLH1 in Artemisia annua leaves increases transcript levels of the genes involved in artemisinin biosynthesis, such as ADS, CYP71AV1 and HMGR
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transcription factor protein glandular trichome-specific WRKY 1, i.e. AaGSW1, promotes artemisinin biosynthesis in Artemisia annua by inducing CYP71AV1 expression. AaGSW1 positively regulates CYP71AV1 and AaORA expression by directly binding to the W-box motifs in their promoters. Overexpression of AaGSW1 in Artemisia annua (via Agrobacterium tumefaciens transformation method) significantly improves artemisinin and dihydroartemisinic acid contents. AaGSW1 can be directly regulated by AaMYC2 and AabZIP1, which are positive regulators of jasmonate- and abscisic acid-mediated artemisinin biosynthetic pathways, respectively. AaGSW1 binds to the W-box in the CYP71AV1 promoter in vitro and activates the transcription of CYP71AV1 in vivo. Global expression profile and phylogenetic analysis of WRKY transcription factors in Artemisia annua, overview
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis