Information on EC 1.14.13.158 - amorpha-4,11-diene 12-monooxygenase

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The expected taxonomic range for this enzyme is: Artemisia

EC NUMBER
COMMENTARY hide
1.14.13.158
transferred to EC 1.14.14.114
RECOMMENDED NAME
GeneOntology No.
amorpha-4,11-diene 12-monooxygenase
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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
amorpha-4,11-diene + 3 O2 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
show the reaction diagram
amorpha-4,11-diene + O2 + NADPH + H+
artemisinic alcohol + NADP+ + H2O
show the reaction diagram
artemisinic alcohol + O2 + NADPH + H+
artemisinic aldehyde + NADP+ + 2 H2O
show the reaction diagram
artemisinic aldehyde + O2 + NADPH + H+
artemisinate + NADP+ + H2O
show the reaction diagram
additional information
?
-
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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
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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 + 3 NADPH + 3 H+
artemisinate + 3 NADP+ + 4 H2O
show the reaction diagram
amorpha-4,11-diene + O2 + NADPH + H+
artemisinic alcohol + NADP+ + H2O
show the reaction diagram
artemisinic alcohol + O2 + NADPH + H+
artemisinic aldehyde + NADP+ + 2 H2O
show the reaction diagram
artemisinic aldehyde + O2 + NADPH + H+
artemisinate + NADP+ + H2O
show the reaction diagram
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
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8
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recombinant enzyme
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
regenerated plantlets
Manually annotated by BRENDA team
artemisinin production in Artemisia annua is localized in glandular trichomes on the surface of leaves, shoots and flowers
Manually annotated by BRENDA team
additional information
callus cannot produce artemisinin
Manually annotated by BRENDA team
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis
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
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Saccharomyces cerevisiae expressing the native Artemisia annua cytochrome P450 monooxygenase (CYP71AV1) and artemisinic aldehyde D11(13) reductase (DBR2) is used as a whole-cell biocatalyst to produce the immediate artemisinin precursor, dihydroartemisinic acid (DHAA)