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 annua

EC NUMBER
COMMENTARY hide
1.14.13.158
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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 NADPH + 3 H+ = artemisinate + 3 NADP+ + 4 H2O
show the reaction diagram
overall reaction
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amorpha-4,11-diene + O2 + NADPH + H+ = artemisinic alcohol + NADP+ + H2O
show the reaction diagram
(1a)
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artemisinic alcohol + O2 + NADPH + H+ = artemisinic aldehyde + NADP+ + 2 H2O
show the reaction diagram
(1b)
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artemisinic aldehyde + O2 + NADPH + H+ = artemisinate + NADP+ + H2O
show the reaction diagram
(1c)
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SYSTEMATIC NAME
IUBMB Comments
amorpha-4,11-diene,NADPH: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
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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the first committed steps in the conversion of farnesyl diphosphate to artemisinin are conducted by amorpha-4,11-diene synthase, amorpha-4,11-diene hydroxylase, a cytochrome P450 monooxygenase, ie. CYP71AV1, and artemisinic aldehyde DELTA11(13) reductase
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 + O2 + NADPH + H+
? + NADP+ + 2 H2O
show the reaction diagram
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-
-
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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
dihydroartemisinic alcohol + O2 + NADPH + H+
dihydroartemisinic aldehyde + NADP+ + 2 H2O
show the reaction diagram
dihydroartemisinic aldehyde + O2 + NADPH + H+
dihydroartemisinate + NADP+ + H2O
show the reaction diagram
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-
-
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octanal + O2 + NADPH + H+
? + NADP+ + 2 H2O
show the reaction diagram
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-
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additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
NADH is as effective as NADPH
NADPH
NADH is as effective as NADPH
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0026
artemisinic aldehyde
pH 8.5, 30C
0.0088
dihydroartemisinic aldehyde
pH 8.5, 30C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.53
artemisinic aldehyde
Artemisia annua
C5I9X1
pH 8.5, 30C
7.74
dihydroartemisinic aldehyde
Artemisia annua
C5I9X1
pH 8.5, 30C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
593
artemisinic aldehyde
Artemisia annua
C5I9X1
pH 8.5, 30C
6337
881
dihydroartemisinic aldehyde
Artemisia annua
C5I9X1
pH 8.5, 30C
19052
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
moderate expression
Manually annotated by BRENDA team
low expression
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
expression in Escherichia coli
expression in Saccharomyces cerevisiae
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis