Information on EC 1.3.1.92 - artemisinic aldehyde DELTA11(13)-reductase

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The expected taxonomic range for this enzyme is: Artemisia annua

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EC NUMBER
COMMENTARY hide
1.3.1.92
-
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RECOMMENDED NAME
GeneOntology No.
artemisinic aldehyde DELTA11(13)-reductase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(11R)-dihydroartemisinic aldehyde + NADP+ = artemisinic aldehyde + NADPH + H+
show the reaction diagram
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
artemisinin biosynthesis
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-
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SYSTEMATIC NAME
IUBMB Comments
artemisinic aldehyde:NADP+ oxidoreductase
Cloned from Artemisia annua. In addition to the reduction of artemisinic aldehyde it is also able to a lesser extent to reduce artemisinic alcohol and artemisinic acid. Part of the biosyntheis of artemisinin.
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
the early steps in artemisinin biosynthesis involve amorpha-4,11-diene hydroxylation to artemisinic alcohol, followed by oxidation to artemisinic aldehyde, reduction of the C11-C13 double bond to dihydroartemisinic aldehyde and oxidation to dihydroartemisinic acid
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-carvone + NADH + H+
(1R,4S)-isodihydrocarvone + NAD+
show the reaction diagram
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plus about 20% of (1S,4S)-dihydrocarvone
-
?
2-cyclohexen-1-one + NADH + H+
cyclohexanone + NAD+
show the reaction diagram
-
-
-
?
2E-nonenal + NADH + H+
nonanal + NAD+
show the reaction diagram
about 12% of the activity with artemisinic aldehyde
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-
?
artemisinic aldehyde + NADH + H+
(11R)-dihydroartemisinic aldehyde + NAD+
show the reaction diagram
-
-
-
?
artemisinic aldehyde + NADPH + H+
dihydroartemisinic aldehyde + NADP+
show the reaction diagram
-
-
-
?
additional information
?
-
no substrate: arteannuin B, artemisinic acid, artemisinic alcohol, artemisitene, coniferyl aldehyde, (2E)-nonenal, alpha-pinene, (+)-pulegone, and sabinone
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
-
NADPH is preferred over NADH
NADPH
-
NADPH is preferred over NADH
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
miconazole
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0.2 mM miconazole induce a 2.5-fold increase of artemisinin production after 24 h, but have severe effects on cell viability
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.65
(+)-carvone
-
30°C, pH 7.5
0.79
2-cyclohexen-1-one
-
30°C, pH 7.5
0.019
artemisinic aldehyde
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30°C, pH 7.5
0.77
NADH
-
30°C, pH 7.5
0.095
NADPH
-
30°C, pH 7.5
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.86
(+)-carvone
Artemisia annua
-
30°C, pH 7.5
1.8
2-cyclohexen-1-one
Artemisia annua
-
30°C, pH 7.5
2.6
artemisinic aldehyde
Artemisia annua
-
30°C, pH 7.5
1.3
NADH
Artemisia annua
-
30°C, pH 7.5
2.5
NADPH
Artemisia annua
-
30°C, pH 7.5
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.3
(+)-carvone
Artemisia annua
-
30°C, pH 7.5
13373
2.3
2-cyclohexen-1-one
Artemisia annua
-
30°C, pH 7.5
2446
140
artemisinic aldehyde
Artemisia annua
-
30°C, pH 7.5
6337
1.7
NADH
Artemisia annua
-
30°C, pH 7.5
8
26
NADPH
Artemisia annua
-
30°C, pH 7.5
5
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
-
complete inhibition
9
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about 25% of maximum activity
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
flower bud, moderate expression
Manually annotated by BRENDA team
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
44000
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gel filtration
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Saccharomyces cerevisiae
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
methyljasmonate does not induce significant changes in the expression of DBR2
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treatment for 30 min and 4 h with miconazole induces about four- und fivefold upregulation of the DBR2 gene, respectively
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
heterologous expression of Artemisia annua amorphadiene synthase and CYP71AV1, the cytochrome P450 responsible for oxidation of amorphadiene, in tobacco lead to the accumulation of amorphadiene and artemisinic alcohol, but not artemisinic acid, in leaf. Additional expression of artemisinic aldehyde DELTA11(13) double-bond reductase with or without aldehyde dehydrogenase 1 leads to the additional accumulation dihydroartemisinic alcohol
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
-
production of artemisin by incubating a mixture of artemisin precursors from engineered Saccharomyces cerevisiae with a cell-free extract of Artemisia annua. Use of cold-acclimated Artemisia annua cell-free extract gives rise to considerable artemisin content up to 0.65%
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LINKS TO OTHER DATABASES (specific for EC-Number 1.3.1.92)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)