Information on EC 1.14.14.145 - abieta-7,13-dien-18-ol hydroxylase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.14.145
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RECOMMENDED NAME
GeneOntology No.
abieta-7,13-dien-18-ol hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
abieta-7,13-dien-18,18-diol = abieta-7,13-dien-18-al + H2O
show the reaction diagram
(1c), spontaneous
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abieta-7,13-dien-18-al + [reduced NADPH-hemoprotein reductase] + O2 = abieta-7,13-dien-18-oate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1c)
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abieta-7,13-dien-18-ol + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = abieta-7,13-dien-18-oate + 2 [oxidized NADPH-hemoprotein reductase] + 3 H2O
show the reaction diagram
overall reaction
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abieta-7,13-dien-18-ol + [reduced NADPH-hemoprotein reductase] + O2 = abieta-7,13-dien-18,18-diol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1a)
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Diterpenoid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
abieta-7,13-dien-18-ol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (18-hydroxylating)
A heme-thiolate protein (P-450). This enzyme catalyses a step in the pathway of abietic acid biosynthesis. The activity has been demonstrated in cell-free stem extracts of Abies grandis (grand fir) and Pinus contorta (lodgepole pine) [1], and the gene encoding the enzyme has been identified in Pinus taeda (loblolly pine) [3]. The recombinant enzyme catalyses the oxidation of multiple diterpene alcohol and aldehydes, including levopimaradienol, isopimara-7,15-dienol, isopimara-7,15-dienal, dehydroabietadienol and dehydroabietadienal. It is not able to oxidize abietadiene.
CAS REGISTRY NUMBER
COMMENTARY hide
160477-93-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Lindl.
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Manually annotated by BRENDA team
Douglas var. latifolia Engelman
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(13S)-pimara-7,15-dien-18-al + [reduced NADPH-hemoprotein reductase] + O2
(13S)-pimara-7,15-dien-18-oate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
?
abieta-7,13-dien-18-al + [reduced NADPH-hemoprotein reductase] + O2
abieta-7,13-dien-18-oate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
?
abieta-7,13-dien-18-ol + 2 [reduced NADPH-hemoprotein reductase] + 2 O2
abieta-7,13-dien-18-oate + 2 [oxidized NADPH-hemoprotein reductase] + 3 H2O
show the reaction diagram
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-
-
?
abieta-7,13-dien-18-ol + [reduced NADPH-hemoprotein reductase] + O2
abieta-7,13-dien-18-al + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
abietadienal + [reduced NADPH-hemoprotein reductase] + O2
abietadienoate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
oxidation at C-18
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-
?
abietadienol + [reduced NADPH-hemoprotein reductase] + O2
abietadienal + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
oxidation at C-18
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-
?
dehydroabietadienal + [reduced NADPH-hemoprotein reductase] + O2
dehydroabietadienal + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
?
dehydroabietadienal + [reduced NADPH-hemoprotein reductase] + O2
dehydroabietadienoate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
oxidation at C-18
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-
?
dehydroabietadienol + [reduced NADPH-hemoprotein reductase] + O2
dehydroabietadienal + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
isopimara-7,15-dienal + [reduced NADPH-hemoprotein reductase] + O2
isopimara-7,15-dien-18-oate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
oxidation at C-18
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?
isopimara-7,15-dienol + [reduced NADPH-hemoprotein reductase] + O2
isopimara-7,15-dienal + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
levopimaradienol + [reduced NADPH-hemoprotein reductase] + O2
levopimaradienal + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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
abieta-7,13-dien-18-ol + 2 [reduced NADPH-hemoprotein reductase] + 2 O2
abieta-7,13-dien-18-oate + 2 [oxidized NADPH-hemoprotein reductase] + 3 H2O
show the reaction diagram
Q50EK3, Q50EK4, Q50EK5, Q50EK6
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?
abieta-7,13-dien-18-ol + [reduced NADPH-hemoprotein reductase] + O2
abieta-7,13-dien-18-al + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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FAD
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omission of flavins results in measurable reduction in both hydroxylation activities
FMN
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omission of flavins results in measurable reduction in both hydroxylation activities
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ancymidol
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clotrimazole
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CO
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blue light reversible inhibition
cytochrome c
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Metyrapone
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miconazole
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0005
abietadienal
pH 7.6, 30°C; pH 7.6, 30°C, recombinant enzyme
0.0008 - 0.003
abietadienol
0.0006
dehydroabietadienal
pH 7.6, 30°C; pH 7.6, 30°C, recombinant enzyme
0.0053
dehydroabietadienol
pH 7.6, 30°C; pH 7.6, 30°C, recombinant enzyme
0.0015
isopimara-7,15-dienol
pH 7.6, 30°C
0.0006
isopimaradienal
pH 7.6, 30°C; pH 7.6, 30°C, recombinant enzyme
0.0015
isopimaradienol
pH 7.6, 30°C, recombinant enzyme
0.0019
levopimaradienol
pH 7.6, 30°C; pH 7.6, 30°C, recombinant enzyme
additional information
additional information
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0013
clotrimazole
Abies grandis
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pH 7.5, 32°C
0.004
cytochrome c
Abies grandis
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pH 7.5, 32°C
0.005
Metyrapone
Abies grandis
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pH 7.5, 32°C
0.307
miconazole
Abies grandis
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pH 7.5, 32°C
additional information
additional information
Abies grandis
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no inhibition detected by ancymidol at 0.2 mM
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 7.6
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
assay at; assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
CYP720B1, functional cDNA screening and expression as FLAG-tagged protein in Saccharomyces cerevisiae, de novo diterpenoid formation in metabolically engineered yeast, overview; CYP720B1, functional cDNA screening and expression as FLAG-tagged protein in Saccharomyces cerevisiae, DNA and amino acid sequence determination and analysis; CYPA, functional cDNA screening and expression as FLAG-tagged protein in Saccharomyces cerevisiae, DNA and amino acid sequence determination and analysis; CYPB, functional cDNA screening and expression as FLAG-tagged protein in Saccharomyces cerevisiae, DNA and amino acid sequence determination and analysis; CYPC, functional cDNA screening and expression as FLAG-tagged protein in Saccharomyces cerevisiae, DNA and amino acid sequence determination and analysis
CYPA1, functional cDNA screening and expression as FLAG-tagged protein in Saccharomyces cerevisiae, DNA and amino acid sequence determination and analysis; CYPA2, functional cDNA screening and expression as FLAG-tagged protein in Saccharomyces cerevisiae, DNA and amino acid sequence determination and analysis
expression of GFP-fusion protein in transiently transformed tobacco cells. The first 48 amino of PtAO are fused to the N-terminus of green fluorescent protein (GFP) and expressed in tobacco under control of Cauliflower Mosaic Virus 35S promoter