Information on EC 1.14.13.109 - abieta-7,13-dien-18-ol hydroxylase

Word Map on EC 1.14.13.109
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.109
-
RECOMMENDED NAME
GeneOntology No.
abieta-7,13-dien-18-ol hydroxylase
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
1b, spontaneous
-
-
-
abieta-7,13-dien-18-ol + NADPH + H+ + O2 = abieta-7,13-dien-18,18-diol + NADP+ + H2O
show the reaction diagram
1a
-
-
-
abieta-7,13-dien-18-ol + NADPH + H+ + O2 = abieta-7,13-dien-18-al + NADP+ + 2 H2O
show the reaction diagram
overall reaction
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Diterpenoid biosynthesis
-
-
Metabolic pathways
-
-
Biosynthesis of secondary metabolites
-
-
SYSTEMATIC NAME
IUBMB Comments
abieta-7,13-dien-18-ol,NADPH: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
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Lindl.
-
-
Manually annotated by BRENDA team
Douglas var. latifolia Engelman
-
-
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
abietadienal + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
abietadienal + NADPH + O2
?
show the reaction diagram
oxidation at C-18
-
-
?
abietadiene + 3 NADPH + H+ + 3 O2
abietic acid + 3 NADP+ + 4 H2O
show the reaction diagram
-
-
-
?
abietadienol + NADPH + H+ + O2
abietadienal + NADP+ + H2O
show the reaction diagram
abietadienol + NADPH + O2
?
show the reaction diagram
oxidation at C-18
-
-
?
dehydroabietadienal + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
dehydroabietadienal + NADPH + O2
?
show the reaction diagram
oxidation at C-18
-
-
?
dehydroabietadienol + NADPH + H+ + O2
dehydroabietadienal + NADP+ + H2O
show the reaction diagram
-
-
-
?
dehydroabietadienol + NADPH + O2
?
show the reaction diagram
oxidation at C-18
-
-
?
isopimara-7,15-dienal + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
?
isopimara-7,15-dienal + NADPH + O2
?
show the reaction diagram
oxidation at C-18
-
-
?
isopimara-7,15-dienol + NADPH + H+ + O2
isopimara-7,15-dienal + NADP+ + H2O
show the reaction diagram
-
-
-
?
isopimara-7,15-dienol + NADPH + O2
?
show the reaction diagram
oxidation at C-18
-
-
?
levopimaradienol + NADPH + H+ + O2
levopimaradienal + NADP+ + H2O
show the reaction diagram
-
-
-
?
levopimaradienol + NADPH + O2
?
show the reaction diagram
oxidation at C-18
-
-
?
additional information
?
-
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
abietadiene + 3 NADPH + H+ + 3 O2
abietic acid + 3 NADP+ + 4 H2O
show the reaction diagram
Q50EK0, Q50EK1, Q50EK3, Q50EK4, Q50EK5, Q50EK6
-
-
-
?
abietadienol + NADPH + H+ + O2
abietadienal + NADP+ + H2O
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
FAD
-
omission of flavins results in measurable reduction in both hydroxylation activities
FMN
-
omission of flavins results in measurable reduction in both hydroxylation activities
NADH
-
hydroxylation activity is maximally supported by NADPH, and NADH is less effective as reductant
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ancymidol
-
-
clotrimazole
-
-
CO
-
blue light reversible inhibition
cytochrome c
-
-
Metyrapone
-
-
miconazole
-
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
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
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0013
clotrimazole
Abies grandis
-
pH 7.5, 32°C
0.004
cytochrome c
Abies grandis
-
pH 7.5, 32°C
0.005
Metyrapone
Abies grandis
-
pH 7.5, 32°C
0.307
miconazole
Abies grandis
-
pH 7.5, 32°C
additional information
additional information
Abies grandis
-
no inhibition detected by ancymidol at 0.2 mM
-
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
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; 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; 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
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