Information on EC 1.14.13.77 - taxane 13alpha-hydroxylase

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The expected taxonomic range for this enzyme is: Taxus cuspidata

EC NUMBER
COMMENTARY hide
1.14.13.77
-
RECOMMENDED NAME
GeneOntology No.
taxane 13alpha-hydroxylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
taxa-4(20),11-dien-5alpha-ol + NADPH + H+ + O2 = taxa-4(20),11-dien-5alpha,13alpha-diol + NADP+ + H2O
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
Diterpenoid biosynthesis
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Metabolic pathways
-
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taxol biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
taxa-4(20),11-dien-5alpha-ol,NADPH:oxygen oxidoreductase (13alpha-hydroxylating)
This cytochrome-P-450-dependent enzyme is involved in the biosynthesis of the diterpenoid antineoplastic drug taxol (paclitaxel).
CAS REGISTRY NUMBER
COMMENTARY hide
399030-58-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Taxus sp.
-
-
-
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
taxa-4(20),11(12)-dien-5alpha-yl acetate + NADPH + O2
taxa-4(20),11(12)-dien-5alpha-yl-acetyl-13alpha-ol + NADP+ + H2O
show the reaction diagram
taxa-4(20),11-dien-5alpha-ol + NADPH + H+ + O2
taxa-4(20),11-dien-5alpha,13alpha-diol + NADP+ + H2O
show the reaction diagram
taxa-4(20),11-dien-5alpha-yl-acetate + NADPH + H+ + O2
taxa-4(20),11-dien-5alpha,13alpha-diol-5-acetate + NADP+ + H2O
show the reaction diagram
taxadien-5a-yl acetate + NADPH + O2 + H+
taxa-4(20),11(12)-dien-5alpha-yl-acetyl-13alpha-ol + NADP+ + H2O
show the reaction diagram
-
the enzyme is involved in the taxol biosynthetic pathway, overview
-
-
?
taxadien-5alpha-yl acetate + NADPH + O2
taxa-4(20),11-dien-5alpha-yl-acetyl-13alpha-ol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
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
taxa-4(20),11(12)-dien-5alpha-yl acetate + NADPH + O2
taxa-4(20),11(12)-dien-5alpha-yl-acetyl-13alpha-ol + NADP+ + H2O
show the reaction diagram
Taxus sp.
-
step in taxol biosynthesis, metabolite analysis and pathway overview
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-
-
taxadien-5a-yl acetate + NADPH + O2 + H+
taxa-4(20),11(12)-dien-5alpha-yl-acetyl-13alpha-ol + NADP+ + H2O
show the reaction diagram
-
the enzyme is involved in the taxol biosynthetic pathway, overview
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
-
heme iron
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.014
taxa-4(20),11-dien-5alpha-ol
0.024
taxa-4(20),11-dien-5alpha-yl-acetate
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.7
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2 - 8.2
-
half-maximal activity at pH 6.2 and pH 8.2
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
31
Taxus sp.
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant VSVG-tagged enzyme from Saccharomyces cerevisiae YPH499 cells
Taxus sp.
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression of the VSVG-tagged enzyme in Saccharomyces cerevisiae YPH499 cells, expression of the enzymes from and reconstruction of the taxol biosynthesis pathway 5 early steps by expression of the participating enzymes in yeast, overview
Taxus sp.
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functional co-expression with taxoid 10beta-hydroxylase in Saccharomyces cerevisiae strain YPH499, subcloning in Escherichia coli
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heterologous expression in Sf9 insect cells