Information on EC 1.14.99.37 - taxadiene 5alpha-hydroxylase

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The expected taxonomic range for this enzyme is: Taxus

EC NUMBER
COMMENTARY hide
1.14.99.37
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RECOMMENDED NAME
GeneOntology No.
taxadiene 5alpha-hydroxylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
taxa-4,11-diene + AH2 + O2 = taxa-4(20),11-dien-5alpha-ol + A + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
taxol biosynthesis
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Diterpenoid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
taxa-4,11-diene,hydrogen-donor:oxygen oxidoreductase (5alpha-hydroxylating)
This microsomal cytochrome-P-450-dependent enzyme is involved in the biosynthesis of the diterpenoid antineoplastic drug Taxol (paclitaxel). The reaction includes rearrangement of the 4(5)-double bond to a 4(20)-double bond, possibly through allylic oxidation.
CAS REGISTRY NUMBER
COMMENTARY hide
253872-99-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Taxus sp.
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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
taxa-4(20),11(12)-diene + NADPH + O2
taxa-4(20),11(12)-dien-5alpha-ol + NADP+ + H2O
show the reaction diagram
preferred substrate
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?
taxa-4(20)-11(12)-diene + AH2 + O2
?
show the reaction diagram
Taxus sp.
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?
taxa-4(5),11(12)-diene + NADPH + O2
5(12)-oxa-3(11)-cyclotaxane + NADP+ + H2O
show the reaction diagram
hydroxylation of the C-5alpha is the first of the oxidations resulting in taxol
OCT is a cyclic ether
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?
taxa-4(5),11(12)-diene + NADPH + O2
taxa-4(20),11(12)-dien-5alpha-ol + NADP+ + H2O
show the reaction diagram
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-
?
taxa-4,11-diene + AH2 + O2
taxa-4(20),11(12)-dien-5alpha-ol + A + H2O
show the reaction diagram
Taxus sp.
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-
-
-
?
taxa-4,11-diene + AH2 + O2
taxa-4(20),11-dien-5alpha-ol + A + H2O
show the reaction diagram
taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
show the reaction diagram
taxadiene + AH2 + O2
taxadiene-5alpha-ol + A + H2O
show the reaction diagram
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?
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
taxa-4(20)-11(12)-diene + AH2 + O2
?
show the reaction diagram
Taxus sp.
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?
taxa-4(5),11(12)-diene + NADPH + O2
5(12)-oxa-3(11)-cyclotaxane + NADP+ + H2O
show the reaction diagram
Q6WG30
hydroxylation of the C-5alpha is the first of the oxidations resulting in taxol
OCT is a cyclic ether
-
?
taxa-4,11-diene + AH2 + O2
taxa-4(20),11(12)-dien-5alpha-ol + A + H2O
show the reaction diagram
Taxus sp.
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-
?
taxa-4,11-diene + AH2 + O2
taxa-4(20),11-dien-5alpha-ol + A + H2O
show the reaction diagram
taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
show the reaction diagram
taxadiene + AH2 + O2
taxadiene-5alpha-ol + A + H2O
show the reaction diagram
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?
additional information
?
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Q6WG30
cDNAs encoding taxa-4(5),11(12)-diene synthase and CYP725A4 are introduced in Nicotiana sylvestris for specific expression in trichome cells. The co-expression does not lead to the production of the expected 5-hydroxytaxa-4(20),11(12)-diene. Instead, taxa-4(5),11(12)-diene is quantitatively converted to a novel taxane
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
clotrimazole
cytochrome c
miconazole
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.016
taxa-4(20),11(12)-diene
pH 7.5
0.0069 - 0.024
taxa-4(5),11(12)-diene
0.006
taxa-4,11-diene
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni-NTA column chromatography
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Ni-NTA resin column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cDNAs encoding taxa-4(5),11(12)-diene synthase and CYP725A4 are introduced in Nicotiana sylvestris for specific expression in trichome cells. Production of truncated TS in Escherichia coli. The TS cDNA coding for a protein truncated at the N-terminus at amino acid position 75 is cloned in the pET-30b expression vector. Furthermore, CYP725A4 is expressed in yeast.; CYP725A4, DNA and amino acid sequence determination and analysis, expression in the Saccharomyces cerevisiae WAT11 strain containing the Arabidopsis reductase ATR1, and co-expression in Nicotiana sylvestris with taxa-4(5),11(12)-diene synthase, which does not lead to 5alpha-hydroxytaxa-4(20),11(12)-diene, but to formation of 5(12)-oxa-3(11)-cyclotaxane, a tritiated oxidized taxane, structural analysis of the compound, phenotype, overview
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expressed in Escherichia coli BL21 (DE3) cells
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expressed in Escherichia coli BL21(DE3) cells
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expressed in Escherichia coli C41(DE3) cells
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expressed in Saccharomyces cerevisiae and Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
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paclitaxel is a successful anticancer drug
medicine