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Enzyme Nomenclature
Information on EC 1.14.99.37 - taxadiene 5alpha-hydroxylase
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The expected taxonomic range for this enzyme is: Taxus
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EC NUMBER 
COMMENTARY 
1.14.99.37
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RECOMMENDED NAME
GeneOntology No.
taxadiene 5alpha-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
taxa-4,11-diene + AH2 + O2 = taxa-4(20),11-dien-5alpha-ol + A + H2O
requires P450, reaction includes rearrangement of the 4(5)-double bound to a 4(20)-double bond, possibly through allylic oxidation, proposed mechanism
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taxa-4,11-diene + AH2 + O2 = taxa-4(20),11-dien-5alpha-ol + A + H2O
requires P450, reaction includes rearrangement of the 4(5)-double bound to a 4(20)-double bond, possibly through allylic oxidation, proposed mechanism
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taxa-4,11-diene + AH2 + O2 = taxa-4(20),11-dien-5alpha-ol + A + H2O
mechanism involving promiscuous radical abstraction with selective oxygen insertion
taxa-4,11-diene + AH2 + O2 = taxa-4(20),11-dien-5alpha-ol + A + H2O
reaction mechanism
taxa-4,11-diene + AH2 + O2 = taxa-4(20),11-dien-5alpha-ol + A + H2O
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
redox reaction
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reduction
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oxidation
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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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.
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CAS REGISTRY NUMBER
COMMENTARY
253872-99-0
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
taxa-4(20),11(12)-diene + NADPH + O2
taxa-4(20),11(12)-dien-5alpha-ol + NADP+ + H2O
preferred substrate
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?
taxa-4(5),11(12)-diene + NADPH + O2
5(12)-oxa-3(11)-cyclotaxane + NADP+ + H2O
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
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?
taxa-4,11-diene + AH2 + O2
taxa-4(20),11-dien-5alpha-ol + A + H2O
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?
taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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reaction is completely dependent on NADPH
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?
taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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reaction is completely dependent on NADPH, enzyme catalyzes the first oxygenating step in taxol biosynthesis pathway
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?
taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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reaction is completely dependent on NADPH
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?
taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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reaction is completely dependent on NADPH, enzyme catalyzes the first oxygenating step in taxol biosynthesis pathway
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?
additional information
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the recombinant enzyme produces 5(12)-oxa-3(11)-cyclotaxane, a tritiated oxidized taxane, instead of taxa-4(20),11-dien-5alpha-ol, structural analysis of the compound, overview
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additional information
?
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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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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
taxa-4(5),11(12)-diene + NADPH + O2
5(12)-oxa-3(11)-cyclotaxane + NADP+ + H2O
Q6WG30
hydroxylation of the C-5alpha is the first of the oxidations resulting in taxol
OCT is a cyclic ether
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?
taxa-4,11-diene + AH2 + O2
taxa-4(20),11-dien-5alpha-ol + A + H2O
Q6WG30
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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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taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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reaction is completely dependent on NADPH, enzyme catalyzes the first oxygenating step in taxol biosynthesis pathway
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?
taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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taxa-4,11-diene + NADPH + O2
taxa-4(20),11-dien-5alpha-ol + NADP+ + H2O
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reaction is completely dependent on NADPH, enzyme catalyzes the first oxygenating step in taxol biosynthesis pathway
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?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
CO
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inhibits taxadiene hydroxylation in the dark, inhihibition is partially reversed by blue light at 450 nm
CO
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inhibits taxadiene hydroxylation in the dark, inhihibition is partially reversed by blue light at 450 nm
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.2
7.2
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activity in extracts, approx. 50% of maximal activity at pH 6.2 and pH 8.2
7.2
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activity in extracts, approx. 50% of maximal activity at pH 6.2 and pH 8.2
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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70% activity resides in light membrane fraction, approx. 25% in dense membrane fraction
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70% activity resides in light membrane fraction, approx. 25% in dense membrane fraction
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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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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
medicine
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enzyme may be useful in the biological production of the potent antimitotic drug taxol which shows activity against a range of cancers
medicine
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enzyme may be useful in the biological production of the potent antimitotic drug taxol which shows activity against a range of cancers
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.99.37)
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