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Information on EC 1.14.14.105 - taxane 10beta-hydroxylase
for references in articles please use BRENDA:EC1.14.14.105
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
1.14.14.105 taxane 10beta-hydroxylase
IUBMB Comments
This microsomal cytochrome-P-450 (heme-thiolate) enzyme from the plant Taxus cuspidata is involved in the biosynthesis of the diterpenoid antineoplastic drug taxol (paclitaxel).
The enzyme appears in viruses and cellular organisms
Reaction Schemes
showSynonyms
taxoid 10beta-hydroxylase, 5-alpha-taxadienol-10-beta-hydroxylase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
EC 1.14.13.76
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-
formerly
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oxygenase, taxane 10beta-mono-
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taxa-4(20),11-dien-5alpha-yl acetate 10beta-hydroxylase
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taxadien-5alpha-yl-acetate 10beta-hydroxylase
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taxane 10beta-hydroxylase
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-
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taxane 10beta-monooxygenase
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taxoid 10beta-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
taxa-4(20),11-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2 = 10beta-hydroxytaxa-4(20),11-dien-5alpha-yl acetate + [oxidized NADPH-hemoprotein reductase] + H2O
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
taxol biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
taxa-4(20),11-dien-5alpha-yl acetate,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (10beta-hydroxylating)
This microsomal cytochrome-P-450 (heme-thiolate) enzyme from the plant Taxus cuspidata is involved in the biosynthesis of the diterpenoid antineoplastic drug taxol (paclitaxel).
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CAS REGISTRY NUMBER
COMMENTARY
337514-75-7
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
cytochrome c + FAD + FMN + O2
?
Substrates: rat cytochrome b5
Products: -
Products: -
?
taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl acetyl-10beta-ol + [oxidized NADPH-hemoprotein reductase] + H2O
taxa-4(20),11-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
10beta-hydroxytaxa-4(20),11-dien-5alpha-yl acetate + [oxidized NADPH-hemoprotein reductase] + H2O
Taxus sp.
-
Substrates: -
Products: -
Products: -
?
taxadien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
10beta-hydroxytaxa-4(20),11-dien-5alpha-yl acetate + [oxidized NADPH-hemoprotein reductase] + H2O
additional information
?
-
Taxus sp.
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Substrates: catalyzes early step in taxol biosynthesis
Products: -
Products: -
?
taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl acetyl-10beta-ol + [oxidized NADPH-hemoprotein reductase] + H2O
Taxus sp.
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Substrates: -
Products: product identification and quantification by HPLC and GC-MS
Products: product identification and quantification by HPLC and GC-MS
?
taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl acetyl-10beta-ol + [oxidized NADPH-hemoprotein reductase] + H2O
Taxus sp.
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Substrates: step in taxol biosynthesis, metabolite analysis and pathway overview
Products: -
Products: -
?
taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl acetyl-10beta-ol + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl acetyl-10beta-ol + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: second P450-dependent step in taxol biosynthesis, regulation mechanism involving elicitors
Products: -
Products: -
?
taxadien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
10beta-hydroxytaxa-4(20),11-dien-5alpha-yl acetate + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: -
Products: -
Products: -
?
taxadien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
10beta-hydroxytaxa-4(20),11-dien-5alpha-yl acetate + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: the enzyme is involved in the taxol biosynthetic pathway, overview
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl acetyl-10beta-ol + [oxidized NADPH-hemoprotein reductase] + H2O
taxadien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
10beta-hydroxytaxa-4(20),11-dien-5alpha-yl acetate + [oxidized NADPH-hemoprotein reductase] + H2O
Substrates: the enzyme is involved in the taxol biosynthetic pathway, overview
Products: -
Products: -
?
additional information
?
-
Taxus sp.
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Substrates: catalyzes early step in taxol biosynthesis
Products: -
Products: -
?
taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl acetyl-10beta-ol + [oxidized NADPH-hemoprotein reductase] + H2O
Taxus sp.
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Substrates: step in taxol biosynthesis, metabolite analysis and pathway overview
Products: -
Products: -
?
taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl acetyl-10beta-ol + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrates: second P450-dependent step in taxol biosynthesis, regulation mechanism involving elicitors
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
elicitors methyl jasmonate, AgNO3, and ammonium ceric sulfate all induce expression of the enzyme
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
Taxus sp.
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in vivo and in vitro assay in yeast for recombinant enzyme
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
-
tissue expression pattern, no expressionin fruits, overview
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). T10H_TAXCU
497
1
56691
Swiss-Prot
other Location (Reliability: 4)
B9TIC7_RICCO
134
1
15571
TrEMBL
Secretory Pathway (Reliability: 1)
B9SBP0_RICCO
455
1
52235
TrEMBL
Secretory Pathway (Reliability: 1)
B9S6I4_RICCO
479
1
54903
TrEMBL
Secretory Pathway (Reliability: 1)
A0A0B2Q144_GLYSO
97
0
11298
TrEMBL
other Location (Reliability: 5)
B9R9F1_RICCO
473
1
54264
TrEMBL
Secretory Pathway (Reliability: 4)
A0A2P6QKV9_ROSCH
132
0
14309
TrEMBL
other Location (Reliability: 2)
B9ST44_RICCO
472
0
54106
TrEMBL
Mitochondrion (Reliability: 5)
B9RLE4_RICCO
475
2
54136
TrEMBL
Secretory Pathway (Reliability: 5)
B9SJJ5_RICCO
487
1
55076
TrEMBL
Secretory Pathway (Reliability: 4)
B9SPD1_RICCO
444
2
50863
TrEMBL
Secretory Pathway (Reliability: 4)
B9R8M6_RICCO
479
1
54416
TrEMBL
Secretory Pathway (Reliability: 2)
B9SJJ7_RICCO
406
0
46140
TrEMBL
other Location (Reliability: 3)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression of the FLAG-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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isolation and cloning of a single-copy gene, DNA and amino acid sequence determination and analysis, expression in insect cells, functional co-expression of full-length and truncated enzyme with taxoid 13beta-hydroxylase or with the organisms' taxoid 10beta-hydroxylase in Saccharomyces cerevisiae strain YPH499, subcloning in Escherichia coli
isolation and cloning of a single-copy gene, DNA and amino acid sequence determination and analysis, functional co-expression with the NADPH:cytochrome P450 reductase, also exhibiting taxoid 10beta-hydroxylase activity, in Saccharomyces cerevisiae strain YPH499, subcloning in Escherichia coli
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Schoendorf, A.; Rithner, C.D.; Williams, R.M.; Croteau, R.B.
Molecular cloning of a cytochrome P450 taxane 10beta-hydroxylase cDNA from Taxus and functional expression in yeast
Proc. Natl. Acad. Sci. USA
98
1501-1506
2001
Taxus sp.
brenda
Jennewein, S.; Park, H.; DeJong, J.M.; Long, R.M.; Bollon, A.P.; Croteau, R.B.
Coexpression in yeast of Taxus cytochrome P450 reductase with cytochrome P450 oxygenases involved in taxol biosynthesis
Biotechnol. Bioeng.
89
588-598
2005
Taxus cuspidata (Q9AXM6), Taxus cuspidata
brenda
DeJong, J.H.; Liu, Y.; Bollon, A.P.; Long, R.M.; Jennewein, S.; Williams, D.; Croteau, R.B.
Genetic engineering of taxol biosynthetic genes in Saccharomyces cerevisiae
Biotechnol. Bioeng.
93
212-224
2006
Taxus sp.
brenda
Kai, G.; Jiang, J.; Zhao, D.; Zhao, L.; Zhang, L.; Li, Z.; Guo, B.; Sun, X.; Miao, Z.; Tang, K.
Isolation and expression profile analysis of a new cDNA encoding 5-alpha-taxadienol-10-beta-hydroxylase from Taxus media
J. Plant Biochem. Biotechnol.
15
1-5
2006
Taxus x media
-
brenda
EXTERNAL LINKS (specific for EC-Number 1.14.14.105)
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