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Information on EC 1.14.14.106 - taxane 13alpha-hydroxylase for references in articles please use BRENDA:EC1.14.14.106
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EC Tree
IUBMB Comments This cytochrome-P-450(heme-thiolate) enzyme from the plant Taxus cuspidata is involved in the biosynthesis of the diterpenoid antineoplastic drug taxol (paclitaxel).
The expected taxonomic range for this enzyme is: Taxus cuspidata
Synonyms
cytochrome P450 taxoid 13alpha-hydroxylase, taxoid 13alpha-hydroxylase, THY13a,
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cytochrome P450 taxoid 13alpha-hydroxylase
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taxoid 13alpha-hydroxylase
taxoid 13alpha-hydroxylase
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taxoid 13alpha-hydroxylase
Taxus sp.
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taxa-4(20),11-dien-5alpha-ol + [reduced NADPH-hemoprotein reductase] + O2 = taxa-4(20),11-dien-5alpha,13alpha-diol + [oxidized NADPH-hemoprotein reductase] + H2O
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taxa-4(20),11-dien-5alpha-ol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (13alpha-hydroxylating)
This 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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taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl-acetyl-13alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O
taxa-4(20),11-dien-5alpha-ol + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11-dien-5alpha,13alpha-diol + [oxidized NADPH-hemoprotein reductase] + H2O
taxa-4(20),11-dien-5alpha-yl-acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11-dien-5alpha,13alpha-diol-5-acetate + [oxidized NADPH-hemoprotein reductase] + H2O
taxadien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl-acetyl-13alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O
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the enzyme is involved in the taxol biosynthetic pathway, overview
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taxadien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11-dien-5alpha-yl-acetyl-13alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O
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taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl-acetyl-13alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O
Taxus sp.
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product identification and quantification by HPLC and GC-MS
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taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl-acetyl-13alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O
Taxus sp.
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step in taxol biosynthesis, metabolite analysis and pathway overview
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taxa-4(20),11-dien-5alpha-ol + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11-dien-5alpha,13alpha-diol + [oxidized NADPH-hemoprotein reductase] + H2O
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taxa-4(20),11-dien-5alpha-ol + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11-dien-5alpha,13alpha-diol + [oxidized NADPH-hemoprotein reductase] + H2O
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taxa-4(20),11-dien-5alpha-yl-acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11-dien-5alpha,13alpha-diol-5-acetate + [oxidized NADPH-hemoprotein reductase] + H2O
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taxa-4(20),11-dien-5alpha-yl-acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11-dien-5alpha,13alpha-diol-5-acetate + [oxidized NADPH-hemoprotein reductase] + H2O
6% of activity with taxa-4(20),11-dien-5alpha-ol
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taxa-4(20),11(12)-dien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl-acetyl-13alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O
Taxus sp.
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step in taxol biosynthesis, metabolite analysis and pathway overview
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taxadien-5alpha-yl acetate + [reduced NADPH-hemoprotein reductase] + O2
taxa-4(20),11(12)-dien-5alpha-yl-acetyl-13alpha-ol + [oxidized NADPH-hemoprotein reductase] + H2O
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the enzyme is involved in the taxol biosynthetic pathway, overview
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cytochrome P-450
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cytochrome P-450
Taxus sp.
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0.014
taxa-4(20),11-dien-5alpha-ol
0.024
taxa-4(20),11-dien-5alpha-yl-acetate
0.014
taxa-4(20),11-dien-5alpha-ol
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0.014
taxa-4(20),11-dien-5alpha-ol
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0.024
taxa-4(20),11-dien-5alpha-yl-acetate
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0.024
taxa-4(20),11-dien-5alpha-yl-acetate
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additional information
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7.5
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6.2 - 8.2
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half-maximal activity at pH 6.2 and pH 8.2
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Taxus sp.
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brenda
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Uniprot
brenda
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brenda
yew
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brenda
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brenda
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brenda
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brenda
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T13H_TAXCU
485
1
54653
Swiss-Prot
B9SLD0_RICCO
480
1
55114
TrEMBL
B9RXN4_RICCO
148
0
17010
TrEMBL
B9S315_RICCO
379
1
42880
TrEMBL
B9SV76_RICCO
473
1
54098
TrEMBL
B9SPT3_RICCO
471
0
53669
TrEMBL
B9SPR3_RICCO
480
1
54500
TrEMBL
B9SV74_RICCO
474
2
53806
TrEMBL
B9SF17_RICCO
523
1
59512
TrEMBL
B9RC34_RICCO
544
1
63202
TrEMBL
B9T864_RICCO
294
0
33536
TrEMBL
B9S060_RICCO
303
0
34869
TrEMBL
B2IWX8_NOSP7
Nostoc punctiforme (strain ATCC 29133 / PCC 73102)
437
0
50024
TrEMBL
B9SAB8_RICCO
480
1
54679
TrEMBL
B9TPY4_RICCO
172
1
19801
TrEMBL
A0A2P6SLS5_ROSCH
480
1
54155
TrEMBL
B9RHG4_RICCO
477
1
54262
TrEMBL
B9SAF0_RICCO
478
0
55437
TrEMBL
B9S713_RICCO
483
0
55250
TrEMBL
B9S4E8_RICCO
167
0
19072
TrEMBL
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recombinant VSVG-tagged enzyme from Saccharomyces cerevisiae YPH499 cells
Taxus sp.
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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
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Wheeler, A.L.; Long, R.M.; Ketchum, R.E.B.; Rithner, C.D.; Williams, R.M.; Croteau, R.
Taxol biosynthesis: differential transformations of taxadien-5alpha-ol and its acetate ester by cytochrome P450 hydroxylases from Taxus suspension cells
Arch. Biochem. Biophys.
390
265-278
2001
Taxus cuspidata
brenda
Jennewein, S.; Rithner, C.D.; Williams, R.M.; Croteau, R.B.
Taxol biosynthesis: taxane 13alpha-hydroxylase is a cytochrome P450-dependent monooxygenase
Proc. Natl. Acad. Sci. USA
98
13595-13600
2001
Taxus cuspidata (Q8W4T9)
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
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
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1.14.14.106 taxane 13alpha-hydroxylase
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