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EC Tree
IUBMB Comments This is the third enzyme in the biosynthesis of the diterpenoid antineoplastic drug taxol (paclitaxel), which is widely used in the treatment of carcinomas, sarcomas and melanomas.
The enzyme appears in viruses and cellular organisms
Synonyms
tmtat, taxadienol acetyl transferase,
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acetyl coenzyme A:taxa-4(20),11(12)-dien-5alpha-ol O-acetyl transferase
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-
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TAX19 acetyltransferase
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taxadienol acetyl transferase
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taxoid-O-acetyltransferase
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acetyl-CoA + taxa-4(20),11-dien-5alpha-ol = CoA + taxa-4(20),11-dien-5alpha-yl acetate
acetyl-CoA + taxa-4(20),11-dien-5alpha-ol = CoA + taxa-4(20),11-dien-5alpha-yl acetate
summary of taxol biosynthesis
acetyl-CoA + taxa-4(20),11-dien-5alpha-ol = CoA + taxa-4(20),11-dien-5alpha-yl acetate
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Acyl group transfer
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acetyl-CoA:taxa-4(20),11-dien-5alpha-ol O-acetyltransferase
This is the third enzyme in the biosynthesis of the diterpenoid antineoplastic drug taxol (paclitaxel), which is widely used in the treatment of carcinomas, sarcomas and melanomas.
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acetyl-CoA + farnesol
CoA + ?
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-
-
?
acetyl-CoA + geranylgeraniol
CoA + ?
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-
-
?
acetyl-CoA + phytol
CoA + ?
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-
-
?
acetyl-CoA + taxa-4(20),11(12)-dien-5alpha-ol
CoA + taxa-4(20),11-dien-5alpha-yl acetate
acetyl-CoA + taxadien-2alpha,5alpha,10beta-triol
CoA + taxadien-10beta-acetoxy-2alpha,5alpha-diol
-
-
?
acetyl-CoA + taxadien-2alpha,5alpha,10beta-triol
CoA + taxadien-5alpha-acetoxy-2alpha,10beta-diol
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-
?
acetyl-CoA + taxadien-2alpha,5alpha-diol
CoA + taxadien-5alpha-acetoxy-2alpha-ol
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-
?
acetyl-CoA + taxadien-5alpha,9alpha,10beta,13alpha-tetraol
CoA + taxadien-10beta-acetoxy-5alpha,9alpha,13alpha-triol
-
-
?
acetyl-CoA + taxadien-5alpha,9alpha,10beta,13alpha-tetraol
CoA + taxadien-13alpha-acetoxy-5alpha,9alpha,10beta-triol
-
-
?
acetyl-CoA + taxadien-5alpha-acetoxy-9alpha,10beta,13alpha-triol + H2O
CoA + taxadien-5alpha,13alpha-diacetoxy-9alpha,10beta-diol
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-
?
acetyl-CoA + taxadien-5alpha-acetoxy-9alpha,10beta,13alpha-triol + H2O
CoA + taxadien-5alpha,9alpha,10beta-triacetoxy-13alpha-ol
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-
?
acetyl-CoA + taxadien-5alpha-ol + H2O
CoA + taxadien-5alpha-yl acetate
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-
?
acetyl-CoA + taxadienol
CoA + ?
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-
-
?
additional information
?
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acetyl-CoA + taxa-4(20),11(12)-dien-5alpha-ol
CoA + taxa-4(20),11-dien-5alpha-yl acetate
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-
-
?
acetyl-CoA + taxa-4(20),11(12)-dien-5alpha-ol
CoA + taxa-4(20),11-dien-5alpha-yl acetate
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-
-
?
acetyl-CoA + taxa-4(20),11(12)-dien-5alpha-ol
CoA + taxa-4(20),11-dien-5alpha-yl acetate
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-
-
?
acetyl-CoA + taxa-4(20),11(12)-dien-5alpha-ol
CoA + taxa-4(20),11-dien-5alpha-yl acetate
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-
?
acetyl-CoA + taxa-4(20),11(12)-dien-5alpha-ol
CoA + taxa-4(20),11-dien-5alpha-yl acetate
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-
?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
additional information
?
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no detectable activity with taxadien-2alpha,5alpha-diol
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?
additional information
?
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no detectable activity with taxadien-2alpha,5alpha-diol
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?
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additional information
?
-
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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-
?
additional information
?
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catalyzes the first acylation step of taxol biosynthesis
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?
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additional information
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monovalent and divalent cations show no effect on the enzyme
additional information
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monovalent and divalent cations show no effect on the enzyme
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CoA
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weak
N-ethylmaleimide
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weak
p-hydroxymercuribenzoate
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weak
p-hydroxymercuribenzoate
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weak
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0.0042
taxa-4(20),11-dien-5alpha-ol
0.0129 - 0.0415
taxadien-2alpha,5alpha,10beta-triol
0.0239
taxadien-2alpha,5alpha-diol
-
0.0173 - 0.0453
taxadien-5alpha,9alpha,10beta,13alpha-tetraol
0.0835 - 0.2794
taxadien-5alpha-acetoxy-9alpha,10beta,13alpha-triol
0.005 - 0.0086
taxadien-5alpha-ol
0.0055
acetyl-CoA
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-
0.0042
taxa-4(20),11-dien-5alpha-ol
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-
0.0042
taxa-4(20),11-dien-5alpha-ol
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0.0129
taxadien-2alpha,5alpha,10beta-triol
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0.0415
taxadien-2alpha,5alpha,10beta-triol
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0.0173
taxadien-5alpha,9alpha,10beta,13alpha-tetraol
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0.0453
taxadien-5alpha,9alpha,10beta,13alpha-tetraol
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0.0835
taxadien-5alpha-acetoxy-9alpha,10beta,13alpha-triol
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0.2794
taxadien-5alpha-acetoxy-9alpha,10beta,13alpha-triol
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0.005
taxadien-5alpha-ol
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0.0086
taxadien-5alpha-ol
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5.77 - 27.92
taxadien-2alpha,5alpha,10beta-triol
52.13
taxadien-2alpha,5alpha-diol
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11.91 - 15.47
taxadien-5alpha,9alpha,10beta,13alpha-tetraol
145 - 297.9
taxadien-5alpha-acetoxy-9alpha,10beta,13alpha-triol
4.28 - 29.59
taxadien-5alpha-ol
5.77
taxadien-2alpha,5alpha,10beta-triol
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27.92
taxadien-2alpha,5alpha,10beta-triol
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11.91
taxadien-5alpha,9alpha,10beta,13alpha-tetraol
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15.47
taxadien-5alpha,9alpha,10beta,13alpha-tetraol
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145
taxadien-5alpha-acetoxy-9alpha,10beta,13alpha-triol
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297.9
taxadien-5alpha-acetoxy-9alpha,10beta,13alpha-triol
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4.28
taxadien-5alpha-ol
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29.59
taxadien-5alpha-ol
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additional information
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9
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pI: 4.7
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7.5 - 10
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50% of maximal activity at pH 7.50 and pH 10.0, enzyme inactive at pH 11.0
7.5 - 10
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50% of maximal activity at pH 7.50 and pH 10.0, enzyme inactive at pH 11.0
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5.4
calculation from nucleotide sequence
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brenda
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SwissProt
brenda
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brenda
methyl jasmonate-induced cells
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brenda
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SwissProt
brenda
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brenda
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SwissProt
brenda
methyl jasmonate-induced cells
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brenda
TAX19 acetyltransferase
SwissProt
brenda
taxoid-O-acetyltransferase; TAX1 acetyltransferase
SwissProt
brenda
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strong expression
brenda
weak expression
brenda
additional information
no expression in fruits
brenda
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T5AT_TAXCU
439
0
49080
Swiss-Prot
other Location (Reliability: 3 )
T5AT_TAXWC
439
0
49183
Swiss-Prot
other Location (Reliability: 2 )
A0A396HCU1_MEDTR
231
0
25981
TrEMBL
other Location (Reliability: 3 )
A0A072UX90_MEDTR
459
0
51217
TrEMBL
other Location (Reliability: 4 )
B9SDE9_RICCO
455
0
51257
TrEMBL
other Location (Reliability: 5 )
A0A396JPB2_MEDTR
150
0
16645
TrEMBL
Secretory Pathway (Reliability: 3 )
A0A396IT09_MEDTR
139
0
15895
TrEMBL
other Location (Reliability: 3 )
A0A396ITJ2_MEDTR
510
0
57748
TrEMBL
Secretory Pathway (Reliability: 1 )
A0A396IR48_MEDTR
407
0
45353
TrEMBL
Chloroplast (Reliability: 3 )
A0A396IT21_MEDTR
438
0
48885
TrEMBL
other Location (Reliability: 5 )
B9RPA0_RICCO
469
0
52568
TrEMBL
other Location (Reliability: 4 )
A0A396ITU9_MEDTR
175
0
19734
TrEMBL
other Location (Reliability: 4 )
G7JKY1_MEDTR
465
0
52052
TrEMBL
other Location (Reliability: 2 )
B9R7Y9_RICCO
455
0
51090
TrEMBL
Chloroplast (Reliability: 3 )
A0A2P6Q4I1_ROSCH
450
0
50179
TrEMBL
other Location (Reliability: 2 )
A0A2G9GVJ8_9LAMI
451
0
50249
TrEMBL
other Location (Reliability: 4 )
A0A396ISZ1_MEDTR
100
1
11499
TrEMBL
other Location (Reliability: 4 )
A0A2G9H2T0_9LAMI
443
0
49549
TrEMBL
other Location (Reliability: 2 )
A0A072UX85_MEDTR
468
0
51793
TrEMBL
other Location (Reliability: 3 )
B9SQQ0_RICCO
438
0
48486
TrEMBL
other Location (Reliability: 5 )
B9RUQ5_RICCO
458
0
51724
TrEMBL
other Location (Reliability: 5 )
G7IK88_MEDTR
449
0
50803
TrEMBL
other Location (Reliability: 2 )
A0A2P6RF41_ROSCH
434
0
48256
TrEMBL
other Location (Reliability: 5 )
A0A2G9HRF2_9LAMI
422
0
46405
TrEMBL
other Location (Reliability: 5 )
A0A396IQ60_MEDTR
97
1
11076
TrEMBL
other Location (Reliability: 3 )
B9SDF5_RICCO
434
0
48667
TrEMBL
other Location (Reliability: 3 )
B9RVG9_RICCO
481
0
53400
TrEMBL
other Location (Reliability: 2 )
Q5Y9C6_TAXCU
442
0
49230
TrEMBL
-
Q5Y9C7_TAXCU
442
0
48970
TrEMBL
-
Q6SPR1_9SPER
439
0
49222
TrEMBL
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49000
x * 49000, calculation from nucleotide sequence
49080
-
recombinant enzyme, calculated from amino acid composition
50000
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gel chromatography
50000
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gel chromatography
50000
-
x * 50000, SDS-PAGE
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?
-
x * 50000, SDS-PAGE
?
x * 49000, calculation from nucleotide sequence
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additional information
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reconstruction of taxoid biosynthesis in Saccharomyces cerevisiae by simultaneous expression of five early pathway steps starting from isoprenoid precursors. Production of taxadiene reaches levels of 0.7 mg/l in YPG media and 1.0 mg/l in selective media
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partially
-
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expression in Escherichia coli
expression in Escherichia coli
expression in Escherichia coli
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medicine
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understanding of biosynthetic pathway of taxol, target: possibly biological production of taxol, taxol or paclitaxel is now well established as a potent chemotherapeutic drug
medicine
understanding of biosynthetic pathway of taxol, target: possibly biological production of taxol, taxol or paclitaxel is now well established as a potent chemotherapeutic drug
medicine
-
understanding of biosynthetic pathway of taxol, target: possibly biological production of taxol, taxol or paclitaxel is now well established as a potent chemotherapeutic drug
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Walker, K.; Croteau, R.
Taxol biosynthetic genes
Phytochemistry
58
1-7
2001
Taxus cuspidata (Q9M6F0)
brenda
Walker, K.; Ketchum, R.E.; Hezari, M.; Gatfield, D.; Goleniowski, M.; Barthol, A.; Croteau, R.
Partial purification and characterization of acetyl coenzyme A: taxa-4(20),11(12)-dien-5alpha-ol O-acetyl transferase that catalyzes the first acylation step of taxol biosynthesis
Arch. Biochem. Biophys.
364
273-279
1999
Taxus canadensis, Taxus cuspidata
brenda
Walker, K.; Schoendorf, A.; Croteau, R.
Molecular cloning of a taxa-4(20),11(12)-dien-5a-ol-O-acetyl transferase cDNA from taxus and functional expression in Escherichia coli
Arch. Biochem. Biophys.
374
371-380
2000
Taxus canadensis, Taxus cuspidata, Taxus cuspidata (Q9M6F0)
brenda
Chau, M.; Walker, K.; Long, R.; Croteau, R.
Regioselectivity of taxoid-O-acetyltransferases: heterologous expression and characterization of a new taxadien-5alpha-ol-O-acetyltransferase
Arch. Biochem. Biophys.
430
237-246
2004
Taxus cuspidata (Q5Y9C6), Taxus cuspidata (Q5Y9C7)
brenda
Kai, G.; Miao, Z.; Qiu, C.; Zhang, L.; Zhao, L.; Li, Z.; Xu, T.; Zhang, L.; Gong, Y.; Zhao, D.; Liu, D.; Sun, X.; Tang, K.
Molecular cloning and characterization of a taxadienol acetyl transferase cDNA from Taxus x media
Plant Sci.
167
759-764
2004
Taxus x media (Q6SPR1)
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 brevifolia
brenda
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2.3.1.162 taxadien-5alpha-ol O-acetyltransferase
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