Information on EC 2.3.1.167 - 10-deacetylbaccatin III 10-O-acetyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.167
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RECOMMENDED NAME
GeneOntology No.
10-deacetylbaccatin III 10-O-acetyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA + 10-deacetylbaccatin III = CoA + baccatin III
show the reaction diagram
The enzyme will not acylate the hydroxy group at 1beta, 7beta or 13alpha of 10-deacetyl baccatin III, or at 5alpha of taxa-4(20),11-dien-5alpha-ol. May be identical to EC 2.3.1.163, 10-hydroxytaxane O-acetyltransferas
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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
acetyl-CoA:taxan-10beta-ol O-acetyltransferase
The enzyme will not acylate the hydroxy group at 1beta, 7beta or 13alpha of 10-deacetyl baccatin III, or at 5alpha of taxa-4(20),11-dien-5alpha-ol. May be identical to EC 2.3.1.163, 10-hydroxytaxane O-acetyltransferase.
CAS REGISTRY NUMBER
COMMENTARY hide
220946-63-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
endophytic taxol-producing fungus strain MD3 isolated from the inner bark of Taxus x media
TREMBL
Manually annotated by BRENDA team
endophytic taxol-producing fungus strain MD2 isolated from the inner bark of Taxus media
TREMBL
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
Taxus sp.
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + 10-deacetylbaccatin III
CoA + baccatin III
show the reaction diagram
acetyl-CoA + 4-deacetylbaccatin III
CoA + baccatin III
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 7,13-diacetyl-4-deacetylbaccatin III
CoA + 13-acetylbaccatin III
show the reaction diagram
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-
-
-
?
butyryl-CoA + 10-deacetylbaccatin III
CoA + 10-deacetyl-10-butyrylbaccatin III
show the reaction diagram
Taxus sp.
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-
-
-
?
n-butyryl-CoA + 10-deacetylbaccatin III
CoA + 10-deacetyl-10-butyrylbaccatin III
show the reaction diagram
Taxus sp.
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-
-
-
?
n-butyryl-CoA + 10-deacetylbaccatin III
CoA + 10-n-butyryl-10-deacetylbaccatin III
show the reaction diagram
Taxus sp.
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-
-
-
?
propionyl-CoA + 10-deacetylbaccatin III
CoA + 10-deacetyl-10-propionylbaccatin III
show the reaction diagram
Taxus sp.
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-
-
-
?
propionyl-CoA + 10-deacetylbaccatin III
CoA + 10-propionyl-10-deacetylbaccatin III
show the reaction diagram
Taxus sp.
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-
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?
additional information
?
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Taxus sp.
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DBAT catalyzes the transfer of acetyl, propionyl or n-butyryl from CoA to the C10-hydroxyl of 10-deacetylbaccatin III
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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
acetyl-CoA + 10-deacetylbaccatin III
CoA + baccatin III
show the reaction diagram
butyryl-CoA + 10-deacetylbaccatin III
CoA + 10-deacetyl-10-butyrylbaccatin III
show the reaction diagram
Taxus sp.
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-
-
-
?
propionyl-CoA + 10-deacetylbaccatin III
CoA + 10-deacetyl-10-propionylbaccatin III
show the reaction diagram
Taxus sp.
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetyl-CoA
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
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required
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ammonium ceric(IV) sulfate
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methyl jasmonate
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Silver nitrate
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01 - 0.0576
10-deacetylbaccatin III
0.008 - 0.0085
acetyl-CoA
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.58
10-deacetylbaccatin III
Taxus cuspidata
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
10.07
10-deacetylbaccatin III
Taxus cuspidata
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5317
0.19
4-deacetylbaccatin III
Taxus cuspidata
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-
156381
0.015
7,13-diacetyl-4-deacetylbaccatin III
Taxus cuspidata
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156382
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.1
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recombinant enzyme with biotinylated peptide tag
16.1
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recombinant glutathione S-transferase-fusion protein
24.4
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recombinant enzyme with a hexahistidine fusion tag
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 8
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half-maximal aactivity of recombinant enzyme at pH 6.0 and 8.0
6.4 - 7.8
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
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assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.05
predicted pI-value
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
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higher content of 10-deacetylbaccatin III in the aerial part of the plantlets than in the roots
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
16000
tag-protein
48980
predicted molecular mass
49050
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calculation from nucleotide sequence
65000
determined by SDS-PAGE, TmDBAT plus fused tag
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 50000, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
by affinity chromatography in Ni-nitrilotriacetic acid columns, the tag is removed by digestion with enterokinase
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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gene dbat, functional expression in Escherichia coli strain JM109, co-expression with acetyl-CoA synthase, gene acs, EC 6.2.1.1, or with acetoacetate:acetyl-CoA CoA-transferase, genes atoAD of the ato operon, EC 2.8.3.8, expressed from and regulated by genes encoded on the bacterial chromosome, overview; into the vector pCWori+ for expression in Escherichia coli JM109 and BL21DE3 cells
Taxus sp.
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into the TA cloning vector pMD19-T for sequencing
into the TA cloning vector pMD19-T for sequencing; into the TA cloning vector pMD19-T for sequencing
into the TA cloning vector pMD19-T for sequencing; into the TA cloning vector pMD19-T for sequencing; into the TA cloning vector pMD19-T for sequencing
overexpression in Escherichia coli. Three kinds of fusion systems with isopropyl-beta-D-1-thiogalactopyranoside inducible promoters are used. The fusion partners are glutathione S-transferase tag, hexahistidine fusion tag, and a biotinylated peptide tag
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the amplified PCR fragment is subcloned into the pGEM-T Easy vector and subsequently into the pET32a+ vector for expression in Escherichia coli BL21DE3 cells
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
10-DBAT is induced by F3, and elicitor isolated from the inner bark of Taxus cuspidata, it is also induced by methyljasmonate, salicylate, and hydrogen peroxide to maximal activities of 6.82, 5.47, 0.97, and 3.30 U, respectively. The metabolite pattern in the suspension cell culture changed due to elicitation, accumulation of baccatin III and 10-DAB III increases slowly, taxol accumulated rapidly, time course of enzyme activity of 10-DBAT, verview
highest level of dbat expression was detected 24 h after inoculation followed by a decrease
subcloned as recombinant protein in Escherichia coli strain BL21(DE3)
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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functional expression in Saccharomyces cerevisiae for reconstruction of taxoid biosynthesis
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
Taxus sp.
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optimizing the semi-biosynthetic method in bacteria potentially provides a practical means of developing commercial-scale production of baccatin III analogs, which serve as key intermediates in the semi-synthesis of second-generation taxols
pharmacology
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use in synthesis of taxol for anticnacer treatment
synthesis