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Information on EC 2.3.1.320 - taxoid C-13 O-(3-amino-3-phenylpropanoyl)transferase
for references in articles please use BRENDA:EC2.3.1.320
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EC Tree 2 Transferases
2.3 Acyltransferases
2.3.1 Transferring groups other than aminoacyl groups
2.3.1.320 taxoid C-13 O-(3-amino-3-phenylpropanoyl)transferase
IUBMB Comments
The enzyme is active in the biosynthetic pathway of paclitaxel (Taxol) in Taxus species (yew).
The expected taxonomic range for this enzyme is: Taxus
Reaction Schemes
showSynonyms
10-deacetylbaccatin III-10-O-acetyl transferase, 3-amino,3-phenylpropanoyltransferase, baccatin III, baccatin III 13-O-(3-amino-3-phenylpropanoyl) transferase, baccatin III 13-O-(3-amino-3-phenylpropanoyl)transferase, baccatin III-3-amino 3-phenylpropanoyltransferase 1, baccatin III:3-amino-3-phenylpropanoyltransferase, baccatin-aminophenylpropanoyl-13-O-transferase, BAPT, phenylpropanoyltransferase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
BAPT
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
baccatin III + (3R)-3-amino-3-phenylpropanoyl-CoA = 3'-N-debenzoyl-2'-deoxytaxol + CoA
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-
-
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SYSTEMATIC NAME
IUBMB Comments
(3R)-3-amino-3-phenylpropanoyl-CoA:baccatin III C-13 O-((3R)-3-amino-3-phenylpropanoyl)transferase
The enzyme is active in the biosynthetic pathway of paclitaxel (Taxol) in Taxus species (yew).
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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
baccatin III + (3R)-3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2-deoxytaxol + CoA
Substrates: -
Products: -
Products: -
?
baccatin III + 3-phenylisoserinoyl-CoA
? + coenzyme A
Substrates: selective for 3-amino-3-phenylpropanoyl-CoA esters with a preference for beta-phenylalanoyl-CoA over 3-phenylisoserinoyl-CoA. Activity with 3-phenylisoserinoyl-CoA is 40% of the activity with beta-phenylalanoyl-CoA. alpha-Phenylalanoyl-CoA and N-benzoyl phenylisoserinoyl-CoA are not productive acyl donors
Products: -
Products: -
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additional information
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Substrates: BAPT catalyses conjugation of the beta-phenylalanoyl-CoA side chain to the C13 hydroxyl group of baccatin III to generate 3'-N-debenzoyl-2'-deoxytaxol
Products: -
Products: -
-
baccatin III + (3R)-3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2'-deoxytaxol + CoA
Substrates: -
Products: -
Products: -
?
baccatin III + (3R)-3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2'-deoxytaxol + CoA
Substrates: -
Products: -
Products: -
?
baccatin III + (3R)-3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2'-deoxytaxol + CoA
Substrates: -
Products: -
Products: -
?
baccatin III + 3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2'-deoxytaxol + coenzyme A
Substrates: the enzyme is involved in taxol biosynthesis
Products: -
Products: -
?
baccatin III + 3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2'-deoxytaxol + coenzyme A
Substrates: selective for 3-amino-3-phenylpropanoyl-CoA esters with a preference for beta-phenylalanoyl-CoA over 3-phenylisoserinoyl-CoA. alpha-Phenylalanoyl-CoA and N-benzoyl phenylisoserinoyl-CoA are not productive acyl donors
Products: this enzymatic product is converted to 2'-deoxytaxol by chemical N-benzoylation, and the identity of this derivative is confirmed by spectrometric analyses
Products: this enzymatic product is converted to 2'-deoxytaxol by chemical N-benzoylation, and the identity of this derivative is confirmed by spectrometric analyses
?
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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
baccatin III + (3R)-3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2-deoxytaxol + CoA
Substrates: -
Products: -
Products: -
?
baccatin III + 3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2'-deoxytaxol + coenzyme A
Substrates: the enzyme is involved in taxol biosynthesis
Products: -
Products: -
?
baccatin III + (3R)-3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2'-deoxytaxol + CoA
Substrates: -
Products: -
Products: -
?
baccatin III + (3R)-3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2'-deoxytaxol + CoA
Substrates: -
Products: -
Products: -
?
baccatin III + (3R)-3-amino-3-phenylpropanoyl-CoA
3'-N-debenzoyl-2'-deoxytaxol + CoA
Substrates: -
Products: -
Products: -
?
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0049
3-amino-3-phenylpropanoyl-CoA
pH and temperature not specified in the publication
0.0024
baccatin III
pH and temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
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
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.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
metabolism
physiological function
3-amino,3-phenyl-propanoyltransferase (BAPT) enzyme integrates baccatin III with phenylisoserine to 3'-N-debenzoyl-2'-deoxytaxol, which is used by 3'-N-debenzoyl-2-deoxytaxol-N-benzoyltransferase (DBTNBT), that catalyzes the final step in paclitaxel (taxol) production
malfunction
the accumulation of taxoids and flavonoids in Taxus cuspidata plantlets is significantly induced by 12 and 24 h of UV-B radiation (3 W/m2), transcriptomic analysis, overview. Baccatin III-3-amino 3-phenylpropanoyltransferase 1, taxadiene-5alpha-hydroxylase, and ethylene response factors 15 are significantly induced, which indicates that UV-B might initiate the jasmonate signaling pathway that contributes to taxoid enhancement in Taxus cuspidata. The baccatin III content is increased
malfunction
overexpression of BAPT and DBTNBT genes in Taxus baccata in vitro cultures enhance the biotechnological production of paclitaxel
metabolism
TXS (taxadiene synthase), BAPT (baccatin III: 3-amino,3-phenylpropanoyltransferase), DBTNBT (3'-N-debenzoyl-2-deoxytaxol-N-benzoyltransferase) and PAM (phenylalanine aminomutase) are involved in paclitaxel biosynthesis, expression profiles of the four genes, overview. The maximum paclitaxel yield is achieved in cultures primed with beta-aminobutyric acid (BABA) for 1 week, highest expression levels of TXS and BAPT genes in hairy roots
metabolism
paclitaxel anticancer drug is produced by plant cell cultures and limited in yield by bottleneck enzymes in the taxane biosynthetic pathway: baccatin-aminophenylpropanoyl-13-O-transferase (BAPT) and 3'-N-debenzoyltaxol N-benzoyltransferase (DBTNBT). Paclitaxel biosynthetic pathway, overview
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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). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
additional information
paclitaxel anticancer drug is produced by plant cell cultures and limited in yield by bottleneck enzymes in the taxane biosynthetic pathway: baccatin-aminophenylpropanoyl-13-O-transferase (BAPT) and 3'-N-debenzoyltaxol N-benzoyltransferase (DBTNBT). Alleviation of the taxane metabolic bottleneck by overexpressing the flux-limiting genes of the taxane biosynthetic pathway, BAPT and DBTNBT, both under the control of one copy of the constitutive CaMV35S promoter. Overexpression of BAPT and DBTNBT genes in Taxus baccata in vitro cultures enhances the biotechnological production of paclitaxel. The content of paclitaxel is almost doubled in the BAPT line (135 mg/l) compared to control
additional information
amelioration and evaluation of Taxus x media hairy root culture productivity in paclitaxel production. Expression profiles over time of BAPT in hairy roots with and without treatment with beta-aminobutyric acid, overview
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene BAPT, overexpressing of the flux-limiting gene BAPT (59.72fold higher at 48 h) through a Rhizobium rhizogenes A4-mediated transformation in Taxus baccata transgenic roots and established faster growing callus lines and cell suspension cultures
gene BAPT, quantitative real-time PCR enzyme expression analysis, overview
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme expression is induced by beta-aminobutyric acid in hairy roots
UV-B radiation induces the enzyme in Taxus cuspidata plantlets, probably via methyl jasmonate (JA) signalling. The wound/defense signaling pathway is to regulate the biosynthesis of secondary metabolites by triggering the production and transduction of some endogenous signal molecules such as JA
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
biotechnology
overexpression of BAPT and DBTNBT genes in Taxus baccata in vitro cultures enhances the biotechnological production of paclitaxel, an important anticancer drug
synthesis
Taxus x media hairy root cultures can produce the anticancer drug paclitaxel involving the enzyme
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Walker, K.; Fujisaki, S.; Long, R.; Croteau, R.
Molecular cloning and heterologous expression of the C-13 phenylpropanoid side chain-CoA acyltransferase that functions in Taxol biosynthesis
Proc. Natl. Acad. Sci. USA
99
12715-12720
2002
Taxus cuspidata (Q8H2B5)
brenda
Onrubia, M.; Moyano, E.; Bonfill, M.; Palazon, J.; Goossens, A.; Cusido, R.M.
The relationship between TXS, DBAT, BAPT and DBTNBT gene expression and taxane production during the development of Taxus baccata plantlets
Plant Sci.
181
282-287
2011
Taxus baccata (L7TC40)
brenda
Perez-Matas, E.; Hidalgo-Martinez, D.; Moyano, E.; Palazon, J.; Bonfill, M.
Overexpression of BAPT and DBTNBT genes in Taxus baccata in vitro cultures to enhance the biotechnological production of paclitaxel
Plant Biotechnol. J.
22
233-247
2024
Taxus baccata (L7TC40)
brenda
Syklowska-Baranek, K.; Sygitowicz, G.; Maciejak-Jastrzebska, A.; Pietrosiuk, A.; Szakiel, A.
Application of priming strategy for enhanced paclitaxel biosynthesis in Taxus x Media hairy root cultures
Cells
11
2062
2022
Taxus x media (Q56V24)
brenda
Jiao, J.; Xu, X.; Lu, Y.; Liu, J.; Fu, Y.; Fu, J.; Gai, Q.
Identification of genes associated with biosynthesis of bioactive flavonoids and taxoids in Taxus cuspidata Sieb. et Zucc. plantlets exposed to UV-B radiation
Gene
823
146384
2022
Taxus cuspidata (Q8H2B5)
brenda
EXTERNAL LINKS (specific for EC-Number 2.3.1.320)
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