Information on EC 2.6.1.28 - tryptophan-phenylpyruvate transaminase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
2.6.1.28
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RECOMMENDED NAME
GeneOntology No.
tryptophan-phenylpyruvate transaminase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-tryptophan + phenylpyruvate = (indol-3-yl)pyruvate + L-phenylalanine
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
amino group transfer
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
L-methionine degradation III
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L-tryptophan degradation VIII (to tryptophol)
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terrequinone A biosynthesis
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tryptophan metabolism
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SYSTEMATIC NAME
IUBMB Comments
L-tryptophan:phenylpyruvate aminotransferase
Valine, leucine and isoleucine can replace tryptophan as amino donor.
CAS REGISTRY NUMBER
COMMENTARY hide
37277-87-5
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
L-phenylalanine + 2-oxobutanoate
phenylpyruvate + 2-aminobutanoate
show the reaction diagram
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low activity
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r
L-phenylalanine + 2-oxohexanoate
phenylpyruvate + L-norleucine
show the reaction diagram
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-
-
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r
L-phenylalanine + 2-oxoisohexanoate
phenylpyruvate + L-leucine
show the reaction diagram
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i.e alpha-ketoisocaproate, highest activity as amino acceptor
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r
L-phenylalanine + 2-oxoisopentanoate
phenylpyruvate + L-valine
show the reaction diagram
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-
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r
L-phenylalanine + pyruvate
phenylpyruvate + L-alanine
show the reaction diagram
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2% of the activity with alpha-ketoisocaproate
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r
L-tryptophan + 2-oxobutanoate
3-indole-2-oxopropanoate + 2-aminobutanoate
show the reaction diagram
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weak activity
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r
L-tryptophan + 2-oxoglutarate
3-indole-2-oxopropanoate + L-glutamate
show the reaction diagram
L-tryptophan + 2-oxohexanoate
3-indole-2-oxopropanoate + L-norleucine
show the reaction diagram
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-
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r
L-tryptophan + 2-oxoisohexanoate
3-indole-2-oxopropanoate + L-leucine
show the reaction diagram
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-
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r
L-tryptophan + 2-oxoisopentanoate
3-indole-2-oxopropanoate + L-valine
show the reaction diagram
L-tryptophan + 2-oxopentanoate
3-indole-2-oxopropanoate + norvaline
show the reaction diagram
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-
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r
L-tryptophan + 4-hydroxyphenylpyruvate
3-indole-2-oxopropanoate + ?
show the reaction diagram
15% of the activity with phenylpyruvate
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?
L-tryptophan + p-hydroxyphenylpyruvate
3-indole-2-oxopropanoate + tyrosine
show the reaction diagram
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r
L-tryptophan + phenylpyruvate
3-indole-2-oxopropanoate + L-phenylalanine
show the reaction diagram
L-tryptophan + pyruvate
3-indole-2-oxopropanoate + L-alanine
show the reaction diagram
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2% of the activity with alpha-ketoisocaproate
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r
phenylpyruvate + DL-5-hydroxytryptophan
phenylalanine + 3-(5-hydroxyindole)-2-oxopropanoate
show the reaction diagram
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r
phenylpyruvate + DL-histidine
phenylalanine + 3-(1H-imidazol-4-yl)-2-oxopropanoate
show the reaction diagram
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low activity
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r
phenylpyruvate + DL-isoleucine
phenylalanine + 3-methyl-2-oxopentanoate
show the reaction diagram
phenylpyruvate + DL-leucine
phenylalanine + 4-methyl-2-oxopentanoate
show the reaction diagram
phenylpyruvate + DL-methionine
phenylalanine + 4-methylsulfanyl-2-oxobutanoate
show the reaction diagram
phenylpyruvate + DL-valine
phenylalanine + 3-methyl-2-oxobutanoate
show the reaction diagram
phenylpyruvate + L-2-iminobutanoate
phenylalanine + ?
show the reaction diagram
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r
phenylpyruvate + L-citrulline
phenylalanine + 2-oxo-5-ureido-pentanoate
show the reaction diagram
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low activity
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r
phenylpyruvate + L-norleucine
phenylalanine + 2-oxohexanoate
show the reaction diagram
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r
phenylpyruvate + L-tyrosine
phenylalanine + 3-(4-hydroxyphenyl)-2-oxopropanoate
show the reaction diagram
phenylpyruvate + norvaline
phenylalanine + 2-oxopentanoate
show the reaction diagram
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r
phenylpyruvate + phenylglycine
phenylalanine + phenylglyoxylate
show the reaction diagram
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r
additional information
?
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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
L-tryptophan + phenylpyruvate
3-indole-2-oxopropanoate + L-phenylalanine
show the reaction diagram
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conversion of tryptophan into the plant indolylacetic acid
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?
additional information
?
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A7XRY8
catalyzes the first enzymatic step specific to the metabolic pathway toward terrequinone A
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxal 5'-phosphate
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.4
2-oxobutanoate
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with L-tryptophan, pH 8.0, 30C
0.08
2-Oxohexanoate
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with tryptophan, pH 8.0, 30C
0.03
2-Oxoisohexanoate
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with L-tryptophan, pH 8.0, 30C
0.11
2-oxoisopentanoate
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with L-tryptophan, pH 8.0, 30C
0.12
2-Oxopentanoate
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with L-tryptophan, pH 8.0, 30C
0.2
Indolepyruvate
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with L-leucine, pH 8.0, 30C
30
L-2-aminobutanoate
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with phenylpyruvate, pH 8.0, 30C
250
L-alanine
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with 2-oxoisohexanoate, pH 8.0, 30C
23.8
L-histidine
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with 2-oxoisohexanoate, pH 8.0, 30C
0.47
L-isoleucine
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with phenylpyruvate, pH 8.0, 30C
0.4
L-leucine
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with phenylpyruvate, pH 8.0, 30C
3.4
L-norleucine
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with phenylpyruvate, pH 8.0, 30C
4.5
L-norvaline
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with phenylpyruvate, pH 8.0, 30C
0.8
L-phenylalanine
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with 2-oxoisohexanoate, pH 8.0, 30C
0.198 - 3.02
L-tryptophan
1
L-tyrosine
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with 2-oxoisohexanoate, pH 8.0, 30C
4.5
L-valine
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with phenylpyruvate, pH 8.0, 30C
1.43
phenylpyruvate
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pH 7.0, 48C
12
pyruvate
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with L-tryptophan, pH 8.0, 30C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0032 - 19.3
L-tryptophan
9.1
phenylpyruvate
Aspergillus nidulans
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pH 7.0, 48C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
76
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purified enzyme
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.6 - 10.6
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pH 8.6: about 70% of activity maximum, pH 10.6: about 80% of activity maximum
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70
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increase in activity from 20C to 70C
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
90000
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sedimentation equilibrium analysis
110000
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gel filtration
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45
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30 min, with pyridoxal 5'-phosphate, no loss of activity
70
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5 min, without substrate or pyridoxal 5'-phosphate, complete loss of activity
additional information
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markedly heat-stable in presence of tryptophan, phenylpyruvate or pyridoxal 5'-phosphate
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
freezing causes loss of activity
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-30C, crude enzyme, stable for more than 3 months
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0-4C, more than 72 h, partially purified enzyme loses activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
to homogeneity
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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expression of complete gene cluster TdiA-TdiE in Escherichia coli, in order to establish the biosynthetic pathway to terrequinone A
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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expression of complete gene cluster TdiA-TdiE in Escherichia coli, in order to establish the biosynthetic pathway to terrequinone A
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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one-pot synthesis of di-demethylasterriquinone D from L-tryptophan and phenylpyruvic acid by use of enzymes TdiA and TdiD