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Information on EC 1.4.1.20 - phenylalanine dehydrogenase
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EC Tree
1.4.1.20 phenylalanine dehydrogenaseIUBMB Comments
The enzymes from Bacillus badius and Sporosarcina ureae are highly specific for L-phenylalanine; that from Bacillus sphaericus also acts on L-tyrosine.
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Word Map
The enzyme appears in viruses and cellular organisms
Synonyms
phenylalanine dehydrogenase, phedh, l-phenylalanine dehydrogenase, recombinant phedh, l-phedh, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
dehydrogenase, phenylalanine
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L-phenylalanine dehydrogenase
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PDH
PHD
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PheDH
phenylalanine dehydrogenase
PheDH
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-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
L-phenylalanine + H2O + NAD+ = phenylpyruvate + NH3 + NADH + H+
the reductive amination proceeds through a sequential ordered ternary-binary mechanism
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L-phenylalanine + H2O + NAD+ = phenylpyruvate + NH3 + NADH + H+
kinetic mechanism is ordered with NAD+ binding prior to Phe and the products being released in the order of ammonia, phenylpyruvate, and NADH
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L-phenylalanine + H2O + NAD+ = phenylpyruvate + NH3 + NADH + H+
the reductive amination proceeds through a sequential ordered ternary-binary mechanism
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L-phenylalanine + H2O + NAD+ = phenylpyruvate + NH3 + NADH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidative deamination
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redox reaction
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reductive amination
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
L-phenylalanine:NAD+ oxidoreductase (deaminating)
The enzymes from Bacillus badius and Sporosarcina ureae are highly specific for L-phenylalanine; that from Bacillus sphaericus also acts on L-tyrosine.
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CAS REGISTRY NUMBER
COMMENTARY
69403-12-9
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-(3-hydroxy-1-adamantyl)-2-oxoethanoic acid + NH3 + NADH
(S)-3-hydroxyadamantylglycine + H2O + NAD+
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modified PDH which contains two amino acid changes at the C-terminus and a 12 amino acid extension of the C-terminus is more effective with keto acid 2-(3-hydroxy-1-adamantyl)-2-oxoethanoic acid and less effective with phenylpyruvate than the wild type PDH
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-
?
2-chloro-phenylpyruvate + NH3 + NADH
2-chloro-L-phenylalanine + H2O + NAD+
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7% of activity with phenylpyruvate
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?
2-fluoro-phenylpyruvate + NH3 + NADH
2-fluoro-L-phenylalanine + H2O + NAD+
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6.6% of activity with phenylpyruvate
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-
?
2-oxo-4-phenylbutanoic acid + NH3 + NADH + H+
(S)-2-amino-4-phenylbutyric acid + H2O + NAD+
2-oxo-4-phenylbutanoic acid + NH3 + NADH + H+
L-homophenylalanine + H2O + NAD+
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-
-
?
2-oxobutanoate + NH3 + NADH
2-aminobutanoate + NAD+ + H2O
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5.5% of the activity with phenylpyruvate
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-
?
3-chloro-phenylpyruvate + NH3 + NADH
3-chloro-L-phenylalanine + H2O + NAD+
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0.8% of activity with phenylpyruvate
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?
3-cyclohexyl-2-oxopropionic acid + NH3 + NADH
3-cyclohexyl-2-aminopropionic acid + H2O + NAD+
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6.1% of activity with phenylpyruvate
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-
?
3-fluoro-phenylpyruvate + NH3 + NADH
3-fluoro-L-phenylalanine + H2O + NAD+
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23% of activity with phenylpyruvate
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?
4-chloro-L-phenylalanine + H2O + NAD+
4-chloro-phenylpyruvate + NH3 + NADH
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-
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?
4-chloro-phenylpyruvate + NH3 + NADH
4-chloro-L-phenylalanine + H2O + NAD+
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62% of activity with phenylpyruvate
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?
4-fluoro-L-phenylalanine + H2O + NAD+
4-fluoro-phenylpyruvate + NH3 + NADH
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-
-
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?
4-methoxy-L-phenylalanine + H2O + NAD+
4-methoxy-phenylpyruvate + NH3 + NADH
-
-
-
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?
4-methyl-2-oxopentanoate + NH3 + NADH + H+
L-leucine + NAD+ + H2O
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-
-
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r
4-methyl-L-phenylalanine + H2O + NAD+
4-methyl-phenylpyruvate + NH3 + NADH
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-
-
-
?
4-methyl-phenylpyruvate + NH3 + NADH
4-methyl-L-phenylalanine + H2O + NAD+
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15% of activity with phenylpyruvate
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?
4-nitro-L-phenylalanine + H2O + NAD+
4-nitro-phenylpyruvate + NH3 + NADH
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-
-
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?
4-nitro-phenylpyruvate + NH3 + NADH
4-nitro-L-phenylalanine + H2O + NAD+
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reaction with the immobilized mutant enzyme N145A
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?
4-phenyl-2-butanone + NH3 + NADH + H+
(R)-1-methyl-3-phenylpropylamine + H2O + NAD+
substrate for mutant enzyme K66Q/S149G/N262C
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?
4-pyridyl-phenylpyruvate + NH3 + NADH
4-pyridyl-L-phenylalanine + H2O + NAD+
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9% of activity with phenylpyruvate
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?
4-trifluoromethyl-phenylpyruvate + NH3 + NADH
4-trifluoromethyl-L-phenylalanine + H2O + NAD+
alpha-ketocaproic acid + NH3 + NADH
alpha-aminocaproic acid + H2O + NAD+
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12.8% of activity with phenylpyruvate
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?
DL-propargylglycine + phenazine ethosulfate + 2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyltetrazolium chloridehydrate + NAD+
? + NADH
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substrate is poorly fertilized by wild type enzyme, but using muteins with different mutations higher turnover can be achieved
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?
L-2-amino-n-butyric acid + H2O + NAD+
2-oxobutanoate + NADH + NH3
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1.0% of the activity with L-Phe
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?
L-2-aminohexanoic acid + H2O + NAD+
2-oxohexanoate + NADH + NH3
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19% of the activity with L-Phe
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?
L-alpha-amino-beta-phenylbutyrate + H2O + NAD+
2-oxo-3-phenylbutyrate + NADH + NH3
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7.0% of the activity with L-Phe
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-
?
L-isoleucine + H2O + NAD+
3-methyl-2-oxopentanoate + NH3 + NADH
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-
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r
L-phenylalanine + H2O + 3-pyridinealdehyde-NAD+
phenylpyruvate + NH3 + 3-pyridinealdehyde-NADH
L-phenylalanine + H2O + oxidized beta-nicotinamide guanine dinucleotide
phenylpyruvate + NH3 + reduced beta-nicotinamide guanine dinucleotide
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at 86% of the activity with NAD+
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?
L-phenylalanine + H2O + oxidized beta-nicotinamide hypoxanthine dinucleotide
phenylpyruvate + NH3 + reduced beta-nicotinamide hypoxanthine dinucleotide
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at 86% of the activity with NAD+
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?
L-phenylalanine + H2O + thio-NAD+
phenylpyruvate + NH3 + thio-NADH
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at 86% of the activity with NAD+
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?
L-phenylalanine + H2O + thionicotinamide-NAD+
phenylpyruvate + NH3 + thionicotinamide-NADH
L-phenylalaninol + H2O + NAD+
1-hydroxyacetone + NADH + NH3
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9.4% of the activity with L-Phe
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?
L-tryptophan + H2O + NAD+
3-(1H-indol-3-yl)-2-oxopropanoate + NH3 + NADH
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2% of activity with L-phenylalanine
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r
L-tyrosine + H2O + NAD+
(4-hydroxyphenyl)pyruvate + NH3 + NADH + H+
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-
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?
phenylacetone + NH3 + NADH + H+
(R)-amphetamine + H2O + NAD+
substrate for mutant enzyme K66Q/S149G/N262C
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?
phenylalaninamide + H2O + NAD+
2-oxo-3-phenylpropionamide + NADH + NH3
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9.0% of the activity with L-Phe
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?
phenylalanine hydroxamate + H2O + NAD+
2-oxo-3-phenylpropionic acid hydroxamate + NADH + NH3
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1.0% of the activity with L-Phe
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?
additional information
?
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specific activity of the chimeric enzyme is 6% of that of the parental phenylalanine dehydrogenase and shows a broad substrate specificity in the oxidative deamination, like phenylalanine dehydrogenase. However, it acts much more effectively than phenylalanine dehydrogenase on Ile and Val. The parent enzyme and the chimeric enzyme belong to the pro-S specific dehydrogenase
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?
2-oxo-4-methylpentanoate + NH3 + NADH
L-Ile + NAD+ + H2O
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13% of the activity with phenylpyruvate
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?
2-oxo-4-methylpentanoate + NH3 + NADH
L-Ile + NAD+ + H2O
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-
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?
2-oxo-4-methylpentanoate + NH3 + NADH
L-Ile + NAD+ + H2O
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16% of the activity with phenylpyruvate
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?
2-oxo-4-methylthiobutanoate + NH3 + NADH
L-Met + NAD+ + H2O
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16% of the activity with phenylpyruvate
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?
2-oxo-4-methylthiobutanoate + NH3 + NADH
L-Met + NAD+ + H2O
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33% of the activity with L-Phe
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?
2-oxo-4-methylthiobutanoate + NH3 + NADH
L-Met + NAD+ + H2O
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-
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?
2-oxo-4-methylthiobutanoate + NH3 + NADH
L-Met + NAD+ + H2O
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55% of the activity with phenylpyruvate
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?
2-oxo-4-phenylbutanoic acid + NH3 + NADH + H+
(S)-2-amino-4-phenylbutyric acid + H2O + NAD+
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-
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r
2-oxo-4-phenylbutanoic acid + NH3 + NADH + H+
(S)-2-amino-4-phenylbutyric acid + H2O + NAD+
-
-
-
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r
2-oxohexanoate + NH3 + NADH
2-aminohexanoate + H2O + NAD+
-
31% of the activity with phenylpyruvate
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-
?
2-oxohexanoate + NH3 + NADH
2-aminohexanoate + H2O + NAD+
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240% of the activity with phenylpyruvate
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?
2-oxohexanoate + NH3 + NADH
2-aminohexanoate + H2O + NAD+
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240% of the activity with phenylpyruvate
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?
2-oxohexanoate + NH3 + NADH
2-aminohexanoate + H2O + NAD+
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-
-
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?
2-oxohexanoate + NH3 + NADH
2-aminohexanoate + H2O + NAD+
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130% of the activity with phenylpyruvate
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?
2-oxoisohexanoate + NH3 + NADH
L-Leu + NAD+ + H2O
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47% of the activity with phenylpyruvate
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?
2-oxopentanoate + NH3 + NADH
L-norvaline + NAD+ + H2O
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12% of the activity with phenylpyruvate
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-
?
2-oxopentanoate + NH3 + NADH
L-norvaline + NAD+ + H2O
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-
-
-
?
2-oxopentanoate + NH3 + NADH
L-norvaline + NAD+ + H2O
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37% of the activity with phenylpyruvate
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-
?
4-fluoro-phenylpyruvate + NH3 + NADH
4-fluoro-L-phenylalanine + H2O + NAD+
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114% of activity with phenylpyruvate
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-
?
4-fluoro-phenylpyruvate + NH3 + NADH
4-fluoro-L-phenylalanine + H2O + NAD+
-
preferred substrate of mutant N145V
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r
4-hydroxyphenylpyruvate + NH3 + NADH
L-Tyr + NAD+ + H2O
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53% of the activity with phenylpyruvate
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-
?
4-hydroxyphenylpyruvate + NH3 + NADH
L-Tyr + NAD+ + H2O
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28% of the activity with phenylpyruvate
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-
?
4-hydroxyphenylpyruvate + NH3 + NADH
L-Tyr + NAD+ + H2O
-
28% of the activity with phenylpyruvate
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-
?
4-hydroxyphenylpyruvate + NH3 + NADH
L-Tyr + NAD+ + H2O
-
5% of the activity with L-Phe
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-
?
4-hydroxyphenylpyruvate + NH3 + NADH
L-Tyr + NAD+ + H2O
-
5% of the activity with L-Phe
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-
?
4-hydroxyphenylpyruvate + NH3 + NADH
L-Tyr + NAD+ + H2O
-
80% of the activity with phenylpyruvate
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-
?
4-hydroxyphenylpyruvate + NH3 + NADH + H+
L-tyrosine + NAD+ + H2O
-
-
-
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r
4-methoxy-phenylpyruvate + NH3 + NADH
4-methoxy-L-phenylalanine + H2O + NAD+
-
15% of activity with phenylpyruvate
-
-
?
4-methoxy-phenylpyruvate + NH3 + NADH
4-methoxy-L-phenylalanine + H2O + NAD+
-
preferred substrate of mutant N145L
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-
r
4-trifluoromethyl-phenylpyruvate + NH3 + NADH
4-trifluoromethyl-L-phenylalanine + H2O + NAD+
-
0.9% of activity with phenylpyruvate
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-
?
4-trifluoromethyl-phenylpyruvate + NH3 + NADH
4-trifluoromethyl-L-phenylalanine + H2O + NAD+
-
preferred substrate of mutant N145A
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-
r
alloisoleucine + H2O + NAD+
3-methyl-2-oxopentanoate + NADH + NH3
-
4.3% of the activity with L-Phe
-
-
?
alloisoleucine + H2O + NAD+
3-methyl-2-oxopentanoate + NADH + NH3
-
26% of the activity with L-Phe
-
-
?
indole-3-pyruvate + NH3 + NADH + H+
L-Trp + NAD+ + H2O
-
54% of the activity with phenylpyruvate
-
-
?
indole-3-pyruvate + NH3 + NADH + H+
L-Trp + NAD+ + H2O
-
54% of the activity with phenylpyruvate
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-
?
L-ethionine + H2O + NAD+
4-ethylthio-2-oxobutanoate + NH3 + NADH
-
7.0% of the activity with L-Phe
-
-
?
L-ethionine + H2O + NAD+
4-ethylthio-2-oxobutanoate + NH3 + NADH
-
13.0% of the activity with L-Phe
-
-
?
L-ethionine + H2O + NAD+
4-ethylthio-2-oxobutanoate + NH3 + NADH
-
-
-
-
?
L-Leu + H2O + NAD+
3-methyl-2-oxopentanoic acid + NH3 + NADH
-
3.0% of the activity with L-Phe
-
-
?
L-Leu + H2O + NAD+
3-methyl-2-oxopentanoic acid + NH3 + NADH
-
-
-
-
?
L-leucine + H2O + NAD+
3,3-dimethyl-2-oxo-butanoate + NH3 + NADH
-
-
-
-
r
L-leucine + H2O + NAD+
3,3-dimethyl-2-oxo-butanoate + NH3 + NADH
-
1% of activity with L-phenylalanine
-
-
r
L-Met + H2O + NAD+
2-oxo-4-methylthiobutanoate + NH3 + NADH
-
8.0% of the activity with L-Phe
-
-
?
L-Met + H2O + NAD+
2-oxo-4-methylthiobutanoate + NH3 + NADH
-
4% of the activity with L-Phe
-
-
?
L-Met + H2O + NAD+
2-oxo-4-methylthiobutanoate + NH3 + NADH
-
4% of the activity with L-Phe
-
-
?
L-Met + H2O + NAD+
2-oxo-4-methylthiobutanoate + NH3 + NADH
-
-
-
-
?
L-Met + H2O + NAD+
2-oxo-4-methylthiobutanoate + NH3 + NADH
-
2.2% of the activity with L-Phe
-
-
?
L-methionine + H2O + NAD+
(4-methylsulfanyl)-2-oxobutanoate + NH3 + NADH
-
-
-
-
r
L-methionine + H2O + NAD+
(4-methylsulfanyl)-2-oxobutanoate + NH3 + NADH
-
3% of activity with L-phenylalanine
-
-
r
L-norleucine + H2O + NAD+
2-oxohexanoate + NH3 + NADH
-
-
-
-
r
L-norleucine + H2O + NAD+
2-oxohexanoate + NH3 + NADH
-
4.5% of activity with L-phenylalanine
-
-
r
L-norleucine + H2O + NAD+
2-oxohexanoic acid + NADH + NH3
-
19% of the activity with L-Phe
-
-
?
L-norleucine + H2O + NAD+
2-oxohexanoic acid + NADH + NH3
-
15.6% of the activity with L-Phe
-
-
?
L-norleucine + H2O + NAD+
2-oxohexanoic acid + NADH + NH3
-
-
-
-
?
L-norleucine + H2O + NAD+
2-oxohexanoic acid + NADH + NH3
-
-
-
-
?
L-norleucine + H2O + NAD+
2-oxohexanoic acid + NADH + NH3
-
30% of the activity with L-Phe
-
-
?
L-norvaline + H2O + NAD+
2-oxopentanoate + NH3 + NADH
-
5.0% of the activity with L-Phe
-
-
?
L-norvaline + H2O + NAD+
2-oxopentanoate + NH3 + NADH
-
-
-
-
r
L-norvaline + H2O + NAD+
2-oxopentanoate + NH3 + NADH
-
28% of the activity with L-Phe
-
-
?
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
-
-
-
?
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
the equilibrium favors L-Phe formation
-
-
r
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
the enzyme is involved in the degradation of Phe
-
?
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
the reductive amination proceeds through a sequential ordered ternary-binary mechanism
-
-
r
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
the reductive amination proceeds through a sequential ordered ternary-binary mechanism
-
-
r
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
-
-
-
r
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
-
-
r
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
-
-
-
r
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
the equilibrium favors L-Phe formation
-
-
r
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
the equilibrium favors L-Phe formation
-
-
r
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
-
-
-
r
L-Phe + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
-
-
-
r
L-phenylalanine + H2O + 3-acetylpyridine-NAD+
phenylpyruvate + NH3 + acetylpyridine-NADH
-
at 241% of the activity with NAD+
-
?
L-phenylalanine + H2O + 3-acetylpyridine-NAD+
phenylpyruvate + NH3 + acetylpyridine-NADH
-
at 241% of the activity with NAD+
-
?
L-phenylalanine + H2O + 3-acetylpyridine-NAD+
phenylpyruvate + NH3 + acetylpyridine-NADH
-
350% of the activity with NAD+
-
-
?
L-phenylalanine + H2O + 3-pyridinealdehyde-NAD+
phenylpyruvate + NH3 + 3-pyridinealdehyde-NADH
-
at 9.2% of the activity with NAD+
-
?
L-phenylalanine + H2O + 3-pyridinealdehyde-NAD+
phenylpyruvate + NH3 + 3-pyridinealdehyde-NADH
-
55% of the activity with NAD+
-
-
?
L-phenylalanine + H2O + deamino-NAD+
phenylpyruvate + NH3 + deamino-NADH
-
at 86% of the activity with NAD+
-
?
L-phenylalanine + H2O + deamino-NAD+
phenylpyruvate + NH3 + deamino-NADH
-
at 86% of the activity with NAD+
-
?
L-phenylalanine + H2O + NAD+
phenylpyruvate + NH3 + NADH
-
-
-
-
r
L-phenylalanine + H2O + NAD+
phenylpyruvate + NH3 + NADH + H+
-
-
-
?
L-phenylalanine + H2O + NAD+
phenylpyruvate + NH3 + NADH + H+
-
-
-
?
L-phenylalanine + H2O + NAD+
phenylpyruvate + NH3 + NADH + H+
Halalkalibacterium halodurans
-
-
-
?
L-phenylalanine + H2O + NAD+
phenylpyruvate + NH3 + NADH + H+
Halalkalibacterium halodurans DSM 18197
-
-
-
?
L-phenylalanine + H2O + NAD+
phenylpyruvate + NH3 + NADH + H+
-
-
-
-
?
L-phenylalanine + H2O + NAD+
phenylpyruvate + NH3 + NADH + H+
-
-
-
?
L-phenylalanine + H2O + NADP+
phenylpyruvate + NH3 + NADPH
-
at 6.6% of the activity with NAD+
-
?
L-phenylalanine + H2O + NADP+
phenylpyruvate + NH3 + NADPH
-
at 6.6% of the activity with NAD+
-
?
L-phenylalanine + H2O + thionicotinamide-NAD+
phenylpyruvate + NH3 + thionicotinamide-NADH
-
at 101% of the activity with NAD+
-
?
L-phenylalanine + H2O + thionicotinamide-NAD+
phenylpyruvate + NH3 + thionicotinamide-NADH
-
at 101% of the activity with NAD+
-
?
L-phenylalanine methyl ester + H2O + NAD+
phenylpyruvic acid methyl ester + NH3 + NADH
-
38% of the activity with L-Phe
-
-
?
L-phenylalanine methyl ester + H2O + NAD+
phenylpyruvic acid methyl ester + NH3 + NADH
-
-
-
-
?
L-Trp + H2O + NAD+
indole-3-pyruvate + NH3 + NADH
-
4% of the activity with L-Phe
-
-
?
L-Trp + H2O + NAD+
indole-3-pyruvate + NH3 + NADH
-
7.5% of the activity with L-Phe
-
-
?
L-Trp + H2O + NAD+
indole-3-pyruvate + NH3 + NADH
-
2% of the activity with L-Phe
-
-
?
L-Trp + H2O + NAD+
indole-3-pyruvate + NH3 + NADH
-
2% of the activity with L-Phe
-
-
?
L-Tyr + H2O + NAD+
4-hydroxyphenylpyruvate + NH3 + NADH
-
9.0% of the activity with L-Phe
-
-
?