Information on EC 2.6.1.18 - beta-alanine-pyruvate transaminase

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

EC NUMBER
COMMENTARY hide
2.6.1.18
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RECOMMENDED NAME
GeneOntology No.
beta-alanine-pyruvate transaminase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-alanine + 3-oxopropanoate = pyruvate + beta-alanine
show the reaction diagram
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-
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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
beta-alanine biosynthesis II
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beta-alanine degradation II
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alanine metabolism
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Valine, leucine and isoleucine degradation
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beta-Alanine metabolism
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Propanoate metabolism
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
L-alanine:3-oxopropanoate aminotransferase
A pyridoxal-phosphate protein.
CAS REGISTRY NUMBER
COMMENTARY hide
9030-47-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain Y2k-2, gene aptA
SwissProt
Manually annotated by BRENDA team
enantioselectivity of the omega-TA from Aspergillus terreus is opposite to that from Ochrobactrum anthropi
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-
Manually annotated by BRENDA team
K-22
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Manually annotated by BRENDA team
K-22
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-
Manually annotated by BRENDA team
ATCC 25416
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
wax bean, var. Kinghorn
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Manually annotated by BRENDA team
ATCC 11250
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain JS17
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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
(R,S)-1,2-dimethylpropylamine + pyruvate
3-methyl-2-oxobutane + alanine
show the reaction diagram
(R,S)-1,5-dimethylhexylamine + pyruvate
6-methyl-2-oxoheptane + alanine
show the reaction diagram
(R,S)-2-aminoheptane + pyruvate
2-oxoheptane + alanine
show the reaction diagram
(R,S)-sec-butylamine + pyruvate
? + alanine
show the reaction diagram
7.3% of activity with L-beta-amino-n-butyric acid
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-
?
(S)-alpha-methylbenzylamine + pyruvate
acetophenone + alanine
show the reaction diagram
(S)-alpha-methylbenzylamine + pyruvate
acetophenone + L-alanine
show the reaction diagram
1-phenylethanamine + 2-oxobutyrate
acetophenone + D-homoalanine
show the reaction diagram
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enantioselectivity of the omega-TA from Aspergillus terreus is opposite to that from Ochrobactrum anthropi, D-homoalanine of more than 99% enantiomeric excess is formed in this coupled reaction
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-
?
1-phenylethanamine + 2-oxobutyrate
acetophenone + L-homoalanine
show the reaction diagram
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-
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?
1-phenylethanamine + propanal
?
show the reaction diagram
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94% relative activity toward propanal compared to pyruvate. Propanal is an inefficient amino acceptor for the kinetic resolution: Enantiomeric excess of (R)-alpha-methylbenzylamine reaches more than 99% with pyruvate at 3 h, whereas enantiomeric excess is only 57% with propanal even after the reaction for 24 h
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-
?
1-phenylethanamine + pyruvate
acetophenone + alanine
show the reaction diagram
1-phenylethylamine + pyruvate
acetophenone + L-alanine
show the reaction diagram
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-
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r
2-oxobutyrate + benzylamine
L-homoalanine + benzaldehyde
show the reaction diagram
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enzyme inhibition by benzaldehyde is the major hurdle in carrying out the omega-TA reaction efficiently. To overcome the product inhibition, a biphasic reaction system in which an organic solvent is employed to extract the inhibitory benzaldehyde from an aqueous system is used
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?
3-fluoropyruvate + (1S)-1-phenyl-ethanamine
(R)-3-fluoroalanine + acetophenone
show the reaction diagram
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to overcome the product inhibition by acetophenone, a biphasic reaction is used
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?
4-phenyl-2-butanone + isopropylamine
3-amino-1-phenylbutane + acetone
show the reaction diagram
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ir
beta-alanine + 2-oxobutanoate
malonic semialdehyde + 2-aminobutanoate
show the reaction diagram
beta-alanine + 2-oxohexanoate
malonic semialdehyde + L-norleucine
show the reaction diagram
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at 6% of the activity with pyruvate
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?
beta-alanine + 2-oxoisohexanoate
malonic semialdehyde + L-isoleucine
show the reaction diagram
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at 4% of the activity with pyruvate
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?
beta-alanine + 2-oxoisopentanoate
malonic semialdehyde + L-valine
show the reaction diagram
beta-alanine + 2-oxopentanoate
malonic semialdehyde + L-norvaline
show the reaction diagram
beta-alanine + acetoacetate
malonic semialdehyde + 3-aminobutanoate
show the reaction diagram
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at 4% of the activity with pyruvate
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?
beta-alanine + glyoxylic acid
malonic semialdehyde + glycine
show the reaction diagram
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at 17% of the activity with pyruvate
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?
beta-alanine + oxaloacetic acid
malonic semialdehyde + L-aspartate
show the reaction diagram
beta-alanine + pyruvate
malonic semialdehyde + L-alanine
show the reaction diagram
beta-alanine + pyruvate
oxaloacetate + alanine
show the reaction diagram
10% of activity with L-beta-amino-n-butyric acid
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?
butyraldehyde + (S)-alpha-methylbenzylamine
? + acetophenone
show the reaction diagram
118% of activity with pyruvate
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?
glyoxylate + (S)-alpha-methylbenzylamine
glycine + acetophenone
show the reaction diagram
13% of activity with pyruvate
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?
L-beta-amino-n-butyric acid + pyruvate
3-oxo-n-butyric acid + alanine
show the reaction diagram
L-beta-amino-n-butyric acid + pyruvate
3-oxobutyrate + alanine
show the reaction diagram
high activity, highly stereoselective enzyme
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?
L-beta-homoleucine + pyruvate
5-methyl-3-oxohexanoate + alanine
show the reaction diagram
2.6% of activity with L-beta-amino-n-butyric acid
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?
L-beta-leucine + pyruvate
4-methyl-3-oxopentanoate + alanine
show the reaction diagram
4.3% of activity with L-beta-amino-n-butyric acid
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?
L-erythrulose + pyruvate
2-amino-1,3,4-butanetriol + ?
show the reaction diagram
propion aldehyde + (S)-alpha-methylbenzylamine
? + acetophenone
show the reaction diagram
105% of activity with pyruvate
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?
pyruvate + (R,S)-1-benzylpyrrolidin-3-amine
L-alanine + (3R)-1-benzylpyrrolidin-3-amine + 1-benzylpyrrolidin-3-one
show the reaction diagram
pyruvate + (R,S)-phenyl 3-aminopyrrolidine-1-carboxylate
L-alanine + phenyl (3R)-3-aminopyrrolidine-1-carboxylate + phenyl 3-oxopyrrolidine-1-carboxylate
show the reaction diagram
pyruvate + (R,S)-piperidin-3-amine
L-alanine + (3R)-piperidin-3-amine + piperidin-3-one
show the reaction diagram
pyruvate + (R,S)-pyrrolidin-3-amine
L-alanine + (3R)-pyrrolidin-3-amine + pyrrolidin-3-one
show the reaction diagram
pyruvate + (R,S)-tert-butyl 3-aminopiperidine-1-carboxylate
L-alanine + tert-butyl (3R)-3-aminopiperidine-1-carboxylate + tert-butyl 3-oxopiperidine-1-carboxylate
show the reaction diagram
pyruvate + (R,S)-tert-butyl 3-aminopyrrolidine-1-carboxylate
L-alanine + tert-butyl (3R)-3-aminopyrrolidine-1-carboxylate + tert-butyl 3-oxopyrrolidine-1-carboxylate
show the reaction diagram
pyruvate + 2-aminoethylphosphonic acid
L-alanine + 2-oxoethylphosphonic acid
show the reaction diagram
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at 28% of the activity with beta-alanine
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?
pyruvate + 2-aminoisobutanoate
L-alanine + 2-oxo-3-methylpropanoate
show the reaction diagram
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at 4% of the activity with beta-alanine
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?
pyruvate + 4-aminobutanoate
L-alanine + succinic semialdehyde
show the reaction diagram
pyruvate + 5-aminopentanoate
L-alanine + 5-oxopentanoate
show the reaction diagram
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at 17% of the activity with beta-alanine
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?
pyruvate + 6-aminohexanoate
L-alanine + 6-oxohexanoate
show the reaction diagram
pyruvate + DL-3-aminoisobutanoate
L-alanine + 3-oxoisobutanoate
show the reaction diagram
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at 160% of the activity with beta-alanine
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?
pyruvate + glycine
L-alanine + glyoxylate
show the reaction diagram
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at 15% of the activity with beta-alanine
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?
pyruvate + L-2,4-diaminobutanoate
L-alanine + ?
show the reaction diagram
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at 4% of the activity with beta-alanine
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?
pyruvate + L-lysine
L-alanine + ?
show the reaction diagram
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at 7% of the activity with beta-alanine
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?
pyruvate + L-ornithine
L-alanine + ?
show the reaction diagram
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at 1% of the activity with beta-alanine
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?
pyruvate + propylamine
L-alanine + propanal
show the reaction diagram
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at 37% of the activity with beta-alanine
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?
pyruvate + taurine
L-alanine + 2-oxoethanesulfonic acid
show the reaction diagram
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at 8% of the activity with beta-alanine
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?
pyruvic aldehyde + (S)-alpha-methylbenzylamine
? + acetophenone
show the reaction diagram
5% of activity with pyruvate
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?
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
beta-alanine + pyruvate
malonic semialdehyde + L-alanine
show the reaction diagram
L-beta-amino-n-butyric acid + pyruvate
3-oxo-n-butyric acid + alanine
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxal 5'-phosphate
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(R)-1-phenylethanol
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is a poor inhibitor which reduces enzyme activity by 10% at 25 mM
3-amino-2,3-dihydrobenzoic acid
i.e. gabaculine, strong inhibition
acetophenone
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in the presence of 5 mM acetophenone, the reactivity of the enzyme towards F-pyruvate decreased by 78%
aminooxyacetic acid
strong inhibition
benzaldehyde
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cysteine
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0.5 mM, 14% inhibition
glutathione
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0.5 mM, 12% inhibition
hydroxylamine
strong inhibition
Monoiodoacetic acid
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0.5 mM, 24% inhibition
p-chloromercuribenzoate
additional information
-
no inhibition by D-glucose
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxamine 5'-phosphate
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shows 20% of pyridoxal 5'-phosphate activation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.1 - 14
beta-Alanine
56
L-beta-amino-n-butyric acid
recombinant enzyme
11 - 62
pyruvate
additional information
additional information
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
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specific activity of the purified enzyme is comparable to the purified native enzyme, pH 7, 37C
77.2
purified recombinant enzyme
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.2 - 7.4
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assay at
8
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assay at
8.5
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above pH 8.5, for reactions with the natural substrates beta-alanine and pyruvate
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 11
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approx. 35% of maximal activity at pH 7.0, approx. 50% of maximal activity at pH 11.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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assay at
33
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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carbon source succinate or glucose
Manually annotated by BRENDA team
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carbon source glucose, 10fold increase in beta-alanine-pyruvate tranasaminase activity compared to ammonium sulfate-grown cells
Manually annotated by BRENDA team
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expression increases with increasing dietary protein levels
Manually annotated by BRENDA team
additional information
-
no activity in brain
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Chromobacterium violaceum (strain ATCC 12472 / DSM 30191 / JCM 1249 / NBRC 12614 / NCIMB 9131 / NCTC 9757)
Chromobacterium violaceum (strain ATCC 12472 / DSM 30191 / JCM 1249 / NBRC 12614 / NCIMB 9131 / NCTC 9757)
Chromobacterium violaceum (strain ATCC 12472 / DSM 30191 / JCM 1249 / NBRC 12614 / NCIMB 9131 / NCTC 9757)
Chromobacterium violaceum (strain ATCC 12472 / DSM 30191 / JCM 1249 / NBRC 12614 / NCIMB 9131 / NCTC 9757)
Chromobacterium violaceum (strain ATCC 12472 / DSM 30191 / JCM 1249 / NBRC 12614 / NCIMB 9131 / NCTC 9757)
Chromobacterium violaceum (strain ATCC 12472 / DSM 30191 / JCM 1249 / NBRC 12614 / NCIMB 9131 / NCTC 9757)
Chromobacterium violaceum (strain ATCC 12472 / DSM 30191 / JCM 1249 / NBRC 12614 / NCIMB 9131 / NCTC 9757)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
100000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 50000, SDS-PAGE
tetramer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
diffraction to 1.7 A. Space group P1
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microbatch method using either 0.05 M HEPES pH 7.5, 5% (v/v) 2-propanol, 10%(w/v) PEG 4000 or 0.1 M lithium sulfate monohydrate, 0.05 M Tris-HCl pH 8.5, 15% (w/v) PEG 4000
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 10.5
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stable
636596
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
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the rate of the reaction with the purified enzyme in 100 mM potassium phosphate buffer, pH 7.0 with 2 mM pyridoxal phosphate cofactor at 25C slows markedly after 50 h with little further product formation up to 75 h
40
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stable up to
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
the rate of the reaction with the purified enzyme in 100 mM potassium phosphate buffer, pH 7.0 with 2 mM pyridoxal phosphate cofactor at 25C slows markedly after 50 h with little further product formation up to 75 h
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, several weeks, no loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
heat treatment, alumina C-gamma gel, protamine sulfate, ammonium sulfate
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K-22, partial purification
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nickel column chromatography
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nickel Sepharose Hi-Performance column chromatography and Superdex 200 Hiload 16/60 gel filtration
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recombinant His-tagged enzyme from Escherichia coli strain BL21
using an Ni-NTA affinity column
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using Ni-NTA chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
expressed in Escherichia coli as a His-tagged fusion protein
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expressed in Escherichia coli BL21gold(DE3) cells
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expressed in Escherichia coli strain BL21 Star (DE3) pLysS
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expression in Escherichia coli
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gene aptA, DNA and amino acid sequence determination and analysis, functional expression of the His-tagged enzyme in Escherichia coli strain BL21
overexpression of the enzyme in Escherichia coli strain BL21
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
synthesis
additional information
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