Information on EC 4.1.2.45 - trans-o-hydroxybenzylidenepyruvate hydratase-aldolase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
4.1.2.45
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RECOMMENDED NAME
GeneOntology No.
trans-o-hydroxybenzylidenepyruvate hydratase-aldolase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O = salicylaldehyde + pyruvate
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
aldol condensation
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Metabolic pathways
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Microbial metabolism in diverse environments
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Naphthalene degradation
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naphthalene degradation (aerobic)
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SYSTEMATIC NAME
IUBMB Comments
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate hydro-lyase
This enzyme is involved in naphthalene degradation. The enzyme catalyses a retro-aldol reaction in vitro, and it accepts a broad range of aldehydes and 4-substituted 2-oxobut-3-enoates as substrates [4].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
strain TA-2, formerly Pseudomonas sp. TA-2
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Manually annotated by BRENDA team
strain TA-2, formerly Pseudomonas sp. TA-2
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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
(3E)-4-(2,4-dihydroxyphenyl)-2-oxobut-3-enoate + H2O
2,4-dihydroxybenzaldehyde + pyruvate
show the reaction diagram
(3E)-4-(2,6-dihydroxyphenyl)-2-oxobut-3-enoate + H2O
2,6-dihydroxybenzaldehyde + pyruvate
show the reaction diagram
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
show the reaction diagram
(E)-2'-hydroxybenzylidenepyruvate + H2O
salicylaldehyde + pyruvate
show the reaction diagram
(E)-2'-hydroxybenzylidenepyruvate + O2
salicylaldehyde + pyruvate
show the reaction diagram
1-hydroxy-2-naphthaldehyde + pyruvate
(3E)-4-(1-hydroxynaphthalen-2-yl)-2-oxobut-3-enoate + H2O
show the reaction diagram
-
-
-
?
1-methylindole-3-carboxaldehyde + pyruvate
(3E)-4-(1-methyl-1H-indol-3-yl)-2-oxobut-3-enoate + H2O
show the reaction diagram
-
-
-
?
1-naphthaldehyde + pyruvate
(3E)-4-naphthalen-1-yl-2-oxobut-3-enoate + H2O
show the reaction diagram
-
-
-
?
2,3-dihydroxybenzaldehyde + pyruvate
(3E)-4-(2,3-dihydroxyphenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
-
-
-
?
2-carboxybenzaldehyde + pyruvate
(3E)-4-(2-carboxyphenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
-
-
-
?
2-chlorobenzaldehyde + pyruvate
(3E)-4-(2-chlorophenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
in the reverse reaction (3E)-4-(2-chlorophenyl)-2-oxobut-3-enoate is cleaved at 1.6% the rate of (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate
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-
?
2-formylbenzenesulfonate + pyruvate
(3E)-2-oxo-4-(2-sulfophenyl)but-3-enoate + H2O
show the reaction diagram
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-
-
?
2-furaldehyde + pyruvate
(3E)-4-furan-2-yl-2-oxobut-3-enoate + H2O
show the reaction diagram
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-
-
?
2-hydroxy-1-naphthaldehyde + pyruvate
(3E)-4-(2-hydroxynaphthalen-1-yl)-2-oxobut-3-enoate + H2O
show the reaction diagram
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-
-
?
2-hydroxy-5-nitrobenzaldehyde + pyruvate
(3E)-4-(2-hydroxy-5-nitrophenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
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-
-
?
2-methoxybenzaldehyde + pyruvate
(3E)-4-(2-methoxyphenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
i.e. o-anisaldehyde
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2-naphthaldehyde + pyruvate
(3E)-4-naphthalen-2-yl-2-oxobut-3-enoate + H2O
show the reaction diagram
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-
-
?
2-nitrobenzaldehyde + pyruvate
(3E)-4-(2-nitrophenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
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-
-
?
2-nitrobenzaldehyde + pyruvate
4-(2-nitrophenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
2-pyridinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-pyridin-2-ylbut-3-enoate + H2O
show the reaction diagram
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-
-
?
2-quinolinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-quinolin-2-ylbut-3-enoate + H2O
show the reaction diagram
-
-
-
?
2-thiophenecarboxaldehyde + pyruvate
(3E)-2-oxo-4-thiophen-2-ylbut-3-enoate + H2O
show the reaction diagram
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-
-
?
3-furaldehyde + pyruvate
(3E)-4-furan-3-yl-2-oxobut-3-enoate + H2O
show the reaction diagram
-
-
-
?
3-hydroxybenzaldehyde + pyruvate
(3E)-4-(3-hydroxyphenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
in the reverse reaction (3E)-4-(3-hydroxyphenyl)-2-oxobut-3-enoate is cleaved at 75% the rate of (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate
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r
3-methoxysalicylaldehyde + pyruvate
(3E)-4-(2-hydroxy-3-methoxyphenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
i.e o-vanillin
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-
?
3-phenylpropionaldehyde + pyruvate
3-hydroxy-5-(2-phenylethyl)furan-2(5H)-one + H2O
show the reaction diagram
3-pyridinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-pyridin-3-ylbut-3-enoate + H2O
show the reaction diagram
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-
?
3-quinolinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-quinolin-3-ylbut-3-enoate + H2O
show the reaction diagram
-
-
-
?
3-thiophenecarboxaldehyde + pyruvate
(3E)-2-oxo-4-thiophen-3-ylbut-3-enoate + H2O
show the reaction diagram
-
-
-
?
4-biphenylcarboxaldehyde + pyruvate
(3E)-4-biphenyl-4-yl-2-oxobut-3-enoate + H2O
show the reaction diagram
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-
-
?
4-hydroxybenzaldehyde + pyruvate
(3E)-4-(4-hydroxyphenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
in the reverse reaction (3E)-4-(4-hydroxyphenyl)-2-oxobut-3-enoate is cleaved at less than 1% the rate of (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate
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?
4-isopropylbenzaldehyde + pyruvate
(3E)-4-[4-(1-methylethyl)phenyl]-2-oxobut-3-enoate + H2O
show the reaction diagram
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-
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?
4-nitrobenzaldehyde + pyruvate
4-(4-nitrophenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
-
-
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?
4-quinolinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-quinolin-4-ylbut-3-enoate + H2O
show the reaction diagram
-
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-
?
benzaldehyde + pyruvate
benzylidenepyruvate + H2O
show the reaction diagram
benzaldehyde + pyruvate
trans-benzylidenepyruvate
show the reaction diagram
benzylidenepyruvate + H2O
benzaldehyde + pyruvate
show the reaction diagram
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with 1% of the activity found with (E)-2'-hydroxybenzylidinepyruvate
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?
cinnamaldehyde + pyruvate
(3E,5E)-2-oxo-6-phenylhexa-3,5-dienoic acid + H2O
show the reaction diagram
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?
crotonaldehyde + pyruvate
(3E,5E)-2-oxohepta-3,5-dienoate + H2O
show the reaction diagram
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?
cyclohexanecarboxaldehyde + pyruvate
(3E)-4-cyclohexyl-2-oxobut-3-enoate + H2O
show the reaction diagram
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?
indole-3-carboxaldehyde + pyruvate
(3E)-4-(1H-indol-3-yl)-2-oxobut-3-enoate + H2O
show the reaction diagram
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?
o-tolualdehyde + pyruvate
(3E)-4-(2-methylphenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
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?
p-tolualdehyde + pyruvate
(3E)-4-(4-methylphenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
in the reverse reaction (3E)-4-(4-methylphenyl)-2-oxobut-3-enoate is cleaved at less than 1% the rate of (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate
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?
phenanthrene-9-carboxaldehyde + pyruvate
(3E)-2-oxo-4-phenanthren-9-ylbut-3-enoate + H2O
show the reaction diagram
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?
phenylacetaldehyde + pyruvate
5-benzyl-3-hydroxyfuran-2(5H)-one + H2O
show the reaction diagram
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?
phthalaldehyde + pyruvate
(3E)-4-(2-formylphenyl)-2-oxobut-3-enoate + H2O
show the reaction diagram
salicylaldehyde + pyruvate
trans-o-hydroxybenzylidenepyruvate
show the reaction diagram
salicylaldehyde + pyruvate
trans-o-hydroxybenzylidenepyruvate + H2O
show the reaction diagram
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?
terephthalaldehyde + pyruvate
4-(4-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)benzaldehyde + H2O
show the reaction diagram
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25% of products
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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
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
show the reaction diagram
(E)-2'-hydroxybenzylidenepyruvate + H2O
salicylaldehyde + pyruvate
show the reaction diagram
(E)-2'-hydroxybenzylidenepyruvate + O2
salicylaldehyde + pyruvate
show the reaction diagram
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naphthalene metabolism
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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no cofactor required
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
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Hg2+
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1 mM, 40% inhibition of fHBP HA B
NEM
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1 mM, 30 min, 25C, 35% inhibition of fHBP HA B, more than 85% of the initial activity of fHBP HA A remains
p-chloromercuribenzoate
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enzyme is partially reactivated by addition of dithiothreitol
PCMB
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1 mM, 30 min, 25C, complete inhibition of fHBP HA B, more than 85% of the initial activity of fHBP HA A remains
Salicylaldehyde
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sodium borhydride
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additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.015
(3E)-4-(2,4-dihydroxyphenyl)-2-oxobut-3-enoate
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pH 7.0
0.006
(3E)-4-(2,6-dihydroxyphenyl)-2-oxobut-3-enoate
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pH 7.0
0.003 - 0.017
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate
8.98
benzaldehyde
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at pH 7.0, 30C
0.4
benzylidenepyruvate
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pH 7.0
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3.58
Salicylaldehyde
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at pH 7.0, 30C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.013
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
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pH 7.0
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
1.55
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recombinant enzyme
7.7
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enzyme form fHBP HA B
11
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enzyme form fHBP HA A
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8
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in Tris/HCl or Na/K-phosphate buffer
9
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enzyme form fHBP HA A and enzyme form fHBP HA B
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 8
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the activity is independent of pH between pH 5.5 and 8.0, but above pH 8.0 activity declines rapidly
6 - 9
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more than 80% of the maximal activity at pH 6.0 and pH 9.0, pH 5.0: 18% of maximal activity, pH 10.0: 14% of maximal activity
6 - 9.5
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pH 6: about 60% of maximal activity, pH 9.5: about 80% of maximal activity, enzyme form fHBP HA A and enzyme form fHBP HA B
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
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at a fixed pH of 7.0
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.3
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enzyme form fHBP HA B, isoelectric focusing
4.8
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enzyme form fHBP HA A, isoelectric focusing
5.4
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calculated from sequence
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
36640
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x * 36640, calculated from sequence
37200
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3 * 37200, enzyme form fHBP HA B, SDS-PAGE
37600
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3 * 37600, enzyme form fHBP HA A, SDS-PAGE
38000
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x * 38000, His-tagged recombinant enzyme, SDS-PAGE
38500
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3 * 38500, SDS-PAGE
104000
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enzyme form fHBP HA B, ultracentrifugation
116000
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enzyme form fHBP HA A, ultracentrifugation
120000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
trimer
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 9.3
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4C, 20 h, enzyme form fHBP HA A is stable
698644
7
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the enzyme was very stable in buffer at pH 7, stored either at 0C or frozen
696061
7.1 - 10.7
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4C, 20 h, enzyme form fHBP HA B is stable
698644
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 40
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after 30 min incubation, the decreases of the activity are 64% at 40C and 24% at 35C, while at 30C, the activity remains unchanged. However, at 30C, the decreases of the activity are 24% after 5 h and 54% after 24 h
50
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pH 7.3, 20 mM Tris-HCl buffer, 5 min, enzyme form fHBP HA A and enzyme form fHBP HA B, stable up to
65
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pH 7.3, 20 mM Tris-HCl buffer, 5 min, enzyme form fHBP HA A and enzyme form fHBP HA B, 80% loss of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
-16C, 4C or 20C, the enzyme is very stable in cell free extracts, after a 1-week incubation (protein concentration: 2.6 mg/ml) in Na/K-phosphate buffer (pH 7.3, 50 mM) the initial enzyme activity is completely recovered
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Co2+ Talon metal affinity resin column chromatography
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presence of at least three trans-o-hydroxybenzylidenepyruvate hydratase-aldolases, purification of two typical trans-o-hydroxybenzylidenepyruvate hydratase-aldolases (fHBP HA A and fHBP HA B)
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a gene cluster is identified on the plasmid pBN6 which codes for several enzymes participating in the degradative pathway for naphthalenesulfonates. A DNA fragment of 16915 bp is sequenced which contains 17 ORFs. The genes encoding the 1,2-dihydroxynaphthalene dioxygenase, 2-hydroxychromene-2-carboxylate isomerase, and 2'-hydroxybenzalpyruvate aldolase of the naphthalenesulfonate pathway are identified on the DNA fragment and the encoded proteins are heterologously expressed in Escherichia coli
expressed in Escherichia coli JM109 (pVLT33-ALD) and M15 (pREP4) cells
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expression in Escherichia coli
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