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Information on EC 4.1.2.45 - trans-o-hydroxybenzylidenepyruvate hydratase-aldolase
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4.1.2.45 trans-o-hydroxybenzylidenepyruvate hydratase-aldolaseIUBMB Comments
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 .
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Word Map
- 4.1.2.45
- naphthalene
- salicylaldehyde
- salicylate
- dioxygenase
-
naphthalenesulfonates
- fluorescens
- putida
- benzaldehyde
- sphingomonas
- 1,2-dihydroxynaphthalene
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
trans-o-hydroxybenzylidenepyruvate hydratase-aldolase, 2'-hydroxybenzalpyruvate aldolase, thbp-ha, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2'-hydroxybenzalpyruvate aldolase
fHBP HA A
fHBP HA B
nsaE
tHBP-HA
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O = salicylaldehyde + pyruvate
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
aldol condensation
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PATHWAY SOURCE
PATHWAYS
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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].
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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
1-hydroxy-2-naphthaldehyde + pyruvate
(3E)-4-(1-hydroxynaphthalen-2-yl)-2-oxobut-3-enoate + H2O
-
-
-
?
1-methylindole-3-carboxaldehyde + pyruvate
(3E)-4-(1-methyl-1H-indol-3-yl)-2-oxobut-3-enoate + H2O
-
-
-
?
1-naphthaldehyde + pyruvate
(3E)-4-naphthalen-1-yl-2-oxobut-3-enoate + H2O
-
-
-
?
2,3-dihydroxybenzaldehyde + pyruvate
(3E)-4-(2,3-dihydroxyphenyl)-2-oxobut-3-enoate + H2O
-
-
-
?
2-carboxybenzaldehyde + pyruvate
(3E)-4-(2-carboxyphenyl)-2-oxobut-3-enoate + H2O
-
-
-
?
2-chlorobenzaldehyde + pyruvate
(3E)-4-(2-chlorophenyl)-2-oxobut-3-enoate + H2O
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
-
-
?
2-formylbenzenesulfonate + pyruvate
(3E)-2-oxo-4-(2-sulfophenyl)but-3-enoate + H2O
-
-
-
?
2-furaldehyde + pyruvate
(3E)-4-furan-2-yl-2-oxobut-3-enoate + H2O
-
-
-
?
2-hydroxy-1-naphthaldehyde + pyruvate
(3E)-4-(2-hydroxynaphthalen-1-yl)-2-oxobut-3-enoate + H2O
-
-
-
?
2-hydroxy-5-nitrobenzaldehyde + pyruvate
(3E)-4-(2-hydroxy-5-nitrophenyl)-2-oxobut-3-enoate + H2O
-
-
-
?
2-methoxybenzaldehyde + pyruvate
(3E)-4-(2-methoxyphenyl)-2-oxobut-3-enoate + H2O
i.e. o-anisaldehyde
-
-
?
2-naphthaldehyde + pyruvate
(3E)-4-naphthalen-2-yl-2-oxobut-3-enoate + H2O
-
-
-
?
2-nitrobenzaldehyde + pyruvate
(3E)-4-(2-nitrophenyl)-2-oxobut-3-enoate + H2O
-
-
-
?
2-pyridinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-pyridin-2-ylbut-3-enoate + H2O
-
-
-
?
2-quinolinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-quinolin-2-ylbut-3-enoate + H2O
-
-
-
?
2-thiophenecarboxaldehyde + pyruvate
(3E)-2-oxo-4-thiophen-2-ylbut-3-enoate + H2O
-
-
-
?
3-furaldehyde + pyruvate
(3E)-4-furan-3-yl-2-oxobut-3-enoate + H2O
-
-
-
?
3-hydroxybenzaldehyde + pyruvate
(3E)-4-(3-hydroxyphenyl)-2-oxobut-3-enoate + H2O
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
-
-
r
3-methoxysalicylaldehyde + pyruvate
(3E)-4-(2-hydroxy-3-methoxyphenyl)-2-oxobut-3-enoate + H2O
i.e o-vanillin
-
-
?
3-pyridinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-pyridin-3-ylbut-3-enoate + H2O
-
-
-
?
3-quinolinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-quinolin-3-ylbut-3-enoate + H2O
-
-
-
?
3-thiophenecarboxaldehyde + pyruvate
(3E)-2-oxo-4-thiophen-3-ylbut-3-enoate + H2O
-
-
-
?
4-biphenylcarboxaldehyde + pyruvate
(3E)-4-biphenyl-4-yl-2-oxobut-3-enoate + H2O
-
-
-
?
4-hydroxybenzaldehyde + pyruvate
(3E)-4-(4-hydroxyphenyl)-2-oxobut-3-enoate + H2O
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
-
-
?
4-isopropylbenzaldehyde + pyruvate
(3E)-4-[4-(1-methylethyl)phenyl]-2-oxobut-3-enoate + H2O
-
-
-
?
4-nitrobenzaldehyde + pyruvate
4-(4-nitrophenyl)-2-oxobut-3-enoate + H2O
-
-
-
-
?
4-quinolinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-quinolin-4-ylbut-3-enoate + H2O
-
-
-
?
benzylidenepyruvate + H2O
benzaldehyde + pyruvate
-
with 1% of the activity found with (E)-2'-hydroxybenzylidinepyruvate
-
-
?
cinnamaldehyde + pyruvate
(3E,5E)-2-oxo-6-phenylhexa-3,5-dienoic acid + H2O
-
-
-
-
?
crotonaldehyde + pyruvate
(3E,5E)-2-oxohepta-3,5-dienoate + H2O
-
-
-
?
cyclohexanecarboxaldehyde + pyruvate
(3E)-4-cyclohexyl-2-oxobut-3-enoate + H2O
-
-
-
?
indole-3-carboxaldehyde + pyruvate
(3E)-4-(1H-indol-3-yl)-2-oxobut-3-enoate + H2O
-
-
-
?
o-tolualdehyde + pyruvate
(3E)-4-(2-methylphenyl)-2-oxobut-3-enoate + H2O
-
-
-
?
p-tolualdehyde + pyruvate
(3E)-4-(4-methylphenyl)-2-oxobut-3-enoate + H2O
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
-
-
?
phenanthrene-9-carboxaldehyde + pyruvate
(3E)-2-oxo-4-phenanthren-9-ylbut-3-enoate + H2O
-
-
-
?
phenylacetaldehyde + pyruvate
5-benzyl-3-hydroxyfuran-2(5H)-one + H2O
-
-
-
-
?
salicylaldehyde + pyruvate
trans-o-hydroxybenzylidenepyruvate + H2O
-
-
-
-
?
terephthalaldehyde + pyruvate
4-(4-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)benzaldehyde + H2O
-
-
25% of products
-
?
(3E)-4-(2,4-dihydroxyphenyl)-2-oxobut-3-enoate + H2O
2,4-dihydroxybenzaldehyde + pyruvate
-
-
-
-
?
(3E)-4-(2,4-dihydroxyphenyl)-2-oxobut-3-enoate + H2O
2,4-dihydroxybenzaldehyde + pyruvate
-
-
-
-
?
(3E)-4-(2,6-dihydroxyphenyl)-2-oxobut-3-enoate + H2O
2,6-dihydroxybenzaldehyde + pyruvate
-
-
-
-
?
(3E)-4-(2,6-dihydroxyphenyl)-2-oxobut-3-enoate + H2O
2,6-dihydroxybenzaldehyde + pyruvate
-
-
-
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
-
-
-
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
Celeribacter indicus P73T
-
-
-
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
i.e. 2'-hydroxybenzylidinepyruvate, i.e. 2'-hydroxybenzalpyruvate, i.e. trans-O-hydroxybenzylidenepyruvate
-
-
r
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
-
this reaction is part of the degradative pathways for naphthalene and naphthalenesulfonates by bacteria
-
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
-
i.e. 2'-hydroxybenzylidinepyruvate, i.e. 2'-hydroxybenzalpyruvate, i.e. trans-O-hydroxybenzylidenepyruvate, intermediate formation of a stable Schiff base between enzyme and substrate
salicylaldehyde i.e. 2-hydroxybenzaldehyde
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
-
this reaction is part of the degradative pathways for naphthalene and naphthalenesulfonates by bacteria
-
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
-
i.e. 2'-hydroxybenzylidinepyruvate, i.e. 2'-hydroxybenzalpyruvate, i.e. trans-O-hydroxybenzylidenepyruvate, intermediate formation of a stable Schiff base between enzyme and substrate
salicylaldehyde i.e. 2-hydroxybenzaldehyde
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
-
i.e. 2'-hydroxybenzylidinepyruvate, i.e. 2'-hydroxybenzalpyruvate
-
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
-
i.e. 2'-hydroxybenzylidinepyruvate, i.e. 2'-hydroxybenzalpyruvate
-
-
?
(E)-2'-hydroxybenzylidenepyruvate + H2O
salicylaldehyde + pyruvate
-
involved in metabolism of naphthalene to salicylate
-
-
?
(E)-2'-hydroxybenzylidenepyruvate + H2O
salicylaldehyde + pyruvate
-
involved in metabolism of naphthalene to salicylate
-
-
?
(E)-2'-hydroxybenzylidenepyruvate + O2
salicylaldehyde + pyruvate
the equilibrium in this reaction favors cleavage
-
-
r
(E)-2'-hydroxybenzylidenepyruvate + O2
salicylaldehyde + pyruvate
-
naphthalene metabolism
-
-
?
2-nitrobenzaldehyde + pyruvate
4-(2-nitrophenyl)-2-oxobut-3-enoate + H2O
-
-
-
-
?
2-nitrobenzaldehyde + pyruvate
4-(2-nitrophenyl)-2-oxobut-3-enoate + H2O
-
-
-
-
?
3-phenylpropionaldehyde + pyruvate
3-hydroxy-5-(2-phenylethyl)furan-2(5H)-one + H2O
-
-
-
-
?
3-phenylpropionaldehyde + pyruvate
3-hydroxy-5-(2-phenylethyl)furan-2(5H)-one + H2O
-
-
-
-
?
benzaldehyde + pyruvate
benzylidenepyruvate + H2O
the product benzylidenepyruvate is not a substrate in the reverse direction
-
-
ir
phthalaldehyde + pyruvate
(3E)-4-(2-formylphenyl)-2-oxobut-3-enoate + H2O
-
-
-
-
?
phthalaldehyde + pyruvate
(3E)-4-(2-formylphenyl)-2-oxobut-3-enoate + H2O
-
-
-
-
?
phthalaldehyde + pyruvate
(3E)-4-(2-formylphenyl)-2-oxobut-3-enoate + H2O
-
-
-
?
salicylaldehyde + pyruvate
trans-o-hydroxybenzylidenepyruvate
-
-
-
-
?
salicylaldehyde + pyruvate
trans-o-hydroxybenzylidenepyruvate
-
-
-
-
?
additional information
?
-
-
enzmye is strictly dependent on pyruvate as donor component. The structure of the products is highly dependent on the electronic characteristics of the aldehyde, and the formation of the furan derivatives is spontaneous during the work up procedure. No donors are: ethyl and methyl pyruvate, 2-oxobutanoic acid, acetyl acetone, and butane-2,3-dione. No acceptor components are: n-octanal, pivalaldehyde, and benzylideneacetone
-
-
?
additional information
?
-
-
enzmye is strictly dependent on pyruvate as donor component. The structure of the products is highly dependent on the electronic characteristics of the aldehyde, and the formation of the furan derivatives is spontaneous during the work up procedure. No donors are: ethyl and methyl pyruvate, 2-oxobutanoic acid, acetyl acetone, and butane-2,3-dione. No acceptor components are: n-octanal, pivalaldehyde, and benzylideneacetone
-
-
?
additional information
?
-
no activity with trans-benzylidenepyruvate, trans-o-methoxybenzylidenepyruvate or trans-o-hydroxycinnamate. The hydratase-aldolase catalyzes the condensation of pyruvate with several other aromatic aldehydes, including benzaldehyde, to give trans-benzylidenepyruvate. Since benzylidenepyruvate is not a substrate for the enzyme, the reaction is irreversible and can be carried out to completion by using relatively low concentrations of the substrates, benzaldehyde and pyruvate
-
-
?
additional information
?
-
the enzyme catalyzes a reversible reaction in vitro (the reverse reaction being an aldol-condensation). It accepts a broad range of aldehydes and 4-substituted 2-keto-but-3-enoates as substrates. Acetophenone, 2'-hydroxyacetophenone, phenylacetaldehyde, and trans-cinnamaldehyde are not substrates
-
-
?
additional information
?
-
-
no activity with: benzylideneacetone and cinnamic acid
-
-
?
additional information
?
-
-
no activity with: benzylideneacetone and cinnamic acid
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
(E)-2'-hydroxybenzylidenepyruvate + O2
salicylaldehyde + pyruvate
-
naphthalene metabolism
-
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
-
-
-
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
Celeribacter indicus P73T
-
-
-
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
-
this reaction is part of the degradative pathways for naphthalene and naphthalenesulfonates by bacteria
-
-
?
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
-
this reaction is part of the degradative pathways for naphthalene and naphthalenesulfonates by bacteria
-
-
?
(E)-2'-hydroxybenzylidenepyruvate + H2O
salicylaldehyde + pyruvate
-
involved in metabolism of naphthalene to salicylate
-
-
?
(E)-2'-hydroxybenzylidenepyruvate + H2O
salicylaldehyde + pyruvate
-
involved in metabolism of naphthalene to salicylate
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NEM
-
1 mM, 30 min, 25°C, 35% inhibition of fHBP HA B, more than 85% of the initial activity of fHBP HA A remains
p-chloromercuribenzoate
-
enzyme is partially reactivated by addition of dithiothreitol
PCMB
-
1 mM, 30 min, 25°C, complete inhibition of fHBP HA B, more than 85% of the initial activity of fHBP HA A remains
additional information
-
no inhibition: benzylideneacetone, cinnamic acid
-
additional information
-
no inhibition: monoiodoacetic acid, N-ethylmaleimide, PCMB, diisopropyl fluorophosphate, phenylmethanesulfonyl fluoride, EDTA, NaN3, KCN, o-phenanthroline, 2,2'-bipyridine, Fe2+, Fe3+, Mg2+, Mn2+, Co2+, Ca2+, Zn2+, Cd2+, Cu2+, Ni2+, EDTA, o-phenanthroline, 2'-bipyridine, KCN
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.003
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate
-
30°C, pH 8.1, enzyme form fHBP HA A
0.009
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate
-
30°C, pH 8.1, enzyme form fHBP HA B
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5 - 8
-
the activity is independent of pH between pH 5.5 and 8.0, but above pH 8.0 activity declines rapidly
6 - 9
-
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
-
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
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
expressed in Escherichia coli JM109, that carries the tHBPA hydratase-aldolase-encoding plasmid pRE701
SwissProt
brenda
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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). A0A840CIC4_9RHOB
331
0
36160
TrEMBL
-
A0A645D266_9ZZZZ
345
0
38181
TrEMBL
other Location (Reliability: 5)
A0A0J5Q5D8_9RHOB
331
0
36558
TrEMBL
-
A0A1V6C3X5_9BACT
319
0
36296
TrEMBL
-
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
trimer
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7
-
the enzyme was very stable in buffer at pH 7, stored either at 0°C or frozen
696061
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30 - 40
-
after 30 min incubation, the decreases of the activity are 64% at 40°C and 24% at 35°C, while at 30°C, the activity remains unchanged. However, at 30°C, the decreases of the activity are 24% after 5 h and 54% after 24 h
50
-
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
-
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
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
-16°C, 4°C or 20°C, 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
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