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Information on EC 4.1.2.45 - trans-o-hydroxybenzylidenepyruvate hydratase-aldolase and Organism(s) Pseudomonas putida and UniProt Accession Q51947
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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 taxonomic range for the selected organisms is: Pseudomonas putida
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
trans-o-hydroxybenzylidenepyruvate hydratase-aldolase, 2'-hydroxybenzalpyruvate aldolase, thbp-ha, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
PATHWAY SOURCE
PATHWAYS
-
-, -
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].
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
(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
(E)-2'-hydroxybenzylidenepyruvate + O2
salicylaldehyde + pyruvate
the equilibrium in this reaction favors cleavage
-
-
r
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-quinolinecarboxaldehyde + pyruvate
(3E)-2-oxo-4-quinolin-4-ylbut-3-enoate + H2O
-
-
-
?
benzaldehyde + pyruvate
benzylidenepyruvate + H2O
the product benzylidenepyruvate is not a substrate in the reverse direction
-
-
ir
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
-
-
-
?
phthalaldehyde + pyruvate
(3E)-4-(2-formylphenyl)-2-oxobut-3-enoate + H2O
-
-
-
?
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
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
expressed in Escherichia coli JM109, that carries the tHBPA hydratase-aldolase-encoding plasmid pRE701
SwissProt
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). PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Eaton, R.W.; Chapman, P.J.
Bacterial metabolism of naphthalene: Construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxynaphthalene and subsequent reactions
J. Bacteriol.
174
7542-7554
1992
Pseudomonas putida (Q51947)
Eaton, R.W.
trans-o-Hydroxybenzylidenepyruvate hydratase-aldolase as a biocatalyst
Appl. Environ. Microbiol.
66
2668-2672
2000
Pseudomonas putida (Q51947)
R. W., Eaton
Organization and evolution of naphthalene catabolic pathways: sequence of the DNA encoding 2-hydroxychromene-2-carboxylate isomerase and trans-o-hydroxybenzylidenepyruvate hydratase-aldolase from the NAH7 plasmid
J. Bacteriol.
176
7757-7762
1994
Pseudomonas putida (Q51947)
EXTERNAL LINKS (specific for EC-Number 4.1.2.45)
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