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Literature summary extracted from

  • Eaton, R.W.
    trans-o-Hydroxybenzylidenepyruvate hydratase-aldolase as a biocatalyst (2000), Appl. Environ. Microbiol., 66, 2668-2672.
    View publication on PubMedView publication on EuropePMC

Organism

EC Number Organism UniProt Comment Textmining
4.1.2.45 Pseudomonas putida Q51947 expressed in Escherichia coli JM109, that carries the tHBPA hydratase-aldolase-encoding plasmid pRE701
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Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.1.2.45 (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate + H2O i.e. 2'-hydroxybenzylidinepyruvate, i.e. 2'-hydroxybenzalpyruvate, i.e. trans-O-hydroxybenzylidenepyruvate Pseudomonas putida salicylaldehyde + pyruvate
-
 r
4.1.2.45 1-hydroxy-2-naphthaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-(1-hydroxynaphthalen-2-yl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 1-methylindole-3-carboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-(1-methyl-1H-indol-3-yl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 1-naphthaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-naphthalen-1-yl-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 2,3-dihydroxybenzaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-(2,3-dihydroxyphenyl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 2-carboxybenzaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-(2-carboxyphenyl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 2-chlorobenzaldehyde + pyruvate 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 Pseudomonas putida (3E)-4-(2-chlorophenyl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 2-formylbenzenesulfonate + pyruvate
-
 Pseudomonas putida (3E)-2-oxo-4-(2-sulfophenyl)but-3-enoate + H2O
-
 ?
4.1.2.45 2-furaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-furan-2-yl-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 2-hydroxy-1-naphthaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-(2-hydroxynaphthalen-1-yl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 2-hydroxy-5-nitrobenzaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-(2-hydroxy-5-nitrophenyl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 2-methoxybenzaldehyde + pyruvate i.e. o-anisaldehyde Pseudomonas putida (3E)-4-(2-methoxyphenyl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 2-naphthaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-naphthalen-2-yl-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 2-nitrobenzaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-(2-nitrophenyl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 2-pyridinecarboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-2-oxo-4-pyridin-2-ylbut-3-enoate + H2O
-
 ?
4.1.2.45 2-quinolinecarboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-2-oxo-4-quinolin-2-ylbut-3-enoate + H2O
-
 ?
4.1.2.45 2-thiophenecarboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-2-oxo-4-thiophen-2-ylbut-3-enoate + H2O
-
 ?
4.1.2.45 3-furaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-furan-3-yl-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 3-hydroxybenzaldehyde + pyruvate 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 Pseudomonas putida (3E)-4-(3-hydroxyphenyl)-2-oxobut-3-enoate + H2O
-
 r
4.1.2.45 3-methoxysalicylaldehyde + pyruvate i.e o-vanillin Pseudomonas putida (3E)-4-(2-hydroxy-3-methoxyphenyl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 3-pyridinecarboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-2-oxo-4-pyridin-3-ylbut-3-enoate + H2O
-
 ?
4.1.2.45 3-quinolinecarboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-2-oxo-4-quinolin-3-ylbut-3-enoate + H2O
-
 ?
4.1.2.45 3-thiophenecarboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-2-oxo-4-thiophen-3-ylbut-3-enoate + H2O
-
 ?
4.1.2.45 4-biphenylcarboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-biphenyl-4-yl-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 4-hydroxybenzaldehyde + pyruvate 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 Pseudomonas putida (3E)-4-(4-hydroxyphenyl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 4-isopropylbenzaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-[4-(1-methylethyl)phenyl]-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 4-quinolinecarboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-2-oxo-4-quinolin-4-ylbut-3-enoate + H2O
-
 ?
4.1.2.45 benzaldehyde + pyruvate the product benzylidenepyruvate is not a substrate in the reverse direction Pseudomonas putida benzylidenepyruvate + H2O
-
 ir
4.1.2.45 crotonaldehyde + pyruvate
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 Pseudomonas putida (3E,5E)-2-oxohepta-3,5-dienoate + H2O
-
 ?
4.1.2.45 cyclohexanecarboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-cyclohexyl-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 indole-3-carboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-(1H-indol-3-yl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 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 Pseudomonas putida ?
-
 ?
4.1.2.45 o-tolualdehyde + pyruvate
-
 Pseudomonas putida (3E)-4-(2-methylphenyl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 p-tolualdehyde + pyruvate 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 Pseudomonas putida (3E)-4-(4-methylphenyl)-2-oxobut-3-enoate + H2O
-
 ?
4.1.2.45 phenanthrene-9-carboxaldehyde + pyruvate
-
 Pseudomonas putida (3E)-2-oxo-4-phenanthren-9-ylbut-3-enoate + H2O
-
 ?
4.1.2.45 phthalaldehyde + pyruvate
-
 Pseudomonas putida (3E)-4-(2-formylphenyl)-2-oxobut-3-enoate + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.1.2.45 o-tHBPA hydratase-aldolase
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 Pseudomonas putida
4.1.2.45 tHBPA hydratase-aldolase
-
 Pseudomonas putida