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(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-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
(E)-2'-hydroxybenzylidenepyruvate + H2O
salicylaldehyde + pyruvate
(E)-2'-hydroxybenzylidenepyruvate + O2
salicylaldehyde + pyruvate
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-nitrobenzaldehyde + pyruvate
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-phenylpropionaldehyde + pyruvate
3-hydroxy-5-(2-phenylethyl)furan-2(5H)-one + H2O
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
-
-
-
?
benzaldehyde + pyruvate
benzylidenepyruvate + H2O
benzaldehyde + pyruvate
trans-benzylidenepyruvate
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
-
-
-
-
?
phthalaldehyde + pyruvate
(3E)-4-(2-formylphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
trans-o-hydroxybenzylidenepyruvate
salicylaldehyde + pyruvate
trans-o-hydroxybenzylidenepyruvate + H2O
-
-
-
-
?
terephthalaldehyde + pyruvate
4-(4-hydroxy-5-oxo-2,5-dihydrofuran-2-yl)benzaldehyde + H2O
-
-
25% of products
-
?
additional information
?
-
(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
-
-
-
-
?
(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
-
-
-
-
?
(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
-
-
-
-
?
benzaldehyde + pyruvate
benzylidenepyruvate + H2O
-
-
-
-
?
benzaldehyde + pyruvate
benzylidenepyruvate + H2O
the product benzylidenepyruvate is not a substrate in the reverse direction
-
-
ir
benzaldehyde + pyruvate
trans-benzylidenepyruvate
-
-
-
-
?
benzaldehyde + pyruvate
trans-benzylidenepyruvate
-
-
-
-
?
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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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)
brenda
Eaton, R.W.
trans-o-Hydroxybenzylidenepyruvate hydratase-aldolase as a biocatalyst
Appl. Environ. Microbiol.
66
2668-2672
2000
Pseudomonas putida (Q51947)
brenda
E.A. Barnsley
Naphthalene metabolism by pseudomonads: The oxidation of 1,2-dihydroxynaphthalene to 2-hydroxychromene-2-carboxylic acid and the formation of 2'-hydroxybenzalpyruvate
Biochem. Biophys. Res. Commun.
72
1116-1121
1976
Pseudomonas sp.
brenda
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)
brenda
Ohmoto, T.; Moriyoshi, K.; Sakai, K.; Hamada, N.; Ohe, T.
Presence of two trans-o-hydroxybenzylidenepyruvate hydratase-aldolases in naphthalenesulfonate-assimilating Sphingomonas paucimobilis TA-2: comparison of some properties
J. Biochem.
127
43-49
2000
Sphingomonas paucimobilis, Sphingomonas paucimobilis TA-2
brenda
Kuhm, A.E.; Knackmuss, H.J.; Stolz, A.
Purification and properties of 2'-hydroxybenzalpyruvate aldolase from a bacterium that degrades naphthalenesulfonates
J. Biol. Chem.
268
9484-9489
1993
Sphingobium xenophagum, Sphingobium xenophagum BN6
brenda
Stolz, A.
Degradation of substituted naphthalenesulfonic acids by Sphingomonas xenophaga BN6
J. Ind. Microbiol. Biotechnol.
23
391-399
1999
Sphingobium xenophagum, Sphingobium xenophagum BN6
brenda
Keck, A.; Conradt, D.; Mahler, A.; Stolz, A.; Mattes, R.; Klein, J.
Identification and functional analysis of the genes for naphthalenesulfonate catabolism by Sphingomonas xenophaga BN6
Microbiology
152
1929-1940
2006
Sphingobium xenophagum (Q9X9Q6), Sphingobium xenophagum, Sphingobium xenophagum BN6 (Q9X9Q6)
brenda
Ferrara, S.; Mapelli, E.; Sello, G.; Di Gennaro, P.
Characterization of the aldol condensation activity of the trans-o-hydroxybenzylidenepyruvate hydratase-aldolase (tHBP-HA) cloned from Pseudomonas fluorescens N3
Biochim. Biophys. Acta
1814
622-629
2011
Pseudomonas fluorescens, Pseudomonas fluorescens N3
brenda
Sello, G.; Di Gennaro, P.
Aldol reactions of the trans-o-hydroxybenzylidenepyruvate hydratase-aldolase (tHBP-HA) from Pseudomonas fluorescens N3
Appl. Biochem. Biotechnol.
170
1702-1712
2013
Pseudomonas fluorescens, Pseudomonas fluorescens N3
brenda
Cao, J.; Lai, Q.; Yuan, J.; Shao, Z.
The phenanthrene degradation mechanism of deep sea bacterium Celeribacter indicus P73T
Chin. J. Appl. Environ. Biol.
22
703-707
2016
Celeribacter indicus, Celeribacter indicus P73T
-
brenda