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Information on EC 4.1.2.45 - trans-o-hydroxybenzylidenepyruvate hydratase-aldolase and Organism(s) Sphingobium xenophagum and UniProt Accession Q9X9Q6

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EC Tree
     4 Lyases
         4.1 Carbon-carbon lyases
             4.1.2 Aldehyde-lyases
                4.1.2.45 trans-o-hydroxybenzylidenepyruvate hydratase-aldolase
IUBMB 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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This record set is specific for:
Sphingobium xenophagum
UNIPROT: Q9X9Q6
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Word Map
The taxonomic range for the selected organisms is: Sphingobium xenophagum
The enzyme appears in selected viruses and cellular organisms
Synonyms
trans-o-hydroxybenzylidenepyruvate hydratase-aldolase, 2'-hydroxybenzalpyruvate aldolase, thbp-ha, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2'-hydroxybenzalpyruvate aldolase
-
2'-hydroxybenzalpyruvate aldolase
-
-
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) 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
-
involved in metabolism of naphthalene to salicylate
-
-
?
benzylidenepyruvate + H2O
benzaldehyde + pyruvate
show the reaction diagram
-
with 1% of the activity found with (E)-2'-hydroxybenzylidinepyruvate
-
-
?
additional information
?
-
-
no activity with: benzylideneacetone and cinnamic acid
-
-
?
NATURAL SUBSTRATE
NATURAL 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-hydroxyphenyl)-2-oxobut-3-enoate + H2O
salicylaldehyde + pyruvate
show the reaction diagram
-
this reaction is part of the degradative pathways for naphthalene and naphthalenesulfonates by bacteria
-
-
?
(E)-2'-hydroxybenzylidenepyruvate + H2O
salicylaldehyde + pyruvate
show the reaction diagram
-
involved in metabolism of naphthalene to salicylate
-
-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
-
-
p-chloromercuribenzoate
-
enzyme is partially reactivated by addition of dithiothreitol
Salicylaldehyde
-
-
sodium borhydride
-
-
additional information
-
no inhibition: benzylideneacetone, cinnamic acid
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.015
(3E)-4-(2,4-dihydroxyphenyl)-2-oxobut-3-enoate
-
pH 7.0
0.006
(3E)-4-(2,6-dihydroxyphenyl)-2-oxobut-3-enoate
-
pH 7.0
0.017
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate
-
pH 7.0
0.4
benzylidenepyruvate
-
pH 7.0
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.013
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
-
pH 7.0
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8
-
in Tris/HCl or Na/K-phosphate buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
BN6
SwissProt
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
NSAE_SPHXE
328
0
35459
Swiss-Prot
-
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
120000
-
gel filtration
38500
-
3 * 38500, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
trimer
-
3 * 38500, SDS-PAGE
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
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
Manually annotated by BRENDA team
Stolz, A.
Degradation of substituted naphthalenesulfonic acids by Sphingomonas xenophaga BN6
J. Ind. Microbiol. Biotechnol.
23
391-399
1999
Sphingobium xenophagum, Sphingobium xenophagum BN6
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team