Information on EC 1.13.11.56 - 1,2-dihydroxynaphthalene dioxygenase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.13.11.56
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RECOMMENDED NAME
GeneOntology No.
1,2-dihydroxynaphthalene dioxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
naphthalene-1,2-diol + O2 = 2-hydroxy-2H-chromene-2-carboxylate
show the reaction diagram
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
naphthalene degradation (aerobic)
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Naphthalene degradation
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Metabolic pathways
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
1,2-dihydroxynaphthalene:oxygen oxidoreductase
This enzyme is involved in naphthalene degradation. Requires Fe2+.
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CAS REGISTRY NUMBER
COMMENTARY hide
55354-35-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
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Manually annotated by BRENDA team
NCIB 9816
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Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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the metabolic pathways of dibenzofuran and dibenzothiophene are controlled by naphthalene-degrading enzymes. Strain JB cannot grow on dibenzofuran or dibenzothiophen as the sole carbon source. 1,2-dihydroxynaphthalene dioxygenase may be responsible for the ring cleavage of 1,2-dihydroxydibenzofuran and 1,2-dihydroxydibenzothiophene to form 2-hydroxy-4-(3'-oxo-3'H-benzofuran-20-yliden)but-2-enoic acid and 4-[2-(3hydroxy)-thianaphthenyl]-2-oxo-3-butenoic acid
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,2,5-trihydroxynaphthalene + O2
?
show the reaction diagram
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-
-
-
?
1,2,6-trihydroxynaphthalene + O2
?
show the reaction diagram
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-
-
-
?
1,2,7-trihydroxynaphthalene + O2
?
show the reaction diagram
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-
-
-
?
1,2-dihydroxynaphthalene + O2
2-hydroxy-2H-chromene-2-carboxylate
show the reaction diagram
1,2-dihydroxynaphthalene + O2
2-hydroxychromene-2-carboxylate
show the reaction diagram
2,3-dihydroxybiphenyl + O2
?
show the reaction diagram
3,4-dihydroxybiphenyl + O2
?
show the reaction diagram
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-
-
-
?
3-methylcatechol + O2
2-hydroxy-6-oxohepta-2,4-dienoic acid
show the reaction diagram
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5% of the activity with 1,2-dihydroxynaphthalene. The product 2-hydroxy-6-oxoheptadienoic acid is not structurally analogous to 2-hydroxychromene-2-carboxylic acid
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?
3-methylcatechol + O2
?
show the reaction diagram
4-methylcatechol + O2
?
show the reaction diagram
catechol + O2
?
show the reaction diagram
additional information
?
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purified enzyme shows no activity with catechol
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1,2-dihydroxynaphthalene + O2
2-hydroxychromene-2-carboxylate
show the reaction diagram
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,2,3-trihydroxybenzene
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0.0005 mM, 76% inhibition
2,2'-dipyridyl
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2,3-dihydroxynaphthalene
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0.0005 mM, 44% inhibition
2,7-dihydroxynaphthalene
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0.0005 mM, 64% inhibition
3,4-dihydroxybenzoic acid
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0.0005 mM, 20% inhibition
3-methylcatechol
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0.0005 mM, 76% inhibition, competitive inhibitor
4-methylcatechol
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0.0005 mM, 36% inhibition, competitive inhibitor
8-hydroxyquinoline
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bathophenanthroline sulfonate
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o-phenanthroline
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.034 - 0.28
1,2-dihydroxynaphthalene
0.15
3-methylcatechol
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pH 6.2, 25°C
0.27
O2
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pH 6.2, 25°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.14
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extract from 1-naphthoic acid
0.17
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extract from acenaphthylene
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
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assay at
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PDB
SCOP
CATH
UNIPROT
ORGANISM
Pseudomonas sp. (strain C18);
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
19000
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x * 19000, SDS-PAGE
33000
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8 * 33000, SDS-PAGE
275000
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gel filtration
290000
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gel filtration
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 19000, SDS-PAGE
octamer
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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the enzyme is more stable at slightly alkaline pH values and better preserved in Na-K phosphate buffer than in Tris-HCI or glycine-NaOH
698539
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
enzyme in crude extract is stable in Na-K phosphate buffer, pH 7.5, after 1 week of storage (2.4 mg of protein per ml) at 4°C, 100% of the original activity is recovered
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the enzyme is inactivated slowly on standing, and inactivation is accelerated by dilution with aerated buffers and by H2O2. The inactive enzyme is reactivated by anaerobic incubation with Fe(SO4) and ferrous ammonium sulfate. Thiol reagents and acetone, ethanol, or glycerol decrease the rate of loss of activity
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ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acetone
Ethanol
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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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 29-hydroxybenzalpyruvate aldolase of the naphthalenesulfonate pathway are identified on the DNA fragment and the encoded proteins heterologously expressed in Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
degradation
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the metabolic pathways of dibenzofuran and dibenzothiophene are controlled by naphthalene-degrading enzymes. Strain JB cannot grow on dibenzofuran or dibenzothiophen as the sole carbon source. 1,2-dihydroxynaphthalene dioxygenase may be responsible for the ring cleavage of 1,2-dihydroxydibenzofuran and 1,2-dihydroxydibenzothiophene to form 2-hydroxy-4-(3'-oxo-3'H-benzofuran-20-yliden)but-2-enoic acid and 4-[2-(3hydroxy)-thianaphthenyl]-2-oxo-3-butenoic acid
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LINKS TO OTHER DATABASES (specific for EC-Number 1.13.11.56)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)