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EC Tree
IUBMB Comments This enzyme is involved in naphthalene degradation. Requires Fe2+.
The enzyme appears in viruses and cellular organisms
Synonyms
1,2-dihydroxynaphthalene dioxygenase, 1,2-dihydroxynaphthalene oxygenase,
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1,2-dihydroxynaphthalene oxygenase
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1,2-DHN dioxygenase
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DHNDO
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nsaC
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naphthalene-1,2-diol + O2 = 2-hydroxy-2H-chromene-2-carboxylate
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1,2-dihydroxynaphthalene:oxygen oxidoreductase
This enzyme is involved in naphthalene degradation. Requires Fe2+.
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1,2,5-trihydroxynaphthalene + O2
?
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-
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?
1,2,6-trihydroxynaphthalene + O2
?
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-
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?
1,2,7-trihydroxynaphthalene + O2
?
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-
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?
1,2-dihydroxynaphthalene + O2
2-hydroxy-2H-chromene-2-carboxylate
1,2-dihydroxynaphthalene + O2
2-hydroxychromene-2-carboxylate
2,3-dihydroxybiphenyl + O2
?
3,4-dihydroxybiphenyl + O2
?
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-
-
?
3-methylcatechol + O2
2-hydroxy-6-oxohepta-2,4-dienoic acid
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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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?
additional information
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purified enzyme shows no activity with catechol
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?
1,2-dihydroxynaphthalene + O2
2-hydroxy-2H-chromene-2-carboxylate
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2-hydroxychromene-2-carboxylic acid may result from cycization of a ring fission product before release from the enzyme
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?
1,2-dihydroxynaphthalene + O2
2-hydroxy-2H-chromene-2-carboxylate
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?
1,2-dihydroxynaphthalene + O2
2-hydroxy-2H-chromene-2-carboxylate
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?
1,2-dihydroxynaphthalene + O2
2-hydroxychromene-2-carboxylate
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induced in presence of naphthalene-2-sulfonic acid
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?
1,2-dihydroxynaphthalene + O2
2-hydroxychromene-2-carboxylate
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induced in presence of naphthalene-2-sulfonic acid
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?
2,3-dihydroxybiphenyl + O2
?
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?
2,3-dihydroxybiphenyl + O2
?
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?
3-methylcatechol + O2
?
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-
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?
3-methylcatechol + O2
?
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-
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?
4-methylcatechol + O2
?
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2% of the activity with 1,2-dihydroxynaphthalene
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?
4-methylcatechol + O2
?
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?
4-methylcatechol + O2
?
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?
catechol + O2
?
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?
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1,2-dihydroxynaphthalene + O2
2-hydroxychromene-2-carboxylate
1,2-dihydroxynaphthalene + O2
2-hydroxychromene-2-carboxylate
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induced in presence of naphthalene-2-sulfonic acid
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?
1,2-dihydroxynaphthalene + O2
2-hydroxychromene-2-carboxylate
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induced in presence of naphthalene-2-sulfonic acid
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?
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Fe2+
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required. Other metal ions (Fe3+, C02+, Ca2+, Cu2+, Hg2+, Ni2+, Zn2+, Mg2+) could not replace Fe2+
Fe2+
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required for maximal activity
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1,2,3-trihydroxybenzene
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0.0005 mM, 76% inhibition
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
bathophenanthroline sulfonate
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-
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0.034 - 0.28
1,2-dihydroxynaphthalene
0.15
3-methylcatechol
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pH 6.2, 25°C
0.034
1,2-dihydroxynaphthalene
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0.28
1,2-dihydroxynaphthalene
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pH 6.2, 25°C
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0.14
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extract from 1-naphthoic acid
0.17
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extract from acenaphthylene
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NCIB 9816
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brenda
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BN6
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BN6
SwissProt
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BN6
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brenda
BN6
SwissProt
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brenda
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brenda
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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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NSAC_SPHXE
298
0
33301
Swiss-Prot
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NAHC1_PSEPU
302
0
33883
Swiss-Prot
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NAHC2_PSEPU
302
0
33942
Swiss-Prot
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NAHC_PSEAI
302
0
33942
Swiss-Prot
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NAHC_PSEU8
302
0
33942
Swiss-Prot
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A0A3P4B4F5_9BURK
287
0
32704
TrEMBL
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A0A2S6U7S2_9PROT
284
0
32206
TrEMBL
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A0A4P6WVD2_HYDPS
286
0
32527
TrEMBL
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A0A2S6QJ79_9PROT
285
0
32655
TrEMBL
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A0A508TF89_9BRAD
295
0
32867
TrEMBL
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A0A644Z4V1_9ZZZZ
302
0
33749
TrEMBL
other Location (Reliability: 2 )
A0A2S6Q8H7_9PROT
285
0
33008
TrEMBL
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A0A2J7V4P4_9BURK
304
0
34182
TrEMBL
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A0A0X8R4Q6_9SPHN
304
0
33823
TrEMBL
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A0A127MWP9_9PSED
306
0
34252
TrEMBL
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A0A446CEC9_9BURK
287
0
32658
TrEMBL
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A0A446CN09_9BURK
287
0
32692
TrEMBL
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19000
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x * 19000, SDS-PAGE
33000
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8 * 33000, SDS-PAGE
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octamer
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8 * 33000, SDS-PAGE
octamer
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8 * 33000, SDS-PAGE
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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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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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Acetone
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storage for 1 week at 4°C in the presence of 10% (v/v) ethanol or acetone, the enzyme in crude extract is completely inactivated
Acetone
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storage for 1 week at 4°C in the presence of 10% (v/v) ethanol or acetone, the enzyme in crude extract is completely inactivated
Ethanol
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storage for 1 week at 4°C in the presence of 10% (v/v) ethanol or acetone, the enzyme in crude extract is completely inactivated
Ethanol
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storage for 1 week at 4°C in the presence of 10% (v/v) ethanol or acetone, the enzyme in crude extract is completely inactivated
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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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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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Nayak, A.S.; Veeranagouda, Y.; Lee, K.; Karegoudar, T.B.
Metabolism of acenaphthylene via 1,2-dihydroxynaphthalene and catechol by Stenotrophomonas sp. RMSK
Biodegradation
20
837-843
2009
Stenotrophomonas sp.
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Patel, T.R.; Barnsley, E.A.
Naphthalene metabolism by pseudomonads: purification and properties of 1,2-dihydroxynaphthalene oxygenase
J. Bacteriol.
143
668-673
1980
Pseudomonas putida
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Kuhm, A.E.; Stolz, A.; Ngai, K.L.; Knackmuss, H.J.
Purification and characterization of a 1,2-dihydroxynaphthalene dioxygenase from a bacterium that degrades naphthalenesulfonic acids
J. Bacteriol.
173
3795-3802
1991
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 (P74836), Sphingobium xenophagum, Sphingobium xenophagum BN6 (P74836)
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Ji, X.; Xu, J.; Ning, S.; Li, N.; Tan, L.; Shi, S.
Cometabolic degradation of dibenzofuran and dibenzothiophene by a naphthalene-degrading Comamonas sp. JB
Curr. Microbiol.
74
1411-1416
2017
Comamonas sp. JB
brenda
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1.13.11.56 1,2-dihydroxynaphthalene dioxygenase
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