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Information on EC 1.13.11.64 - 5-nitrosalicylate dioxygenase for references in articles please use BRENDA:EC1.13.11.64Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
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The expected taxonomic range for this enzyme is: Bradyrhizobium
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5-nitrosalicylate dioxygenase
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4-nitro-6-oxohepta-2,4-dienedioate = 2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite
spontaneous
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5-nitrosalicylate + O2 = 2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite
overall reaction
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5-nitrosalicylate + O2 = 4-nitro-6-oxohepta-2,4-dienedioate
(1a)
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5-nitrosalicylate:oxygen 1,2-oxidoreductase (decyclizing)
The enzyme, characterized from the soil bacterium Bradyrhizobium sp. JS329, is involved in the pathway of 5-nitroanthranilate degradation. It is unusual in being able to catalyse the ring fission without the requirement for prior removal of the nitro group. The product undergoes spontaneous lactonization, with concurrent elimination of the nitro group.
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5NSA dioxygenase
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naaB
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gene name
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UniProt
brenda
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UniProt
brenda
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4-nitro-6-oxohepta-2,4-dienedioate
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite
5-chlorosalicylate + O2
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + chloride
5-nitrosalicylate + O2
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite
5-nitrosalicylate + O2
4-nitro-6-oxohepta-2,4-dienedioate
additional information
?
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4-nitro-6-oxohepta-2,4-dienedioate
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite
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2nd step of reaction, spontaneous
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?
4-nitro-6-oxohepta-2,4-dienedioate
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite
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2nd step of reaction, spontaneous
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?
5-chlorosalicylate + O2
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + chloride
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overall reaction
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?
5-chlorosalicylate + O2
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + chloride
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overall reaction
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?
5-nitrosalicylate + O2
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite
oxidation catalyzed by cell extracts requires 0.97 mol O2/mol 5-nitrosalicylate
overall reaction
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?
5-nitrosalicylate + O2
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite
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results are consistent with a dioxygenase-catalyzed ring opening followed by spontaneous lactonization and nitrite elimination and enzyme-catalyzed hydrolysis of the lactone to produce maleylpyruvate
overall reaction. The initial ring fission product of 5-nitrosalicylate dioxygenation is spontaneously and rapidly cyclized to form lactones, accompanied by the release of NO2-
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?
5-nitrosalicylate + O2
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite
oxidation catalyzed by cell extracts requires 0.97 mol O2/mol 5-nitrosalicylate
overall reaction
-
?
5-nitrosalicylate + O2
2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite
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results are consistent with a dioxygenase-catalyzed ring opening followed by spontaneous lactonization and nitrite elimination and enzyme-catalyzed hydrolysis of the lactone to produce maleylpyruvate
overall reaction. The initial ring fission product of 5-nitrosalicylate dioxygenation is spontaneously and rapidly cyclized to form lactones, accompanied by the release of NO2-
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?
5-nitrosalicylate + O2
4-nitro-6-oxohepta-2,4-dienedioate
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1st step of reaction
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?
5-nitrosalicylate + O2
4-nitro-6-oxohepta-2,4-dienedioate
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1st step of reaction
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?
salicylate + O2
?
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salicylate + O2
?
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additional information
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no substrates: 4-chlorocatechol, 4-nitrocatechol
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additional information
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no substrates: 4-chlorocatechol, 4-nitrocatechol
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additional information
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no requirement of NADPH
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Fe2+
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ultrafiltration abolishes the enzymatic activity against 5-nitrosalicylate, which is restored by addition of ferrous but not ferric ions
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2,2'-dipyridyl
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1 mM, 98% loss of activity
o-phenanthroline
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1 mM, complete loss of activity
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-20°C, 40% to 50% loss of original activity after 1 week of storage
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ultrafiltration abolishes the enzymatic activity against 5-nitrosalicylate, which is restored by addition of ferrous but not ferric ions
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NAAB_BRASZ
207
23624
Swiss-Prot
A0A1B9BJK5_CLOBE
102
11570
TrEMBL
A0A1Y2MV46_PSEAH
373
40943
TrEMBL
A0A1M7YYZ8_9VIBR
170
19429
TrEMBL
A0A1Y5TRZ6_9PROT
211
24103
TrEMBL
A0A2S6Q5D9_9PROT
382
43321
TrEMBL
A0A2K8QW18_9ACTN
355
40076
TrEMBL
A0A0F7KTK2_9SPHN
371
42059
TrEMBL
A0A1V5FQF8_9BACT
123
13788
TrEMBL
A0A2H5W1J5_9BACT
169
19138
TrEMBL
A0A2J7W7T7_9BURK
192
22124
TrEMBL
A0A1B8YFN9_9GAMM
149
16753
TrEMBL
A0A0X1U7B4_CLOPR
113
12330
TrEMBL
A0A2S5D220_LYSSH
182
20111
TrEMBL
A0A1Y2NIU2_STRPT
144
16026
TrEMBL
A0A2H5VLH3_9BACT
169
19086
TrEMBL
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Qu, Y.; Spain, J.C.
Biodegradation of 5-nitroanthranilic acid by Bradyrhizobium sp. strain JS329
Appl. Environ. Microbiol.
76
1417-1422
2010
Bradyrhizobium sp., Bradyrhizobium sp. (D3WZ86), Bradyrhizobium sp. JS329 (D3WZ86)
brenda
Qu, Y.; Spain, J.C.
Molecular and biochemical characterization of the 5-nitroanthranilic acid degradation pathway in Bradyrhizobium sp. strain JS329
J. Bacteriol.
193
3057-3063
2011
Bradyrhizobium sp., Bradyrhizobium sp. (D3WZ86), Bradyrhizobium sp. JS329 (D3WZ86)
brenda
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