Entry
Name
5-nitrosalicylate dioxygenase;
naaB (gene name);
5-nitrosalicylate:oxygen 1,2-oxidoreductase (decyclizing)
Class
Oxidoreductases;
Acting on single donors with incorporation of molecular oxygen (oxygenases);
With incorporation of two atoms of oxygen
BRITE hierarchy
Sysname
5-nitrosalicylate:oxygen 1,2-oxidoreductase (ring-opening)
Reaction(IUBMB)
5-nitrosalicylate + O2 = 2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite (overall reaction) [RN:
R10109 ];
(1a) 5-nitrosalicylate + O2 = 4-nitro-6-oxohepta-2,4-dienedioate [RN:
R10110 ];
(1b) 4-nitro-6-oxohepta-2,4-dienedioate = 2-oxo-3-(5-oxofuran-2-ylidene)propanoate + nitrite (spontaneous) [RN:
R10111 ]
Reaction(KEGG)
Substrate
5-nitrosalicylate [CPD:
C19789 ];
O2 [CPD:
C00007 ];
4-nitro-6-oxohepta-2,4-dienedioate [CPD:
C20367 ]
Product
2-oxo-3-(5-oxofuran-2-ylidene)propanoate [CPD:
C20366 ];
nitrite [CPD:
C00088 ];
4-nitro-6-oxohepta-2,4-dienedioate [CPD:
C20367 ]
Comment
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.
History
EC 1.13.11.64 created 2012
Orthology
K18250 5-nitrosalicylate dioxygenase
Reference
Authors
Qu Y, Spain JC
Title
Biodegradation of 5-nitroanthranilic acid by Bradyrhizobium sp. strain JS329.
Journal
Sequence
Reference
Authors
Qu Y, Spain JC
Title
Molecular and biochemical characterization of the 5-nitroanthranilic acid degradation pathway in Bradyrhizobium sp. strain JS329.
Journal
Sequence
Other DBs
UM-BBD (Biocatalysis/Biodegradation Database): 1.13.11.64