Nitrobenzene → 2-Aminophenol
Reaction equation
[NH2:1]/[C:2](=[CH:6]\[CH:7]=[CH:8]\[C:9]([O-:11])=[O:10])/[C:3]([O-:5])=[O:4].[N+](C1C=CC=CC=1)([O-])=O>>[NH2:1]/[C:2](=[CH:6]\[CH:7]=[CH:8]\[C:9]([O-:11])=[O:10])/[C:3]([O-:5])=[O:4].[NH2:1][C:2]1[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=1[OH:5].[CH:7](/[CH:6]=[C:2](/[NH2:1])\[C:3]([OH:5])=[O:4])=[CH:8]/[CH:9]=[O:10]Participants
Procedure
Recently, we found that 2-aminomuconate is one of the intermediates in the pathway for the biodegradation of nitrobenzene by the bacterium Pseudomonas pseudoalcaligenes JS45. 2-Aminomuconate is produced from 2-aminophenol by the action of 2-aminophenol 1,6-dioxygenase and 2-aminomuconic semialdehyde dehydrogenase. We have prepared 2-aminomuconate with these two enzymes either in crude extracts or in the fractions from a DEAE-Sepharose column, and separated it by anion exchange chromatography for use in investigating the properties of 2-aminomuconate deaminase from P. pseudoalcaligenes JS45. However, attempts to prepare the material in large quantities for general use failed because the partially purified dioxygenase was unstable even during storage at −70° C. In crude extracts the dioxygenase was relatively stable, but the presence of 2-aminomuconate deaminase precluded accumulation of 2-aminomuconate.
Sources & evidence
- ORD record
- ord-351843caa81145329214b968869904c2
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06432683B1
Reaction notes
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