This Article
Right arrow Full Text
Right arrow Full Text (PDF)
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Download to citation manager
Right arrowReprints and Permissions
Right arrow Copyright Information
Right arrow Books from ASM Press
Right arrow MicrobeWorld
Citing Articles
Right arrow Citing Articles via HighWire
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by Zhao, J.-S.
Right arrow Articles by Ward, O. P.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Zhao, J.-S.
Right arrow Articles by Ward, O. P.
Agricola
Right arrow Articles by Zhao, J.-S.
Right arrow Articles by Ward, O. P.

 Previous Article  |  Next Article 

Applied and Environmental Microbiology, June 2000, p. 2336-2342, Vol. 66, No. 6
0099-2240/00/$04.00+0
Copyright © 2000, American Society for Microbiology. All rights reserved.

Biotransformation of Hydroxylaminobenzene and Aminophenol by Pseudomonas putida 2NP8 Cells Grown in the Presence of 3-Nitrophenol

Jian-Shen Zhao, Ajay Singh, Xiao-Dong Huang, and Owen P. Ward*

Department of Biology, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1

Received 22 December 1999/Accepted 16 March 2000

Biotransformation products of hydroxylaminobenzene and aminophenol produced by 3-nitrophenol-grown cells of Pseudomonas putida 2NP8, a strain grown on 2- and 3-nitrophenol, were characterized. Ammonia, 2-aminophenol, 4-aminophenol, 4-benzoquinone, N-acetyl-4-aminophenol, N-acetyl-2-aminophenol, 2-aminophenoxazine-3-one, 4-hydroquinone, and catechol were produced from hydroxylaminobenzene. Ammonia, N-acetyl-2-aminophenol, and 2-aminophenoxazine-3-one were produced from 2-aminophenol. All of these metabolites were also found in the nitrobenzene transformation medium, and this demonstrated that they were metabolites of nitrobenzene transformation via hydroxylaminobenzene. Production of 2-aminophenoxazine-3-one indicated that oxidation of 2-aminophenol via imine occurred. Rapid release of ammonia from 2-aminophenol transformation indicated that hydrolysis of the imine intermediate was the dominant reaction. The low level of 2-aminophenoxazine-3-one indicated that formation of this compound was probably due to a spontaneous reaction accompanying oxidation of 2-aminophenol via imine. 4-Hydroquinone and catechol were reduction products of 2- and 4-benzoquinones. Based on these transformation products, we propose a new ammonia release pathway via oxidation of aminophenol to benzoquinone monoimine and subsequent hydrolysis for transformation of nitroaromatic compounds by 3-nitrophenol-grown cells of P. putida 2NP8. We propose a parallel mechanism for 3-nitrophenol degradation in P. putida 2NP8, in which all of the possible intermediates are postulated.

* Corresponding author. Mailing address: Department of Biology, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1. Phone: (519) 888-4567, ext. 2427. Fax: (519) 746-4989. E-mail: opward{at}sciborg.uwaterloo.ca.

Applied and Environmental Microbiology, June 2000, p. 2336-2342, Vol. 66, No. 6
0099-2240/00/$04.00+0
Copyright © 2000, American Society for Microbiology. All rights reserved.


This article has been cited by other articles:

  • (2008). Annual Review of Cosmetic Ingredient Safety Assessments: 2005/2006. International Journal of Toxicology 27: 77-142 [Full Text]  
  • Kadiyala, V., Nadeau, L. J., Spain, J. C. (2003). Construction of Escherichia coli Strains for Conversion of Nitroacetophenones to ortho-Aminophenols. Appl. Environ. Microbiol. 69: 6520-6526 [Abstract] [Full Text]  
  • Takenaka, S., Okugawa, S., Kadowaki, M., Murakami, S., Aoki, K. (2003). The Metabolic Pathway of 4-Aminophenol in Burkholderia sp. Strain AK-5 Differs from That of Aniline and Aniline with C-4 Substituents. Appl. Environ. Microbiol. 69: 5410-5413 [Abstract] [Full Text]  
  • Nadeau, L. J., He, Z., Spain, J. C. (2003). Bacterial Conversion of Hydroxylamino Aromatic Compounds by both Lyase and Mutase Enzymes Involves Intramolecular Transfer of Hydroxyl Groups. Appl. Environ. Microbiol. 69: 2786-2793 [Abstract] [Full Text]  
  • Zhao, J.-S., Halasz, A., Paquet, L., Beaulieu, C., Hawari, J. (2002). Biodegradation of Hexahydro-1,3,5-Trinitro-1,3,5-Triazine and Its Mononitroso Derivative Hexahydro-1-Nitroso-3,5-Dinitro-1,3,5-Triazine by Klebsiella pneumoniae Strain SCZ-1 Isolated from an Anaerobic Sludge. Appl. Environ. Microbiol. 68: 5336-5341 [Abstract] [Full Text]  
  • Hughes, M. A., Baggs, M. J., al-Dulayymi, J.'a, Baird, M. S., Williams, P. A. (2002). Accumulation of 2-Aminophenoxazin-3-one-7-Carboxylate during Growth of Pseudomonas putida TW3 on 4-Nitro-Substituted Substrates Requires 4-Hydroxylaminobenzoate Lyase (PnbB). Appl. Environ. Microbiol. 68: 4965-4970 [Abstract] [Full Text]  
  • Zhao, J.-S., Ward, O. P. (2001). Substrate Selectivity of a 3-Nitrophenol-Induced Metabolic System in Pseudomonas putida 2NP8 Transforming Nitroaromatic Compounds into Ammonia under Aerobic Conditions. Appl. Environ. Microbiol. 67: 1388-1391 [Abstract] [Full Text]  


Copyright © 2009 by the American Society for Microbiology.   For an alternate route to Journals.ASM.org, visit: http://intl-journals.asm.org | More Info»