3-Hydroxylaminophenol mutase from Ralstonia eutropha JMP134 catalyzes a Bamberger rearrangement

Journal of Bacteriology

Volumn 181, Issue 5, 1999, Pages 1444-1450

  Schenzle, Andreas ^a,b   Lenke, Hiltrud ^a   Spain, Jim C ^c   Knackmuss, Hans Joachim ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b DUPONT COMPANY   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

MUTASE;

ARTICLE; BACTERIAL GENE; BIODEGRADATION; ENZYME SUBSTRATE COMPLEX; GENE REARRANGEMENT; NONHUMAN; PRIORITY JOURNAL; PROTEIN PURIFICATION; WAUTERSIA EUTROPHA;

RALSTONIA EUTROPHA;

EID: 0033026362     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/jb.181.5.1444-1450.1999     Document Type: Article

References (56)

1. Almassy, R. J., C. A. Janson, R. Hamlin, N. H. Xuong, and D. Eisenberg. 1986. Novel subunit-subunit interactions in the structure of glutamine synthetase. Nature 323:304-309.
2. Altschul, S. F., T. L. Madden, A. A. Schäffer, J. Zhang, Z. Zhang, W. Miller, and D. J. Lipman. 1997. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res. 25:3389-3402.
3. Bamberger, E. 1984. Über das Phenylhydroxylamin. Chem. Ber. 27:1548-1557.
4. Becker, A. R., and L. A. Sternson. 1980. Nonenzymatic reduction of nitrosobenzene to phenylhydroxylamine by NAD(P)H. Bioorg. Chem. 9:305-312.
5. Bisswanger, H. 1979. Theorie und Methoden der Enzymkinetik. Verlag Chemie, Weinheim, Germany.
6. Booth, J., and E. Boyland. 1964. The biochemistry of aromatic amines. 10. Enzymic N-hydroxylation of arylamines and conversion of arylhydroxylamines into o-aminophenols. Biochem. J. 91:362-369.
7. Bosold, F., and G. Boche. 1990. The ultimate carcinogen. O-acetyl-N-2-(fluorenyl)-hydrosylamine ("N-acetoxy-2-aminofluorene"), and its reaction in vitro to form 2-[N-(deoxyguanosin-8-yl)amino]fluorene. Angew. Chem. Int. Ed. Engl. 29:63-64.
8. Boteju, L. W., and P. E. Hanna. 1993. Bioactivation of N-hydroxylaminofluorenes by N,O-acyltransferase: substituent effects on covalent binding to DNA. Carcinogenesis 14:1651-1675.
9. Bradford, M. M. 1976. A rapid and sensitive method for the quantification of micrograms quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:248-254.
10. Bruhn, C., H. Lenke, and H.-J. Knackmuss. 1987. Nitrosubstituted aromatic compounds as nitrogen source for bacteria. Appl. Environ. Microbiol. 53: 208-210.
11. Cardy, D. L., and J. C. Murrell. 1990. Cloning, sequencing and expression of the glutamine synthetase structural gene (glnA) from the obligate methanotroph Methylococcus capsulatus (Bath). J. Gen. Microbiol, 136:343-352.
12. Colombo, G., and J. J. Villafranca. 1986. Amino acid sequence of Escherichia coli glutamine synthetase deduced from the DNA nucleotide sequence. J. Biol. Chem. 261:10587-10591.
13. Corbett, M. D., and B. R. Corbett. 1981. Metabolism of 4-chloronitrobenzene by the yeast Rhodosporidium sp. Appl. Environ. Microbiol. 41:942-949.
14. Corbett, M. D., and B. R. Corbett. 1995. Bioorganic chemistry of the arylhydroxylamine and nitrosoarene functional groups, p. 151-182. In J. C. Spain (ed.), Biodegradation of nitroaromatic compounds. Plenum Press, New York, N.Y.
15. Corbett, M. D., B. R. Corbett, and D. R. Doerge. 1982. Hydroxamic acid production and active-site induced Bamberger rearrangement from the action of α-ketoglutarate dehydrogenase on 4-chloronitrosobenzene. J. Chem. Soc. Perkin Trans. I 1982:345-350.
16. Fleischmann, R. D., M. D. Adams, O. White, R. A. Clayton, E. F. Kirkness, A. R. Kerlavage, C. J. Bult, J.-F. Tomb, B. A. Dougherty, J. M. Merrick, K. McKenney, G. Sutton, W. Fitzhugh, C. A. Fields, J. D. Gocayne, J. D. Scott, R. Shirley, L.-I. Liu, A. Glodek, J. M. Kelley, J. F. Weidman, C. A. Phillips, T. Spriggs, E. Hedblom, M. D. Cotton, T. R. Utterback, M. C. Hanna, D. T. Nguyen, D. M. Saudek, R. C. Brandon, L. D. Fine, J. L. Fritchman, J. L. Fuhrmann, N. S. M. Geoghagen, C. L. Gnehm, L. A. McDonald, K. V. Small, C. M. Fraser, H. O. Smith, and J. C. Venter. 1995. Whole-genome random sequencing and assembly of Haemophilus influenzae Rd. Science 269:496-512.
17. Furniss, B. S., A. J. Hannaford, P. W. G. Smith, and A. R. Tatchell. 1989. Vogel's textbook of practical organic chemistry, 5th ed. John Wiley & Sons, Inc., New York, N.Y.
18. Gorontzky, T., O. Drzyzga, M. W. Kahl, D. Bruns-Nagel, J. Breitung, E. von Loew, and K.-H. Blotevogel. 1994. Microbial degradation of explosives and related compounds. Crit. Rev. Microbiol. 20:265-284.
19. Groenewegen, P. E. J., and J. A. M. de Bont. 1992. Degradation of 4-nitrobenzoate via 4-hydroxylaminobenzoate and 3,4-dihydroxybenzoate in Comamonas acidovorans NBA-10. Arch. Microbiol. 158:381-386.
20. Haigler, B. E., and J. C. Spain. 1993. Biodegradation of 4-nitrotoluene by Pseudomonas sp. strain 4NT. Appl. Environ. Microbiol. 59:2239-2243.
21. Higson, F. K. 1992. Microbial degradation of nitroaromatic compounds. Adv. Appl. Microbiol. 37:1-19.
22. Hughes, J. Personal communication.
23. Jakoby, M., M. Tesch, H. Sahm, R. Kraemer, and A. Burkovski. 1997. Isolation of the Corynebacterium glutamicum glnA gene encoding glutamine synthetase I. FEMS Microbiol. Lett. 154:81-88.
24. Knight, G. T., and B. Saville. 1973. Hydrogen transfer from N-arylhydroxylamines to nitrosoarenes: an accompaniment to azoxyarene formation. J. Chem. Soc. Perkin Trans. II 1973:1550-1553.
25. Koerber, S. C., P. Schack, A. M.-J. Au, and M. F. Dunn. 1980. Investigations of a novel liver alcohol dehydrogenase catalyzed redox-elimination reaction involving arylnitroso substrate analogues. Biochemistry 19:731-738.
26. Kolanczyk, R. C., H. R. Gutmann, and I. R. Rutks. 1992. Effect of bovine serum albumin on the extent of ortho rearrangement of N-(sulfooxy)-2-fluorenylacetamide and of enzymatically activated N-hydroxy-2-fluorenylacetamide and on the binding of reactive esters to nucleic acids. Chem. Res. Toxicol. 5:274-279.
27. Laemmli, U. K. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature (London) 227:680-685.
28. Lenke, H., and H.-J. Knackmuss. 1992. Initial hydrogenation during catabolism of picric acid by Rhodococcus erythropolis HL 24-2. Appl. Environ. Microbiol. 58:2933-2937.
29. Lenke, H., and H.-J. Knackmuss. 1996. Initial hydrogenation and extensive reduction of substituted 2,4-dinitrophenols. Appl. Environ. Microbiol. 62: 784-790.
30. Leskovac, V., J. Svircevic, S. Trivic, M. Popovic, and M. Radulovic. 1989. Reduction of aryl-nitroso compounds by pyridine and flavin coenzymes. Int. J. Biochem. 21:825-834.
31. Maharaj, R., E. Rumbak, W. A. Jones, S. M. Robb, F. T. Robb, and D. R. Woods. 1989. Nucleotide sequence of the Vibrio alginolyticus glnA region. Arch. Microbiol. 152:542-549.
32. Marvin-Sikkema, F. D., and J. A. M. de Bont. 1994. Degradation of nitroaromatic compounds by microorganisms. Appl. Microbiol. Biotechnol. 42:499-507.
33. Maskos, Z., and G. W. Winston. 1993. Alcohol dehydrogenase-dependent reduction of 2-nitrosofluorene and rearrangement of N-hydroxy-2-aminofluorene. Biochemistry 32:12768-12773.
34. Meulenberg, R., and J. A. M. de Bont. 1995. Microbial production of catechols from nitroaromatic compounds, p. 37-52. In J. C. Spain (ed.), Biodegradation of nitroaromatic compounds. Plenum Press, New York, N.Y.
35. Meulenberg, R., M. Pepi, and J. A. M. de Bont. 1996. Degradation of 3-nitrophenol by Pseudomonas putida B2 occurs via 1,2,4-benzenetriol. Biodegradation 7:303-311.
36. Müller, O. 1977. Grundlagen der Biochemie. 1. Biochemische Reaktionen. Thieme, Stuttgart, Germany.
37. Nishino, S. F., and J. C. Spain. 1993. Degradation of nitrobenzene by a Pseudomonas pseudoalcaligenes. Appl. Environ. Microbiol. 59:2520-2525.
38. Novak, M., M. J. Kahley, E. Eiger, J. S. Helmick, and H. E. Peters. 1993. Reactivity and selectivity of nitrenium ions derived from ester derivatives of carcinogenic N-(4-biphenyl)hydroxylamine and the corresponding hydroxamic acid. J. Am. Chem. Soc. 115:9453-9460.
39. Pemberton, J. M., B. Corney, and R. H. Don. 1979. Evolution and spread of pesticide degrading ability among soil micro-organisms, p. 287-299. In K. N. Timmis and A. Pühler (ed.). Plasmids of medical, environmental and commercial importance. Elsevier North Holland Biomedical Press, Amsterdam, The Netherlands.
40. Rawlings, D. E., W. A. Jones, E. G. O'Neill, and D. R. Woods. 1987. Nucleotide sequence of the glutamine synthetase gene and its controlling region from the acidophilic autotroph Thiobacillus ferrooxidans. Gene 53:211-217.
41. Rhys-Williams, W., S. C. Taylor, and P. A. Williams. 1993. A novel pathway for the catabolism of 4-nitrotoluene by Pseudomonas. J. Gen. Microbiol. 139:1967-1972.
42. Rigo, L. U., M. B. R. Steffens, E. M. Souza, and F. O. Pedrosa. Sequence and structural organization of the glnAntrBC operon from Herbaspirillum seropedicae strain Z78. Submitted for publication.
43. Schenzle, A., H. Lenke, P. Fischer, P. A. Williams, and H.-J. Knackmuss. 1997. Catabolism of 3-nitrophenol by Ralstonia eutropha JMP134. Appl. Environ. Microbiol. 63:1421-1427.
44. Schenzle, A., H. Lenke, and H.-J. Knackmuss. 1997. Catabolism of 2-chloro-5-nitrophenol by Ralstonia eutropha JMP 134, abstr. Q-117, p. 475. In Abstracts of the 97th General Meeting of the American Society for Microbiology 1997. American Society for Microbiology, Washington, D.C.
45. Shine, H. J. 1967. The rearrangement of phenylhydroxylamines, p. 182-190. In C. Eaborn and N. B. Chapmann (ed.), Reaction mechanisms in organic chemistry. Elsevier Biomedical Publishing Co., Amsterdam, The Netherlands.
46. Sone, T., Y. Tokuda, T. Sakai, S. Shinkai, and O. Manabe. 1981. Kinetics and mechanisms of the Bamberger rearrangement. 3. Rearrangement of phenylhydroxylamines to p-aminophenols in aqueous sulphuric acid solutions. J. Chem. Soc. Perkin Trans. II 1981:298-302.
47. Spain, J. C. (ed.). 1995. Biodegradation of nitroaromatic compounds. Plenum Press, New York, N.Y.
48. Spain, J. C. 1995. Biodegradation of nitroaromatic compounds. Annu. Rev. Microbiol. 49:523-555.
49. Spain, J. C. 1995. Bacterial degradation of nitroaromatic compounds under aerobic conditions, p. 19-35. In Spain, J. C. (ed.). Biodegradation of nitroaromatic compounds. Plenum Press, New York, N.Y.
50. Spiess, T., F. Desiere, P. Fischer, J. C. Spain, H.-J. Knackmuss, and H. Lenke. 1998. A novel degradative pathway of 4-nitrotoluene by a Mycobacterium sp. strain. Appl. Environ. Microbiol. 64:446-452.
51. Sternson, L. A., and R. E. Gammans. 1975. A mechanistic study of aromatic hydroxylamine rearrangement in the rat. Bioorg. Chem. 4:58-63.
52. Stone, K. L., and K. R. Williams. 1993. 2. Enzymatic digestion of proteins, p. 54-68. In P. Matsudaira (ed.), A practical guide to protein and peptide purification for microsequencing, 2nd ed. Academic Press, Inc., New York, N.Y.
53. Toukdarian, A., G. Saunders, G. Selman-Sosa, E. Santero, P. Woodley, and C. Kennedy. 1990. Molecular analysis of the Azotobacter vinelandii glnA gene encoding glutamine synthetase. J. Bacteriol. 172:6529-6539.
54. Vorbeck, C., H. Lenke, P. Fischer, and H.-J. Knackmuss. 1994. Identification of a hydride-Meisenheimer complex as a metabolite of 2,4,6-trinitrotoluene by a Mycobacterium strain. J. Bacteriol. 176:932-934.
55. Vorbeck, C., H. Lenke, P. Fischer, J. C. Spain, and H.-J. Knackmuss. 1998. Initial reductive reactions in aerobic microbial metabolism of 2,4,6-trinitrotoluene. Appl. Environ. Microbiol. 64:246-252.
56. Zhou, J., L. D. Bowler, and B. G. Spratt. 1997. Interspecies recombination, and phylogenetic distortions, within the glutamine synthetase and shikimate dehydrogenase genes of Neisseria meningitidis and commensal Neisseria species. Mol. Microbiol. 23:799-812.