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Bioorganic Chemistry of the Arylhydroxylamine and Nitrosoarene Functional Groups

  • Chapter
Biodegradation of Nitroaromatic Compounds

Part of the book series: Environmental Science Research ((ESRH,volume 49))

Abstract

Arylamine and nitroaromatic chemicals make up one of the largest groups of man-made chemicals that find their way into our environment, including food, water and air. The vast majority of herbicides, the mainstay of no-till agriculture, are derivatives of these classes of compounds. Even cooking high protein foods leads to the formation of arylamine chemicals, some of which are potent mutagens and probable human carcinogens. Arylamine and nitroaromatic compounds are at either end of an oxidation/reduction equilibrium and are both relatively unreactive. Both arylamine and nitroaromatic compounds can be metabolized into the more reactive intermediates between the two, that is, the arylhydroxylamine and nitrosoarene compounds (Fig. 1). This review will focus attention on the chemistry of these arylhydroxylamine and nitrosoarene intermediates under biological conditions.

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References

  1. Becker, A. R., and L. A. Sternson. 1980. Nonenzymatic reduction of nitrosobenzene to phenylhydroxylamine by NAD(P)H. Bioorg. Chem. 9:305–312.

    Article  CAS  Google Scholar 

  2. Bernheim, M. L. C. 1972. The non-enzymic oxidation of NADH by nitrosobenzene. Biochem. Biophys. Res. Commun. 46:1598–1602.

    Article  PubMed  CAS  Google Scholar 

  3. Boche, G., F. Bosold and S. Schröder. 1988. N-Aryl-O-acylhydroxylamines; preparation by O-acylation or N→O transacylation and reaction with amines; model reactions for key steps connected with the carcinogenicity of aromatic amines. Angew. Chem. Int. Ed. Engl. 27:973–974.

    Article  Google Scholar 

  4. Boche, G., R. H. Sommerlade and F. Bosold. 1986. N-Aryl-O-(diphenylphosphinoyl)hydroxylamines: electrophilic amination of amines to hydrazines; a model reaction for the carcinogenicity of aromatic amines. Angew. Chem. Int. Ed. Engl. 25:562–563.

    Article  Google Scholar 

  5. Bosold, F. and G. Boche. 1990. The ultimate carcinogen, O-acetyl-N-2-(fluorenyl)hydroxylamine (“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.

    Article  Google Scholar 

  6. Boteju, L. W. and P. E. Hanna. 1993. Bioactivation of N-hydroxyaminofluorenes by N,O-acyltransferase: substituent effects on covalent binding to DNA. Carcinogenesis 14:1651–1657.

    Article  PubMed  CAS  Google Scholar 

  7. Channon, H. J., G. T. Mills, and R. T. Williams. 1944. The metabolism of 2,4,6-trinitrotoluene. Biochem. J. 38:70–85.

    PubMed  CAS  Google Scholar 

  8. Corbett, M. D. 1974. Hydroxamic acids from the reaction of active acetaldehyde with aromatic nitroso compounds. Bioorg. Chem. 3:361–365.

    Article  CAS  Google Scholar 

  9. Corbett, M. D., D. G. Baden and B. R. Chipko. 1979. The nonmicrosomal production of N-(4-chlorophenyl)-glycolhydroxamic acid from 4-chloronitrosobenzene by rat liver homogenates. Bioorg. Chem. 8:227–235.

    Article  CAS  Google Scholar 

  10. Corbett, M. D. and B. R. Chipko. 1977. N-Phenylglycolylhydroxamate production by the action of transketolase on nitrosobenzene. Biochem. J. 165:263–267.

    PubMed  CAS  Google Scholar 

  11. Corbett, M. D., B. R. Chipko and J. H. Paul. 1978. The production of hydroxamic acid metabolites of nitrosobenzene by Chlorella pyrenoidosa. J. Environ. Path. Toxicol. 1:259–266.

    CAS  Google Scholar 

  12. Corbett, M. D. and B. R. Chipko. 1980. Comparative aspects of hydroxamic acid production by thiamine-dependent enzymes. Bioorg. Chem. 9:273–287.

    Article  CAS  Google Scholar 

  13. Corbett, M. D. and B. R. Corbett. 1980. The reaction of nitroso aromatics with glyoxylic acid: a new path to hydroxamic acids. J. Org. Chem. 45:2834–2838.

    Article  CAS  Google Scholar 

  14. Corbett, M. D. and B. R. Corbett. 1981. Reductive formylation of N,N-dimethyl-p-nitrosoaniline by glyoxylic acid. Evidence for a hydroxamic acid intermediate. J. Org. Chem. 46:466–468.

    Article  CAS  Google Scholar 

  15. Corbett, M. D. and B. R. Corbett. 1981. Metabolism of 4-chloronitrobenzene by the yeast Rhodosporidium sp. Appl. Environ. Microbiol. 41:942–949.

    PubMed  CAS  Google Scholar 

  16. Corbett, M. D. and B. R. Corbett. 1982. Enzymic generation of N-[4-(dimethylamino)phenyl]acetohydroxamic acid by the action of pyruvate decarboxylase on 4-(dimethylamino)nitrosobenzene. Bioorg. Chem. 11:328–337.

    Article  CAS  Google Scholar 

  17. Corbett, M. D. and B. R. Corbett. 1983. Enzymatic preparation of [U-14C]-4-chloronitrosobenzene. Experientia 39:487–488.

    Article  CAS  Google Scholar 

  18. Corbett, M. D. and B. R. Corbett. 1985. The reactions of C-nitroso aromatics with a-oxo acids, p. 400–408. In J.W. Gorrod and L.A. Damani (ed.), Biological oxidation of nitrogen in organic molecules. Ellis Horwood, Ltd., Chichester.

    Google Scholar 

  19. Corbett, M. D. and B. R. Corbett. 1986. Effect of ring substituents on the transketolase catalyzed conversion of nitroso aromatics to hydroxamic acids. Biochem. Pharmacol. 35:3613–3621.

    Article  PubMed  CAS  Google Scholar 

  20. Corbett, M. D. and B. R. Corbett. 1987. HRP-catalyzed bioactivation of carcinogenic hydroxamic acids. The greater reactivity of glycolyl-versus acetyl-derived hydroxamic acids. Chem.-Biol. Interact. 63:249–264.

    Article  PubMed  CAS  Google Scholar 

  21. Corbett, M. D. and B. R. Corbett. 1990. Biochemical studies on the putative nitroso metabolite of chloramphenicol: a new model for the cause of aplastic anemia, p. 245–255. In P.C. Howard, S.S. Hecht and F.A. Beland (ed.), Nitroarenes: occurrence, metabolism and biological impact. Plenum Press, New York.

    Chapter  Google Scholar 

  22. Corbett, M. D. and B. R. Corbett. 1993. Studies on the nitroso-glyoxylate reaction. Relative hydroxamic acid production by glyoxylate, pyruvate, and formaldehyde in reactions with 4-nitrosobiphenyl. Chem. Res. Toxicol. 6:82–90.

    Article  PubMed  CAS  Google Scholar 

  23. Corbett, M. D., B. R. Corbett and A. O. Batchelor. 1980. The action of chloride peroxidase on 4-chloroaniline. Biochem. J. 187:893–903.

    PubMed  CAS  Google Scholar 

  24. Corbett, M. D., B. R. Corbett and D. R. Doerge. 1982. Hydroxamic acid production and active-site induced Bamberger rearrangement from the action of a-ketoglutarate dehydrogenase on 4-chloronitrosobenzene. J. Chem. Soc. Perkin I 1982:345–350.

    Article  Google Scholar 

  25. Corbett, M. D., B. R. Corbett, M.-H. Hannothiaux and S. J. Quintana. 1992. The covalent binding of acetaminophen to cellular nucleic acids as the result of the respiratory burst of neutrophils derived from the HL-60 cell line. Toxicol. Appl. Pharmacol. 113:80–86.

    Article  PubMed  CAS  Google Scholar 

  26. Corbett, M. D., D. R. Doerge and B. R. Corbett. 1983. Hydroxamic acid production by a-ketoglutarate dehydrogenase. Part 2. Evidence for an electrophilic reaction intermediate at the enzyme active site. J. Chem. Soc. Perkin I 1983:765–769.

    Article  Google Scholar 

  27. Corbett, M. D., L. O. Lim, B. R. Corbett, J. J. Johnston and P. Wiebkin. 1988. Covalent binding of N-hydroxy-2-acetylaminofluorene and N-hydroxy-2-glycolylaminofluorene to rat hepatocyte DNA: In vitro and cell-suspension studies. Chem. Res. Toxicol. 1:41–46.

    Article  PubMed  CAS  Google Scholar 

  28. Corbett, M. D., C. Wei and B. R. Corbett. 1985. Nitroreductase-dependent mutagenicity of p-nitrophenyl-hydroxylamine and its N-acetyl and N-formyl hydroxamic acids. Carcinogenesis 6:727–732.

    Article  PubMed  CAS  Google Scholar 

  29. Cramer, J. W., J. A. Miller and E. C. Miller. 1960. A new metabolic reaction observed in the rat with the carcinogen 2-AAF. J. Biol. Chem. 235:885–888.

    PubMed  CAS  Google Scholar 

  30. Doerge, D. R. and M. D. Corbett. 1985. The action of a-ketoglutarate dehydrogenase on 4-chloronitrosobenzene: evidence for species-dependent differences in active site properties. Comp. Biochem. Physiol. 80C:161–165.

    CAS  Google Scholar 

  31. Doerge, D. R. and M. D. Corbett. 1991. Peroxygenation mechanism for chloroperoxidase-catalyzed N-oxidation of arylamines. Chem. Res. Toxicol. 4:556–560.

    Article  PubMed  CAS  Google Scholar 

  32. Dölle, B., W. Töpner and H.-G. Neumann. 1980. Reaction of arylnitroso compounds with mercaptans. Xenobiotica 10:527–536.

    Article  PubMed  Google Scholar 

  33. Eyer, P. 1979. Reactions of nitrosobenzene with reduced glutathione. Chem.-Biol. Interact. 24:227–239.

    Article  PubMed  CAS  Google Scholar 

  34. Eyer, P. 1985. Reactions of nitrosoarenes with sulphydryl groups: reaction mechanism and biological significance, p. 386–399. In J.W. Gorrod and L.A. Damani (ed.), Biological oxidation of nitrogen in organic molecules. Ellis Horwood, Ltd., Chichester.

    Google Scholar 

  35. Eyer, P. 1988. Detoxication of N-oxygenated arylamines in erythrocytes. Xenobiotica 18:1327–1333.

    Article  PubMed  CAS  Google Scholar 

  36. Famulok, M., F. Bosold and G. Boche. 1989. Synthesis of N-acetoxy-2-aminonaphthalene, an ultimate carcinogen of the carcinogenic 2-naphthylamine, and its in vitro reactions with (bio)nucleophiles. Tetrahedron Lett. 30:321–324.

    Article  CAS  Google Scholar 

  37. Forrester, A. R. and R. H. Thomson. 1985. Reaction of quinones with nitrosoarenes. Z. Naturforsch. 40B:1515–1518.

    CAS  Google Scholar 

  38. Gassman, P. G. and G. A. Campbell. 1971. The mechanism of the chlorination of anilines and related aromatic amines. The Involvement of nitrenium ions. J. Amer. Chem. Soc. 93:2567–2569.

    Article  CAS  Google Scholar 

  39. Gassman, P. G., G. A. Campbell and R. C. Frederick. 1972. Nucleophilic aromatic substitution of anilines via aryl nitrenium ions (Anilenium Ions). J. Amer. Chem. Soc. 94:3884–3890.

    Article  CAS  Google Scholar 

  40. Gassman, P. G. and J. E. Granrud. 1984. Synthesis and rearrangement of methanesulfonate esters of N-hydroxyacetanilides. A model for a penultimate carcinogen. J. Amer. Chem. Soc. 106:1498–1499.

    Article  CAS  Google Scholar 

  41. Gassman, P. G. and J. E. Granrud. 1984. Isolation, characterization, and rearrangement of cis-and trans-N-acetyl-2-amino-5,6-dimethoxy-5-methylcyclohexa-l,3-diene. Models for the proposed precursors of meta-substituted products from carcinogenic aromatic amines. J. Amer. Chem. Soc. 106:2448–2449.

    Article  CAS  Google Scholar 

  42. Gilissen, R. A. H. J., D. P. Ringer, H. J. F. C. Stavenuiter, G. J. Mulder and J. H. N. Meerman. 1992. Sulfation of hydroxylamines and hydroxamic acids in liver cytosol from male and female rats and purified aryl sulfotransferase IV. Carcinogenesis 13:1699–1703.

    Article  PubMed  CAS  Google Scholar 

  43. Gorrod, J. W. and D. Manson. 1986. The metabolism of aromatic amines. Xenobiotica 16:933–955.

    Article  PubMed  CAS  Google Scholar 

  44. Gowenlock, B. G. and W. Lüttke. 1958. Structure and properties of C-nitroso-compounds. Quarterly Rev. 12:321–340.

    Article  CAS  Google Scholar 

  45. Gowenlock, B. G. and K. J. McCullough. 1989. Structure of the trans-dimer of 2,6-di-isopropylni-trosobenzene. J. Chem. Soc. Perkin Trans. II 1989:551–553.

    Article  Google Scholar 

  46. Groenewegen, P. E. J., P. Breeuwer, J. M. L. M. van Helvoort, A. A. M. Langenhoff, F. P. deVries and J. A. M. deBont. 1992. Novel degradative pathway of 4-nitrobenzoate in Comamonas acidovorans NBA-10. J. Gen. Microbiol. 138:1599–1605.

    Article  PubMed  CAS  Google Scholar 

  47. Guengerich, F. P. and T. Shimada. 1991. Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem. Res. Toxicol. 4:391–407.

    Article  PubMed  CAS  Google Scholar 

  48. Haigler, B. E. and J. C. Spain. 1993. Biodegradation of 4-nitrotoluene by Pseudomonas sp. strain 4NT. Appl. Environ. Microbiol. 59:2239–2243.

    PubMed  CAS  Google Scholar 

  49. Halliwell, B., J. M. C. Gutteridge, and C. E. Cross. 1992. Free radicals, antioxidants and human disease: where are we now. J. Lab. Clin. Med. 119:598–620.

    PubMed  CAS  Google Scholar 

  50. Hanna, P. E. and R. B. Banks. 1985. Arylhydroxylamines and arylhydroxamic acids: conjugation reactions, p. 375–402. In M.W. Anders (ed), Bioactivation of foreign compounds. Academic Press, Orlando.

    Google Scholar 

  51. Hein, D. W. 1988. Acetylator genotype and arylamine-induced carcinogenesis. Biochim. Biophys. Acta 948:37–66.

    PubMed  CAS  Google Scholar 

  52. Helmick, J. S., K. A. Martin, J. L. Heinrich and M. Novak. 1991. Mechanism of the reaction of carbon and nitrogen nucleophiles with the model carcinogens O-pivaloyl-N-arylhydroxylamines: competing SN2 substitution and SN1 solvolysis. J. Amer. Chem. Soc. 113:3459–3466.

    Article  CAS  Google Scholar 

  53. Helmick, J. S. and M. Novak. 1991. Nucleophilic substitution at nitrogen and carboxyl carbon of N-aryl-O-pivaloylhydroxylamines in aqueous solution: competition with SN1 solvolysis of model carcinogens. J. Org. Chem. 56:2925–2927.

    Article  CAS  Google Scholar 

  54. Hlavica, P. 1982. Biological oxidation of nitrogen in organic compounds and disposition of N-oxidized products. CRC Crit. Rev. Biochem. 12:39–101.

    Article  PubMed  CAS  Google Scholar 

  55. Hlavica, P., I. Golly and J. Mietaschk. 1983. Comparative studies on the cumene hydroperoxide-and NADPH-supported N-oxidation of 4-chloroaniline by cytochrome P-450. Biochem. J. 212:539–547.

    PubMed  CAS  Google Scholar 

  56. Ibne-Rasa, K. M. and J. O. Edwards. 1962. The mechanism of the oxidation of some aromatic amines by peroxyacetic acid. J. Amer. Chem. Soc. 84:763–768.

    Article  CAS  Google Scholar 

  57. Kalhorn, T., A. R. Becker and L. A. Sternson. 1981. Evidence for general catalysis and formation of nitrobenzene in the oxidation of phenylhydroxylamine in aqueous phosphate buffer. Bioorg. Chem. 10:144–151.

    Article  CAS  Google Scholar 

  58. Kazanis, S. and R. A. McClelland. 1992. Electrophilic intermediate in the reaction of glutathione and nitrosoarenes. J. Amer. Chem. Soc. 114:3052–3059.

    Article  CAS  Google Scholar 

  59. Klehr, H., P. Eyer and W. Schäfer. 1985. On the mechanism of reactions of nitrosoarenes with thiols. Biol. Chem. Hoppe-Seyler 366:755–760.

    Article  PubMed  CAS  Google Scholar 

  60. 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.

    Article  Google Scholar 

  61. Koerber, S. C., P. Schack, A. M.-J. Au and M. F. Dunn. 1980. Investigation of a novel liver alcohol dehydrogenase catalyzed redox-elimination reaction involving arylnitroso substrate analogues. Biochemistry 19:731–738.

    Article  PubMed  CAS  Google Scholar 

  62. Kohnstam, G., W. A. Petch and D. L. H. Williams. 1984. Kinetic substituent and isotope effects in the acid-catalyzed rearrangement of N-phenylhydroxylamines. Are nitrenium ions involved? J. Chem. Soc. Perkin Trans. II 1984:423–427.

    Article  Google Scholar 

  63. 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.

    Article  PubMed  CAS  Google Scholar 

  64. Land, S. J., K. Zukowski, M.-S. Lee, C. Y. Wang and C. M. King. 1993. Purification and characterization of a rat hepatic acetyltransferase that can metabolize aromatic amine derivatives. Carcinogenesis 14:1441–1449.

    Article  PubMed  CAS  Google Scholar 

  65. 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.

    Article  PubMed  CAS  Google Scholar 

  66. Lim, L. O., B. R. Corbett and M. D. Corbett. 1987. Irreversible inhibition of the cytosolic metabolism of N-hydroxy-2-acetylaminofluorene by its glycolyl analog. Cancer Lett. 37:205–211.

    Article  PubMed  CAS  Google Scholar 

  67. Liu, Y.-Y., A. Y. H. Lu, R. A. Stearns and S.-H. L. Chiu. 1992. In vivo covalent binding of [14C]trinitrotoluene to proteins in the rat. Chem.-Biol. Interact. 82:1–19.

    Article  PubMed  CAS  Google Scholar 

  68. Lobo, A. M., M. M. Marques, S. Prabhakar and J. S. Rzepa. 1987. Tetrahedral intermediates formed by nitrogen and oxygen attack of aromatic hydroxylamines on acetyl cyanide. J. Org. Chem. 52:2925–2927.

    Article  CAS  Google Scholar 

  69. Lutz, R. E. and M. R. Lytton. 1937. Oxidation-reduction potentials of a series of nitrosobenzene-phenyl-hydroxylamine systems. J. Org. Chem. 2:68–75.

    Article  CAS  Google Scholar 

  70. Mangold, B. L. K., J. Erickson, C. Lohr, D. J. McCann and J. B. Mangold. 1990. Self-catalyzed irreversible inactivation of rat hepatic aryl sulfotransferase IV by N-hydroxy-2-acetylaminofluorene. Carcinogenesis 11:1563–1567.

    Article  PubMed  CAS  Google Scholar 

  71. Maples, K. R., P. Eyer and R. P. Mason. 1990. Aniline-, phenylhydroxylamine-, nitrosobenzene-, and nitrobenzene-induced hemoglobin thiyl free radical formation in vivo and in vitro. Molec. Pharmacol. 37:311–318.

    CAS  Google Scholar 

  72. 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.

    Article  PubMed  CAS  Google Scholar 

  73. Mason, R. P. 1982. Free-radical intermediates in the metabolism of toxic chemicals, p. 161–222. In W.A. Pryor (ed.), Free radicals in biology. Academic Press, New York.

    Google Scholar 

  74. Michels, J. and G. Gottschalk. 1994. Inhibition of the lignin peroxidase of Phanerochaete chrysosporium by hydroxylamino-dinitrotoluene, an early intermediate in the degradation of 2,4,6-trinitrotoluene. Appl. Environ. Microbiol. 60:187–194.

    PubMed  CAS  Google Scholar 

  75. Minchin, R. F., K. F. Ilett, C. H. Teitel, P. T. Reeves and F. F. Kadlubar. 1992. Direct O-acetylation of N-hydroxy arylamines by acetylsalicylic acid to form carcinogen-DNA adducts. Carcinogenesis 13:663–667.

    Article  PubMed  CAS  Google Scholar 

  76. Nishino, S. F. and J. C. Spain. 1993. Degradation of nitrobenzene by a Pseudomonas pseudoalcaligenes. Appl. Environ. Microbiol. 59:2520–2525.

    PubMed  CAS  Google Scholar 

  77. 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. Amer. Chem. Soc. 115:9453–9460.

    Article  CAS  Google Scholar 

  78. Novak, M. and R. K. Lagerman. 1988. Hydrolysis of Fe2+-induced reduction of N-aryl-O-pivaloylhydroxylamines: aqueous solution chemistry of model carcinogens. J. Org. Chem. 53:4762–4769.

    Article  CAS  Google Scholar 

  79. Novak, M., K. A. Martin and J. L. Heinrich. 1989. SN2 reactions of a carbon nucleophile with N-aryl-O-pivaloylhydroxylamines: a model for in vivo reactions of carcinogenic metabolites of aromatic amines. J. Org. Chem. 54:5430–5431.

    Article  CAS  Google Scholar 

  80. Novak, M., M. Pelecanou. A. K. Roy, A. F. Andronico, F. M. Plourde, T. M. Olefirowicz and T. J. Curtin. 1984. Solvolysis of N-sulfonoxyacetanilides in aqueous and alcohol solutions: generation of electrophilic species. J. Amer. Chem. Soc. 106:5623–5631.

    Article  CAS  Google Scholar 

  81. Novak, M. and A. K. Roy. 1985. Hydrolysis of N-(sulfonatooxy)-p-acetotoluidide: solution chemistry of models for carcinogenic metabolites of aromatic amides. J. Org. Chem. 50:571–580.

    Article  CAS  Google Scholar 

  82. Panda, M., M. Novak and J. Magonski. 1989. Hydrolysis kinetics of the ultimate hepatocarcinogen N-(sulfonatooxy)-2-(acetylamino)fluorene: detection of long-lived hydrolysis intermediates. J. Amer. Chem. Soc. 111:4524–4525.

    Article  CAS  Google Scholar 

  83. Pearson, R. G. and J. Songstad. 1967. Application of the principle of hard and soft acids and bases to organic chemistry. J. Amer. Chem. Soc. 89:1827–1836.

    Article  CAS  Google Scholar 

  84. Pelecanou, M. and M. Novak. 1985. Oxidation-reduction reactions of N-sulfonoxyacetanilides: mechanisms of the halide-induced reduction of models for the carcinogenic metabolites of aromatic amides. J. Amer. Chem. Soc. 107:4499–4503.

    Article  CAS  Google Scholar 

  85. Ringer, D. P., T. R. Norton and R. R. Self. 1992. Reaction product inactivation of aryl sulfotransferase IV following electrophilic substitution by the sulfuric acid ester of N-hydroxy-2-acetylaminofluorene. Carcinogenesis 13:107–112.

    Article  PubMed  CAS  Google Scholar 

  86. Sakamoto, Y., T. Yoshioka and T. Uematsu. 1989. N-Arylhydroxamic acids: reaction of nitroso aromatics with α-oxo acids. J. Org. Chem. 54:4449–4453.

    Article  CAS  Google Scholar 

  87. Sone, T., Y. Tokuda, T. Sakai, S. Shinkai and O. Manabe. 1981. Kinetics and mechanisms of the Bamberger rearrangement. Part 3. Rearrangement of phenylhydroxylamines to p-aminophenols in aqueous sulphuric acid solution. J. Chem. Soc. Perkin. Trans. II 1981:298–302.

    Article  Google Scholar 

  88. Ulbrich, R., M. Famulok, F. Bosold and G. Boche. 1990. SN2 at nitrogen: the reaction of N-(4-cyanophenyl)-O-diphenylphosphinoylhydroxylamine with N-methylaniline. A model for the reactions of ultimate carcinogens of aromatic amines with (bio)nucleophiles. Tetrahedron Lett. 31:1689–1692.

    Article  CAS  Google Scholar 

  89. Weisburger, E. K. 1978. Mechanism of chemical carcinogenesis. Ann. Rev. Pharmacol. Toxicol. 18:395–415.

    Article  CAS  Google Scholar 

  90. Yoshioka, T., T. Suzuki and T. Uematsu. 1989. Biotransformation of N-substituted aromatic compounds in mammalian spermatozoa. Nonoxidative formation of N-hydroxy-N-arylacetamides from nitroso aromatic compounds. J. Biol. Chem. 264:12432–12438.

    PubMed  CAS  Google Scholar 

  91. Yoshioka, T. and T. Uematsu. 1993. Formation of N-hydroxy-N-arylacetamides from nitrosoaromatic compounds by the mammalian pyruvate dehydrogenase complex. Biochem. J. 290:783–790.

    PubMed  CAS  Google Scholar 

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  1. Eppley Institute for Cancer Research, University of Nebraska Medical Center, 600 S. 42nd Street, Omaha, NE, 68198-6805, USA

    Michael D. Corbett & Bernadette R. Corbett

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  1. Armstrong Laboratory, Tyndall Air Force Base, Florida, USA

    Jim C. Spain

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Corbett, M.D., Corbett, B.R. (1995). Bioorganic Chemistry of the Arylhydroxylamine and Nitrosoarene Functional Groups. In: Spain, J.C. (eds) Biodegradation of Nitroaromatic Compounds. Environmental Science Research, vol 49. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-9447-2_10

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