By Richard A. Scanlan and Steven R. Tannenbaum (Eds.)
content material: Activation of nitrosamines to organic alkylating brokers / C.J. Michejda, M.B. Kroeger-Koepke, S.R. Koepke, and D.H. Sieh --
Chemical and biochemical alterations of [beta]-oxidized nitrosamines / Richard N. Loeppky, Jerry R. Outram, Witold Tomasik, and Wayne McKinley --
Mechanisms of alkylation of DNA through N-nitrosodialkylamines / Michael C. Archer and Kwang-Hang Leung --
The metabolism of cyclic nitrosamines / Stephen S. Hecht, G. David McCoy, Chi-Hong B. Chen, and Dietrich Hoffmann --
results of constitution at the carcinogenic habit of nitrosamines / John S. Wishnok --
Structure-activity relationships between N-nitroso compounds / William Lijinsky --
Chemistry of a few N-nitrosamides / Clive N. Berry, Brian C. Challis, Andrew D. Gribble, and Susan P. Jones --
fuel section reactions of N, N-dimethylhydrazine with ozone and NOx in simulated atmospheres : facile formation of N-nitrosodimethylamine / William P.L. Carter, Ernesto C. Tuazon, Arthur M. Winer, and J.N. Pitts, Jr. --
attainable mechanisms of nitrosamine formation in insecticides / Larry ok. Keefer --
Formation and inhibition of N-nitrosodiethanolamine in an anionic oil-water emulsion / B.L. Kabacoff, R.J. Lechnir, S.F. Vielhuber, and M.L. Douglass --
The function of micro organism in nitrosamine formation / D. Ralt and S.R. Tannenbaum --
Formation of N-nitroso compounds in meals / J. Ian grey --
N-nitrosomorpholine synthesis in rodents uncovered to nitrogen dioxide and morpholine / Sidney S. Mirvish, Phillip Issenberg, and James P. Sams --
blockading nitrosation reactions in vivo / William J. Mergens and Harold L. Newmark --
prevalence of N-nitrosamines within the place of work : a few fresh advancements / D.H. nice and D.P. Rounbehler --
relief of human publicity to environmental N-nitroso compounds / R. Preussmann, B. Spiegelhalder, and G. Eisenbrand --
N-nitrosamines in beer / Mario M. Mangino, Richard A. Scanlan, and Terence J. O'Brien --
Formation, incidence, and carcinogenicity of N-nitrosamines in tobacco items / Dietrich Hoffmann, John D. Adams, Klaus D. Brunnemann, and Stephen S. Hecht --
N-nitrosamine formation in soil from the herbicide glyphosate and its uptake through crops / Shahamat U. Khan --
response of meat materials with nitrite / R.G. Cassens, okay. Izumi, M. Lee, M.L. Greaser, and J. Lozano --
N-nitroso compounds : nutrition and melanoma tendencies : an method of the prevention of gastric melanoma / John H. Weisburger --
The microecology of gastric melanoma / Pelayo Correa and Steven R. Tannenbaum --
Analytical tools for nitrosamines / Phillip Issenberg --
Pesticide-derived nitrosamines : incidence and environmental destiny / James E. Oliver --
relief of nitrosamine impurities in pesticide formulations / G.W. Probst --
coverage and regulatory features of N-nitroso contaminants in pesticide items / Gunter Zweig and Willa Garner.
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Extra info for N-Nitroso Compounds
Example text
2 CHj-N=N-OH • 3 CH 3 CHfty C H C H C H 2 lVcH 2 C or NO OH CHjCHjCHjN-CHj-CH-CHjA 3 2 2 3 3 OH * NO CH CH,ÇH-NCH, A -> C H C H C H N C H A uthors' explanation for Kriiger's experiments. ch002 32 N-NITROSO COMPOUNDS Scheme 5. OH Transformation expected to spontaneously follow enzymatic a'-hydroxylation of a β-hydroxynitrosamine. NO -C—CH OH 3 W> - C - C H 3 + H+ NO 2. LOEPPKY ET AL. ch002 The Discovery of the Biochemical Retroaldol Cleavage of βHydroxynitrosamines. With due consideration to the forgoing we have taken up ex periments to demonstrate whether or not our hypothesis relating to a biochemical retroaldol cleavage of β-hydroxynitrosamines has any v a l i d i t y .
Food Chem. 1977,25, 422. 24. L. Scientia Sinica. 1979, 22, 471. 25. ; Eisenbrand, G. Z. Krebsforsch. 1976, 85, 125. 26. ; Enders, D. Angew. Chem. Internat. Ed. 1975, 14, 15. 27. ; Enders, D. Chem. Ber. 1975, 108, 1293. 28. ; Seebach, D. Chem. Ber. 1977, 110, 1866. 29. ; Seebach, D. Chem. Ber. 1978, 111, 2630. 30. ; Wykpiel, W. Synthesis 1979, 1979, 423. 31. ; Seebach, D. Tetrahedron Lett. 1980, 21, 1927. 32. ; Chuaqui-Offermanns, N. J . Amer. Chem. Soc. 1980, 102, 1426. 33. ; Faulconer, J . R. manuscript i n preparation.
Ch002 The Discovery of the Biochemical Retroaldol Cleavage of βHydroxynitrosamines. With due consideration to the forgoing we have taken up ex periments to demonstrate whether or not our hypothesis relating to a biochemical retroaldol cleavage of β-hydroxynitrosamines has any v a l i d i t y . As a result of our research on the base induced fragmentation of β-hydroxynitrosamines we chose four substrates to investigate this p o s s i b i l i t y . A l l of these compounds have been shown to undergo the base induced cleavage with the f a c i l i t y and we reasoned that a biochemical cleavage of these compounds would l i k e l y have a similar transition state to the organochemical transformation.