| he mechanisms of bioactivation of ethanolnitrosamines such as N-nitrosodiethanolamine (NDELA) are still under intensive investigation. Several hypotheses have been proposed based on individual experimental observations by others. In this work, the chemistry of some reactive nitrosamines related to those hypotheses were studied.;The reaction of 3-methyl-1,2,3-oxadiazolinium tosylate (MeOX) with acyclovir was re-examined. Using NMR NOESY experiments, the structure of the reaction intermediate and the major products from the hydrolysates were confirmed as N;The reactive epoxide intermediate N-nitroso-2,3-epoxymorpholine (NEMOR) was synthesized by reacting dimethyldioxirane (DMD) with N-nitroso-2,3-didehydromorpholine (NDMOR) in high yield and purity. Treatment of NEMOR with 1 equivalent of glacial acetic acid afforded N-nitroso-2-acetoxy-3-hydroxymorpholine (NAHMOR). Both NEMOR and NAHMOR decompose in aqueous solution rapidly while the decomposition of NEMOR is much faster. Reaction of NEMOR and dG generated O;Two standards for the development of ;The important precursor for the NDELA... |
