Franzén R, Morita M, Tanabe K, Takagi H, Shibata Y
National Institute for Environmental Studies, Ibaraki, Japan.
Chem Res Toxicol. 1997 Oct;10(10):1186-91. doi: 10.1021/tx970036d.
Several genotoxic butenedioic acids present in chlorine-disinfected drinking water were allowed to react with adenosine, guanosine, and cytidine in aqueous solution. HPLC analyses, with detection at 254 and 310 nm, showed that clearly detectable products were formed only in the reactions with adenosine. The major products from the reactions between either 2-chloro-3-methyl-2-butenedioic acid (ox-MCF) or 2-chloro-3-(chloromethyl)-2-butenedioic acid (ox-CMCF) and adenosine were the same. This substance was isolated by C18 column chromatography and characterized by UV absorbance, 1H and 13C NMR spectroscopy, and mass spectrometry. It was identified as 3-(beta-D-ribofuranosyl)-7-carboxy-7-formyl-8-[9'-(beta-D-ribofuranosyl) -N6- adenosinyl]-1,N6-ethanoadenosine (cf epsilon A,A). The yields of cf epsilon A,A in reactions performed at pH 7.4 and 37 degrees C were 0.7% and 0.3% with ox-MCF and ox-CMCF, respectively.
让氯消毒饮用水中存在的几种具有基因毒性的丁烯二酸与水溶液中的腺苷、鸟苷和胞苷发生反应。通过在254和310 nm处进行检测的高效液相色谱分析表明，仅在与腺苷的反应中形成了可清晰检测到的产物。2-氯-3-甲基-2-丁烯二酸（ox-MCF）或2-氯-3-（氯甲基）-2-丁烯二酸（ox-CMCF）与腺苷反应的主要产物相同。该物质通过C18柱色谱法分离，并通过紫外吸收、1H和13C核磁共振光谱以及质谱进行表征。它被鉴定为3-（β-D-呋喃核糖基）-7-羧基-7-甲酰基-8-[9'-（β-D-呋喃核糖基）-N6-腺苷基]-1,N6-乙撑腺苷（cf εA,A）。在pH 7.4和37℃下进行的反应中，ox-MCF和ox-CMCF生成cf εA,A的产率分别为0.7%和0.3%。
