Underwood G R, Price M F, Shapiro R
Department of Chemistry, New York University, NY 10003.
Carcinogenesis. 1988 Oct;9(10):1817-21. doi: 10.1093/carcin/9.10.1817.
The carcinogen N-acetoxy-N-2-acetylaminofluorene reacts with dG and dG-containing nucleotides to give good yields of the C-8 adducts, but the analogous 4-aminobiphenyl derivative does not. Replacement of the N-acetoxy group by 2,6-dichlorobenzoyloxy circumvents this difficulty. This reaction is shown to be generally applicable, and biphenylamido adducts with dG, d(CpG), d(GpC) and d(ApG) have been prepared. A new, useful deacetylation procedure employing the heterogeneous system sodium carbonate/methanol which leads to the corresponding biphenylamino derivative without appreciable imidazole ring opening is also reported.
致癌物N-乙酰氧基-N-2-乙酰氨基芴与dG及含dG的核苷酸反应，能高产率地生成C-8加合物，但类似的4-氨基联苯衍生物则不能。用2,6-二氯苯甲酰氧基取代N-乙酰氧基可避免这一难题。该反应被证明具有普遍适用性，已制备出与dG、d(CpG)、d(GpC)和d(ApG)的联苯酰胺加合物。还报道了一种新的、有用的脱乙酰化方法，该方法采用碳酸钠/甲醇非均相体系，能生成相应的联苯氨基衍生物，且咪唑环无明显开环。
