在烷基化多核苷酸中存在开环7-甲基鸟嘌呤的两种旋转异构体形式。
Two rotameric forms of open ring 7-methylguanine are present in alkylated polynucleotides.
作者信息
Boiteux S, Belleney J, Roques B P, Laval J
出版信息
Nucleic Acids Res. 1984 Jul 11;12(13):5429-39. doi: 10.1093/nar/12.13.5429.
Abstract
High performance liquid chromatography analysis of imidazole open ring 7-methylguanine, 2-6 diamino-4-hydroxy-5N-methyl-formamidopyrimidine (rom7G), showed two well-separated peaks (fI and fII) of the same magnitude. Rechromatography of each isolated component indicated that they are slowly interconverted to give a 1:1 mixture. NMR analysis demonstrated that the two species observed on reversed phase HPLC are rotational isomers. Thermodynamic measurements strongly suggested that the equilibrium can be assigned to rotation around the N-methyl formamido bond. The two species, fI and fII, separated by HPLC were identified as rotamers E and Z, respectively. The structures of fI and fII were also determined. A polynucleotide containing rom7G was obtained by alkaline treatment of poly (dGC) containing 7-methylguanine. In order to study its structure within the polynucleotide, rom7G was enzymatically excized by E.coli rom7G-DNA glycosylase. The analysis of the products released by the enzyme showed a 1:4 mixture of the two rotamers favoring the Z form (fII).
摘要
对咪唑开环的7-甲基鸟嘌呤、2,6-二氨基-4-羟基-5N-甲基-甲酰胺基嘧啶（rom7G）进行高效液相色谱分析，结果显示出两个大小相同、分离良好的峰（fI和fII）。对每个分离组分进行再色谱分析表明，它们会缓慢相互转化，形成1:1的混合物。核磁共振分析表明，在反相高效液相色谱上观察到的这两种物质是旋转异构体。热力学测量结果有力地表明，该平衡可归因于围绕N-甲基甲酰胺键的旋转。通过高效液相色谱分离出的两种物质fI和fII，分别被鉴定为旋转异构体E和Z。还确定了fI和fII的结构。通过对含有7-甲基鸟嘌呤的聚（dGC）进行碱性处理，得到了一种含有rom7G的多核苷酸。为了研究其在多核苷酸中的结构，利用大肠杆菌rom7G-DNA糖基化酶酶切去除rom7G。对该酶释放产物的分析表明，两种旋转异构体的混合物比例为1:4，其中Z型（fII）占优势。
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