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1
Two rotameric forms of open ring 7-methylguanine are present in alkylated polynucleotides.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。
Nucleic Acids Res. 1984 Jul 11;12(13):5429-39. doi: 10.1093/nar/12.13.5429.
2
Imidazole open ring 7-methylguanine: an inhibitor of DNA synthesis.咪唑开环7-甲基鸟嘌呤：一种DNA合成抑制剂。
Biochem Biophys Res Commun. 1983 Jan 27;110(2):552-8. doi: 10.1016/0006-291x(83)91185-3.
3
Ring-opened alkylated guanine is not repaired in Z-DNA.开环烷基化鸟嘌呤在Z-DNA中无法修复。
Nature. 1984;310(5980):798-800. doi: 10.1038/310798a0.
4
Mutagenic specificity of imidazole ring-opened 7-methylpurines in M13mp18 phage DNA.M13mp18噬菌体DNA中咪唑环开环的7-甲基嘌呤的诱变特异性。
Acta Biochim Pol. 1999;46(3):785-99.
5
Detection of the sites of alkylation in DNA and polynucleotides by laser Raman spectroscopy.用激光拉曼光谱法检测DNA和多核苷酸中的烷基化位点
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6
Release of 7-methylguanine residues whose imidazole rings have been opened from damaged DNA by a DNA glycosylase from Escherichia coli.通过来自大肠杆菌的一种DNA糖基化酶从受损DNA中释放出咪唑环已打开的7-甲基鸟嘌呤残基。
Nucleic Acids Res. 1979 Aug 10;6(11):3673-84. doi: 10.1093/nar/6.11.3673.
7
Alkaline opening of imidazole ring of 7-methylguanosine. 2. Further studies on reaction mechanisms and products.
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8
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9
Interaction of the antitumor antibiotic mitomycin C with Z-DNA.
J Biomol Struct Dyn. 1988 Dec;6(3):459-70. doi: 10.1080/07391102.1988.10506500.
10
Formamidopyrimidine DNA glycosylase in the yeast Saccharomyces cerevisiae.酿酒酵母中的甲酰胺基嘧啶DNA糖基化酶
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N-(2-Deoxy-d- erythro-pentofuranosyl)-2,6-diamino-3,4-dihydro-4-oxo-5- N-(2-hydroxy-3-buten-1-yl)-formamidopyrimidine Adducts of 1,3-Butadiene: Synthesis, Structural Identification, and Detection in Human Cells.N-(2-脱氧-d-赤戊呋喃糖基)-2,6-二氨基-3,4-二氢-4-氧代-5-N-(2-羟基-3-丁烯-1-基)-甲酰胺嘧啶与 1,3-丁二烯的加合物：合成、结构鉴定及在人细胞中的检测。
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本文引用的文献

1
Purification and characterization of Escherichia coli formamidopyrimidine-DNA glycosylase that excises damaged 7-methylguanine from deoxyribonucleic acid.从脱氧核糖核酸中切除受损7-甲基鸟嘌呤的大肠杆菌甲酰胺基嘧啶-DNA糖基化酶的纯化与特性分析
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2
Enzymatic release of 7-methylguanine from methylated DNA by rodent liver extracts.啮齿动物肝脏提取物对甲基化DNA中7-甲基鸟嘌呤的酶促释放。
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3
Release of 7-methylguanine residues from alkylated DNA by extracts of Micrococcus luteus and Escherichia coli.藤黄微球菌和大肠杆菌提取物对烷基化DNA中7-甲基鸟嘌呤残基的释放作用
Proc Natl Acad Sci U S A. 1981 Feb;78(2):852-5. doi: 10.1073/pnas.78.2.852.
4
Escherichia coli mutants deficient in 3-methyladenine-DNA glycosylase.缺乏3-甲基腺嘌呤-DNA糖基化酶的大肠杆菌突变体。
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Identification of N5-methyl-N5-formyl-2,5,6-triamino-4-hydroxypyrimidine as a major adduct in rat liver DNA after treatment with the carcinogens, N,N-dimethylnitrosamine or 1,2-dimethylhydrazine.鉴定 N5-甲基-N5-甲酰基-2,5,6-三氨基-4-羟基嘧啶为大鼠肝脏 DNA 在经致癌物 N,N-二甲基亚硝胺或 1,2-二甲基肼处理后形成的主要加合物。
Biochem Biophys Res Commun. 1983 Jan 27;110(2):625-31. doi: 10.1016/0006-291x(83)91195-6.
6
Imidazole open ring 7-methylguanine: an inhibitor of DNA synthesis.咪唑开环7-甲基鸟嘌呤：一种DNA合成抑制剂。
Biochem Biophys Res Commun. 1983 Jan 27;110(2):552-8. doi: 10.1016/0006-291x(83)91185-3.
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DNA repair enzymes.DNA修复酶
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8
Possible relevance of O-6 alkylation of deoxyguanosine to the mutagenicity and carcinogenicity of nitrosamines and nitrosamides.脱氧鸟苷的O-6烷基化与亚硝胺和亚硝酰胺的致突变性和致癌性之间可能存在的关联。
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9
Specific excision of methylation products from DNA of Escherichia coli treated with N-methyl-N'-nitro-N-nitrosoguanidine.从用N-甲基-N'-硝基-N-亚硝基胍处理的大肠杆菌DNA中特异性切除甲基化产物
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10
Methylation of ribonucleic acid by the carcinogens dimethyl sulphate, N-methyl-N-nitrosourea and N-methyl-N'-nitro-N-nitrosoguanidine. Comparisons of chemical analyses at the nucleoside and base levels.致癌物质硫酸二甲酯、N-甲基-N-亚硝基脲和N-甲基-N'-硝基-N-亚硝基胍对核糖核酸的甲基化作用。核苷和碱基水平化学分析的比较。
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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.

DOI:10.1093/nar/12.13.5429
PMID:6462910
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC318929/
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。