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单核苷酸乙基化的氢键催化作用支持N-乙基-N-亚硝基脲对DNA的非随机烷基化作用。

Hydrogen bond catalysis of mononucleotide ethylation supports non-random DNA alkylations by N-ethyl, N-nitrosourea.

作者信息

Stahl K W, Köster F E

出版信息

Experientia. 1984 Jul 15;40(7):734-6. doi: 10.1007/BF01949749.

DOI:10.1007/BF01949749
PMID:6745405
Abstract

The axial (ax.) and equatorial (eq.) diastereomeric forms of phosphate triesters resulting from reactions of N-ethyl, N-nitrosourea with 3 cyclic mononucleotides were analyzed by column liquid chromatography (CLC). Evidence is presented that the 2'OH group of 3', 5'cAMP essentially contributes to the stereoselective eq. alkyl substitution, most probably by hydrogen bonding catalysis. The neighboring group direction of ethylation gives substantial support to non-random DNA alkylations by NEU.

摘要

通过柱液相色谱（CLC）分析了N-乙基-N-亚硝基脲与3种环状单核苷酸反应生成的磷酸三酯的轴向（ax.）和赤道（eq.）非对映体形式。有证据表明，3',5'-环磷酸腺苷（cAMP）的2'-OH基团主要通过氢键催化作用，对立体选择性赤道烷基取代有贡献。乙基化的邻基定向为NEU对DNA的非随机烷基化提供了有力支持。

相似文献

1
Hydrogen bond catalysis of mononucleotide ethylation supports non-random DNA alkylations by N-ethyl, N-nitrosourea.单核苷酸乙基化的氢键催化作用支持N-乙基-N-亚硝基脲对DNA的非随机烷基化作用。
Experientia. 1984 Jul 15;40(7):734-6. doi: 10.1007/BF01949749.
2
Effect of alkylation with N-methyl-N-nitrosourea and N-ethyl-N-nitrosourea on the secondary structure of DNA.用N-甲基-N-亚硝基脲和N-乙基-N-亚硝基脲进行烷基化对DNA二级结构的影响。
Biosci Rep. 1984 Sep;4(9):729-35. doi: 10.1007/BF01128813.
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Alkylation of deoxyribonucleic acid by carcinogens dimethyl sulphate, ethyl methanesulphonate, N-ethyl-N-nitrosourea and N-methyl-N-nitrosourea. Relative reactivity of the phosphodiester site thymidylyl(3'-5')thymidine.致癌物硫酸二甲酯、甲磺酸乙酯、N-乙基-N-亚硝基脲和N-甲基-N-亚硝基脲对脱氧核糖核酸的烷基化作用。磷酸二酯位点胸苷酰（3'-5'）胸苷的相对反应活性。
Biochem J. 1978 Jun 1;171(3):575-87. doi: 10.1042/bj1710575.
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Alkylation of ribose in RNA reacted with ethylnitrosourea at neutrality.在中性条件下，RNA中的核糖与乙基亚硝基脲发生烷基化反应。
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Nature. 1978 Nov 2;276(5683):85-8. doi: 10.1038/276085a0.
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The alkaline hydrolysis of phosphotriesters in alkylated mammalian DNA.烷基化哺乳动物DNA中磷酸三酯的碱性水解
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The specificity of different classes of ethylating agents toward various sites in RNA.不同种类的乙基化剂对RNA中各个位点的特异性。
Biochemistry. 1975 Feb 25;14(4):772-82. doi: 10.1021/bi00675a020.

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本文引用的文献

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Persistence of alkylated DNA bases in the Mongolian gerbil (Meriones unguiculatus) following a single dose of methylnitrosourea +.亚硝脲单剂量处理后蒙古沙鼠（Meriones unguiculatus）体内烷基化 DNA 碱基的持续存在。
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N-Acetoxy-acetylaminofluorene reacts preferentially with a control region of intracellular SV40 chromosome.N-乙酰氧基-乙酰氨基芴优先与细胞内SV40染色体的一个调控区域发生反应。
Nature. 1981 May 7;291(5810):84-5. doi: 10.1038/291084a0.
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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。
Nature. 1969 Jul 12;223(5202):206-7. doi: 10.1038/223206a0.
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High-pressure liquid chromatography of modified purine mononucleotides and nucleosides.修饰嘌呤单核苷酸和核苷的高压液相色谱法
J Chromatogr. 1973 Aug 29;83:395-404. doi: 10.1016/s0021-9673(00)97056-0.