含诱变碱基类似物4-O-乙基胸腺嘧啶的寡脱氧核苷酸的合成与表征
Synthesis and characterization of oligodeoxynucleotides containing the mutagenic base analogue 4-O-ethylthymine.
作者信息
Fernandez-Forner D, Palom Y, Ikuta S, Pedroso E, Eritja R
机构信息
Department of Organic Chemistry, University of Barcelona, Spain.
出版信息
Nucleic Acids Res. 1990 Oct 11;18(19):5729-34. doi: 10.1093/nar/18.19.5729.
Abstract
A method for the preparation of oligonucleotides containing the mutagenic base 4-O-ethylthymine is described for the first time. Use of p-nitrophenylethyl type base protecting groups together with phosphitetriester solid-phase methodology makes possible the rapid and efficient preparation of oligonucleotides bearing 4-O-ethylthymine, while standard base protecting groups are not compatible with the presence of this base. Possible applications of this methodology are discussed.
摘要
首次描述了一种制备含有诱变碱基4-O-乙基胸腺嘧啶的寡核苷酸的方法。对硝基苯乙基型碱基保护基团与亚磷酸三酯固相方法的使用使得快速有效地制备带有4-O-乙基胸腺嘧啶的寡核苷酸成为可能，而标准碱基保护基团与该碱基的存在不相容。讨论了该方法的可能应用。
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本文引用的文献
1
Mechanisms of carcinogenesis induced by alkylating agents.烷化剂诱导的致癌机制。
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2
Hybridization triggered cross-linking of deoxyoligonucleotides.杂交引发脱氧寡核苷酸的交联。
Nucleic Acids Res. 1986 Oct 10;14(19):7661-74. doi: 10.1093/nar/14.19.7661.
3
Application of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite for in situ preparation of deoxyribonucleoside phosphoramidites and their use in polymer-supported synthesis of oligodeoxyribonucleotides.2-氰基乙基-N,N,N',N'-四异丙基亚磷酰胺在原位制备脱氧核糖核苷亚磷酰胺中的应用及其在聚合物支持的寡脱氧核苷酸合成中的用途。
Nucleic Acids Res. 1986 Sep 25;14(18):7391-403. doi: 10.1093/nar/14.18.7391.
4
A study of side reactions occurring during synthesis of oligodeoxynucleotides containing O6-alkyldeoxyguanosine residues at preselected sites.一项关于在预选位点含有O6-烷基脱氧鸟苷残基的寡脱氧核苷酸合成过程中发生的副反应的研究。
Biochemistry. 1987 May 5;26(9):2465-71. doi: 10.1021/bi00383a010.
5
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6
O-alkyl pyrimidines in mutagenesis and carcinogenesis: occurrence and significance.诱变与致癌过程中的O-烷基嘧啶：存在情况及意义
Cancer Res. 1986 Oct;46(10):4879-85.
7
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8
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Nucleic Acids Res. 1989 Jul 11;17(13):4957-74. doi: 10.1093/nar/17.13.4957.
9
Solid-phase synthesis and side reactions of oligonucleotides containing O-alkylthymine residues.
Biochemistry. 1989 Feb 21;28(4):1471-7. doi: 10.1021/bi00430a007.
10
Formation and metabolism of alkylated nucleosides: possible role in carcinogenesis by nitroso compounds and alkylating agents.烷基化核苷的形成与代谢：在亚硝基化合物和烷基化剂致癌过程中的可能作用。
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