含有致癌物质3-硝基苯并蒽酮形成的C8-2 ' -脱氧鸟苷加合物的寡脱氧核苷酸的合成

Q4 Chemistry
Arindom Chatterjee, Chanchal K. Malik, Ashis K. Basu
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引用次数: 1

摘要

本单元分五个部分详细介绍了位于寡核苷酸所需位置的C8-2 ' -脱氧鸟苷-3-氨基苯并蒽酮加合物的合成过程。第一部分描述了受保护的2 ' -脱氧鸟苷O - 6-苄基- n -2 - dmtr -3 ' -5 ' -bisTBDMS-C8-Br-2 ' -脱氧鸟苷的合成。第二部分详细介绍了还原致癌物3-氨基苯并蒽醌的合成。第三部分概述了通过钯催化的交叉偶联反应在还原的致癌物和受保护的核苷之间形成加合物的关键步骤。最后两部分描述了从核苷致癌物质加合物合成的酰胺磷,然后通过固相寡核苷酸合成将其特定位点并入DNA中。加合寡核苷酸采用反相高效液相色谱法纯化,质谱法表征。©2017 by John Wiley &儿子,Inc。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Synthesis of Oligodeoxynucleotides Containing a C8-2′-Deoxyguanosine Adduct Formed by the Carcinogen 3-Nitrobenzanthrone

Synthesis of Oligodeoxynucleotides Containing a C8-2′-Deoxyguanosine Adduct Formed by the Carcinogen 3-Nitrobenzanthrone

Synthesis of Oligodeoxynucleotides Containing a C8-2′-Deoxyguanosine Adduct Formed by the Carcinogen 3-Nitrobenzanthrone

This unit describes the detailed procedure in five parts for the synthesis of the C8-2′-deoxyguanosine-3-aminobenzanthrone adduct located in a desired site in an oligonucleotide. The synthesis of the protected 2′-deoxyguanosine, O 6-benzyl-N 2-DMTr-3′-5′-bisTBDMS-C8-Br-2′-deoxyguanosine, is described in the first part. The synthesis of the reduced carcinogen 3-aminobenzanthrone is detailed in part two. The third part outlines the key step of the adduct formation between the reduced carcinogen and the protected nucleoside by a palladium-catalyzed cross coupling reaction. The final two parts describe phosphoramidite synthesis from the nucleoside-carcinogen adduct followed by its site-specific incorporation into DNA by solid-phase oligonucleotide synthesis. The adducted oligonucleotides are purified by reversed-phase HPLC and characterized by mass spectrometry. © 2017 by John Wiley & Sons, Inc.

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来源期刊
Current Protocols in Nucleic Acid Chemistry
Current Protocols in Nucleic Acid Chemistry Chemistry-Organic Chemistry
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期刊介绍: Published in association with International Society for Nucleosides, Nucleotides & Nucleic Acids (IS3NA) , Current Protocols in Nucleic Acid Chemistry is equally valuable for biotech, pharmaceutical, and academic labs. It is the resource for designing and running successful research projects in the rapidly growing and changing field of nucleic acid, nucleotide, and nucleoside research.
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