通过涉及二胺连接物和互补寡脱氧核苷酸上的无碱基位点的顺序还原胺化反应合成含有特定位置链间交联的 DNA 双链体。
Synthesis of DNA Duplexes Containing Site-Specific Interstrand Cross-Links via Sequential Reductive Amination Reactions Involving Diamine Linkers and Abasic Sites on Complementary Oligodeoxynucleotides.
机构信息
Department of Chemistry, University of Missouri, 125 Chemistry Building, Columbia, Missouri 65211, United States.
Department of Biochemistry, University of Missouri, 125 Chemistry Building, Columbia, Missouri 65211, United States.
出版信息
Chem Res Toxicol. 2021 Nov 15;34(11):2384-2391. doi: 10.1021/acs.chemrestox.1c00293. Epub 2021 Oct 25.
Abstract
Interstrand DNA cross-links are important in biology, medicinal chemistry, and materials science. Accordingly, methods for the targeted installation of interstrand cross-links in DNA duplexes may be useful in diverse fields. Here, a simple procedure is reported for the preparation of DNA duplexes containing site-specific, chemically defined interstrand cross-links. The approach involves sequential reductive amination reactions between diamine linkers and two abasic (apurinic/apyrimidinic, AP) sites on complementary oligodeoxynucleotides. Use of the symmetrical triamine, tris(2-aminoethyl)amine, in this reaction sequence enabled the preparation of a cross-linked DNA duplex bearing a derivatizable aminoethyl group.
摘要
链间 DNA 交联在生物学、药物化学和材料科学中很重要。因此，在 DNA 双螺旋中靶向安装链间交联的方法可能在多个领域都有应用。本文报道了一种在 DNA 双链中制备具有特定位置、化学定义的链间交联的简单方法。该方法涉及通过二胺接头与互补寡脱氧核苷酸上的两个无碱基（嘌呤/嘧啶缺失，AP）位点之间的顺序还原胺化反应。在该反应序列中使用对称三胺，三（2-氨基乙基）胺，可制备带有可衍生氨基乙基的交联 DNA 双链。
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