用于连接两个不同报告基团的寡核苷酸的位点特异性功能化。
Site specific functionalization of oligonucleotides for attaching two different reporter groups.
作者信息
Agrawal S, Zamecnik P C
机构信息
Worcester Foundation for Experimental Biology, Shrewsbury, MA 01545.
出版信息
Nucleic Acids Res. 1990 Sep 25;18(18):5419-23. doi: 10.1093/nar/18.18.5419.
Abstract
The synthesis of an oligonucleotide functionalized to attach two different reporter groups at specific internucleotide linkages is described. To incorporate the amine specific reporter group the internucleotide linkage is modified to phosphoramidate (N-1-aminoalkyl) and for a thiol specific reporter group the internucleotide linkage is modified to a phosphorothioate diester. The synthetic cycle for introducing the modified internucleotide linkages at specific sites can be carried out using an automated DNA synthesizer. Combination of reporter groups have been attached successfully.
摘要
描述了一种寡核苷酸的合成，该寡核苷酸经功能化处理后可在特定的核苷酸间连接处以连接两个不同的报告基团。为了引入胺特异性报告基团，将核苷酸间连接修饰为磷酰胺酸酯（N-1-氨基烷基）；为了引入硫醇特异性报告基团，将核苷酸间连接修饰为硫代磷酸二酯。可以使用自动DNA合成仪在特定位点引入修饰的核苷酸间连接的合成循环。报告基团的组合已成功连接。
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3
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