Design and synthesis of boronic-acid-labeled thymidine triphosphate for incorporation into DNA.
Design and synthesis of boronic-acid-labeled thymidine triphosphate for incorporation into DNA.
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DOI：
10.1093/nar/gkl1091
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发表时间：
2007
影响因子：
14.9
通讯作者：
Wang B
中科院分区：
文献类型：
--
作者：
Lin N;Yan J;Huang Z;Altier C;Li M;Carrasco N;Suyemoto M;Johnston L;Wang S;Wang Q;Fang H;Caton-Williams J;Wang B
硼酸部分是在碳水化合物识别、糖蛋白下拉、水解酶抑制和硼中子俘获疗法中有用的通用官能团。将硼酸基团结合到DNA中可以产生具有各种生物功能的分子。我们成功地合成了一个硼酸标记的胸苷三磷酸（B-TTP）通过14个原子的系链连接，并有效地将其纳入DNA的酶促聚合。以Huisgen环加成反应为关键反应进行合成。我们已经证明，DNA聚合酶可以有效地识别硼酸标记的DNA作为DNA聚合的模板，允许PCR扩增硼酸标记的DNA。以B-TTP为底物，硼酸标记的DNA为模板的DNA聚合酶解是通过体外选择开发基于DNA的凝集素模拟物的关键问题。
The boronic acid moiety is a versatile functional group useful in carbohydrate recognition, glycoprotein pull-down, inhibition of hydrolytic enzymes and boron neutron capture therapy. The incorporation of the boronic-acid group into DNA could lead to molecules of various biological functions. We have successfully synthesized a boronic acid-labeled thymidine triphosphate (B-TTP) linked through a 14-atom tether and effectively incorporated it into DNA by enzymatic polymerization. The synthesis was achieved using the Huisgen cycloaddition as the key reaction. We have demonstrated that DNA polymerase can effectively recognize the boronic acid-labeled DNA as the template for DNA polymerization, that allows PCR amplification of boronic acid-labeled DNA. DNA polymerase recognitions of the B-TTP as a substrate and the boronic acid-labeled DNA as a template are critical issues for the development of DNA-based lectin mimics via in vitro selection.
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