PDF(Sci-hub)
Abstract：
Linear or branched 1,3-diketone-linked thymidine 5\'-O-mono- and triphosphate were synthesized through CuAAC click reaction of diketone-alkynes with 5-azidomethyl-dUMP or -dUTP. The triphosphates were good substrates for KOD XL DNA polymerase in primer extension synthesis of modified DNA. The nucleotide bearing linear 3,5-dioxohexyl group (HDO) efficiently reacted with arginine-containing peptides to form stable pyrimidine-linked conjugates, whereas the branched 2-acetyl-3-oxo-butyl (PDO) group was not reactive. Reaction with Lys or a terminal amino group formed enamine adducts that were prone to hydrolysis. This reactive HDO modification in DNA was used for bioconjugations and cross-linking with Arg-containing peptides or proteins (e.g. histones).
摘要：
通过二酮-炔与5-叠氮基甲基-dUMP或-dUTP的CuAAC点击反应，合成了直链或支链的1,3-二酮连接的胸苷5'-O-单-和三磷酸酯。在修饰DNA的引物延伸合成中，三磷酸盐是KODXLDNA聚合酶的良好底物。带有线性3,5-二氧己基（HDO）的核苷酸与含精氨酸的肽有效反应形成稳定的嘧啶连接的缀合物，而支链的2-乙酰基-3-氧代丁基（PDO）基团没有反应性。与Lys或末端氨基反应形成易于水解的烯胺加合物。DNA中的这种反应性HDO修饰用于与含Arg的肽或蛋白质(例如组蛋白)的生物缀合和交联。
