Synthesis of Naphthyridine Carbamate Dimer (NCD) Derivatives Modified with Alkanethiol and Binding Properties of G?G Mismatch DNA
Synthesis of Naphthyridine Carbamate Dimer (NCD) Derivatives Modified with Alkanethiol and Binding Properties of G?G Mismatch DNA
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烷硫醇修饰的萘啶氨基甲酸酯二聚体 (NCD) 衍生物的合成及 G?G 错配 DNA 的结合特性
DOI：
10.1021/acs.orglett.7b01632
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发表时间：
2017
期刊：
影响因子：
5.2
通讯作者：
Nakatani Kazuhiko
中科院分区：
文献类型：
--
作者：
Yamada Takeshi;Miki Shouta;Ul’Husna Anisa;Michikawa Akiko;Nakatani Kazuhiko
报道了一系列新的脱氧核糖核酸结合分子NCD-CN-SH(n=3、4、5和6)，其结构域选择性地与5‘-CGG-3’/5‘-CGG-3’序列中的G-G错配结合，并含有硫醇部分，在有氧条件下氧化时发生自发二聚为(NCD-CN-S)2。S-S二聚体(NCD-CN-S)2生成了1：1的结合络合物，热稳定性提高。与CGG/CGG DNA结合的二聚体表现出比单体和先前合成的NCTn衍生物更高的正协同作用。NCD-CN-SH二聚体在CGG重复DNA上选择性地加速，而在CAG重复DNA上不被选择性地加速。
A series of new DNA binding moleculesNCD–Cn–SH(n= 3, 4, 5, and 6) is reported, which possesses theNCD(naphthyridine carbamate dimer) domain selectively binding to the G–G mismatch in the 5′-CGG-3′/5′-CGG-3′ sequence and a thiol moiety, which undergoes spontaneous dimerization to(NCD–Cn–S)2upon oxidation under aerobic conditions. The S–S dimer(NCD–Cn–S)2produced the 1:1 binding complex with improved thermal stability. The dimer binding to the CGG/CGG DNA showed higher positive cooperativity than the binding of monomer and previously synthesized NCTn derivative. The dimerization ofNCD–Cn–SHwas selectively accelerated on the CGG repeat DNA but not on the CAG repeat DNA.