Department of Life Science, Tokyo Institute of Technology, 4259 Nagatsuta, Yokohama 226-8501, Japan.
Bioorg Med Chem. 2009 Oct 15;17(20):7275-80. doi: 10.1016/j.bmc.2009.08.053. Epub 2009 Sep 2.
2'-O-Carbamoyluridine (U(cm)) was synthesized and incorporated into DNAs and 2'-O-Me-RNAs. The oligonucleotides incorporating U(cm) formed less stable duplexes with their complementary and U(cm)-U, U(cm)-C single-base mismatched DNAs and RNAs in comparison with those without the carbamoyl group. On the contrary, the T(m) analyses revealed that the duplexes with a mismatched U(cm)-G base pair showed almost the same thermostability as the corresponding unmodified duplexes. Molecular dynamics (MD) simulations of the U(cm)-modified 2'-O-Me-RNA/RNA duplexes with U(cm)-G mismatched base pair suggested that the carbamoyl group could participate in the U(cm)-G base pair by an additional intermolecular hydrogen bond between the carbamoyl oxygen and the H2 of the guanine base.
2'-O- 甲酰基尿苷（U(cm)）被合成并掺入 DNA 和 2'-O-Me-RNAs 中。与没有甲酰基的寡核苷酸相比，掺入 U(cm)的寡核苷酸与其互补和 U(cm)-U、U(cm)-C 单碱基错配 DNA 和 RNA 形成的双链体稳定性较差。相反，T(m)分析表明，具有错配 U(cm)-G 碱基对的双链体与相应的未修饰双链体具有几乎相同的热稳定性。U(cm)-修饰的 2'-O-Me-RNA/RNA 双链体与 U(cm)-G 错配碱基对的分子动力学（MD）模拟表明，甲酰基可以通过甲酰基氧和鸟嘌呤碱基的 H2 之间的额外分子间氢键参与 U(cm)-G 碱基对。
