Foundation for Applied Molecular Evolution (FfAME), 720 SW Second Avenue, Suite 201, Gainesville, Florida 32601, USA.
J Org Chem. 2012 Apr 6;77(7):3664-9. doi: 10.1021/jo300230z. Epub 2012 Mar 13.
6-Aminopyridin-2-ones form Watson-Crick pairs with complementary purine analogues to add a third nucleobase pair to DNA and RNA, if an electron-withdrawing group at position 5 slows oxidation and epimerization. In previous work with a nucleoside analogue trivially named dZ, the electron withdrawing unit was a nitro group. Here, we describe an analogue of dZ (cyano-dZ) having a cyano group instead of a nitro group, including its synthesis, pK(a), rates of acid-catalyzed epimerization, and enzymatic incorporation.
6-氨基吡啶-2-酮与互补嘌呤类似物形成 Watson-Crick 对，为 DNA 和 RNA 添加第三个碱基对，如果在 5 位引入吸电子基团则可以减缓氧化和差向异构化。在之前关于核苷类似物 dZ 的研究中，吸电子单元是硝基。在此，我们描述了一种 dZ 的类似物（氰基-dZ），其 5 位取代基为氰基而不是硝基，包括其合成、pK(a)、酸催化差向异构化速率和酶促掺入。
