Synthesis and properties of 5-cyano-substituted nucleoside analog with a donor–donor–acceptor hydrogen-bonding pattern

HJ Kim, F Chen, SA Benner

Index: Kim, Hyo-Joong; Chen, Fei; Benner, Steven A. Journal of Organic Chemistry, 2012 , vol. 77, # 7 p. 3664 - 3669

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Citation Number: 11

Abstract

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 d Z, the electron withdrawing unit was a nitro group. Here, we describe an analogue of d Z (cyano-d Z) having a cyano group instead of a nitro group, including its synthesis, p ...