jo300230z_si_001.pdf (765.66 kB)
Synthesis and Properties of 5-Cyano-Substituted Nucleoside Analog with a Donor–Donor–Acceptor Hydrogen-Bonding Pattern
journal contribution
posted on 2012-04-06, 00:00 authored by Hyo-Joong Kim, Fei Chen, Steven A. Benner6-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, pKa, rates of acid-catalyzed
epimerization, and enzymatic incorporation.