Synthesis and Properties
of 5-Cyano-Substituted Nucleoside
Analog with a Donor–Donor–Acceptor Hydrogen-Bonding
Pattern
Hyo-Joong Kim
Fei Chen
Steven A. Benner
10.1021/jo300230z.s001
https://acs.figshare.com/articles/journal_contribution/Synthesis_and_Properties_of_5_Cyano_Substituted_Nucleoside_Analog_with_a_Donor_Donor_Acceptor_Hydrogen_Bonding_Pattern/2533459
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<b>Z</b>, the electron withdrawing unit was
a nitro group. Here, we describe an analogue of d<b>Z</b> (cyano-d<b>Z</b>) having a cyano group instead of a nitro group, including
its synthesis, p<i>K</i><sub>a</sub>, rates of acid-catalyzed
epimerization, and enzymatic incorporation.
2012-04-06 00:00:00
nucleoside analogue trivially
DNA
epimerization
nitro group
RNA
dZ