title: Synthesis and properties of 5-cyano-substituted nucleoside analog with a donor-donor-acceptor hydrogen-bonding pattern.
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 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.
authors.affiliation: Foundation for Applied Molecular Evolution (FfAME), 720 SW Second Avenue, Suite 201, Gainesville, Florida 32601, USA.
authors.forename: Hyo-Joong
authors.initials: HJ
authors.lastname: Kim
authors.forename: Fei
authors.initials: F
authors.lastname: Chen
authors.forename: Steven A
authors.initials: SA
authors.lastname: Benner
mesh_terms: D020029:Base Pairing; D002384:Catalysis; D004247:DNA / Q000737:chemistry*; D006860:Hydrogen Bonding; D007536:Isomerism; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: C547309:6-amino-5-nitro-3-(1'-beta-D-2'-deoxyribofuranosyl)-2(1H)-pyridone; D009005:Monosaccharides; D009570:Nitriles; D009705:Nucleosides; D004247:DNA