title: Expanding the genetic alphabet: non-epimerizing nucleoside with the pyDDA hydrogen-bonding pattern.
abstract: 6-Amino-3-(2'-deoxy-beta-D-ribofuranosyl)-5-nitro-1H-pyridin-2-one (4), a C-glycoside exhibiting the nonstandard pyDDA hydrogen-bonding pattern, was synthesized via Heck coupling. The nitro group greatly enhances the stability of the nucleoside toward acid-catalyzed epimerization without leading to significant deprotonation of the heterocycle at physiological pH. These results make nucleoside 4 a promising candidate for an expanded genetic alphabet.
authors.affiliation: Department of Chemistry and Department of Anatomy and Cell Biology, University of Florida, Gainesville, Florida 32611-7200 benner@chem.ufl.edu
authors.forename: Daniel
authors.initials: D
authors.lastname: Hutter
authors.forename: Steven A
authors.initials: SA
authors.lastname: Benner
mesh_terms: D020029:Base Pairing; D002384:Catalysis; D006860:Hydrogen Bonding; D006863:Hydrogen-Ion Concentration; D007536:Isomerism; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry; D009705:Nucleosides / Q000737:chemistry* / Q000235:genetics; D011687:Purines / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry
chemical_list: D009574:Nitro Compounds; D009705:Nucleosides; D011687:Purines; D011743:Pyrimidines