Expanding the genetic alphabet: non-epimerizing nucleoside with the pyDDA hydrogen-bonding pattern.
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.
Hutter
Daniel
D
Department of Chemistry and Department of Anatomy and Cell Biology, University of Florida, Gainesville, Florida 32611-7200 benner@chem.ufl.edu
Benner
Steven A
SA
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
D009574:Nitro Compounds; D009705:Nucleosides; D011687:Purines; D011743:Pyrimidines