title: Ribonucleosides for an artificially expanded genetic information system.
abstract: Rearranging hydrogen bonding groups adds nucleobases to an artificially expanded genetic information system (AEGIS), pairing orthogonally to standard nucleotides. We report here a large-scale synthesis of the AEGIS nucleotide carrying 2-amino-3-nitropyridin-6-one (trivially Z) via Heck coupling and a hydroboration/oxidation sequence. RiboZ is more stable against epimerization than its 2'-deoxyribo analogue. Further, T7 RNA polymerase incorporates ZTP opposite its Watson-Crick complement, imidazo[1,2-a]-1,3,5-triazin-4(8H)one (trivially P), laying grounds for using this "second-generation" AEGIS Z:P pair to add amino acids encoded by mRNA.
authors.affiliation: Foundation for Applied Molecular Evolution (FfAME), 720 SW Second Avenue, Suite 201, Gainesville, Florida 32601, United States.
authors.forename: Hyo-Joong
authors.initials: HJ
authors.lastname: Kim
authors.forename: Nicole A
authors.initials: NA
authors.lastname: Leal
authors.forename: Shuichi
authors.initials: S
authors.lastname: Hoshika
authors.forename: Steven A
authors.initials: SA
authors.lastname: Benner
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D020029:Base Pairing; D001894:Borohydrides / Q000737:chemistry*; D012321:DNA-Directed RNA Polymerases / Q000737:chemistry*; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D012333:RNA, Messenger / Q000737:chemistry*; D012263:Ribonucleosides / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry*; D014764:Viral Proteins / Q000737:chemistry*
chemical_list: C000594399:2-amino-3-nitropyridin-6-one; D000596:Amino Acids; D001894:Borohydrides; D007093:Imidazoles; D009705:Nucleosides; D009711:Nucleotides; D011725:Pyridines; D012333:RNA, Messenger; D012263:Ribonucleosides; D014227:Triazines; D014764:Viral Proteins; C000594401:imidazo(1,2-a)-1,3,5-triazin-4(8H)one; C062210:bacteriophage T7 RNA polymerase; D012321:DNA-Directed RNA Polymerases