Ribonucleosides for an Artificially Expanded Genetic Information System
| Autor: | Hyo-Joong Kim, Nicole A. Leal, Shuichi Hoshika, Steven A. Benner |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Base pair
Stereochemistry Pyridines Borohydrides 010402 general chemistry 01 natural sciences Nucleobase Viral Proteins medicine T7 RNA polymerase Nucleotide RNA Messenger Amino Acids Base Pairing chemistry.chemical_classification 010405 organic chemistry Nucleotides Triazines Organic Chemistry Imidazoles RNA Hydrogen Bonding Nucleosides DNA-Directed RNA Polymerases Note 0104 chemical sciences Amino acid Hydroboration chemistry Artificially Expanded Genetic Information System Ribonucleosides medicine.drug |
| Zdroj: | The Journal of Organic Chemistry |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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