Ribonucleosides for an Artificially Expanded Genetic Information System

[Image: see text] 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...

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Autores principales: Kim, Hyo-Joong, Leal, Nicole A., Hoshika, Shuichi, Benner, Steven A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985877/
https://www.ncbi.nlm.nih.gov/pubmed/24597611
http://dx.doi.org/10.1021/jo402665d
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author Kim, Hyo-Joong
Leal, Nicole A.
Hoshika, Shuichi
Benner, Steven A.
author_facet Kim, Hyo-Joong
Leal, Nicole A.
Hoshika, Shuichi
Benner, Steven A.
author_sort Kim, Hyo-Joong
collection PubMed
description [Image: see text] 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.
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spelling pubmed-39858772015-03-05 Ribonucleosides for an Artificially Expanded Genetic Information System Kim, Hyo-Joong Leal, Nicole A. Hoshika, Shuichi Benner, Steven A. J Org Chem [Image: see text] 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. American Chemical Society 2014-03-05 2014-04-04 /pmc/articles/PMC3985877/ /pubmed/24597611 http://dx.doi.org/10.1021/jo402665d Text en Copyright © 2014 American Chemical Society
spellingShingle Kim, Hyo-Joong
Leal, Nicole A.
Hoshika, Shuichi
Benner, Steven A.
Ribonucleosides for an Artificially Expanded Genetic Information System
title Ribonucleosides for an Artificially Expanded Genetic Information System
title_full Ribonucleosides for an Artificially Expanded Genetic Information System
title_fullStr Ribonucleosides for an Artificially Expanded Genetic Information System
title_full_unstemmed Ribonucleosides for an Artificially Expanded Genetic Information System
title_short Ribonucleosides for an Artificially Expanded Genetic Information System
title_sort ribonucleosides for an artificially expanded genetic information system
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985877/
https://www.ncbi.nlm.nih.gov/pubmed/24597611
http://dx.doi.org/10.1021/jo402665d
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