用于人工扩展遗传信息系统的核糖核苷。
Ribonucleosides for an artificially expanded genetic information system.
作者信息
Kim Hyo-Joong, Leal Nicole A, Hoshika Shuichi, Benner Steven A
机构信息
Foundation for Applied Molecular Evolution (FfAME), 720 SW Second Avenue, Suite 201, Gainesville, Florida 32601, United States.
出版信息
J Org Chem. 2014 Apr 4;79(7):3194-9. doi: 10.1021/jo402665d. Epub 2014 Mar 18.
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.
摘要
重新排列氢键基团可将核碱基添加到人工扩展遗传信息系统（AEGIS）中，与标准核苷酸正交配对。我们在此报告了通过Heck偶联和硼氢化/氧化序列大规模合成携带2-氨基-3-硝基吡啶-6-酮（简称为Z）的AEGIS核苷酸。与2'-脱氧核糖类似物相比，核糖Z对差向异构化更稳定。此外，T7 RNA聚合酶将ZTP与其沃森-克里克互补物咪唑并[1,2-a]-1,3,5-三嗪-4(8H)酮（简称为P）配对，为使用这种“第二代”AEGIS Z:P对添加由mRNA编码的氨基酸奠定了基础。
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