Ribonucleosides for an Artificially Expanded Genetic Information System

被引：21

作者：

Kim, Hyo-Joong ^{[1
,2
]}

Leal, Nicole A. ^{[1
,2
]}

Hoshika, Shuichi ^{[1
,3
]}

Benner, Steven A. ^{[1
,3
]}

机构：

[1] Fdn Appl Mol Evolut FfAME, Gainesville, FL 32601 USA

[2] Firebird Biomol Sci LLC, Alachua, FL 32615 USA

[3] Westheimer Inst Sci & Technol TWIST, Gainesville, FL 32601 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 07期

关键词：

DONOR PYRIMIDINE ANALOG; UNNATURAL BASE-PAIR; EFFICIENT SYNTHESIS; AMINO-ACID; DNA; AMPLIFICATION; REPLICATION; RECOGNITION; NUCLEOSIDE; EXPANSION;

D O I：

10.1021/jo402665d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3194 / 3199

页数：6

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