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
收藏
页码：3194 / 3199
页数：6
相关论文
共 43 条
  • [1] Biochemical analysis with the expanded genetic lexicon
    Ai, Hui-wang
    [J]. ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2012, 403 (08) : 2089 - 2102
  • [2] New nitrogenated siloxy butadienes from 1,3-dichloroacetone
    Alonso, Dulce
    Caballero, Esther
    Medarde, Manuel
    Tome, Fernando
    [J]. TETRAHEDRON LETTERS, 2007, 48 (06) : 907 - 910
  • [3] Comparison of the Eragen Multi-Code Respiratory Virus Panel with Conventional Viral Testing and Real-Time Multiplex PCR Assays for Detection of Respiratory Viruses
    Arens, Max Q.
    Buller, Richard S.
    Rankin, Anne
    Mason, Sheila
    Whetsell, Amy
    Agapov, Eugene
    Lee, Wai-Ming
    Storch, Gregory A.
    [J]. JOURNAL OF CLINICAL MICROBIOLOGY, 2010, 48 (07) : 2387 - 2395
  • [4] RIBOSOME-MEDIATED INCORPORATION OF A NONSTANDARD AMINO-ACID INTO A PEPTIDE THROUGH EXPANSION OF THE GENETIC-CODE
    BAIN, JD
    SWITZER, C
    CHAMBERLIN, AR
    BENNER, SA
    [J]. NATURE, 1992, 356 (6369) : 537 - 539
  • [5] Understanding nucleic acids using synthetic chemistry
    Benner, SA
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (10) : 784 - 797
  • [6] CHEMISTRY OF PSEUDOURIDINE - SYNTHESIS OF PSEUDOURIDINE-5'-DIPHOSPHATE
    CHAMBERS, RW
    KURKOV, V
    SHAPIRO, R
    [J]. BIOCHEMISTRY, 1963, 2 (06) : 1192 - &
  • [7] COHN WE, 1960, J BIOL CHEM, V235, P1488
  • [8] A branched DNA signal amplification assay for quantification of nucleic acid targets below 100 molecules/ml
    Collins, ML
    Irvine, B
    Tyner, D
    Fine, E
    Zayati, C
    Chang, CA
    Horn, T
    Ahle, D
    Detmer, J
    Shen, LP
    Kolberg, J
    Bushnell, S
    Urdea, MS
    Ho, DD
    [J]. NUCLEIC ACIDS RESEARCH, 1997, 25 (15) : 2979 - 2984
  • [9] ENANTIOSPECIFIC SYNTHESIS OF D-MYO-INOSITOL 1,4,5-TRISPHOSPHATE FROM (-)-QUINIC ACID
    FALCK, JR
    YADAGIRI, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) : 5851 - 5852
  • [10] Nucleobase pairing in Watson-Crick-like genetic expanded information systems
    Geyer, CR
    Battersby, TR
    Benner, SA
    [J]. STRUCTURE, 2003, 11 (12) : 1485 - 1498
12345