TY - JOUR
T1 - Chimeric RNA Oligonucleotides Incorporating Triazole-Linked Trinucleotides
T2 - Synthesis and Function as mRNA in Cell-Free Translation Reactions
AU - Fujino, Tomoko
AU - Suzuki, Takeru
AU - Okada, Koudai
AU - Kogashi, Kanako
AU - Yasumoto, Ken Ichi
AU - Sogawa, Kazuhiro
AU - Isobe, Hiroyuki
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/10/7
Y1 - 2016/10/7
N2 - A method for the synthesis of chimeric oligonucleotides was developed to incorporate purine nucleobases and multiple triazole linkers in natural, phosphate-linked structures of RNA. A solution-phase synthesis method for triazole-linked RNA oligomers via copper-catalyzed azide-alkyne cycloaddition reaction was optimized and tolerated purine nucleobases and protecting groups for further transformations. Three TLRNA trinucleotides with 5′-protected hydroxy and 3′-phosphoramidite groups were prepared, and one congener with a representative sequence was subjected to automated, solid-phase phosphoramidite synthesis. The synthesis allowed the efficient preparation of 13-mer chimeric RNA oligonucleotides with two triazole linkers, ten phosphate linkers and purine/pyrimidine nucleobases. The chimeric oligonucleotide was found applicable to a cell-free translation system as mRNA and provided the genetic code for dipeptide production.
AB - A method for the synthesis of chimeric oligonucleotides was developed to incorporate purine nucleobases and multiple triazole linkers in natural, phosphate-linked structures of RNA. A solution-phase synthesis method for triazole-linked RNA oligomers via copper-catalyzed azide-alkyne cycloaddition reaction was optimized and tolerated purine nucleobases and protecting groups for further transformations. Three TLRNA trinucleotides with 5′-protected hydroxy and 3′-phosphoramidite groups were prepared, and one congener with a representative sequence was subjected to automated, solid-phase phosphoramidite synthesis. The synthesis allowed the efficient preparation of 13-mer chimeric RNA oligonucleotides with two triazole linkers, ten phosphate linkers and purine/pyrimidine nucleobases. The chimeric oligonucleotide was found applicable to a cell-free translation system as mRNA and provided the genetic code for dipeptide production.
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U2 - 10.1021/acs.joc.6b01618
DO - 10.1021/acs.joc.6b01618
M3 - Article
C2 - 27579606
AN - SCOPUS:84990996962
VL - 81
SP - 8967
EP - 8976
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 19
ER -