title: Chimeric RNA Oligonucleotides Incorporating Triazole-Linked Trinucleotides: Synthesis and Function as mRNA in Cell-Free Translation Reactions.
abstract: 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. ThreeTLRNA 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.
authors: Department of Chemistry, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors: Tomoko
authors: T
authors: Fujino
authors: Department of Chemistry, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors: Takeru
authors: T
authors: Suzuki
authors: Department of Chemistry, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors: Koudai
authors: K
authors: Okada
authors: Department of Chemistry, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors: Kanako
authors: K
authors: Kogashi
authors: Department of Biomolecular Sciences, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors: Ken-Ichi
authors: KI
authors: Yasumoto
authors: Department of Biomolecular Sciences, Tohoku University , Aoba-ku, Sendai 980-8578, Japan.
authors: Kazuhiro
authors: K
authors: Sogawa
authors: JST ERATO, Isobe Degenerate π-Integration Project and Advanced Institute for Materials Research, Tohoku University , Aoba-ku, Sendai 980-8577, Japan.|Department of Chemistry, The University of Tokyo , Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors: Hiroyuki
authors: H
authors: Isobe
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002474:Cell-Free System; D002851:Chromatography, High Pressure Liquid; D009841:Oligonucleotides / Q000737:chemistry*; D014176:Protein Biosynthesis; D066244:Proton Magnetic Resonance Spectroscopy; D012333:RNA, Messenger / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D014230:Triazoles / Q000737:chemistry*
chemical_list: D009841:Oligonucleotides; D012333:RNA, Messenger; D014230:Triazoles