Synthesis Of RNA Oligomers Research Articles

Development of new methods for the synthesis of RNA oligonucleotides having baselabile functional groups

In the previous study, we developed a method for O-selective phosphorylation, i.e., "the activated phosphite method" for DNA synthesis without base protection. However, the O-selectivity was low in RNA synthesis when the activated phosphite method was used. In this paper, we developed two new methods for synthesis of RNA oligomers having base-labile functional groups on polymer supports. One is the N-unprotected phosphoramidite method involving P(III)-N bond cleavage. The selectivity of the phosphorylation in RNA synthesis increased to more than 99% by posttreatment of the undesired P(III)-N bonds with 6-nitoro-HOBt and was independent of the kind of protecting groups at the 2' position. Another method is the RNA synthesis involving deprotection of protecting groups of the nucleobases under acidic conditions. It was found that an N,N-dialkylaminomethlene (DAF) group could be easily removed by heat-induced deprotection using HOBt as an acidic promoter.

A novel RNA synthetic method with a 2′-O-(2-cyanoethoxymethyl) protecting group

A novel method for the synthesis of RNA oligomers with 2-cyanoethoxymethyl (CEM) as the 2'-hydroxyl protecting group has been developed. The new method allows the synthesis of oligonucleotides with an efficiency and final purity comparable to that obtained in DNA synthesis.(1) In addition, the CEM method has the potential for application to the synthesis of very long RNA oligonucleotides.

Chemical synthesis of RNA including 5-taurinomethyluridine

Recently, a novel base-modified uridine derivative, 5-taurinomethyluridine (taum(5)U) was discovered from bovine and human mitochondrial tRNAs, and this modified ribonucleoside was found to existed at the first position of the anti-codon. We report efficient reactions for the synthesis of RNA oligomers including this base-modified ribonucleotide.

ChemInform Abstract: Synthesis of RNA Oligomers and Their Template Properties

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Synthesis of RNA oligomers on heterogeneous templates.

The concept of an RNA world in the chemical origin of life is appealing, as nucleic acids are capable of both information storage and acting as templates that catalyse the synthesis of complementary molecules. Template-directed synthesis has been demonstrated for homogeneous oligonucleotides that, like natural nucleic acids, have 3',5' linkages between the nucleotide monomers. But it seems likely that prebiotic routes to RNA-like molecules would have produced heterogeneous molecules with various kinds of phosphodiester linkages and both linear and cyclic nucleotide chains. Here we show that such heterogeneity need be no obstacle to the templating of complementary molecules. Specifically, we show that heterogeneous oligocytidylates, formed by the montmorillonite clay-catalysed condensation of actuated monomers, can serve as templates for the synthesis of oligoguanylates. Furthermore, we show that oligocytidylates that are exclusively 2',5'-linked can also direct synthesis of oligoguanylates. Such heterogeneous templating reactions could have increased the diversity of the pool of protonucleic acids from which life ultimately emerged.