Oligoribonucleotides synthesis

Milligan, J., Groebe, D., Witherell, G., and Uhlenbeck, O. (1987). Oligoribonucleotide synthesis using T7 RNA polymerase and synthetic DNA templates. Nucleic Acids Res. 15, 8783. 

In 1968 Miller and Stirling showed that the 2-tosylethyl ester function (abbreviated TSE) underwent easy base-catalysed elimination in the presence of 1 M sodium hydroxide or sodium carbonate (but not sodium hydrogen carbonate) in aqueous dioxane at room temperature to give p-toluenesulfinate anion, ethylene. and a carboxylate 215 Thus, this ester function complements the methylsul-fonylmethyl function (see section 6.4) derived from methylthiomethyl esters in its base-sensitivity. Electron withdrawing groups (e.g., p-nitro) on the aryl ring increase base lability — a feature that has been exploited for the protection of the 2f hydroxyl function in oligoribonucleotide synthesis.216... 

Table 3 Summary of a 0.2-/amol-Scale Cycle for Oligoribonucleotide Synthesis...

Wu T, Ogilvie KK, Pon RT. N-Phenoxyacetylated guanosine and adenosine phosphoramidities in the solid-phase synthesis of oligoribonucleotides Synthesis of a ribozyme sequence. Tetrahedron Lett 34 4249-4252, 1988. 

Gait MJ, Pritchard C, Slim G. Oligoribonucleotide synthesis. In Eckstein F, ed. Oligonucleotides and Analogues, a Practical Approach. Oxford Oxford University Press, 1991, pp 25-48. 

Capaldi DC, Reese CB. Use of the l-(2-fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) and related protecting groups in oligoribonucleotide synthesis Stability of intemucleotide linkages to aqueous acid. Nucleic Acids Res 22 2209-2216, 1994. 

Reese CB, Serfinowska HT, Zappia G. An acetal group suitable for the protection of 2 -hydroxy functions in rapid oligoribonucleotide synthesis. Tetrahedron Lett 27 2291-2294, 1986. 

Wincott F, Usman N. 2 -(Trimethylsilyl)ethoxymethyl protection of the 2 -hydroxyl group in oligoribonucleotide synthesis. Tetrahedron Lett 35 6827-6830, 1994. 

Stawinski J, Stromberg R, Thelin M, Westman E. Studies on the t-butyldi-methylsilyl group as 2 -(9-protection in oligoribonucleotide synthesis via the i7-phosphonate approach. Nucleic Acids Res 16 9285-9298, 1988. 

Chaix C, Molko D, Teoule R. The use of labile base protecting groups in oligoribonucleotide synthesis. Tetrahedron Lett 30 71-74, 1989. 

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