The Synthesis of 2′-O-[(Triisopropylsilyl)oxy] methyl (TOM) Phosphoramidites of Methylated Ribonucleosides (m1G, m2G, m22G, m1I, m3U, m4C, m6A, m62A) for Use in Automated RNA Solid-Phase Synthesis

Article abstract of DOI:10.1007/s00706-003-0592-1

The straightforward synthesis of eight methylated ribonucleoside phosphoramidites is described. These building blocks allow for incorporation of the naturally occuring nucleosides 1-methylguanosine (m¹G), N ²-methylguanosine (m²G), N²N ²-dimethylguanosine (m²₂G), 1-methylinosine (m¹I), 3-methyluridine (m³U), N⁴- methylcytidine (m⁴C), N⁶-methyladenosine (m⁶A), and N⁶,N⁶-dimethyladenosine (m⁶₂A) into oligoribonucleotides by automated RNA solid-phase synthesis. In all cases, the ribose 2′-hydroxyl group of the building blocks is masked by the recently introduced [(triisopropylsilyl)oxy]methyl (TOM) group.