Advertisement

Monatshefte für Chemie / Chemical Monthly

, Volume 134, Issue 6, pp 851–873 | Cite as

The Synthesis of 2′-O-[(Triisopropylsilyl)oxy] methyl (TOM) Phosphoramidites of Methylated Ribonucleosides (m 1 G, m 2 G, m 2 2 G, m 1 I, m 3 U, m 4 C, m 6 A, m 6 2 A) for Use in Automated RNA Solid-Phase Synthesis

  • Claudia Höbartner
  • Christoph Kreutz
  • Elke Flecker
  • Elke Ottenschläger
  • Werner Pils
  • Karl Grubmayr
  • Ronald Micura

Summary.

 The straightforward synthesis of eight methylated ribonucleoside phosphoramidites is described. These building blocks allow for incorporation of the naturally occuring nucleosides 1-methylguanosine (m 1 G), N2-methylguanosine (m 2 G), N2,N2-dimethylguanosine (m 2 2 G), 1-methylinosine (m 1 I), 3-methyluridine (m 3 U), N4-methylcytidine (m 4 C), N6-methyladenosine (m 6 A), and N6,N6-dimethyladenosine (m 6 2 A) 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.

Keywords. Phosphoramidites; TOM-chemistry; RNA solid-phase synthesis; Methylation; Modified nucleosides. 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Copyright information

© Springer-Verlag/Wien 2003

Authors and Affiliations

  • Claudia Höbartner
    • 1
  • Christoph Kreutz
    • 1
  • Elke Flecker
    • 2
  • Elke Ottenschläger
    • 2
  • Werner Pils
    • 2
  • Karl Grubmayr
    • 2
  • Ronald Micura
    • 1
  1. 1.Institute of Organic Chemistry, University of Innsbruck, AustriaAT
  2. 2.Institute of Chemistry, University of Linz, AustriaAT

Personalised recommendations