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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

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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), N 2-methylguanosine (m 2 G), N 2,N 2-dimethylguanosine (m 2 2 G), 1-methylinosine (m 1 I), 3-methyluridine (m 3 U), N 4-methylcytidine (m 4 C), N 6-methyladenosine (m 6 A), and N 6,N 6-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.

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Authors and Affiliations

  1. Institute of Organic Chemistry, University of Innsbruck, Austria, , , , , , AT

    Claudia Höbartner, Christoph Kreutz & Ronald Micura

  2. Institute of Chemistry, University of Linz, Austria, , , , , , AT

    Elke Flecker, Elke Ottenschläger, Werner Pils & Karl Grubmayr

Authors
  1. Claudia Höbartner
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  2. Christoph Kreutz
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  3. Elke Flecker
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  4. Elke Ottenschläger
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  5. Werner Pils
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  6. Karl Grubmayr
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  7. Ronald Micura
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Additional information

Present address: Voestalpine, Voest-Alpine Strasse 3, A-4031 Linz

Present address: Baxter AG Austria, Lange Allee 51, A-1221 Vienna

Present address: DSM Fine Chemicals Austria, St. Peter Strasse 25, A-4021 Linz

Corresponding author. E-mail: ronald.micura@uibk.ac.at

Received January 14, 2003; accepted January 20, 2003 Published online May 2, 2003

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Höbartner, C., Kreutz, C., Flecker, E. et al. 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. Monatshefte für Chemie 134, 851–873 (2003). https://doi.org/10.1007/s00706-003-0592-1

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  • DOI: https://doi.org/10.1007/s00706-003-0592-1

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