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Updated: Jan 2, 2026

Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism
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Solid-Phase Synthesis of Oligo-ADP-Ribose.

Hans A V Kistemaker1, Nico J Meeuwenoord1, Herman S Overkleeft1

  • 1Department of Bio-organic Synthesis, Leiden Institute of Chemistry, Leiden University, Leiden, The Netherlands.

Current Protocols in Nucleic Acid Chemistry
|December 11, 2019
PubMed
Summary

Researchers developed a solid-phase method to synthesize adenosine diphosphate ribose oligomers (ADPr-oligomers) of specific lengths. This advancement aids in studying ADP-ribosylation, a crucial protein modification.

Keywords:
phosphorylationpoly(ADP-ribose)pyrophosphatesolid-phase synthesis

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Area of Science:

  • Biochemistry and Molecular Biology
  • Chemical Synthesis

Background:

  • ADP-ribosylation is a significant post-translational modification.
  • The precise biological roles of ADP-ribosylation are not fully understood.
  • A need exists for tools to study ADP-ribosylation, such as defined ADPr-oligomers.

Purpose of the Study:

  • To present a novel solid-phase methodology for synthesizing adenosine diphosphate ribose oligomers (ADPr-oligomers).
  • To enable the creation of ADPr-oligomers with precisely defined lengths.
  • To provide researchers with a tool for investigating ADP-ribosylation.

Main Methods:

  • Development of an advanced 2-ribosyl adenosine phosphoramidite building block.
  • Preparation of the building block in solution using an efficient, high-yielding method.
  • Implementation of a solid-phase synthesis protocol featuring phosphitylation of a phosphomonoester as the key condensation step.

Main Results:

  • Successful establishment of a solid-phase synthesis for ADPr-oligomers.
  • The methodology allows for the synthesis of ADPr-oligomers of exact, defined lengths.
  • The key phosphitylation step is efficient within the solid-phase protocol.

Conclusions:

  • The presented solid-phase methodology offers a rapid and reliable way to synthesize defined ADPr-oligomers.
  • This technique is valuable for researchers in structural biology and cell biology.
  • The ability to create specific ADPr-fragments will facilitate the study of ADP-ribosylation.