Changed reactivity of secondary hydroxyl groups in C8-modified adenosine – lessons learned from silylation

Submitting author affiliation:
University Greifswald, Greifswald, Germany

Beilstein Arch. 2020, 2020102.

Published 09 Sep 2020

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Synthesis of site-specifically modified oligonucleotides has become a major tool for RNA structure and function studies. Reporter groups or specific functional entities are required to be attached at a pre-defined site of the oligomer.  An attractive strategy is the incorporation of suitably functionalized building blocks that allow post-synthetic conjugation of the desired moiety. A C8-alkynyl modified adenosine derivative was synthesized, reviving an old synthetic pathway for iodination of purine nucleobases. Silylation of the C8-alkynyl modified adenosine revealed unexpected selectivity of the two secondary sugar hydroxyl groups, with the 3'-O-isomer being preferentially formed. Optimization of the protection scheme lead to a new and economic route to the desired C8-alkynylated building block and its incorporation in RNA.

Keywords: Nucleoside Chemistry; Protecting groups; Sonogashira reaction; RNA synthesis

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Frommer, J.; Müller, S. Beilstein Arch. 2020, 2020102. doi:10.3762/bxiv.2020.102.v1

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