4.7 Article

6-Iodopurine as a Versatile Building Block for RNA Purine Architecture Modifications

Journal

BIOCONJUGATE CHEMISTRY
Volume 33, Issue 2, Pages 353-362

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.bioconjchem.1c00595

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Funding

  1. Natural Science Foundation of China [91753201, 21721005]

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Natural modified bases in RNA play a crucial role in basic biological processes, and artificial RNA modifications have been widely used for studying RNA interference, structure, and dynamics. This study presents a chemical method for the synthesis of RNA containing C-6 modified purine, which provides a convenient approach for synthesizing oligonucleotides with specific structures.
Natural modified bases in RNA were found to be indispensable for basic biological processes. In addition, artificial RNA modifications have been a versatile toolbox for the study of RNA interference, structure, and dynamics. Here, we present a chemical method for the facile synthesis of RNA containing C-6-modified purine. 6-Iodopurine, as a postsynthetic building block with high reactivity, was used for metal-free construction of C-N, C-O, and C-S bonds under mild conditions and C-C bond formation by Suzuki-Miyaura cross-coupling. Our strategy provides a convenient approach for the synthesis of various RNA modifications, especially for oligonucleotides containing specific structures.

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