Facile synthesis of a 3-deazaadenosine phosphoramidite for RNA solid-phase synthesis

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Abstract

Access to 3-deazaadenosine (c3A) building blocks for RNA solid-phase synthesis represents a severe bottleneck in modern RNA research, in particular for atomic mutagenesis experiments to explore mechanistic aspects of ribozyme catalysis. Here, we report the 5-step synthesis of a c3A phosphoramidite from cost-affordable starting materials. The key reaction is a silyl-Hilbert-Johnson nucleosidation using unprotected 6-amino-3-deazapurine and benzoyl-protected 1-O-acetylribose. The novel path is superior to previously described syntheses in terms of efficacy and ease of laboratory handling.

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Mairhofer, E., Fuchs, E., & Micura, R. (2016). Facile synthesis of a 3-deazaadenosine phosphoramidite for RNA solid-phase synthesis. Beilstein Journal of Organic Chemistry, 12, 2556–2562. https://doi.org/10.3762/bjoc.12.250

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