C-Nucleosides

C-Nucleosides

General structure of a C-nucleoside featuring D-ribose as the sugar unit. Note the C-C bond that links the nucleobase to the sugar.

In C-nucleosides, a carbon-carbon bond links the nucleobase (or nucleobase analog) to the sugar. This is in contrast to canonical nucleosides, where a nitrogen atom links the base to the ribose or 2'-deoxyribose. The best-known natural C-nucleoside is pseudouridine. Several therapeutic nucleosides (or their prodrug forms used as active pharmaceutical ingredients) are known that are C-nucleosides.

References

Review

[1] M. Hocek, C-Nucleosides: synthetic strategies and biological applications. Chem. Rev. 2009, 109, 6729–6764. https://doi.org/10.1021/cr9002165

Synthetic Papers

[2]  H.-J. Kim, N. A. Leal, S. Hoshika, S. A. Benner, Ribonucleosides for an artificially expanded genetic information system. J. Org. Chem. 2014, 79, 3194−3199. https://doi.org/10.1021/jo402665d

[3]  T. Gniech, C. Richert, Diastereoselective synthesis of pyridone ribo-C-nucleosides via Heck reaction and oxidation. Eur. J. Org. Chem. 2024, e202400342. https://doi.org/10.1002/ejoc.202400342