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Modification Of Purine And Pyrimidine Nucleosides By Direct C-H Bond Activation, Yong Liang, Stanislaw F. Wnuk
Modification Of Purine And Pyrimidine Nucleosides By Direct C-H Bond Activation, Yong Liang, Stanislaw F. Wnuk
Stanislaw Wnuk
Transition metal-catalyzed modifications of the activated heterocyclic bases of nucleosides as well as DNA or RNA fragments employing traditional cross-coupling methods have been well-established in nucleic acid chemistry. This review covers advances in the area of cross-coupling reactions in which nucleosides are functionalized via direct activation of the C8-H bond in purine and the C5-H or C6-H bond in uracil bases. The review focuses on Pd/Cu-catalyzed couplings between unactivated nucleoside bases with aryl halides. It also discusses cross-dehydrogenative arylations and alkenylations as well as other reactions used for modification of nucleoside bases that avoid the use of organometallic precursors and …
Strain Promoted Click Chemistry Of 2- Or 8-Azidopurine And 5-Azidopyrimidine Nucleosides And 8-Azidoadenosine Triphosphate With Cyclooctynes. Application To Living Cell Fluorescent Imaging, Jessica Zayas, Marie Annoual, Jayanta K. Das, Quentin Felty, Walter Gonzalez, Jaroslava Miksovska, Nima Sharifai, Akira Chiba, Stanislaw F. Wnuk
Strain Promoted Click Chemistry Of 2- Or 8-Azidopurine And 5-Azidopyrimidine Nucleosides And 8-Azidoadenosine Triphosphate With Cyclooctynes. Application To Living Cell Fluorescent Imaging, Jessica Zayas, Marie Annoual, Jayanta K. Das, Quentin Felty, Walter Gonzalez, Jaroslava Miksovska, Nima Sharifai, Akira Chiba, Stanislaw F. Wnuk
Stanislaw Wnuk
Strain-promoted click chemistry of nucleosides and nucleotides with an azido group directly attached to the purine and pyrimidine rings with various cyclooctynes in aqueous solution at ambient temperature resulted in efficient formation (3 min to 3 h) of fluorescent, light-up, triazole products. The 2- and 8-azidoadenine nucleosides reacted with fused cyclopropyl cyclooctyne, dibenzylcyclooctyne, or monofluorocyclooctyne to produce click products functionalized with hydroxyl, amino, N-hydroxysuccinimide, or biotin moieties. The 5-azidouridine and 5-azido-2'-deoxyuridine were similarly converted to the analogous triazole products in quantitative yields in less than 5 min. The 8-azido-ATP quantitatively afforded the triazole product with fused cyclopropyl cyclooctyne in aqueous …