Open Access. Powered by Scholars. Published by Universities.®
Medicinal-Pharmaceutical Chemistry Commons™
Open Access. Powered by Scholars. Published by Universities.®
Articles 1 - 1 of 1
Full-Text Articles in Medicinal-Pharmaceutical Chemistry
Strain Promoted Click Chemistry Of 8-Azidopurine And 5-Azidopyrimidine Nucleosides And Nucleotides With Cyclooctynes And Applications To Living Cell Imaging, Jessica Zayas
FIU Electronic Theses and Dissertations
The strain promoted azide alkyne cycloaddition (SPAAC) of azido nucleobase modified nucleosides and nucleotides with cyclooctynes to give fluorescent triazoles has been relatively unexplored. Thus, SPAAC between azido-nucleobases and various cyclooctynes in aqueous solution at ambient temperature resulted in the efficient formation (3 min - 2 h) of triazole products with inherent fluorescent properties. 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 previously unexplored 5-azidouridine and labile 5-azido-2'-deoxyuridine were similarly converted to the analogous triazole products in quantitative yields in less …