Purine Functionalization via Bis-Triazolyl Derivatives

Balticum Organicum Syntheticum: Program and Abstracts 2016
Kristers Ozols, Dace Cīrule, Ērika Bizdēna, Māris Turks

2,6-Diazidopurine deoxyribonucleoside has been employed for synthesis of 2,6-bis-triazolyl derivatives using the Cu(I) catalyzed azide-alkyne cycloaddition. These compounds undergo neat, regioselective and high-yielding reactions with N- and S- nucleophiles. Since the N- products exhibit visible fluorescence, one of the adenosine analogues (λ emission = 420 nm, QY = 12% in water) has been further investigated as a fluorescent label. After incorporation in trinucleotide, 7% fluorescence quantum yield was determined.

Keywords
Purine, Nucleoside, Fluorescent adenosine, Click chemistry, Aromatic substitution
Hyperlink
http://www.boschem.eu/public/BOS2016/BOS-2016_Anstract-Book_Final.pdf

Ozols, K., Cīrule, D., Bizdēna, Ē., Turks, M. Purine Functionalization via Bis-Triazolyl Derivatives. In: Balticum Organicum Syntheticum: Program and Abstracts, Latvia, Rīga, 3-6 July, 2016. Riga: 2016, pp.125-125.

Publication language
English (en)