Fluorescent Purine Nucleosides Containing Amino Acid Side Chain
Balticum Organicum Syntheticum: Program and Abstracts 2016
Dace Cīrule, Kristers Ozols, oskars Platnieks, Ērika Bizdēna, Māris Turks

Azolylpurine nucleoside derivatives exhibit a broad range of notable biological activities. Our group has recently investigated regioselective SNAr reactions of 2,6-bis-triazolyl purine nucleosides with primary and secondary amines and thiols. The obtained N6-substituted 2-triazolyl adenosine analogs possessed good fluorescent properties. Herein, we report the synthesis of purine nucleoside – amino acid conjugates. The obtained nucleosides showed useful levels of fluorescence with quantum yields up to 38% and Stoke shifts up to 91 nm. The chemoselectivity of nucleophilic aromatic substitution between bis-triazolylderivative and amino acids containing both N- and S-nucleophilic sites are discussed.


Keywords
Purine, Nucleosides, Nucleoside-amino acid conjugates, Click chemistry
Hyperlink
http://www.boschem.eu/public/BOS2016/BOS-2016_Anstract-Book_Final.pdf

Cīrule, D., Ozols, K., Platnieks, O., Bizdēna, Ē., Turks, M. Fluorescent Purine Nucleosides Containing Amino Acid Side Chain. In: Balticum Organicum Syntheticum: Program and Abstracts, Latvia, Riga, 3-6 July, 2016. Riga: 2016, pp.53-53.

Publication language
English (en)
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