Development of N6-methyl-2-(1,2,3-triazol-1-yl)-2′-deoxyadenosine as a Novel Fluorophore and Its Application in Nucleotide Synthesis

Tetrahedron Letters 2016
Kristers Ozols, Dace Cīrule, Irina Novosjolova, Dmitrijs Stepanovs, Edvards Liepiņš, Ērika Bizdēna, Māris Turks

The synthesis of fluorescent N6-methyl-2-(1,2,3-triazol-1-yl)-2′-deoxyriboadenosine (AOz) was achieved by methylamine induced nucleophilic aromatic substitution of the corresponding 2,6-bis-(1,2,3-triazol-1-yl)purine 2′-deoxyribonucleoside. The developed fluorophore exhibits quantum yields of 20% and 12% in methanol and water, respectively. It was further applied in the synthesis of trinucleotide GAOzC which sustains a reasonable Stokes shift of 121 nm and 7% quantum yield upon irradiation at 310 nm. It was also demonstrated that Cu(I) species reduce 2,6-diazido purine derivatives regioselectively at C(6) providing a practical entry to 6-amino-2-azido-purine nucleosides.

Keywords
Triazolyl purine derivatives; Nucleophilic aromatic substitution; Azide reduction; Fluorescence; Oligonucleotides
DOI
10.1016/j.tetlet.2016.02.003
Hyperlink
http://www.sciencedirect.com/science/article/pii/S0040403916301137

Ozols, K., Cīrule, D., Novosjolova, I., Stepanovs, D., Liepiņš, E., Bizdēna, Ē., Turks, M. Development of N6-methyl-2-(1,2,3-triazol-1-yl)-2′-deoxyadenosine as a Novel Fluorophore and Its Application in Nucleotide Synthesis. Tetrahedron Letters, 2016, Vol.57, Iss.10, pp.1174-1178. ISSN 0040-4039. Available from: doi:10.1016/j.tetlet.2016.02.003

Publication language
English (en)