Development of N⁶-methyl-2-(1,2,3-triazol-1-yl)-2′-deoxyadenosine as a novel fluorophore and its application in nucleotide synthesis

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• 作者：Kristers Ozols^a ; Dace Cīrule^a ; Irina Novosjolova^a ; Dmitrijs Stepanovs^a ; ^b ; Edvards Liepinsh^b ; Ērika Bizdēna^a ; Māris Turks^a ; ^{maris_turks@ktf.rtu.lv" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Triazolyl purine derivatives ; Nucleophilic aromatic substitution ; Azide reduction ; Fluorescence ; Oligonucleotides
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：9 March 2016
• 年：2016
• 卷：57
• 期：10
• 页码：1174-1178
• 全文大小：1101 K

文摘

The synthesis of fluorescent N⁶-methyl-2-(1,2,3-triazol-1-yl)-2′-deoxyriboadenosine (A^Oz) 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 GA^OzC 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.