857684-40-3Relevant academic research and scientific papers
Replacement of canonical DNA nucleobases by benzotriazole and 1,2,3-triazolo[4,5-d]pyrimidine: Synthesis, fluorescence, and ambiguous base pairing
Seela, Frank,Jawalekar, Anup M.,Muenster, Ingo
, p. 751 - 765 (2005)
The syntheses and the fluorescence properties of 7H-3,6-dihydro-1,2,3- triazolo[4,5-d]pyrimidin-7-one 2′-deoxy-β-D-ribonucleosides (=2′-deoxy-8-azainosine) 3 (N3), 15 (N2), and 16 (N1) as well as of 1,2,3-benzotriazole 2′-O-methyl-β- or -α-D-ribofuranosides 6 (N1) and 24 (N1) are described. Also the fluorescence properties of 1,2,3-benzotriazole 2′-deoxy-β-D-ribofuranosides 4 (N1) and 5 (N2) are evaluated. From the nucleosides 3-6, the phosphoramidites 19, 26a, 26b, and 28 are prepared and employed in solid-phase oligonucleotide synthesis. In 12-mer DNA duplexes, compound 3 shows similar ambiguous base-pairing properties as 2′-deoxyinosine (1), while the nucleosides 4-6 show strong pairing with each other and discriminate very little the four canonical DNA constituents.
