Replacement of Canonical DNA Nucleobases by Benzotriazole and 1,2,3-Triazolo[4,5-d]pyrimidine: Synthesis, Fluorescence, and Ambiguous Base Pairing

✍ Scribed by Frank Seela; Anup M. Jawalekar; Ingo Münster

• Book ID: 102260138
• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: German
• Weight: 164 KB
• Volume: 88
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200590052

✦ Synopsis

Abstract

The syntheses and the fluorescence properties of 7__H__‐3,6‐dihydro‐1,2,3‐triazolo[4,5‐d]pyrimidin‐7‐one 2′‐deoxy‐β‐D‐ribonucleosides (=2′‐deoxy‐8‐azainosine) 3 (N^3^), 15 (N^2^), and 16 (N^1^) as well as of 1,2,3‐benzotriazole 2′‐O‐methyl‐β‐ or ‐α‐D‐ribofuranosides 6 (N^1^) and 24 (N^1^) are described. Also the fluorescence properties of 1,2,3‐benzotriazole 2′‐deoxy‐β‐D‐ribofuranosides 4 (N^1^) and 5 (N^2^) 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.