2-Aminopyridine as a Nucleobase Substitute for Adenine in DNA-like Architectures: Synthesis of Alkynyl C-Nucleotides and Their Hybridization Characteristics

Kurosaki, Fumihiro; Chiba, Junya; Oda, Yutaro; Hino, Airi; Inouye, Masahiko

2-Aminopyridine as a Nucleobase Substitute for Adenine in DNA-like Architectures: Synthesis of Alkynyl C-Nucleotides and Their Hybridization Characteristics

2019

Kurosaki, Fumihiro | Chiba, Junya | Oda, Yutaro | Hino, Airi | Inouye, Masahiko

Halogenated 2-aminopyridine was attached to the acetylene terminal of ethynyl C-2-deoxy-β-d-ribofuranoside as a nucleobase substitute, and then, the C-nucleoside was incorporated into natural DNAs. The resulting chimeric DNA constructed double helical structures with the complementary chimeric DNA. In the duplex, 2-aminopyridine functioned as an adenine analogue that formed a base pair with a non-natural thymine isostere. Artificial homooligomers were also prepared only from the adenine-type C-nucleoside and proven to form completely artificial double helices with the corresponding artificial thymine-type homooligomers.

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