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

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

March 24, 2020

  • Year

  • Technique

  • Industry

Title

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

Author

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

Year

2020

Journal

Journal of Organic Chemistry

Abstract

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.

Full Article

https://pubs.acs.org/doi/abs/10.1021/acs.joc.9b02750

Instrument

V-560, J-720

Keywords

Absorption, DNA structure, Thermal stability, Circular dichroism, Chemical stability, Organic chemistry, Biochemistry