TY - JOUR
T1 - 2-Aminopyridine as a Nucleobase Substitute for Adenine in DNA-like Architectures
T2 - Synthesis of Alkynyl C-Nucleotides and Their Hybridization Characteristics
AU - Kurosaki, Fumihiro
AU - Chiba, Junya
AU - Oda, Yutaro
AU - Hino, Airi
AU - Inouye, Masahiko
N1 - Publisher Copyright:
© 2019 American Chemical Society.
PY - 2020/2/21
Y1 - 2020/2/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85078655536&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.9b02750
DO - 10.1021/acs.joc.9b02750
M3 - 学術論文
C2 - 31875396
AN - SCOPUS:85078655536
SN - 0022-3263
VL - 85
SP - 2666
EP - 2671
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -