A new modified cytosine base capable of base pairing with guanine using four hydrogen bonds

作者：Yamada Ken; Masaki Yoshiaki; Tsunoda Hirosuke; Ohkubo Akihiro; Seio Kohji; Sekine Mitsuo^*

来源：Organic and Biomolecular Chemistry, 2014, 12(14): 2255-2262.

DOI：10.1039/c3ob42420k

Oligonucleotides, containing 4-N-(1H-pyrrol-2-ylcarbonyl)deoxycytidine (dC(Pyc)) and related derivatives, were synthesized via deprotection using 1.5 M NaOMe/MeOH. Among them, oligodeoxynucleotides containing dC(Pyc) exhibited a higher hybridization affinity for DNA and RNA than the unmodified oligodeoxynucleotides. Comparative analysis between dC(Pyc) and its derivatives by molecular dynamic simulation indicated that the C-Pyc residue could form four hydrogen bonds with the opposite G nucleobase keeping a more planar structure than the C-Inc residue where the Pyc group was replaced with a 1H-indol-2-yl-carbonyl group.

• 出版日期2014