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Short Paper | Special issue | Vol 97, No. 2, 2018, pp.1149-1156
Published online, 30th May, 2018
DOI: 10.3987/COM-18-S(T)53
Design and Synthesis of a DNA-Like Structure Composed of Alkynyl C-Nucleotide with 2-Aminopyrimidin-4-one as a Nucleobase

Fumihiro Kurosaki, Junya Chiba,* and Masahiko Inouye*

*Graduate School of Medicines and Pharmaceutical Sciences for Research, Toyama University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan


A heterocyclic compound, 2-aminopyrimidin-4-one, was found to be a new candidate of a non-natural nucleobase that forms a novel base pair by self-dimerization. 2-Aminopyrimidin-4-one was connected to a deoxyribose through an acetylene linkage. The non-natural nucleoside was derivatized to its phosphoramidite that could be subjected to a conventional solid-phase DNA synthesis. The solid-phase auto-synthesis successfully afforded a non-natural DNA-like oligomer bearing 2-aminopyrimidin-4-one as a nucleobase. The synthetic oligomer exhibited reversible formation of a higher-order structure that would be a duplex like natural DNA. The present study means creation of a novel artificial DNA-like system with unordinary odd numbers of genetic alphabets.