Organic Letters
Organic Letters
4 years ago

Synthesis of Naphthyridine Carbamate Dimer (NCD) Derivatives Modified with Alkanethiol and Binding Properties of G–G Mismatch DNA

Synthesis of Naphthyridine Carbamate Dimer (NCD) Derivatives Modified with Alkanethiol and Binding Properties of G–G Mismatch DNA
Shouta Miki, Takeshi Yamada, Anisa Ul’Husna, Akiko Michikawa, Kazuhiko Nakatani
A series of new DNA binding molecules NCD–Cn–SH (n = 3, 4, 5, and 6) is reported, which possesses the NCD (naphthyridine carbamate dimer) domain selectively binding to the G–G mismatch in the 5′-CGG-3′/5′-CGG-3′ sequence and a thiol moiety, which undergoes spontaneous dimerization to (NCD–Cn–S)2 upon oxidation under aerobic conditions. The S–S dimer (NCD–Cn–S)2 produced the 1:1 binding complex with improved thermal stability. The dimer binding to the CGG/CGG DNA showed higher positive cooperativity than the binding of monomer and previously synthesized NCTn derivative. The dimerization of NCD–Cn–SH was selectively accelerated on the CGG repeat DNA but not on the CAG repeat DNA.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01632

DOI: 10.1021/acs.orglett.7b01632

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