Synthesis and characterization of oligodeoxynucleotides containing a novel tetraazabenzo[cd]azulene:naphthyridine base pair |
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Authors: | Hirama Yasuyuki Minakawa Noriaki Matsuda Akira |
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Institution: | a Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan b Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi 1-78-1, Tokushima 770-8505, Japan |
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Abstract: | The synthesis and thermal stability of oligodeoxynucleotides (ODNs) containing 4-amino-2,3,5,6-tetraazabenzocd]azulen-7-one nucleosides 5 (BaON) with the aim of developing new base pairing motif is described. The tricyclic nucleoside 5 was prepared starting with the 7-deaza-7-iodopurine derivative 1 via a palladium catalyzed cross-coupling reaction with methyl acrylate, followed by an intramolecular cyclization. The resulting nucleoside was incorporated into ODNs, and the base pairing property of the BaON:NaNO (2-amino-7-hydroxy-1,8-naphthyridine nucleoside) pair in the duplex was evaluated by a thermal denaturation study. The melting temperature (Tm) of the duplex containing the BaON:NaNO pair showed a higher value than that of the duplexes containing the adenine:thymine (A:T) and the guanine:cytosine (G:C) pairs, however it was lower than that of the ImON:NaNO (ImON = 7-amino-imidazo5′,4′:4,5]pyrido2,3-d]pyrimidin-4(5H)-one nucleoside) pair. A temperature-dependent 1H NMR study revealed that the H-bonding ability of BaON was lower than that of ImON, which would explain why the BaON:NaNO pair was less thermally stable than the ImON:NaNO pair. |
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Keywords: | Tetraazabenzo[cd]azulene Hydrogen bond Nucleobase Nucleoside Oligodeoxynucleotide |
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