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Angewandte Chemie International Edition
Communication

Synthesis of 1,8‐Naphthyridine C‐Nucleosides and Their Base‐Pairing Properties in Oligodeoxynucleotides: Thermally Stable Naphthyridine:Imidazopyridopyrimidine Base‐Pairing Motifs*

Sadao Hikishima

Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita‐12, Nishi‐6, Kita‐ku, Sapporo 060‐0812, Japan, Fax: (+81) 11‐706‐4980

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Noriaki Minakawa Prof.

E-mail address:noriaki@pharm.hokudai.ac.jp

Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita‐12, Nishi‐6, Kita‐ku, Sapporo 060‐0812, Japan, Fax: (+81) 11‐706‐4980

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Kazuyuki Kuramoto

Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita‐12, Nishi‐6, Kita‐ku, Sapporo 060‐0812, Japan, Fax: (+81) 11‐706‐4980

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Yuki Fujisawa

Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita‐12, Nishi‐6, Kita‐ku, Sapporo 060‐0812, Japan, Fax: (+81) 11‐706‐4980

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Maki Ogawa

Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita‐12, Nishi‐6, Kita‐ku, Sapporo 060‐0812, Japan, Fax: (+81) 11‐706‐4980

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Akira Matsuda Prof.

E-mail address:matuda@pharm.hokudai.ac.jp

Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita‐12, Nishi‐6, Kita‐ku, Sapporo 060‐0812, Japan, Fax: (+81) 11‐706‐4980

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First published: 11 January 2005
Cited by: 47
*

This work was supported in part by a Grant‐in‐Aid for Scientific Research on Priority Areas and Encouragement of Young Scientists from the Ministry of Education, Science, Sports, and Culture of Japan. This paper constitutes Part 229 of Nucleosides and Nucleotides. Part 228 is reference [15].

Abstract

Out with the old, in with the new: Novel 1,8‐naphthyridine C‐nucleosides, Na‐NO and Na‐ON (see formulae), were synthesized through Heck coupling reactions. Oligodeoxynucleotides containing the Na‐NO and Na‐ON nucleosides formed extremely stable duplexes by the base‐pairing motifs Na‐NO:Im‐ON and Na‐ON:Im‐NO.

Number of times cited: 47

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