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Nucleic Acids Research, 1992, Vol. 20, No. 4 777-782
© 1992

CHEMISTRY

The synthesis and properties of oligodeoxyribonucleotides containing N6-methoxyadenine

Hisayoshi Nishio, Akira Ono, Akira Matsuda* and Tohru Ueda

Faculty of Pharmaceutical Sciences, Hokkaido University Kita-12, Nishi-6, Kita-ku, Sapporo 060, Japan

*To whom correspondence should be addressed

Received November 20, 1991. Revised January 28, 1992. Accepted January 28, 1992.

Oligodeoxyribonucleotides containing N6-methoxy-adenine (M) have been synthesized. The order of stability of duplexes consisting of synthesized oligodeoxyribonucleotides, 5d(CCTGGTAXCAGGTCC)3-5'd(GGACCTGNTACCAGG)3' (X = M, A, G. N = A, G, T, C), was M: A (Tm = 52°C) >M: T (50°C) >M: G (48°C) >M: C (46°C) observed by thermal denaturation in a buffer of 0.01 M Na cacodylate, and 0.1 M NaCI at pH 7.0. The Tms are within a range of 6 degrees of difference, which Is smaller than those of Tms of the duplexes containing A:N pairs (11 degrees) and G:N pairs (11 degrees). DNA replication study on a template-primer system, 5'd(32P-CAGCTTTCGC)3' 3'd(GTCGAAAGCGMAGTCG)5',showed that TTP and dCTP were incorporated into DNA strands at a site opposite to M by Klenow DNA polymerase, but dATP and dGTP were not.


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