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Nucleic Acids Symposium Series 2001 1(1):9-10; doi:10.1093/nass/1.1.9
© 2001 by Oxford University Press
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Synthesis of 5-substituted [N3-15N]-pyrimidine nucleosides: Developing model systems for NMR studies of substituent effects on the N-H···N hydrogen bond in duplex DNA

Rei Ishikawa1, Chojiro Kojima1,2, Akira Ono1 and Masatsune Kainosho1

1 Department of Chemistry, CREST and Graduate School of Science, Tokyo Metropolitan University, 1-1 Minami-ohsawa, Hachioji, Tokyo 192-0397, Japan, 2 Present address: Graduate School of Biological Sciences, Nara Institute of Science and Technology

The effects on various NMR parameters of substitutions, which may influence the hydrogen bond strengths of Watson-Crick-type base pairs, were investigated for DNA dodecamers containing 5-substituted-2'-deoxyuridine derivatives in oligomers, 5'-d(CGCGAATXCGCG)-3', where A and X were [ul-15N]-2'-deoxyadenosine and [3-15N]-2'-deoxyuridine derivatives. The substitution effects on the NMR parameters were linearly correlated with the pKa values of the 2'-deoxyuridine derivatives.


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