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Nucleic Acids Symposium Series 2006 50(1):59-60; doi:10.1093/nass/nrl029
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© 2006 Oxford University Press

Synthesis and cross-linking activities of oligodeoxynucleotides containing a 4-oxoalkenal group

Akio Kobori, Takashi Kobuchi, Masato Ikeda and Akira Murakami

Department of Biomolecular Engineering, Graduate School of Science and Technolog, Kyoto Institute of Technology, Gosyokaidocho, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan

The 4-oxoalkenal group, which has been characterized as part of a novel lipid-peroxidation-derived genotoxin, reacts with dG, dC, and dA, yielding etheno adducts. To develop a new interstrand cross-linking system based on the covalent bond formed between the 4-oxoalkenal group and DNA bases, we prepared 4-oxoalkenal-derivatized oligodeoxynucleotides. The protected 4-oxoalkenal derivative with a primary amino group was synthesized and incorporated to the 5' end of the oligodeoxynucleotide. In the presence of the complementary strand, cross-linking products were observed by HPLC and MALDI-MS analysis.


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