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Nucleic Acids Research, 1984, Vol. 12, No. 3 1581-1592
© 1984

CHEMISTRY

Identification of oligonucleotide fragments produced in a strand scisslon reaction of the d(C-G-C-G-C-G) duplex by bleomycin

Seiichi Uesugi, Toshio Shida, Morio Ikehara, Yuji Kobayashi* and Yoshimasa Kyogoku*

Faculty of Pharmaceutical Sciences Suita Osaka 565, Japan *Institute for Protein Research, Osaka University Suita Osaka 565, Japan

Received November 29, 1983. Accepted January 3, 1983.

To elucidate the mechanism of DNA strand scission by bleomycin, a d(C-G C-G-C-G) duplex was treated with the bleomycin-iron ion complex in the presence of H2 O2 and degradation products (1, 2, cytosine and deoxyguanosine 5'-phosphate were identified. 1 and 2 contain a carboxyinethyl group attached to the 3'-terminal phosphoryl group of d(C{intcal}Gp) and31 d(C-G-C-Gp), respectively. These compounds were identified by UV, H and P NMR spectroscopy and paper electrophoresis. 1 was synthesized from the protected dinucleotide and glycolic acid and the proton NMR spectrum was identical to that of 1 obtained as a degradation product. Thus the oligonucleotide fragments produced by the action of bleomycin on DNA were directly identified and cleavage of the C3'-C4' bond of the sugar residues was proved.


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