Open AccessIdentification of oligonucleotide fragments produced in a strand scisslon reaction of the d(C-G-C-G-C-G) duplex by bleomycin
Author(s) -
Seiichi Uesugi,
Toshio Shida,
Morio Ikehara,
Yuji Kobayashi,
Yoshimasa Kyōgoku
Publication year - 1984
Publication title -
nucleic acids research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 9.008
H-Index - 537
eISSN - 1362-4954
pISSN - 0305-1048
DOI - 10.1093/nar/12.3.1581
Subject(s) - oligonucleotide , biology , duplex (building) , cytosine , bond cleavage , dna , cleavage (geology) , stereochemistry , nuclear magnetic resonance spectroscopy , deoxyguanosine , biochemistry , microbiology and biotechnology , chemistry , paleontology , fracture (geology) , catalysis
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 H2O2 and degradation products (1, 2, cytosine and deoxyguanosine 5'-phosphate) were identified. 1 and 2 contain a carboxymethyl group attached to the 3'-terminal phosphoryl group of d(C-Gp) and d(C-G-C-Gp), respectively. These compounds were identified by UV, 1H and 31P 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.