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Nucleic Acids Symposium Series 2005 49(1):23-24; doi:10.1093/nass/49.1.23
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© 2005 Oxford University Press

Novel post DNA synthesis chemistry for preparing oligonucleotides containing O6-modified purines

Takayuki Shibata and David M. Williams

Centre for Chemical Biology, Department of Chemistry, Richard Roberts Building, University of Sheffield, Sheffield S3 7HF, UK

O6-Alkylguanine DNA alkyltransferase (AGT) is a key target for inhibition during cancer chemotherapy. A large number of O6-modified-guanine analogues have been developed as AGT inhibitors, of which benzyl and (4-bromothenyl) have been used clinically. Since the normal AGT substrate is the alkylated guanine in DNA, the inhibition of AGT by oligonucleotides containing these compounds offers a promising therapeutic approach in terms of efficacy. In order to prepare such oligonucleotides, we have synthesised the novel phosphoramidite analogue of the 2'-deoxyriboside of 2-amino-6-methylsulfonylpurine. Following the incorporation of the analogue into DNA, the subsequent nucleophilic displacement of the methylsulfanyl group by alkoxide provides a convenient route to a variety of oligonucleotides containing O6-modified guanines.


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