Oligonucleotide incorporation of 8-thio-2'-deoxyguanosine
Michelle L Hamm1, Rushina Cholera, Courtney L Hoey
1Department of Chemistry, University of Richmond, Gottwald N-113, Richmond, Virginia 23173, USA. mhamm@richmond.edu
Abstract:
[reaction: see text] 8-Thio-2'-deoxyguanosine (SdG) is a useful analogue of the abundant promutagen 8-oxo-2'-deoxyguanosine (OdG). Its synthesis and DNA incorporation using standard phosphoramidite chemistry is reported. To prevent oxidation during DNA synthesis, the sulfur was protected as a 2-(trimethylsilyl)ethyl sulfide. Subsequent treatment with TBAF yielded the desired 8-thiocarbonyl functionality. Melting studies with SdG revealed almost equal stabilities of SdG:dC and SdG:dA base pairs, lending insight into the base-pairing preferences of OdG.
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