Hamm Michelle L, Cholera Rushina, Hoey Courtney L, Gill Timothy J
Department of Chemistry, University of Richmond, Gottwald N-113, Richmond, Virginia 23173, USA.
Org Lett. 2004 Oct 14;6(21):3817-20. doi: 10.1021/ol0484097.
[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.
