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Oligonucleotide Incorporation of 8-Thio-2‘-deoxyguanosine

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journal contribution
posted on 14.10.2004 by Michelle L. Hamm, Rushina Cholera, Courtney L. Hoey, Timothy J. Gill
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.