Oligonucleotide incorporation of 8-thio-2'-deoxyguanosine.
[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.
Department of Chemistry, University of Richmond, Gottwald N-113, Richmond, Virginia 23173, USA. mhamm@richmond.edu
Michelle L
ML
Hamm
Rushina
R
Cholera
Courtney L
CL
Hoey
Timothy J
TJ
Gill
D001483:Base Sequence; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000138:chemical synthesis; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D009841:Oligonucleotides / Q000737:chemistry*; D010084:Oxidation-Reduction
C508466:8-thio-2'-deoxyguanosine; D009841:Oligonucleotides; D004247:DNA; D003849:Deoxyguanosine