1.
J Am Chem Soc
; 129(25): 7724-5, 2007 Jun 27.
Artículo
en Inglés
| MEDLINE
| ID: mdl-17536801
2.
Org Lett
; 6(21): 3817-20, 2004 Oct 14.
Artículo
en Inglés
| MEDLINE
| ID: mdl-15469357
RESUMEN
[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.