Oligonucleotide incorporation of 8-thio-2′-deoxyguanosine

被引：23

作者：

Hamm, ML ^{[1
]}

Cholera, R ^{[1
]}

Hoey, CL ^{[1
]}

Gill, TJ ^{[1
]}

机构：

[1] Univ Richmond, Dept Chem, Richmond, VA 23173 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 21期

关键词：

D O I：

10.1021/ol0484097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(GRAPHICS) 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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页码：3817 / 3820

页数：4

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