Onizuka Kazumitsu, Taniguchi Yosuke, Sasaki Shigeki
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
Nucleosides Nucleotides Nucleic Acids. 2009 Aug;28(8):752-60. doi: 10.1080/15257770903155576.
6-S-[2-[(2-ethylhexyl)oxycarbonyl]ethyl)}-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxy-6-thiogua nosine (2) was synthesized in high yield from the corresponding 6-O-mesitylenesulfonyl derivative by the reaction with 2-ethylhexyl 3-mercapto-propionate. The phosphoramidite precursor derived from 2 was successfully applied to an automated DNA synthesizer to produce 2'-deoxy-6-thioguanosine containing ODN. The results showed that 2-ethylhexyl 3-mercaptopropionate is useful as an odor less reagent and also as an S-protecting group of 2'-deoxy-6-thioguanosine.
6 - S - [2 - [(2 - 乙基己基)氧羰基]乙基] - 3',5' - O - 双(叔丁基二甲基甲硅烷基) - 2' - 脱氧 - 6 - 硫代鸟苷(2)由相应的6 - O - 均三甲苯磺酰基衍生物与2 - 乙基己基3 - 巯基丙酸反应高产率合成。衍生自2的亚磷酰胺前体成功应用于自动DNA合成仪以制备含2' - 脱氧 - 6 - 硫代鸟苷的寡脱氧核苷酸。结果表明，2 - 乙基己基3 - 巯基丙酸作为无臭试剂以及2' - 脱氧 - 6 - 硫代鸟苷的S - 保护基团是有用的。
