A NEW ODORLESS PROCEDURE FOR THE SYNTHESIS OF 2′-DEOXY-6-THIOGUANOSINE AND ITS INCORPORATION INTO OLIGODEOXYNUCLEOTIDES
A NEW ODORLESS PROCEDURE FOR THE SYNTHESIS OF 2′-DEOXY-6-THIOGUANOSINE AND ITS INCORPORATION INTO OLIGODEOXYNUCLEOTIDES
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DOI：
10.1080/15257770903155576
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发表时间：
2009-01-01
影响因子：
1.3
通讯作者：
Sasaki, Shigeki
中科院分区：
文献类型：
--
作者：
Onizuka, Kazumitsu;Taniguchi, Yosuke;Sasaki, Shigeki
6-S-{2-[（2-乙基己基）氧羰基]乙基）}-3 ′，5 ′-O-双（叔丁基二甲基硅基）-2 ′-脱氧-6-硫代胍基（2）由相应的6-O-均三甲苯磺酰基衍生物与3-巯基丙酸2-乙基己酯反应，以高产率合成。将2的亚磷酰胺前体成功地应用于全自动DNA合成仪，制备了含2 '-脱氧-6-硫代鸟苷的ODN。结果表明，3-巯基丙酸2-乙基己酯可用作无味试剂，也可用作2 ′-脱氧-6-硫代鸟苷的S-保护基。
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.