First Synthesis of Fully Modified 4鈥?SelenoRNA and 2鈥?OMe-4鈥?selenoRNA Based on the Mechanistic Considerations of an Unexpected Strand Break

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• 作者：Noriko Tarashima ; Koya Hayashi ; Maki Terasaki ; Hirotsugu Taniike ; Yusuke Inagaki ; Kenji Hirose ; Kazuhiro Furukawa ; Akira Matsuda ; Noriaki Minakawa
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：September 19, 2014
• 年：2014
• 卷：16
• 期：18
• 页码：4710-4713
• 全文大小：262K
• ISSN：1523-7052

文摘

This study investigated oligonucleotide (ON) synthesis containing 4鈥?selenoribonucleoside(s) under standard phosphoramidite conditions. Careful operation using a manual ON synthetic system revealed that an unexpected strand break occurred to afford a C2-symmetric homodimer as a byproduct. In addition, this side reaction occurred during I₂ oxidation. On the basis of these findings, the first synthesis of fully modified 4鈥?selenoRNA and 2鈥?OMe-4鈥?selenoRNA was achieved using tert-butyl hydroperoxide (TBHP) as the alternative oxidant.