New oligodeoxyribonucleotide derivatives bearing internucleotide N-tosyl phosphoramidate groups: Synthesis and complementary binding to DNA and RNA

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• 作者：D. V. Prokhorova ; B. P. Chelobanov…
• 关键词：β ; cyanoethyl phosphite ; solid ; phase synthesis ; Staudinger reaction ; p ; toluenesulfonyl azide
• 刊名：Russian Journal of Bioorganic Chemistry
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：43
• 期：1
• 页码：38-42
• 全文大小：
• 刊物类别：Biomedical and Life Sciences
• 刊物主题：Biochemistry, general; Bioorganic Chemistry; Organic Chemistry; Biomedicine general;
• 出版者：Pleiades Publishing
• ISSN：1608-330X
• 卷排序：43

文摘

N-Sulfonyl phosphoramidate derivatives of oligodeoxyribonucleotides containing N-tosyl phosphoramidate groups are first reported. The synthesis is based on Staudinger reaction between tosyl azide and 3′,5′-dinucleoside β-cyanoethyl phosphite comprising the immobilized oligonucleotide, which is obtained by the phosphoramidite coupling during the solid-phase oligonucleotide synthesis. The N-tosyl phosphoramidate group was stable under conditions of the oligonucleotide synthesis, in particular, upon acidic detritylation followed by the removal of protective groups and cleavage from the polymer support by the treatment with concentrated aqueous ammonia at 55°C. The stability of DNA and RNA duplexes of the model oligonucleotides containing N-tosyl phosphoramidate groups was only slightly lower than that of native DNA:DNA and DNA:RNA duplexes, respectively.