New oligodeoxynucleotide derivatives containing N-(methanesulfonyl)-phosphoramidate (mesyl phosphoramidate) internucleotide group
- 作者: Chelobanov B.1,2, Burakova E.1, Prokhorova D.1,2, Fokina A.1, Stetsenko D.1,2
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隶属关系:
- Institute of Chemical Biology and Fundamental Medicine, Siberian Branch
- Novosibirsk State University
- 期: 卷 43, 编号 6 (2017)
- 页面: 664-668
- 栏目: Article
- URL: https://journals.rcsi.science/1068-1620/article/view/228731
- DOI: https://doi.org/10.1134/S1068162017060024
- ID: 228731
如何引用文章
详细
Novel oligonucleotide derivatives containing N-(methanesulfonyl)-phosphoramidate (mesyl phosphoramidate) group have been described. Solid-phase synthesis of these compounds using an automated DNA synthesizer has been performed for the first time, including the Staudinger reaction between methanesulfonyl azide (mesyl azide) and 3′,5′-dinucleoside 2-cyanoethyl phosphite within an oligonucleotide immobilized on the polymer support, which is a product of phosphoramidite coupling. The mesyl phosphoramidate group is stable to the conditions of oligonucleotide synthesis, in particular, during acidic detritylation and subsequent removal of protecting groups and cleavage of an oligonucleotide from the polymer support by concentrated aqueous ammonia or methylamine at 55°C. It has been shown that the stability of complementary duplexes of oligodeoxynucleotides containing the mesyl phosphoramidate group with a single-stranded DNA is not inferior to the stability of native DNA:DNA duplex. Furthermore, mesyl phosphoramidate oligonucleotides are able to form a complementary duplex with RNA, which is only slightly less stable than the equivalent DNA:RNA duplex. This raises the possibility of their application as potential antisense therapeutic agents.
作者简介
B. Chelobanov
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch; Novosibirsk State University
Email: dast@niboch.nsc.ru
俄罗斯联邦, Novosibirsk, 630090; Novosibirsk, 630090
E. Burakova
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch
Email: dast@niboch.nsc.ru
俄罗斯联邦, Novosibirsk, 630090
D. Prokhorova
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch; Novosibirsk State University
Email: dast@niboch.nsc.ru
俄罗斯联邦, Novosibirsk, 630090; Novosibirsk, 630090
A. Fokina
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch
Email: dast@niboch.nsc.ru
俄罗斯联邦, Novosibirsk, 630090
D. Stetsenko
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch; Novosibirsk State University
编辑信件的主要联系方式.
Email: dast@niboch.nsc.ru
俄罗斯联邦, Novosibirsk, 630090; Novosibirsk, 630090