New oligodeoxynucleotide derivatives containing N-(methanesulfonyl)-phosphoramidate (mesyl phosphoramidate) internucleotide group
- Autores: Chelobanov B.1,2, Burakova E.1, Prokhorova D.1,2, Fokina A.1, Stetsenko D.1,2
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Afiliações:
- Institute of Chemical Biology and Fundamental Medicine, Siberian Branch
- Novosibirsk State University
- Edição: Volume 43, Nº 6 (2017)
- Páginas: 664-668
- Seção: Article
- URL: https://journals.rcsi.science/1068-1620/article/view/228731
- DOI: https://doi.org/10.1134/S1068162017060024
- ID: 228731
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Resumo
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.
Sobre autores
B. Chelobanov
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch; Novosibirsk State University
Email: dast@niboch.nsc.ru
Rússia, Novosibirsk, 630090; Novosibirsk, 630090
E. Burakova
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch
Email: dast@niboch.nsc.ru
Rússia, Novosibirsk, 630090
D. Prokhorova
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch; Novosibirsk State University
Email: dast@niboch.nsc.ru
Rússia, Novosibirsk, 630090; Novosibirsk, 630090
A. Fokina
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch
Email: dast@niboch.nsc.ru
Rússia, Novosibirsk, 630090
D. Stetsenko
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch; Novosibirsk State University
Autor responsável pela correspondência
Email: dast@niboch.nsc.ru
Rússia, Novosibirsk, 630090; Novosibirsk, 630090