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

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New oligodeoxyribonucleotide derivatives bearing internucleotide N-tosyl phosphoramidate groups: Synthesis and complementary binding to DNA and RNA. / Prokhorova, D. V.; Chelobanov, B. P.; Burakova, E. A. et al.

In: Russian Journal of Bioorganic Chemistry, Vol. 43, No. 1, 01.01.2017, p. 38-42.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{0d58ca766b924c39b6d7fa35e0296f8c,

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

abstract = "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.",

keywords = "p-toluenesulfonyl azide, solid-phase synthesis, Staudinger reaction, β-cyanoethyl phosphite, beta-cyanoethyl phosphite, ANTISENSE OLIGONUCLEOTIDES",

author = "Prokhorova, {D. V.} and Chelobanov, {B. P.} and Burakova, {E. A.} and Fokina, {A. A.} and Stetsenko, {D. A.}",

note = "The work was supported by the Russian Foundation for Basic Research (project nos. 15-03-06331, 15-29-01334, 15-54-10049, and 16-03-01055). The oligonucleotide synthesis was supported by the Russian Science Foundation (project no. 15-15-00121). The authors are grateful to M.F. Kassakin for the assistance in recording the mass spectra and M.I. Mesh-chaninova for the oligoribonucleotide synthesis.",

year = "2017",

month = jan,

day = "1",

doi = "10.1134/S1068162017010071",

language = "English",

volume = "43",

pages = "38--42",

journal = "Russian Journal of Bioorganic Chemistry",

issn = "1068-1620",

publisher = "MAIK NAUKA/INTERPERIODICA/SPRINGER",

number = "1",

}

RIS

TY - JOUR

T1 - New oligodeoxyribonucleotide derivatives bearing internucleotide N-tosyl phosphoramidate groups: Synthesis and complementary binding to DNA and RNA

AU - Prokhorova, D. V.

AU - Chelobanov, B. P.

AU - Burakova, E. A.

AU - Fokina, A. A.

AU - Stetsenko, D. A.

N1 - The work was supported by the Russian Foundation for Basic Research (project nos. 15-03-06331, 15-29-01334, 15-54-10049, and 16-03-01055). The oligonucleotide synthesis was supported by the Russian Science Foundation (project no. 15-15-00121). The authors are grateful to M.F. Kassakin for the assistance in recording the mass spectra and M.I. Mesh-chaninova for the oligoribonucleotide synthesis.

PY - 2017/1/1

Y1 - 2017/1/1

N2 - 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.

AB - 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.

KW - p-toluenesulfonyl azide

KW - solid-phase synthesis

KW - Staudinger reaction

KW - β-cyanoethyl phosphite

KW - beta-cyanoethyl phosphite

KW - ANTISENSE OLIGONUCLEOTIDES

UR - http://www.scopus.com/inward/record.url?scp=85012886465&partnerID=8YFLogxK

U2 - 10.1134/S1068162017010071

DO - 10.1134/S1068162017010071

M3 - Article

AN - SCOPUS:85012886465

VL - 43

SP - 38

EP - 42

JO - Russian Journal of Bioorganic Chemistry

JF - Russian Journal of Bioorganic Chemistry

SN - 1068-1620

IS - 1

ER -

ID: 10310095