Email this article Phosphoryl Guanidines: A New Type of Nucleic Acid Analogues
- Authors: Kupryushkin M.S.1, Pyshnyi D.V.1, Stetsenko D.A.1
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Affiliations:
- Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences
- Issue: Vol 6, No 4 (2014)
- Pages: 116-118
- Section: Short communications
- Submitted: 17.01.2020
- Published: 15.12.2014
- URL: https://actanaturae.ru/2075-8251/article/view/10536
- DOI: https://doi.org/10.32607/20758251-2014-6-4-116-118
- ID: 10536
Cite item
Abstract
A new type of nucleic acid analogues with a phosphoryl guanidine group is described. Oxidation of polymer-supported dinucleoside 2-cyanoethyl phosphite by iodine in the presence of 1,1,3,3-tetramethyl guanidine yields a dinucleotide with an internucleoside tetramethyl phosphoryl guanidine (Tmg) group as the main product. The Tmg group is stable under conditions of solid-phase DNA synthesis and subsequent cleavage and deprotection with ammonia. Oligonucleotides with one or more Tmg groups bind their complementary DNA or RNA with affinity similar to that of natural oligodeoxyribonucleotides.
About the authors
M. S. Kupryushkin
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences
Author for correspondence.
Email: dast@niboch.nsc.ru
Россия
D. V. Pyshnyi
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences
Email: dast@niboch.nsc.ru
Россия
D. A. Stetsenko
Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences
Email: dast@niboch.nsc.ru
Россия
References
- Goodchild J. N.Y. // Therapeutic Oligonucleotides: Methods and Protocols. Methods Mol. Biol. / Humana Press, 2011 2011, V.764, P.340
- Bell N.M., Micklefield J. // ChemBioChem. 2009, V.10, №17, P.2691-2703
- Egholm M., Buchardt O., Nielsen P.E., Berg R.H. // J. Am. Chem. Soc. 1992, V.114, №5, P.1895-1897
- Summerton J., Weller D. // Antisense Nucleic Acid Drug Dev. 1997, V.7, №3, P.187-195
- Nielsen P.E. // Mol. Biotechnol. 2004, V.26, №3, P.233-248
- Karkare S., Bhatnagar D. // Appl. Microbiol. Biotechnol. 2006, V.71, №5, P.575-586
- Jäger A., Levy M.J., Hecht S.M. // Biochemistry. 1988, V.27, №19, P.7237-7246
- Stetsenko D.A., Kupryushkin M.S., Pyshnyi D.V. // WO patent application PCT /RU 2014/000647, priority from 22.08.2014. 2014
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