Phosphoryl Guanidines: A New Type of Nucleic Acid Analogues

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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.


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

Russian Federation

D. V. Pyshnyi

Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences

Email: dast@niboch.nsc.ru

Russian Federation

D. A. Stetsenko

Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences

Email: dast@niboch.nsc.ru

Russian Federation

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Copyright (c) 2014 Kupryushkin M.S., Pyshnyi D.V., Stetsenko D.A.

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