Chemical reactions in double-stranded nucleic acids. XIII. Directed introduction of acylphosphate bond into DNA duplex structure

S. A. Kuznetsova, M. G. Ivanovskaya, Z. A. Shabarova

Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow

Abstract: DNA duplex, containing an acylphosphate internucleotide bond in a predetermined position of the sugar-phosphate backbone, was synthesized. The synthesis was carried out by condensing on the complementary matrix two heptanudeotides, one of which possessed at the 3'-end a glycine residue, connected with the oligonucleotide by the phosphoramide bond, whereas the 5'-end phosphate group of the other was activated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDAC). The yield of the oligonucleotide with an acylphosphate bond was 24%. The stability and chemical properties of the synthesized compound were studied in comparison with analogous oligonucleotide containing a substituted pyrophosphate internucleotide bond. The former was shown to be an effective acylating agent in the aqueous medium in contrast to the latter which is a phosphorylating agent.

Russian Journal of Bioorganic Chemistry 1991, 17 (12):1633-1639

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