Synthesis of Novel Representatives of Phosphoryl Guanidine Oligonucleotides

S. A. Zhukov, D. V. Pyshnyi, M. S. Kupryushkin

Research output: Contribution to journalArticlepeer-review

Abstract

Novel representatives of phosphoryl guanidine oligonucleotide derivatives were prepared in this study. A synthetic scheme has been proposed and implemented suitable for the preparation of a wide range of diaminocarbenium azides starting from various secondary amines for subsequent incorporation of tetrasubstituted guanidine residues into the oligonucleotides by the Staudinger reaction. A number of factors which affected the yield of the phosphoryl guanidine derivative were identified, in particular, the size of the alkyl substituents in the azide used, the purity of the azide, and the conditions for elimination of the protecting cyanoethyl group before the final deprotection of the oligonucleotide.

Original languageEnglish
Pages (from-to)380-389
Number of pages10
JournalRussian Journal of Bioorganic Chemistry
Volume47
Issue number2
DOIs
Publication statusPublished - Mar 2021

Keywords

  • automatic oligonucleotide synthesis
  • modified oligonucleotides
  • organic azides
  • phosphoryl guanidine oligonucleotides (PGOs)
  • phosphoryl guanidines
  • the Staudinger reaction

OECD FOS+WOS

  • 1.06 BIOLOGICAL SCIENCES
  • 1.04 CHEMICAL SCIENCES

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