Problems of the Synthesis of Oligonucleotide Derivatives in the Realization of the Anchimeric Effect

E. S. Dyudeeva, A. S. Pavlova, M. S. Kupryushkin, D. V. Pyshnyi, I. A. Pyshnaya

Research output: Contribution to journalArticlepeer-review

Abstract

It has been found that the presence of a free OH group at the 3'-terminal residue of the substituted ethylene glycol fragment in a phosphoryl guanidine oligodeoxyribonucleotide derivative is a factor that determines the instability of the structure of the target oligonucleotide product under the conditions of a standard deblocking protocol. It has been shown that the main by-products of the realization of the anchimeric effect of the OH group are the products of the transesterification of the phosphoryl guanidine (PG) unit carrying the O-substituted ethylene glycol residue. The data of the mass spectrometry analysis indicate that, under alkaline conditions, the accumulation of derivatives devoid of the N,N,N',N'-substituted guanidine residue (1,3-dimethylimidazolidin-2-imine, DMI) or the entire 3'-terminal PG-containing nonnucleotide unit occurs.

Original languageEnglish
Pages (from-to)505-513
Number of pages9
JournalRussian Journal of Bioorganic Chemistry
Volume47
Issue number2
DOIs
Publication statusPublished - Mar 2021

Keywords

  • anchimeric effect
  • mass spectrometry
  • modified oligonucleotides
  • phosphoryl guanidines

OECD FOS+WOS

  • 1.06 BIOLOGICAL SCIENCES
  • 1.04 CHEMICAL SCIENCES

Fingerprint

Dive into the research topics of 'Problems of the Synthesis of Oligonucleotide Derivatives in the Realization of the Anchimeric Effect'. Together they form a unique fingerprint.

Cite this