[Chemical reactions in double-stranded nucleic acids. IX. Directed introduction of substituted pyrophosphate bonds into DNA structure]

Bioorg Khim. 1990 Feb;16(2):219-25.
[Article in Russian]

Abstract

An effective synthesis of oligodeoxyribonucleotides containing a substituted pyrophosphate bond in the definite position of the sugar-phosphate backbone has been developed by template-directed condensation of two heptanucleotides. One of them containing 5'-phosphate group to be activated and 3'-phosphate group of the other being substituted with ethoxy-, buthylamino-, morpholino- or ethyl glycinate residues. Water-soluble carbodiimide (EDAC) proved to be more efficient in the phosphate group activation than N-hydroxybenzotriazole ester (yields of substituted pyrophosphates 35-80 and 10-15% respectively). The substituted pyrophosphate bong is quite stable in neutral aqueous solution. Mild conditions of selective cleavage of this bond yielding the initial oligonucleotides were found.

Publication types

  • English Abstract

MeSH terms

  • Base Sequence
  • Chemical Phenomena
  • Chemistry
  • DNA*
  • Diphosphates*
  • Molecular Sequence Data
  • Oligodeoxyribonucleotides / chemical synthesis*

Substances

  • Diphosphates
  • Oligodeoxyribonucleotides
  • DNA