Synthesis and incorporation into DNA of a chemically stable, functional abasic site analogue

Org Lett. 2005 Nov 10;7(23):5211-4. doi: 10.1021/ol052045g.

Abstract

[reaction: see text] The abasic site building block 7 for DNA synthesis, containing a methylenephosphinic acid group at C3', was prepared in six steps and was incorporated into DNA via a combination of H-phosphonate and phosphoramidite chemistry. Corresponding oligodeoxynucleotides were shown to be chemically stable under basic conditions and fully functional at the respective hemiacetal center.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • DNA / chemical synthesis
  • DNA / chemistry*
  • DNA Repair
  • Indicators and Reagents
  • Molecular Structure
  • Oligodeoxyribonucleotides / chemical synthesis*
  • Phosphines / chemical synthesis*

Substances

  • Indicators and Reagents
  • Oligodeoxyribonucleotides
  • Phosphines
  • DNA