2-Amino-alpha-2'-deoxyadenosine increased duplex stability of methoxyethylphosphoramidate alpha-oligodeoxynucleotides with RNA target

Bioorg Med Chem Lett. 2002 Jun 3;12(11):1435-8. doi: 10.1016/s0960-894x(02)00215-9.

Abstract

A new efficient synthesis of 2-amino-alpha-2'-deoxyadenosine and its incorporation into methoxyethylphosphoramidate alpha-oligodeoxynucleotides (ODNs) via H-phosphonate chemistry were reported. Thermal denaturation experiments demonstrated a significant stabilization of the complexes formed between these analogues and their RNA target (+2 degrees C/NH2A) relative to adenosine-containing phosphoramidate alpha-oligonucleotides. Concerning the binding specificity of these modified ODNs, unlike natural ODNs, discrimination against G pairing is higher and against C pairing is lower.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry
  • Base Sequence
  • Cytosine / chemistry
  • DNA, Complementary / chemistry
  • Deoxyadenosines / chemical synthesis
  • Deoxyadenosines / chemistry*
  • Guanosine / analogs & derivatives
  • Guanosine / chemistry
  • Hot Temperature
  • Nucleic Acid Denaturation
  • Nucleic Acid Heteroduplexes / chemistry
  • Nucleic Acid Hybridization
  • Oligodeoxyribonucleotides / chemical synthesis*
  • Oligodeoxyribonucleotides / chemistry
  • Phosphoric Acids / chemical synthesis
  • Phosphoric Acids / chemistry
  • RNA / chemistry*

Substances

  • Amides
  • DNA, Complementary
  • Deoxyadenosines
  • Nucleic Acid Heteroduplexes
  • Oligodeoxyribonucleotides
  • Phosphoric Acids
  • 2'-amino-2'-deoxyadenosine
  • Guanosine
  • RNA
  • Cytosine
  • phosphoramidic acid