Convenient synthesis of 8-amino-2'-deoxyadenosine

Nucleosides Nucleotides Nucleic Acids. 2003 Feb;22(2):193-202. doi: 10.1081/NCN-120019521.

Abstract

We studied the behaviour of 8-azido-2'-deoxyadenosine and 8-bromo-2'-deoxyadenosine in aqueous solutions of ammonia and primary and secondary amines. Unexpectedly, 8-Azido-2'-deoxyadenosine is converted to 8-amino-2'-deoxyadenosine in excellent yields. The use of this reaction for the preparation of 8-aminoadenine derivatives needed for the preparation of oligonucleotides carrying 8-aminoadenine is discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Ammonia / chemistry
  • Azides / chemistry*
  • Chromatography, High Pressure Liquid
  • Deoxyadenosines / chemical synthesis*
  • Deoxyadenosines / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Oligonucleotides
  • Purines / chemistry

Substances

  • 8-azido-2'-deoxyadenosine
  • Amines
  • Azides
  • Deoxyadenosines
  • Oligonucleotides
  • Purines
  • 8-amino-2'-deoxyadenosine
  • 8-bromo-2'-deoxyadenosine
  • Ammonia