Improved synthesis of 2'-amino-2'-deoxyguanosine and its phosphoramidite

Bioorg Med Chem. 2006 Feb 1;14(3):705-13. doi: 10.1016/j.bmc.2005.08.050. Epub 2005 Oct 3.

Abstract

2'-Amino-2'-deoxynucleosides and oligonucleotides containing them have proven highly effective for an array of biochemical applications. The guanosine analogue and its phosphoramidite derivatives have been accessed previously from 2'-amino-2'-deoxyuridine by transglycosylation, but with limited overall efficiency and convenience. Using simple modifications of known reaction types, we have developed useful protocols to obtain 2'-amino-2'-deoxyguanosine and two of its phosphoramidite derivatives with greater convenience, fewer steps, and higher yields than reported previously. These phosphoramidites provide effective synthons for the incorporation of 2'-amino-2'-deoxyguanosine into oligonucleotides.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / chemical synthesis
  • Deoxyguanosine / chemistry
  • Methods
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry

Substances

  • Oligonucleotides
  • Organophosphorus Compounds
  • phosphoramidite
  • 2'-amino-2'-deoxyguanosine
  • Deoxyguanosine