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

Qing Dai, Shirshendu K. Deb, James L. Hougland, Joseph A. Piccirilli

Research output: Contribution to journalArticle

11 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)705-713
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume14
Issue number3
DOIs
StatePublished - Feb 1 2006
Externally publishedYes

Keywords

  • 2′-Amino-2′-deoxyguanosine
  • Oligonucleotide
  • Phosphoramidite
  • Transglycosylation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Improved synthesis of 2′-amino-2′-deoxyguanosine and its phosphoramidite'. Together they form a unique fingerprint.

  • Cite this