Jump to main content
Jump to site search

Issue 19, 2008
Previous Article Next Article

DNA with stable fluorinated dA and dG substitutes: syntheses, base pairing and 19F-NMR spectra of 7-fluoro-7-deaza-2′-deoxyadenosine and 7-fluoro-7-deaza-2′-deoxyguanosine

Author affiliations

Abstract

Fluorinated DNA containing stable fluorine substituents in the “purine” base were synthesized for the first time. For this, the phosphoramidites of 7-fluoro-7-deaza-2′-deoxyadenosine and 7-fluoro-7-deaza-2′-deoxyguanosine were prepared and oligonucleotides were synthesized. The 7-fluoro substitution leads to increased duplex stability and more selective base pairing compared to the non-functionalized 7-deazapurine oligonucleotides. 19F NMR spectra of fluorinated nucleosides, single stranded oligonucleotides and DNA duplex show only a single signal for one fluorine modification. The NMR sensitive 19F spin or the positron emitting 18F isotope make these compounds applicable for DNA detection or imaging in vitro and in vivo.

Graphical abstract: DNA with stable fluorinated dA and dG substitutes: syntheses, base pairing and 19F-NMR spectra of 7-fluoro-7-deaza-2′-deoxyadenosine and 7-fluoro-7-deaza-2′-deoxyguanosine

Back to tab navigation

Publication details

The article was received on 11 Apr 2008, accepted on 06 Jun 2008 and first published on 17 Jul 2008


Article type: Paper
DOI: 10.1039/B806145A
Citation: Org. Biomol. Chem., 2008,6, 3552-3560

  •   Request permissions

    DNA with stable fluorinated dA and dG substitutes: syntheses, base pairing and 19F-NMR spectra of 7-fluoro-7-deaza-2′-deoxyadenosine and 7-fluoro-7-deaza-2′-deoxyguanosine

    F. Seela and K. Xu, Org. Biomol. Chem., 2008, 6, 3552
    DOI: 10.1039/B806145A

Search articles by author

Spotlight

Advertisements