Issue 19, 2008

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

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

Article information

Article type
Paper
Submitted
11 Apr 2008
Accepted
06 Jun 2008
First published
17 Jul 2008

Org. Biomol. Chem., 2008,6, 3552-3560

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

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