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

Autor(en): Seela, Frank
Xu, Kuiying
Stichwörter: 2'-DEOXYTUBERCIDIN; 2-FLUOROADENINE; 7-DEAZAPURINE; Chemistry; Chemistry, Organic; CONFORMATION; CRYSTAL; DUPLEX STABILITY; MODIFIED OLIGONUCLEOTIDES; MOLECULAR STRUCTURE; NMR-SPECTROSCOPY; NUCLEOSIDES
Erscheinungsdatum: 2008
Herausgeber: ROYAL SOC CHEMISTRY
Journal: ORGANIC & BIOMOLECULAR CHEMISTRY
Volumen: 6
Ausgabe: 19
Startseite: 3552
Seitenende: 3560
Zusammenfassung: 
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. F-19 NMR spectra of fluorinated nucleosides, single stranded oligonucleotides and DNA duplex show only a single signal for one fluorine modification. The NMR sensitive F-19 spin or the positron emitting F-18 isotope make these compounds applicable for DNA detection or imaging in vitro and in vivo.
ISSN: 14770520
DOI: 10.1039/b806145a

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