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

DC FieldValueLanguage
dc.contributor.authorSeela, Frank
dc.contributor.authorXu, Kuiying
dc.date.accessioned2021-12-23T16:05:53Z-
dc.date.available2021-12-23T16:05:53Z-
dc.date.issued2008
dc.identifier.issn14770520
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/7265-
dc.description.abstractFluorinated 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.
dc.description.sponsorshipIdenix Pharmaceuticals, Cambridge, US; Montpellier, France; ChemBiotech, Munster, Germany; We thank Dr Peter Leonard and Dr Simone Budow for helpful discussions during the preparation of the manuscript. We thank also Ms Padmaja Chittipu, Mr Dawei Jiang for the measurements of the NMR spectra and Dr I Koch. Roche Diagnostics GmbH, for the MALDI-TOF mass spectra. We gratefully acknowledge financial support by Idenix Pharmaceuticals, Cambridge, US and Montpellier, France and ChemBiotech, Munster, Germany
dc.language.isoen
dc.publisherROYAL SOC CHEMISTRY
dc.relation.ispartofORGANIC & BIOMOLECULAR CHEMISTRY
dc.subject2'-DEOXYTUBERCIDIN
dc.subject2-FLUOROADENINE
dc.subject7-DEAZAPURINE
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectCONFORMATION
dc.subjectCRYSTAL
dc.subjectDUPLEX STABILITY
dc.subjectMODIFIED OLIGONUCLEOTIDES
dc.subjectMOLECULAR STRUCTURE
dc.subjectNMR-SPECTROSCOPY
dc.subjectNUCLEOSIDES
dc.titleDNA 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
dc.typejournal article
dc.identifier.doi10.1039/b806145a
dc.identifier.isiISI:000259813400014
dc.description.volume6
dc.description.issue19
dc.description.startpage3552
dc.description.endpage3560
dc.publisher.placeTHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
dcterms.isPartOf.abbreviationOrg. Biomol. Chem.
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