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http://hdl.handle.net/2445/129851
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DC Field | Value | Language |
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dc.contributor.author | Martínez-Montero, Saúl | - |
dc.contributor.author | Deleavey, Glen F. | - |
dc.contributor.author | Dierker-Viil, Arden | - |
dc.contributor.author | Lindovska, Petra | - |
dc.contributor.author | Ilina, Tatiana | - |
dc.contributor.author | Portella, Guillem | - |
dc.contributor.author | Orozco López, Modesto | - |
dc.contributor.author | Parniak, Michael A. | - |
dc.contributor.author | Damha, Masad J. | - |
dc.date.accessioned | 2019-03-06T15:11:28Z | - |
dc.date.available | 2019-03-06T15:11:28Z | - |
dc.date.issued | 2015-02-27 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/2445/129851 | - |
dc.description.abstract | We report the synthesis, thermal stability, and RNase H substrate activity of 2′-deoxy-2′,4′-difluoroarabino-modified nucleic acids. 2′-Deoxy-2′,4′-difluoroarabinouridine (2,′4′-diF-araU) was prepared in a stereoselective way in six steps from 2′-deoxy-2′-fluoroarabinouridine (2′-F-araU). NMR analysis and quantum mechanical calculations at the nucleoside level reveal that introduction of 4′-fluorine introduces a strong bias toward the North conformation, despite the presence of the 2′-βF, which generally steers the sugar pucker toward the South/East conformation. Incorporation of the novel monomer into DNA results on a neutral to slightly stabilizing thermal effect on DNA-RNA hybrids. Insertion of 2′,4′-diF-araU nucleotides in the DNA strand of a DNA-RNA hybrid decreases the rate of both human and HIV reverse transcriptase-associated RNase H-mediated cleavage of the complement RNA strand compared to that for an all-DNA strand or a DNA strand containing the corresponding 2′-F-araU nucleotide units, consistent with the notion that a 4′-fluorine in 2′-F-araU switches the preferred sugar conformation from DNA-like (South/East) to RNA-like (North). | - |
dc.format.extent | 9 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | American Chemical Society | - |
dc.relation.isformatof | Versió postprint del document publicat a: https://doi.org/10.1021/jo502948t | - |
dc.relation.ispartof | Journal of Organic Chemistry, 2015, vol. 80, num. 6, p. 3083-3091 | - |
dc.relation.uri | https://doi.org/10.1021/jo502948t | - |
dc.rights | (c) American Chemical Society , 2015 | - |
dc.source | Articles publicats en revistes (Bioquímica i Biomedicina Molecular) | - |
dc.subject.classification | Síntesi de l'ADN | - |
dc.subject.classification | Química orgànica | - |
dc.subject.other | DNA synthesis | - |
dc.subject.other | Organic chemistry | - |
dc.title | Synthesis and Properties of 2′-Deoxy-2′,4′-difluoroarabinose-Modified Nucleic Acids | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 652658 | - |
dc.date.updated | 2019-03-06T15:11:28Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
dc.identifier.pmid | 25723361 | - |
Appears in Collections: | Articles publicats en revistes (Bioquímica i Biomedicina Molecular) |
Files in This Item:
File | Description | Size | Format | |
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652658.pdf | 1.13 MB | Adobe PDF | View/Open |
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