Por favor, use este identificador para citar o enlazar a este item:
http://hdl.handle.net/10261/130723
COMPARTIR / EXPORTAR:
SHARE CORE BASE | |
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE | |
Título: | Synthesis and properties of 2′-deoxy-2′,4′-difluoroarabinose-modified nucleic acids |
Autor: | Martínez-Montero, S.; Deleavey, G.F.; Dierker-Viik, A.; Lindovska, P.; Ilina, T.; Portella, G.; Orozco, Modesto; Parniak, M.A.; González, Carlos CSIC ; González, Carlos CSIC ; Damha, Masad J. | Fecha de publicación: | 2015 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 80: 3083- 3091 (2015) | Resumen: | © 2015 American Chemical Society. 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). | URI: | http://hdl.handle.net/10261/130723 | DOI: | 10.1021/jo502948t | Identificadores: | doi: 10.1021/jo502948t issn: 1520-6904 |
Aparece en las colecciones: | (IQF) Artículos |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
---|---|---|---|---|
accesoRestringido.pdf | 15,38 kB | Adobe PDF | Visualizar/Abrir |
CORE Recommender
PubMed Central
Citations
11
checked on 20-abr-2024
SCOPUSTM
Citations
30
checked on 18-abr-2024
WEB OF SCIENCETM
Citations
30
checked on 29-feb-2024
Page view(s)
194
checked on 24-abr-2024
Download(s)
73
checked on 24-abr-2024
Google ScholarTM
Check
Altmetric
Altmetric
Artículos relacionados:
NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.