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Title: Isoguanine and 5-Methyl-Isocytosine Bases, In Vitro and In Vivo
Authors: Bande, Omprakash ×
Abou El Asrar, Rania
Braddick, Darren
Dumbre, Shrinivas
Pezo, Valérie
Schepers, Guy
Pinheiro, Vitor B
Lescrinier, Eveline
Holliger, Philipp
Marlière, Philippe
Herdewijn, Piet #
Issue Date: Mar-2015
Publisher: VCH Verlagsgesellschaft
Series Title: Chemistry - a European Journal vol:21 issue:13 pages:5009-22
Article number: 10.1002/chem.201406392
Abstract: The synthesis, base-pairing properties and in vitro and in vivo characteristics of 5-methyl-isocytosine (isoC(Me) ) and isoguanine (isoG) nucleosides, incorporated in an HNA(h) (hexitol nucleic acid)-DNA(d) mosaic backbone, are described. The required h-isoG phosphoramidite was prepared by a selective deamination as a key step. As demonstrated by Tm measurements the hexitol sugar showed slightly better mismatch discrimination against dT. The d-isoG base mispairing follows the order T>G>C while the h-isoG base mispairing follows the order G>C>T. The h- and d-isoC(Me) bases mainly mispair with G. Enzymatic incorporation experiments show that the hexitol backbone has a variable effect on selectivity. In the enzymatic assays, isoG misincorporates mainly with T, and isoC(Me) misincorporates mainly with A. Further analysis in vivo confirmed the patterns of base-pair interpretation for the deoxyribose and hexitol isoC(Me) /isoG bases in a cellular context, through incorporation of the bases into plasmidic DNA. Results in vivo demonstrated that mispairing and misincorporation was dependent on the backbone scaffold of the base, which indicates rational advances towards orthogonality.
URI: 
ISSN: 0947-6539
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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