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Isoguanine and 5-Methyl-Isocytosine Bases, In Vitro and In Vivo

Bande, O; Abu El Asrar, R; Braddick, D; Dumbre, S; Pezo, V; Schepers, G; Pinheiro, VB; ... Herdewijn, P; + view all (2015) Isoguanine and 5-Methyl-Isocytosine Bases, In Vitro and In Vivo. Chem. Eur. J. , 21 (13) pp. 5009-5022. 10.1002/chem.201406392. Green open access

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Abstract

The synthesis, base-pairing properties and in vitro and in vivo characteristics of 5-methyl-isocytosine (isoCMe) 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-isoCMe 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 isoCMe misincorporates mainly with A. Further analysis in vivo confirmed the patterns of base-pair interpretation for the deoxyribose and hexitol isoCMe/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.

Type: Article
Title: Isoguanine and 5-Methyl-Isocytosine Bases, In Vitro and In Vivo
Open access status: An open access version is available from UCL Discovery
DOI: 10.1002/chem.201406392
Publisher version: http://dx.doi.org/10.1002/chem.201406392
Language: English
Additional information: © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Keywords: Science & Technology, Physical Sciences, Chemistry, Multidisciplinary, Chemistry, Hna, Isog, Polymerase, Nucleosides, Xna Plasmid, Antiparallel Chain Orientation, Synthetic Genetic Polymers, Oligonucleotide Duplexes, Photochemical-Synthesis, Nucleic-Acids, Pair, Isoguanosine, 2'-Deoxyisoguanosine, Replication, Nucleosides
UCL classification: UCL > School of Life and Medical Sciences
UCL > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > School of Life and Medical Sciences > Faculty of Life Sciences > Biosciences (Division of) > Structural and Molecular Biology
URI: http://discovery.ucl.ac.uk/id/eprint/1551648
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