Jabgunde, AM;
Jaziri, F;
Bande, O;
Froeyen, M;
Abramov, M;
Hoai, N;
Schepers, G;
... Herdewijn, P; + view all
(2018)
Methylated Nucleobases: Synthesis and Evaluation for Base Pairing In Vitro and In Vivo.
Chemistry - A European Journal
, 24
(48)
pp. 12695-12707.
10.1002/chem.201802304.
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Abstract
The synthesis, base pairing properties and in vitro (polymerase) and in vivo (E. coli) recognition of 2′‐deoxynucleotides with a 2‐amino‐6‐methyl‐8‐oxo‐7,8‐dihydro‐purine (X), a 2‐methyl‐6‐thiopurine (Y) and a 6‐methyl‐4‐pyrimidone (Z) base moiety are described. As demonstrated by Tm measurements, the X and Y bases fail to form a self‐complementary base pair. Despite this failure, enzymatic incorporation experiments show that selected DNA polymerases recognize the X nucleotide and incorporate this modified nucleotide versus X in the template. In vivo, X is mainly recognized as a A/G or C base; Y is recognized as a G or C base and Z is mostly recognized as T or C. Replacing functional groups in nucleobases normally involved in W−C recognition (6‐carbonyl and 2‐amino group of purine; 6‐carbonyl of pyrimidine) readily leads to orthogonality (absence of base pairing with natural bases).
| Type: | Article |
|---|---|
| Title: | Methylated Nucleobases: Synthesis and Evaluation for Base Pairing In Vitro and In Vivo |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/chem.201802304 |
| Publisher version: | https://doi.org/10.1002/chem.201802304 |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| Keywords: | duplex stability, methylated nucleobases, polymerases, self-pairing, transliteration |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > Div of Biosciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > Div of Biosciences > Structural and Molecular Biology |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10067423 |
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