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Hydrogen-Bonding Interactions of Methylated Adenine Derivatives
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SYSNO ASEP 0545118 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Hydrogen-Bonding Interactions of Methylated Adenine Derivatives Author(s) Osifová, Zuzana (UOCHB-X)
Socha, Ondřej (UOCHB-X) ORCID, RID
Mužíková Čechová, Lucie (UOCHB-X) ORCID, RID
Šála, Michal (UOCHB-X) RID, ORCID
Janeba, Zlatko (UOCHB-X) RID, ORCID
Dračínský, Martin (UOCHB-X) RID, ORCIDSource Title European Journal of Organic Chemistry - ISSN 1434-193X
Roč. 2021, č. 29 (2021), s. 4166-4173Number of pages 8 s. Language eng - English Country DE - Germany Keywords DFT calculations ; Hoogsteen pairing ; hydrogen bonds ; NMR spectroscopy ; nucleic acids OECD category Physical chemistry R&D Projects GA20-01472S GA ČR - Czech Science Foundation (CSF) Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 UT WOS 000687136200029 EID SCOPUS 85113199113 DOI 10.1002/ejoc.202100721 Annotation Hydrogen bonding between nucleobases is a crucial noncovalent interaction for the life on Earth. Apart from Watson-Crick binding, Hoogsteen pairing has been found in many structures of nucleic acids. Methylation of nucleic acids (NAs) is a post-replication or post-transcription mechanism that can modulate the structure and function of a NA without changing its sequence. Methylation of adenine at the N6 position to form m6A is one of the most important and common epigenetic markers. This paper describes an investigation of intermolecular H-bonding interactions of methylated derivatives of adenine with its complementary partner, thymine. Adenine derivatives with (di)methylamino groups in positions 2 or 6 have been prepared and their interactions with a thymine derivative have been studied by NMR spectroscopy and DFT calculations. It has been found that Hoogsteen pairing is preferred for adenine derivatives, which offer two hydrogen-bond sites on both Watson-Crick and Hoogsteen sides of the molecule. Methylation of the N6 position leads to further stabilization of the Hoogsteen pair. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2022 Electronic address https://doi.org/10.1002/ejoc.202100721
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