Hydrogen-Bonding Interactions of Methylated Adenine Derivatives
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F21%3A00545118" target="_blank" >RIV/61388963:_____/21:00545118 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/21:10430712
Result on the web
<a href="https://doi.org/10.1002/ejoc.202100721" target="_blank" >https://doi.org/10.1002/ejoc.202100721</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.202100721" target="_blank" >10.1002/ejoc.202100721</a>
Alternative languages
Result language
angličtina
Original language name
Hydrogen-Bonding Interactions of Methylated Adenine Derivatives
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
<a href="/en/project/GA20-01472S" target="_blank" >GA20-01472S: NMR crystallography of disordered systems</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
1099-0690
Volume of the periodical
2021
Issue of the periodical within the volume
29
Country of publishing house
DE - GERMANY
Number of pages
8
Pages from-to
4166-4173
UT code for WoS article
000687136200029
EID of the result in the Scopus database
2-s2.0-85113199113