Hydrogen-Bonding Interactions of Methylated Adenine Derivatives

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/00216208:11310/21:10430712

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Hydrogen-Bonding Interactions of Methylated Adenine Derivatives

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Hydrogen-Bonding Interactions of Methylated Adenine Derivatives

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/GA20-01472S" target="_blank" >GA20-01472S: NMR krystalografie neuspořádaných systémů</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

1099-0690

Svazek periodika

2021

Číslo periodika v rámci svazku

29

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

8

Strana od-do

4166-4173

Kód UT WoS článku

000687136200029

EID výsledku v databázi Scopus

2-s2.0-85113199113