Tautomerism of guanine analogues

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00521852" target="_blank" >RIV/61388963:_____/20:00521852 - isvavai.cz</a>

Result on the web

<a href="https://www.mdpi.com/2218-273X/10/2/170" target="_blank" >https://www.mdpi.com/2218-273X/10/2/170</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/biom10020170" target="_blank" >10.3390/biom10020170</a>

Result language

angličtina

Original language name

Tautomerism of guanine analogues

Original language description

Tautomerism of nucleic acid (NA) bases is a crucial factor for the maintenance and translation of genetic information in organisms. Only canonical tautomers of NA bases can form hydrogen-bonded complexes with their natural counterparts. On the other hand, rare tautomers of nucleobases have been proposed to be involved in processes catalysed by NA enzymes. Isocytosine, which can be considered as a structural fragment of guanine, is known to have two stable tautomers both in solution and solid states. The tautomer equilibrium of isocytosine contrasts with the remarkable stability of the canonical tautomer of guanine. This paper investigates the factors contributing to the stability of the canonical tautomer of guanine by a combination of NMR experiments and theoretical calculations. The electronic effects of substituents on the stability of the rare tautomers of isocytosine and guanine derivatives are studied by density functional theory (DFT) calculations. Selected derivatives are studied by variable-temperature NMR spectroscopy. Rare tautomers can be stabilised in solution by intermolecular hydrogen-bonding interactions with suitable partners. These intermolecular interactions give rise to characteristic signals in proton NMR spectra, which make it possible to undoubtedly confirm the presence of a rare tautomer.

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10403 - Physical chemistry

Project

<a href="/en/project/GA18-11851S" target="_blank" >GA18-11851S: Intermolecular interactions studied by NMR spectroscopy and advanced quantum-chemical calculations</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2020

Confidentiality

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

Name of the periodical

Biomolecules

ISSN

2218-273X

e-ISSN

—

Volume of the periodical

10

Issue of the periodical within the volume

2

Country of publishing house

CH - SWITZERLAND

Number of pages

10

Pages from-to

170

UT code for WoS article

000522138500121

EID of the result in the Scopus database

2-s2.0-85078231994