Počet záznamů: 1
Tautomerism of guanine analogues
- 1.
SYSNO ASEP 0521852 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Tautomerism of guanine analogues Tvůrce(i) Štoček, Jakub Radek (UOCHB-X) ORCID
Dračínský, Martin (UOCHB-X) RID, ORCIDČíslo článku 170 Zdroj.dok. Biomolecules. - : MDPI
Roč. 10, č. 2 (2020)Poč.str. 10 s. Jazyk dok. eng - angličtina Země vyd. CH - Švýcarsko Klíč. slova nucleic acids ; tautomerism ; NMR spectroscopy ; DFT calculations Vědní obor RIV CF - Fyzikální chemie a teoretická chemie Obor OECD Physical chemistry CEP GA18-11851S GA ČR - Grantová agentura ČR Způsob publikování Open access Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000522138500121 EID SCOPUS 85078231994 DOI 10.3390/biom10020170 Anotace 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. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Rok sběru 2021 Elektronická adresa https://www.mdpi.com/2218-273X/10/2/170
Počet záznamů: 1