The Control of the Tautomeric Equilibrium of Isocytosine by Intermolecular Interactions

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00495590" target="_blank" >RIV/61388963:_____/18:00495590 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201800506" target="_blank" >http://dx.doi.org/10.1002/ejoc.201800506</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201800506" target="_blank" >10.1002/ejoc.201800506</a>

Result language
angličtina
Original language name
The Control of the Tautomeric Equilibrium of Isocytosine by Intermolecular Interactions
Original language description
Isocytosine has two stable tautomers, which can form a dimer with each other, stabilised by three intermolecular hydrogen bonds similar to those in the guanine-cytosine base pair. Molecules with suitable donor/acceptor hydrogen-bonding patterns can form intermolecular complexes with one or the other isocytosine tautomer. These intermolecular interactions stabilise the selected isocytosine tautomer, leading to an increase of its relative concentration. The integration of the H-1 NMR spectra acquired at various temperatures and concentrations was used for the determination of free-energy changes of the formation of the isocytosine dimer/complex. The experimental free-energy changes contain contributions from the formation of the isocytosine dimer/complex itself and from the rearrangement of the solvation shell. The latter contribution was estimated through a comparison of the experimental free-energy changes with those calculated for the dimer/complex formation at the DFT level. The study demonstrates that the molecular environment can change relative tautomer stabilities, which supports the hypothesis of the involvement of rare nucleobase tautomers in the catalytic function of RNA enzymes.
Czech name
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Czech description
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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

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
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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