NMR Quantification of Tautomeric Populations in Biogenic Purine Bases

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F09%3A00034755" target="_blank" >RIV/00216224:14310/09:00034755 - isvavai.cz</a>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

NMR Quantification of Tautomeric Populations in Biogenic Purine Bases

Popis výsledku v původním jazyce

Purine bases such as purine, adenine, hypoxanthine, and mercaptopurine are known to exist in several tautomeric forms. Characterization of their tautomeric equilibria is important not only for predicting the regioselectivity of their N-alkylation reactions but also for gaining knowledge of the patterns with which these compounds of significant biological activity form hydrogen bonds with their biological targets. Low-temperature 1H- and 13C-NMR spectroscopy were used to investigate the tautomeric equilibria for purine and some purine derivatives in methanol and N,N-dimethylformamide solutions. The N(7)H and N(9)H tautomeric forms were quantified by integrating the individual 1H NMR signals at low temperatures. The Gibbs free energy differences were calculated, and the effects of substitution on the N(7)H/N(9)H ratio discussed. A previously published theoretically predicted mechanism of the tautomeric exchange is compared with our measurements in deuterated solvents.

Název v anglickém jazyce

NMR Quantification of Tautomeric Populations in Biogenic Purine Bases

Popis výsledku anglicky

Purine bases such as purine, adenine, hypoxanthine, and mercaptopurine are known to exist in several tautomeric forms. Characterization of their tautomeric equilibria is important not only for predicting the regioselectivity of their N-alkylation reactions but also for gaining knowledge of the patterns with which these compounds of significant biological activity form hydrogen bonds with their biological targets. Low-temperature 1H- and 13C-NMR spectroscopy were used to investigate the tautomeric equilibria for purine and some purine derivatives in methanol and N,N-dimethylformamide solutions. The N(7)H and N(9)H tautomeric forms were quantified by integrating the individual 1H NMR signals at low temperatures. The Gibbs free energy differences were calculated, and the effects of substitution on the N(7)H/N(9)H ratio discussed. A previously published theoretically predicted mechanism of the tautomeric exchange is compared with our measurements in deuterated solvents.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/LC06030" target="_blank" >LC06030: Biomolekulární centrum</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2009

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

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Svazek periodika

2009

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

7

Strana od-do

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Kód UT WoS článku

000264683800014

EID výsledku v databázi Scopus

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