BARTL, Tomáš, Zuzana ZACHAROVÁ, Pavlína SEČKÁŘOVÁ, Erkki KOLEHMAINEN and Radek MAREK. NMR Quantification of Tautomeric Populations in Biogenic Purine Bases. European Journal of Organic Chemistry. Weinheim: WILEY-VCH, 2009, vol. 2009, No 9, p. 1377-1383. ISSN 1434-193X. doi:10.1002/ejoc.200801016.
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Basic information
Original name NMR Quantification of Tautomeric Populations in Biogenic Purine Bases
Name in Czech NMR kvantifikace tautomerních populací pro biogenní purinové báze
Authors BARTL, Tomáš (203 Czech Republic, belonging to the institution), Zuzana ZACHAROVÁ (703 Slovakia, belonging to the institution), Pavlína SEČKÁŘOVÁ (203 Czech Republic, belonging to the institution), Erkki KOLEHMAINEN (246 Finland) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution).
Edition European Journal of Organic Chemistry, Weinheim, WILEY-VCH, 2009, 1434-193X.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10401 Organic chemistry
Country of publisher Germany
Confidentiality degree is not subject to a state or trade secret
WWW DOI: 10.1002/ejoc.200801016
Impact factor Impact factor: 3.096
RIV identification code RIV/00216224:14310/09:00034755
Organization unit Faculty of Science
UT WoS 000264683800014
Keywords in English Purine; Adenine; Low-temperature NMR; Tautomerism; Population
Tags adenine, Low-temperature NMR, Population, purine, tautomerism
Tags International impact, Reviewed
Changed by Changed by: prof. RNDr. Radek Marek, Ph.D., učo 381. Changed: 17. 6. 2013 14:28.
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. The influence of concentration on the temperature of coalescence indicates that supramolecular clusters play a significant role in this proton transfer process.
Abstract (in Czech)
Purinové báze, jako je purin, adenin, hypoxanthin a merkaptopurin, mohou existovat v několika tautomerních formách. Ke studiu tautomerních dějů některých derivátů byla využita nízkoteplotní 1H- a 13C-NMR spektroskopie vzorků v methanolu a N,N-dimethylformamidu. Byla vypočítána Gibbsova volná energie a diskutován vliv substituce na pomět N(7)/N(9) forem.
LC06030, research and development projectName: Biomolekulární centrum
Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular centre
MSM0021622413, plan (intention)Name: Proteiny v metabolismu a při interakci organismů s prostředím
Investor: Ministry of Education, Youth and Sports of the CR, Proteins in metabolism and interaction of organisms with the environment
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