| 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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@article{815785,
author = {Bartl, Tomáš and Zacharová, Zuzana and Sečkářová, Pavlína and Kolehmainen, Erkki and Marek, Radek},
article_location = {Weinheim},
article_number = {9},
doi = {http://dx.doi.org/10.1002/ejoc.200801016},
keywords = {Purine; Adenine; Low-temperature NMR; Tautomerism; Population},
language = {eng},
issn = {1434-193X},
journal = {European Journal of Organic Chemistry},
title = {NMR Quantification of Tautomeric Populations in Biogenic Purine Bases},
url = {http://dx.doi.org/10.1002/ejoc.200801016},
volume = {2009},
year = {2009}
}
TY - JOUR
ID - 815785
AU - Bartl, Tomáš - Zacharová, Zuzana - Sečkářová, Pavlína - Kolehmainen, Erkki - Marek, Radek
PY - 2009
TI - NMR Quantification of Tautomeric Populations in Biogenic Purine Bases
JF - European Journal of Organic Chemistry
VL - 2009
IS - 9
SP - 1377-1383
EP - 1377-1383
PB - WILEY-VCH
SN - 1434193X
KW - Purine
KW - Adenine
KW - Low-temperature NMR
KW - Tautomerism
KW - Population
UR - http://dx.doi.org/10.1002/ejoc.200801016
L2 - http://dx.doi.org/10.1002/ejoc.200801016
N2 - 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.
ER -
BARTL, Tomáš, Zuzana ZACHAROVÁ, Pavlína SEČKÁŘOVÁ, Erkki KOLEHMAINEN and Radek MAREK. NMR Quantification of Tautomeric Populations in Biogenic Purine Bases. \textit{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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