About: NMR Quantification of Tautomeric Populations in Biogenic Purine Bases

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	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. 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. (en)
Title	NMR Quantification of Tautomeric Populations in Biogenic Purine Bases NMR Quantification of Tautomeric Populations in Biogenic Purine Bases (en)
skos:prefLabel	NMR Quantification of Tautomeric Populations in Biogenic Purine Bases NMR Quantification of Tautomeric Populations in Biogenic Purine Bases (en)
skos:notation	RIV/00216224:14310/09:00034755!RIV10-MSM-14310___
http://linked.open...avai/riv/aktivita	P S Z
http://linked.open...avai/riv/aktivity	P(LC06030), S, Z(MSM0021622413)
http://linked.open...iv/cisloPeriodika	9
http://linked.open...vai/riv/dodaniDat	2010
http://linked.open...aciTvurceVysledku	Bartl, Tomáš Marek, Radek Zacharová, Zuzana Sečkářová, Pavlína
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Masarykova univerzita / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	329613
http://linked.open...ai/riv/idVysledku	RIV/00216224:14310/09:00034755
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Purine; Adenine; Low-temperature NMR; Tautomerism; Population (en)
http://linked.open.../riv/klicoveSlovo	Population Purine Adenine Tautomerism Low-temperature NMR
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[64F0CCAF7D7A]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	4 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...vavai/riv/projekt	Biomolecular centre
http://linked.open...UplatneniVysledku	2009
http://linked.open...v/svazekPeriodika	2009
http://linked.open...iv/tvurceVysledku	Marek, Radek Bartl, Tomáš Zacharová, Zuzana Sečkářová, Pavlína Kolehmainen, Erkki
http://linked.open...ain/vavai/riv/wos	000264683800014
http://linked.open...n/vavai/riv/zamer	Proteiny v metabolismu a při interakci organismů s prostředím
issn	1434-193X
number of pages	7 (xsd:int)
http://localhost/t...ganizacniJednotka	14310

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