Original title: The mechanism of isotopic exchange reaction of hydrogen H-5 of uracil derivatives in water and in non-protic solvents
Authors: Dračínský, Martin ; Jansa, Petr ; Chocholoušová, Jana ; Vacek, Jaroslav ; Kovačková, Soňa ; Holý, Antonín
Document type: Papers
Conference/Event: Chemistry of Nucleic Acid Components /15./, Český Krumlov (CZ), 2011-06-05 / 2011-06-10
Year: 2011
Language: eng
Abstract: The mechanism of isotopic exchange reaction of hydrogen H-5 of uracil and its methyl-derivatives in water and in organic solvents was studied. The key intermediate of the reaction is a C-5 tautomer of uracil. We have used 1H NMR spectroscopy to follow the kinetics of the hydrogen-to-deuterium exchange reaction. In aqueous media, a general base catalysis was observed and in organic solvents we propose a reaction mechanism with participation of the solvent molecules. These findings could be effectively used for the tritium labeling of pyrimidine nucleic acid bases.
Keywords: isotope labeling; pyrimidines; reaction mechanism
Project no.: CEZ:AV0Z40550506 (CEP), KJB400550903 (CEP)
Funding provider: GA AV ČR
Host item entry: Chemistry of Nucleic Acid Components. 15th Symposium, ISBN 978-80-86241-37-1

Institution: Institute of Organic Chemistry and Biochemistry AS ČR (web)
Document availability information: Fulltext is available at the institute of the Academy of Sciences.
Original record: http://hdl.handle.net/11104/0198873

Permalink: http://www.nusl.cz/ntk/nusl-55842


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Research > Institutes ASCR > Institute of Organic Chemistry and Biochemistry
Conference materials > Papers