The mechanism of isotopic exchange reaction of hydrogen H-5 of uracil derivatives in water and in non-protic solvents

0361589 - ÚOCHB 2012 CZ eng C - Conference Paper (international conference)
Dračínský, Martin - Jansa, Petr - Chocholoušová, Jana - Vacek, Jaroslav - Kovačková, Soňa - Holý, Antonín
The mechanism of isotopic exchange reaction of hydrogen H-5 of uracil derivatives in water and in non-protic solvents.
Chemistry of Nucleic Acid Components. 15th Symposium. Praha: Institute of Organic Chemistry and Biochemistry AS CR, v. v. i., 2011 - (Hocek, M.), s. 323-324. Collection Symposium Series, 12. ISBN 978-80-86241-37-1.
[Chemistry of Nucleic Acid Components /15./. Český Krumlov (CZ), 05.06.2011-10.06.2011]
R&D Projects: GA AV ČR KJB400550903
Institutional research plan: CEZ:AV0Z40550506
Keywords : pyrimidines * isotope labeling * reaction mechanism
Subject RIV: CC - Organic Chemistry

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.
Permanent Link: http://hdl.handle.net/11104/0198873