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Base-promoted reaction of 5-hydroxyuracil derivatives with peroxyl radicals
Authors:
- Riccardo Amorati,
- Luca Valgimigli,
- Gian Franco Pedulli,
- Stanislav A. Grabovskiy,
- Natalia N. Kabalnova,
- Chryssostomos Chatgilialoglu
Abstract
Addition of millimolar amounts of a weak base (pyridines) dramatically accelerates the reaction with peroxyl radicals of two biologically relevant uracil derivatives, 5-hydroxyuracil (HU) and 5-hydroxy-6-methyluracil (HMU). This is due to the formation of small amounts of the deprotonated form (pK a = 8.1-8.5 in water), which reacts with peroxyl radicals much faster than the parent undissociated form, via formal H-atom transfer from the OH in the 5 position. © 2010 American Chemical Society.
- Record ID
- UAM4e2572292a2844308b8bf272cdc2a9b0
- Author
- Journal series
- Organic Letters, ISSN 1523-7060
- Issue year
- 2010
- Vol
- 12
- Pages
- 4130-4133
- ASJC Classification
- ; ;
- DOI
- DOI:10.1021/ol1017245 Opening in a new tab
- Language
- (en) English
- Score (nominal)
- 0
- Score source
- journalList
- Publication indicators
- = 23; = 28; : 2010 = 1.304; : 2010 (2 years) = 5.250 - 2010 (5 years) =4.962
- Citation count
- 41
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- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAM4e2572292a2844308b8bf272cdc2a9b0/
- URN
urn:amu-prod:UAM4e2572292a2844308b8bf272cdc2a9b0
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.