Base-Promoted Reaction of 5-Hydroxyuracil Derivatives with Peroxyl Radicals

Base-Promoted Reaction of 5-Hydroxyuracil Derivatives with Peroxyl Radicals

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...

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Bibliographic Details
Published in:Organic letters Vol. 12; no. 18; pp. 4130 - 4133
Main Authors: Amorati, Riccardo, Valgimigli, Luca, Pedulli, Gian Franco, Grabovskiy, Stanislav A, Kabal’nova, Natalia N, Chatgilialoglu, Chryssostomos
Format: Journal Article
Language:English
Published: United States American Chemical Society 17-09-2010
Subjects:
Molecular Structure
Oxygen - chemistry
Peroxides - chemistry
Uracil - analogs & derivatives
Uracil - chemistry
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol1017245